Title: TOP 10 Hotels in Windsor, MA (from $77) 2026 - Competitive Prices | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx6005427)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d6005427.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d6005427.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Feb 7 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 8 - Feb 9](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-08&endDate=2026-02-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor hotels ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold [](https://www.expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) Lenox 9.0/10 Wonderful (853 reviews) "So charming, clean, thoughtful touches and a really special place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juliana $98 nightly $110 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/30e56504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn [](https://www.expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) Williamstown 9.6/10 Exceptional (573 reviews) "Great stay. Comfortable hotel and very friendly staff. Restaurant is very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica $189 nightly $212 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms | Iron/ironing board, free cribs/infant beds, WiFi, bed sheets](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG [](https://www.expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) South Lee 9.0/10 Wonderful (832 reviews) "Great overnights stay, wish I was here longer " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas $123 nightly $137 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive King Room | Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/4ae0b464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/efe975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/cab085ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### D. Hotel Suites & Spa [](https://www.expedia.com/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) Holyoke 9.2/10 Wonderful (2,239 reviews) "Great service, clean & quiet rooms, and a solid breakfast to start the day" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie $127 nightly $141 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/94cb14a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4e4268ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3e2d816d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn [](https://www.expedia.com/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) Stockbridge 8.8/10 Excellent (1,002 reviews) "As always, our stay at The Red Lion Inn was memorable. Everything was top notch." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary $190 nightly $213 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/73ad73a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds | Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/6a901d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony Queen | Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/1845c2ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/0d0e7da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Northampton [](https://www.expedia.com/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information) Northampton 9.2/10 Wonderful (1,000 reviews) "The staff were amazing and the room was perfect. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shaun $999 nightly $1,116 total Mar 6 - Mar 7 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/77fe0507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/201806cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge [](https://www.expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) Pittsfield 9.0/10 Wonderful (831 reviews) "Very comfortable and very close to ski slope and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick $121 nightly $136 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/bb79982b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/3670f3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Private Bathroom (Field of Dreams) | Individually decorated, individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/903dd1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn [](https://www.expedia.com/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) Cheshire 9.4/10 Exceptional (53 reviews) "Nice place for a weekend away." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory $204 nightly $216 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room, 1 King Bed, Non Smoking, No Children Allowed | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/8cd694d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1,010 reviews) "Very friendly staff comfy beds!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giselle $98 nightly $110 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.0/10 Wonderful (1,002 reviews) "Room was clean and the staff was super friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ethan $98 nightly $109 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, 1 King Bed, Garden View | Egyptian cotton sheets, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/f581b284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/be4af91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Cabin, 1 King Bed, Lake View | Egyptian cotton sheets, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/f1533622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prospect Berkshires [](https://www.expedia.com/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) Egremont 9.6/10 Exceptional (19 reviews) "Excellent local stay - would recommend to all" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gentian $196 nightly $219 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a97806ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/e88abd9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) Pittsfield 8.0/10 Very Good (1,001 reviews) "Staff was