Title: 20 Best B&B in Windsor, VT - Bed and Breakfast from $152 | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx7881)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d7881.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d7881.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d7881.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d7881.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d7881.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-05-15&endDate=2026-05-17&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor bed & breakfast ![Porch](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/1e0ac20a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/c10f6d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![River View | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/3b283cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/0ee737a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harvest Barn Inn [](https://www.expedia.com/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.Hotel-Information) Bellows Falls 9.8/10 Exceptional (253 reviews) "Everything was great. Awesome hosts, room, common areas and a fabulous breakfast. Can’t recommend too highly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark $139 nightly $152 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/0ba93825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/589572bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room | Individually decorated, individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/2970ae6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/676cb54e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vesper [](https://www.expedia.com/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) Woodstock 9.2/10 Wonderful (57 reviews) "Uniqueness of rooms, breakfast options and walking distance to so many great spots!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily $154 nightly $170 total Mar 28 - Mar 29 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/9a1e2ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/b9dbfee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/e0958349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jackson [](https://www.expedia.com/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) West Woodstock 9.6/10 Exceptional (275 reviews) "Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly," ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael $199 nightly $219 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/ae105a01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, Mountain View | Individually decorated, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/48815e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/7060d495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Hearth Inn and Eatery [](https://www.expedia.com/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) Chester 9.2/10 Wonderful (115 reviews) "Great stay! Very cozy and homey. Very yummy breakfast! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olena $193 nightly $211 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![Building design](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/71e55c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/f20a7a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/w768h580x0y0-90dad15b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/3ab17c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dexter's Inn [](https://www.expedia.com/Sunapee-Hotels-Dexters-Inn.h2042604.Hotel-Information) Sunapee 8.8/10 Excellent (70 reviews) "This was my 3rd time staying at Dexter’s Inn and hopefully not the last. It is a wonderful inn with easy access to Mount Sunapee. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa $263 nightly $285 total Mar 21 - Mar 22 Total with taxes and fees [](https://www.expedia.com/Sunapee-Hotels-Dexters-Inn.h2042604.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/53db29c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/b1b23979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/4d2bc29e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/97b53e6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deer Brook Inn [](https://www.expedia.com/Woodstock-Hotels-Deer-Brook-Inn.h122648718.Hotel-Information) Woodstock 10/10 Exceptional (1 review) "The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara $227 nightly $250 total Mar 25 - Mar 26 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-Deer-Brook-Inn.h122648718.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/d7baa23b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/33fd758e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Double Room, Courtyard View | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/ce0b45d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Double Room, Garden View | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/5423776f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stay At Jimmy's [](https://www.expedia.com/Woodstock-Hotels-Stay-At-Jimmys.h103188664.Hotel-Information) Woodstock 10/10 Exceptional (49 reviews) "Wonderful amenities, location, and team, Highly recommend and would love to stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather $249 nightly $274 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-Stay-At-Jimmys.h103188664.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/86a78166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/efed55f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/832ba4c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/8b78ee8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Snowed Inn [](https://www.expedia.com/Killington-Hotels-Snowed-Inn.h1153997.Hotel-Information) Killington 9.8/10 Exceptional (390 reviews) "Wonderful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory $172 nightly $189 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-Snowed-Inn.h1153997.