very courteous and rooms clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven $102 nightly $114 total Mar 7 - Mar 8 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/5bcca6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/2bb92acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![28-inch TV with digital channels, Netflix, pay movies](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/be3999ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/d0afa322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Trail in Adams - Berkshires’ Art Hotel [](https://www.expedia.com/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information) Adams 9.0/10 Wonderful (144 reviews) "Staff was great, very clean, Breakfast was terrific" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael $156 nightly $175 total Feb 11 - Feb 12 Total with taxes and fees [](https://www.expedia.com/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/143e42a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed | Iron/ironing board, free cribs/infant beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/df38277f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/9e7aab54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed | Iron/ironing board, free cribs/infant beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/7d7cb3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ellery [](https://www.expedia.com/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) Northampton 9.2/10 Wonderful (959 reviews) "clean room, nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) david $115 nightly $128 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/66dde072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/4417504a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/59498ff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/a1e89c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Porches Inn at Mass MoCA [](https://www.expedia.com/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) North Adams 9.4/10 Exceptional (454 reviews) "The great people!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie $164 nightly $183 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/980000/973700/973618/f968e782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Studio Suite | Floor plan](https://images.trvl-media.com/lodging/1000000/980000/973700/973618/c84c8cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook [](https://www.expedia.com/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information) Hancock 9.2/10 Wonderful (569 reviews) "Good place to take your family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria [](https://www.expedia.com/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/58d2b953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/a856ec31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/eb4406db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Farm Inn [](https://www.expedia.com/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) Lenox 9.4/10 Exceptional (164 reviews) "Everything was perfect - location and accommodation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher $191 nightly $217 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library Suite, 1 King Bed | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c5c7040f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/e65bd9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/e57afaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North [](https://www.expedia.com/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) Pittsfield 9.6/10 Exceptional (821 reviews) "Great staff, beautiful hotel. Would definitely recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawn $149 nightly $166 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/9903b094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/39644ba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/1294364a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 6:00 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/70229688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Downstreet, an Ascend Collection Hotel [](https://www.expedia.com/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) North Adams 8.8/10 Excellent (1,001 reviews) "Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly $126 nightly $140 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-22&endDate=2026-02-23®ionId=6005427&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Hotels.d6005427.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Hotels.d6005427.Travel-Guide-Hotels) ## Top Windsor Hotel Reviews ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay." [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Spacious 2 bed 2 bath!" [](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Rooms were clean and spacious. Our room had 2 queen beds and they easily accommodated 2 of us and our late teen children. It's only 20 minutes from Jiminy Peak skiing area. There are several breakfast and food places nearby. " [](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "loved " [](https://expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Room was clean and nicely equipped with kitchen. Will return if the future. " [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel." [](https://expedia.com/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "The great people!!!" [](https://expedia.com/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Clean" [](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg) ### Red Roof Inn PLUS+ South Deerfield – Amherst 10/10 Excellent "All good. Strange stay as there was a large storm approaching." [](https://expedia.com/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ## More cheap stays in Windsor ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Howard Johnson by Wyndham Lenox 462 Pittsfield Rd Lenox MA $69 nightly $77 total Feb 9 - Feb 10 Total