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/77eb994f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/ea7ecfec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/594556d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/0a80171b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Echo Lake Inn [](https://www.expedia.com/Ludlow-Hotels-Echo-Lake-Inn.h893657.Hotel-Information) Plymouth 8.6/10 Excellent (100 reviews) "Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle $214 nightly $234 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Ludlow-Hotels-Echo-Lake-Inn.h893657.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/6f38eb9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/c2bef1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/447cd0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/99b8436e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Woodstocker B&B [](https://www.expedia.com/Woodstock-Hotels-The-Woodstocker-BB.h25079404.Hotel-Information) Woodstock 10/10 Exceptional (51 reviews) "This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kavina $266 nightly $293 total Mar 27 - Mar 28 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-The-Woodstocker-BB.h25079404.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=2026-04-03&endDate=2026-04-04®ionId=7881&adults=2&lodging=BED_AND_BREAKFAST&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-Bed-And-Breakfast.d7881-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Bed-And-Breakfast.d7881-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/bdef58fa_y.jpg) ### Summit Lodge 10/10 Excellent "Great stay " [](https://expedia.com/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Clean, comfortable and quiet. Great retreat for skiers. Nice hot tub, comfy beds and convenient parking." [](https://expedia.com/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/17fcad53_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Really friendly and helpful staff. Excellent bar and grille, pool and exercise room with generous hours. A little noisy as some parents let their kids free range about. However, very comfortable room, beds and great views." [](https://expedia.com/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/f9bd2dd9_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 8/10 Good "Yes" [](https://expedia.com/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg) ### On The River Inn 10/10 Excellent "Just a great property all around. For going a few minutes down the road from downtown you get a very well appointed, updated hotel. Breakfast was excellent, pool and Sauna are is nicely updated. Amazingly kid friendly, will be back soon! " [](https://expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Hilton Garden Inn Hanover Lebanon](https://images.trvl-media.com/lodging/22000000/21500000/21490500/21490448/9e678e0d_y.jpg) ### Hilton Garden Inn Hanover Lebanon 10/10 Excellent "We were disappointed that the bar was not open. My friends and I were looking forward to sitting and having a drink together. We rarely all get together." [](https://expedia.com/Lebanon-Hotels-Hilton-Garden-Inn-HanoverLebanon.h21490448.Hotel-Information) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07b171_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Excellent!!" [](https://expedia.com/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/4cc53d97_y.jpg) ### Align Inn Vermont 10/10 Excellent "Absolute perfect stay, Chelsea was so kind and helpful. The room was immaculate and cozy. This is always our go to when in the area. " [](https://expedia.com/White-River-Junction-Hotels-Align-Inn-Vermont.h1108.Hotel-Information) ![Fireside Inn & Suites West Lebanon](https://images.trvl-media.com/lodging/1000000/20000/12300/12300/43f4036d_y.jpg) ### Fireside Inn & Suites West Lebanon 8/10 Good "Very convenient location. Helpful, kind staff." [](https://expedia.com/Lebanon-Hotels-Fireside-Inn-Suites-West-Lebanon.h12300.Hotel-Information) ## Find out more about Windsor ## Windsor B&B information | Number of reviews | 1,261 | | ----------------- | ------ | | Accommodation | 26 B&B | | Lowest Price | $152 | | Highest Price | $293 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in Windsor? ### When is the best time to book a Bed & Breakfast in Windsor? > June is particularly popular, as it heralds the start of summer festivities, including music events and farmers' markets brimming with fresh local produce. The lively atmosphere of the town, combined with the colorful gardens in full bloom, offers a delightful experience for those seeking to connect with the community. > > > For those looking for a more budget-friendly option, consider visiting in late fall, around November. This time offers a quieter ambiance, great for enjoying the beautiful autumn foliage and indulging in local culinary delights without the hustle and bustle of peak tourist season. ### What is the difference between a Windsor B&B and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Windsor Station ](https://www.expedia.com/Windsor-Station-Hotels.d6195274.Travel-Guide-Hotels) - [Hotels near South Congregational Church ](https://www.expedia.com/South-Congregational-Church-Hotels.0-l6330774-0.Travel-Guide-Filter-Hotels) - [Hotels near American Precision Museum ](https://www.expedia.com/American-Precision-Museum-Hotels.0-l6330768-0.Travel-Guide-Filter-Hotels) - [Hotels near Harpoon Brewery ](https://www.expedia.com/Harpoon-Brewery-Hotels.0-l553248635975913439-0.Travel-Guide-Filter-Hotels) - [Hotels near Mt Ascutney State Park ](https://www.expedia.com/Mt-Ascutney-State-Park-Hotels.0-l6175264-0.Travel-Guide-Filter-Hotels) - 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