with taxes and fees 7.4/10 Good! (829 reviews) [](https://expedia.com/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 170 Housatonic Street Lee MA $84 nightly $94 total Feb 22 - Feb 23 Total with taxes and fees 8.2/10 Very Good! (1,000 reviews) [](https://expedia.com/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Red Roof Inn PLUS+ South Deerfield – Amherst 9 Greenfield Rd South Deerfield MA $89 nightly $100 total Mar 1 - Mar 2 Total with taxes and fees 7/10 Good! (1,007 reviews) [](https://expedia.com/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd Lenox MA $98 nightly $110 total Feb 9 - Feb 10 Total with taxes and fees 9/10 Wonderful! (1,010 reviews) [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Berkshires-Lenox 445 Pittsfield Rd Lenox MA $119 nightly $133 total Mar 1 - Mar 2 Total with taxes and fees 9/10 Wonderful! (999 reviews) [](https://expedia.com/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Fairfield Inn & Suites by Marriott Williamstown](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5d49dcf2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Fairfield Inn & Suites by Marriott Williamstown 430 Main St Williamstown MA $158 nightly $176 total Feb 22 - Feb 23 Total with taxes and fees 8.8/10 Excellent! (402 reviews) [](https://expedia.com/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information) ## Hotels in Windsor with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 11 properties [](https://expedia.com/4Star-Windsor-Hotels.s40-0-d6005427.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 102 properties [](https://expedia.com/3Star-Windsor-Hotels.s30-0-d6005427.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 102 properties [](https://expedia.com/2Star-Windsor-Hotels.s20-0-d6005427.Travel-Guide-Filter-Hotels) ## Find out more about Windsor ### Top reasons to visit Windsor - **Outdoor Adventure:** Windsor is a haven for outdoor enthusiasts, offering skiing, breathtaking mountain views, and nearby nature reserves. - **Wellness Retreats:** After an active day, unwind at local wellness centers for a rejuvenating experience. - **Scenic Wine Country:** Explore charming local wineries that provide a romantic atmosphere and stunning vistas. - **Diverse Accommodations:** Choose from cozy motels to inviting resorts, perfect for families and couples alike. - **Year-Round Activities:** Enjoy a mix of thrilling winter sports and peaceful summer escapes in this picturesque area. ### Find great hotels near Windsor Discover the charm of Windsor, Massachusetts, with a range of hotel accommodations designed for every type of traveler. From cozy motels to inviting resorts, you'll find the perfect spot for family getaways, romantic retreats, or thrilling ski vacations. Explore our top-rated hotels, read reviews, and enjoy a memorable stay in this picturesque area. - **[Holiday Inn & Suites Pittsfield-Berkshires by IHG: ](https://www.expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)** This 3-star hotel offers a unique blend of business and leisure, making it an ideal choice for travelers seeking a professional yet welcoming atmosphere. Located 11 miles from Windsor, it features a fully-equipped Business Center with 24-hour access, meeting rooms, and a conference center. The hotel's commitment to inclusivity is evident, as it is LGBTQIA-friendly and affiliated with LGBTQI travel guides. Guests can also indulge in nearby winery experiences, adding a delightful touch to their stay. - **[Berkshire Mountain Lodge: ](https://www.expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)** Nestled 13 miles from Windsor, this 3-star lodge is perfect for adventure enthusiasts and ski lovers. With easy access to ski shuttles and lifts, guests can hit the slopes with ease. The lodge offers golf experiences and a range of adventure sports, including biking, kayaking, and ziplining. Its proximity to nature trails and snow tubing locations ensures that every guest can find an exciting outdoor activity to enjoy during their stay. - **[Club Wyndham Bentley Brook: ](https://www.expedia.com/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information)** Located 13 miles from Windsor, this 3-star hotel is a haven for adventure seekers and winter sports fans. With close access to ski shuttles and lifts, guests can partake in downhill and cross-country skiing, as well as snowboarding right onsite. The property also provides hiking and biking opportunities nearby, making it a great choice for those looking to immerse themselves in the stunning Berkshire outdoors. The welcoming atmosphere and recreational facilities ensure a memorable stay for all guests. ### Where to stay near Windsor Windsor, Massachusetts, offers an exciting blend of adventure and scenic beauty, perfect for outdoor enthusiasts and families alike. Explore the nearby wine country with local wineries that provide a romantic atmosphere and stunning views. Whether you're seeking a thrilling ski vacation or a peaceful escape, Windsor and its surrounding areas cater to all types of travelers, making it an ideal destination for unforgettable experiences. - **[Pittsfield: ](https://www.expedia.com/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)** Located 11 miles from Windsor, Pittsfield is a vibrant city nestled in the heart of the Berkshires. Known for its year-round appeal, the city attracts visitors especially during the summer months from June to August. Outdoor enthusiasts flock to Pittsfield for thrilling ski experiences, with access to top-notch ski fields and resorts. Beyond skiing, the area boasts beautiful lakes and mountains ideal for hiking and relaxation. Families can also enjoy local waterparks, making Pittsfield a great destination for all ages. - **[North Adams: ](https://www.expedia.com/North-Adams-Hotels.d9137.Travel-Guide-Hotels)** Situated 14 miles away from Windsor, North Adams is a charming city that invites adventure seekers and outdoor lovers alike. With visitor numbers peaking in June, July, and September, this city offers an array of outdoor activities, including skiing at nearby resorts. Art lovers will appreciate the local art museum and vibrant public art scene, which reflect the city’s cultural richness. North Adams is perfect for those looking to combine outdoor exploration with artistic experiences. - **[Savoy: ](https://www.expedia.com/Savoy-Hotels.d6005417.Travel-Guide-Hotels)** Just 4 miles from Windsor, Savoy is a quaint city known for its scenic beauty and outdoor adventures. Popular among visitors from March to April and in July, Savoy offers excellent skiing opportunities and access to stunning mountain peaks and serene lakes. This small town is ideal for nature lovers and those looking to escape the hustle and bustle, providing a peaceful retreat amid picturesque landscapes. Whether you're skiing or hiking, Savoy has something for every outdoor enthusiast. ### Things to do near Windsor Windsor, Massachusetts, is a fantastic destination for adventure seekers and outdoor enthusiasts, offering thrilling activities like skiing at its local ski fields and resorts. In addition to winter sports, visitors can unwind at wellness centers to rejuvenate after an adventurous day. Whether you're hitting the slopes or relaxing, Windsor provides a perfect blend of excitement and relaxation for your vacation. **Shopping** In Windsor, you can enjoy shopping at [Guido's Marketplace](https://www.expedia.com/Guidos-Marketplace-Hotels.0-l553248621532665282-0.Travel-Guide-Filter-Hotels), a public market offering a variety of goods. If you're up for a drive, visit North Adams Center and North Adams Gateway Center, both just 13 and 14 miles away, featuring family-friendly shopping experiences in a vibrant setting. **Recreation** At [Bas Ridge Golf Course](https://www.expedia.com/Bas-Ridge-Golf-Course-Hotels.0-l553248621560926698-0.Travel-Guide-Filter-Hotels), enjoy a day of golfing surrounded by beautiful landscapes just 6 miles from Windsor. For a serene escape, visit [Windsor Lake Park](https://www.expedia.com/Windsor-Lake-Park-Hotels.0-l553248621560926712-0.Travel-Guide-Filter-Hotels), 12 miles away, where you can relax by the water and immerse yourself in nature. [Skyline Country Club](https://www.expedia.com/Skyline-Country-Club-Hotels.0-l553248621532665295-0.Travel-Guide-Filter-Hotels) offers another excellent golfing experience just 10 miles from town. **Adventure** Experience the thrill of winter sports at [Jiminy Peak Mountain Resort](https://www.expedia.com/Jiminy-Peak-Mountain-Resort-Hotels.0-l553248621532665536-0.Travel-Guide-Filter-Hotels), located 13 miles from Windsor. For a diverse range of outdoor activities, visit [Berkshire East Ski Resort](https://www.expedia.com/Berkshire-East-Ski-Resort-Hotels.0-l553248621532666707-0.Travel-Guide-Filter-Hotels), 12 miles away. Enjoy picturesque views and challenging trails at [Skyline Trail](https://www.expedia.com/Skyline-Trail-Hotels.0-l553248621532666608-0.Travel-Guide-Filter-Hotels), just 10 miles away, perfect for hiking enthusiasts. **Nightlife** Experience the vibrant nightlife in Windsor by catching a show at the nearby [Adams Theater](https://www.expedia.com/Adams-Theater-Hotels.0-l811533410309558272-0.Travel-Guide-Filter-Hotels) or [Colonial Theater](https://www.expedia.com/Colonial-Theater-Hotels.0-l553248621532665289-0.Travel-Guide-Filter-Hotels), both offering a mix of culture and romance. For a unique experience, check out the [Barrington Stage Company](https://www.expedia.com/Barrington-Stage-Company-Hotels.0-l553248621532665294-0.Travel-Guide-Filter-Hotels), where you can enjoy captivating performances in a welcoming atmosphere. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Windsor To save money during your trip to Windsor, consider visiting in January or March to April when hotel prices are lower. Tuesdays offer the cheapest stays, while Saturdays are the most expensive. Use Expedia’s search tool to compare room rates and find budget-friendly accommodations, and consider bundling your hotel, flights, and activities for additional savings. Joining Expedia's One Key membership can provide exclusive discounts and cash back on future stays. Lastly, take advantage of free local activities and explore the area on foot to further reduce costs. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Windsor are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Windsor is Tuesday. The most expensive day to stay in Windsor is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool lets you set your budget, choose your desired location, and much more. You can arrange your search results by price, from lowest to highest, ensuring you spot the most affordable hotels at the top. Additionally, you have the option to refine your choices by hotel category; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels available for booking. - **Consider bundling your trip:** You can save money by combining your Windsor hotel reservation with your flights and activities through an Expedia package deal. - **Become a One Key member:** Join [Expedia's One Key membership](https://www.expedia.com/welcome-one-key) program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels. ### Find the best attractions near Windsor Windsor, Massachusetts, is a fantastic destination for outdoor enthusiasts and adventure seekers. Visitors can enjoy breathtaking mountain views, explore nearby nature reserves, and experience the thrill of skiing. The area offers a diverse range of attractions that cater to those looking for adventure, cultural experiences, and outdoor activities, making it an ideal spot for a memorable vacation. - **[Mount Greylock: ](https://www.expedia.com/Mount-Greylock-Hotels.0-l6091829-0.Travel-Guide-Filter-Hotels)** Experience breathtaking views from the highest peak in Massachusetts, located 11 miles from Windsor. Outdoor enthusiasts can hike scenic trails that showcase the stunning natural beauty of the Berkshires, making it a perfect spot for adventure seekers. - **[Wahconah Falls State Park: ](https://www.expedia.com/Wahconah-Falls-State-Park-Hotels.0-l553248621532665297-0.Travel-Guide-Filter-Hotels)** Just 4 miles from Windsor, this park features picturesque waterfalls and lush landscapes. Enjoy hiking and exploring the scenic trails while taking in the refreshing sounds of nature, ideal for those looking for an outdoor adventure. - **[Berkshire East Ski Resort: ](https://www.expedia.com/Berkshire-East-Ski-Resort-Hotels.0-l553248621532666707-0.Travel-Guide-Filter-Hotels)** Located 12 miles away, this ski resort offers thrilling winter sports opportunities. Whether skiing, snowboarding, or enjoying the beautiful mountain scenery, it's a must-visit for adventure lovers year-round. ### Best time to go to Windsor The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, visitor numbers are average and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 19.9°F (-6.7°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 22.1°F (-5.5°C) | Light Rain | Mostly Cloudy | Moderately Low | Average | | March | 29.7°F (-1.3°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | April | 41.4°F (5.2°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | May | 53.8°F (12.1°C) | Light Rain | Mostly Sunny | Average | Average | | June | 61.5°F (16.4°C) | Light Rain | Mostly Sunny | Average | Average | | July | 67.6°F (19.8°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | August | 65.7°F (18.7°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly High | | September | 58.6°F (14.8°C) | Light Rain | Mostly Sunny | Average | Average | | October | 47.7°F (8.7°C) | Light Rain | Mostly Cloudy | Moderately High | Slightly High | | November | 35.4°F (1.9°C) | Light Rain | Mostly Sunny | Moderately High | Average | | December | 27.0°F (-2.8°C) | Light Rain | Mostly Cloudy | Moderately Low | Average | ### The nearest major airports for your trip to Windsor To reach Windsor, Massachusetts, you have several airport options. Hartford, CT's Bradley International Airport ([BDL](https://www.expedia.com/Bradley-Intl-Airport-Hotels.0-aBDL-0.Travel-Guide-Filter-Hotels)) is 44 miles away, with nearby accommodations like the [DoubleTree by Hilton Hartford - Bradley Airport](https://www.expedia.com/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information), just 1 mile from the airport, and the [Simsbury 1820 House](https://www.expedia.com/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information), 7 miles away. Albany, NY's Albany International Airport ([ALB](https://www.expedia.com/Albany-Intl-Airport-Hotels.0-aALB-0.Travel-Guide-Filter-Hotels)) is 42 miles from Windsor, offering hotel choices such as the [Park Manor Hotel](https://www.expedia.com/Clifton-Park-Hotels-Park-Manor-Hotel.h895584.Hotel-Information) and [The Landing Hotel at Rivers Casino & Resort](https://www.expedia.com/Albany-Hotels-The-Landing-Hotel-At-Rivers-Casino-Resort.h19093277.Hotel-Information), both 8 miles from the airport. Additionally, Pittsfield Municipal Airport ([PSF](https://www.expedia.com/Pittsfield-Municipal-Airport-Hotels.0-aPSF-0.Travel-Guide-Filter-Hotels)) is the closest, located 14 miles away, with options like The Stockbridge Country Inn and [The Central Downtown Inn & Suites](https://www.expedia.com/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) nearby. ## Frequently asked questions ### What is the best area to stay in Windsor? > Windsor itself is a small, quiet town known for its natural beauty and outdoor activities. Staying near the town center provides easy access to the Windsor Historical Society and the local general store. This area is ideal for travelers seeking a peaceful retreat and proximity to hiking trails and scenic drives. > > > For couples looking for a tranquil getaway with access to nature, staying in a guesthouse or inn located in the hills surrounding the town center is an excellent choice. These accommodations often offer picturesque views and a chance to relax away from any hustle, while still being a short drive from attractions like the Windsor State Forest. ### When is the best time to go to Windsor? > Summer in Windsor offers pleasant temperatures, typically ranging from the mid-60s to high 70s Fahrenheit, making it ideal for exploring the natural beauty of the Berkshires. This season is great for hiking trails, enjoying the numerous lakes and ponds, and participating in local outdoor events. The longer daylight hours also allow for more extensive sightseeing. > > > For those who appreciate natural beauty, early to mid-fall is a spectacular time to visit. The Berkshire region is renowned for its vibrant autumn colors, with the hillsides transforming into a canvas of reds, oranges, and yellows. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Windsor hotel booking with Expedia? > \*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo. ### How much is the nightly rate at a Windsor hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Wahconah Falls State Park ](https://www.expedia.com/Wahconah-Falls-State-Park-Hotels.0-l553248621532665297-0.Travel-Guide-Filter-Hotels) - [Savoy Hotels ](https://www.expedia.com/Savoy-Hotels.d6005417.Travel-Guide-Hotels) - [Cabin Rentals in Savoy ](https://www.expedia.com/Savoy-Cabins.d6005417-aaCabins.Travel-Guide-Accommodation) - [B&B in Savoy ](https://www.expedia.com/Savoy-Bed-And-Breakfast.d6005417-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Savoy ](https://www.expedia.com/Savoy-Cottages.d6005417-aaCottages.Travel-Guide-Accommodation) - [Peru Hotels ](https://www.expedia.com/Peru-Hotels.d553248634999167831.Travel-Guide-Hotels) - [Hotels near Bas Ridge Golf Course ](https://www.expedia.com/Bas-Ridge-Golf-Course-Hotels.0-l553248621560926698-0.Travel-Guide-Filter-Hotels) - 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