Title: 20 Best B&B in Windsor, VT - Bed and Breakfast from $124 | 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 [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-04-10&endDate=2026-04-12&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) ![Exterior](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/0ee737a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/096e29dd.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 (248 reviews) "Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) RICHARD $147 nightly $161 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/7ed84417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Room with View | 2 bedrooms, down comforters, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/dc02869f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Room with Spring | 2 bedrooms, down comforters, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/23d8da75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/b90ec0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Valley Retreat [](https://www.expedia.com/Killington-Hotels-Mountain-Valley-Retreat.h8270194.Hotel-Information) Killington 9.6/10 Exceptional (196 reviews) "Superb stay all the way around! Mike and Barbara work very hard for their guests and it shows with all the room details and breakfast is 5 out of 5 stars everytime. Check in and out is very easy as well as parking even on snow covered days as the property is very well kept and cleared. Loved it and want to return!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven $110 nightly $124 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-Mountain-Valley-Retreat.h8270194.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) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/91483dc1.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) ![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) ### The Jackson [](https://www.expedia.com/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) West Woodstock 9.8/10 Exceptional (265 reviews) "The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby $169 nightly $186 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-The-Jackson-House-Inn.h181337.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) ![Deluxe Room | Individually decorated, individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/2533d22f.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) ![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 (55 reviews) "Charming bed and breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas $179 nightly $197 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-The-Vesper.h103415437.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) ![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/7060d495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/450d23d8.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) ### Stone Hearth Inn and Eatery [](https://www.expedia.com/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) Chester 9.2/10 Wonderful (112 reviews) "So great all around!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet $247 nightly $270 total Mar 13 - Mar 14 Total with taxes and fees [](https://www.expedia.com/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.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) ![Classic Suite | Interior](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/85691467.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) ### Deer Brook Inn [](https://www.expedia.com/Woodstock-Hotels-Deer-Brook-Inn.h122648718.Hotel-Information) Woodstock $228 nightly $251 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-Deer-Brook-Inn.h122648718.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) ![Interior](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/3ab17c06.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) ![Room, Multiple Beds, Private Bathroom | Individually decorated, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2050000/2042700/2042604/bf739072.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 $252 nightly $274 total Feb 18 - Feb 19 Total with taxes and fees [](https://www.expedia.com/Sunapee-Hotels-Dexters-Inn.h2042604.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) ![Golf](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/8b78ee8c.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) ### Snowed Inn [](https://www.expedia.com/Killington-Hotels-Snowed-Inn.h1153997.Hotel-Information) Killington 9.8/10 Exceptional (382 reviews) "Wonderful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory $314 nightly $345 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-Snowed-Inn.h1153997.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) ![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) ![Signature Suite, Garden View | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/4c69dfd7.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) ### Stay At Jimmy's [](https://www.expedia.com/Woodstock-Hotels-Stay-At-Jimmys.h103188664.Hotel-Information) Woodstock 10/10 Exceptional (47 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 $299 nightly $329 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-Stay-At-Jimmys.h103188664.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) ![Free daily cooked-to-order breakfast](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/94881046.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) ![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 (99 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 $280 nightly $306 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Ludlow-Hotels-Echo-Lake-Inn.h893657.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=2026-02-25&endDate=2026-02-26®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 ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Everything worked and was as expected for the price. " [](https://expedia.com/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Highly recommend this hotel! It was great for families, very clean, and had a wonderful restaurant on-site. We will definitely be coming again!" [](https://expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/5da3617c_y.jpg) ### Summit Lodge 10/10 Excellent "This was our 3rd stay at the Summit Lodge for a long ski weekend. It’s very clean, with old school charm, and their staff is so nice. There is a hot buffet breakfast, a heated outdoor pool, an extra large jacuzzi, and a wonderful Irish pub in the basement, that has live music on Saturday nights. We will be back. " [](https://expedia.com/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Staff are so friendly ,great place very clean rooms a lot of activities " [](https://expedia.com/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Fireside Inn & Suites West Lebanon](https://images.trvl-media.com/lodging/1000000/20000/12300/12300/adb27d13_y.jpg) ### Fireside Inn & Suites West Lebanon 10/10 Excellent "Environment, upgraded room and food" [](https://expedia.com/Lebanon-Hotels-Fireside-Inn-Suites-West-Lebanon.h12300.Hotel-Information) ![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "The staff could not have been more accommodating. From the front desk to the shuttle drivers, to the wait staff in the restaurant, they were all friendly, helpful and pleasant." [](https://expedia.com/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Very clean room, kind staff and excellent breakfast. " [](https://expedia.com/White-River-Junction-Hotels-Align-Inn-Vermont.h1108.Hotel-Information) ![Hilton Garden Inn Hanover Lebanon](https://images.trvl-media.com/lodging/22000000/21500000/21490500/21490448/0ffc6821_y.jpg) ### Hilton Garden Inn Hanover Lebanon 10/10 Excellent "Everything was great. It was quiet and clean." [](https://expedia.com/Lebanon-Hotels-Hilton-Garden-Inn-HanoverLebanon.h21490448.Hotel-Information) ![Hideaway Inn Mt.Sunapee](https://images.trvl-media.com/lodging/121000000/120350000/120341300/120341253/7f350a77_y.jpg) ### Hideaway Inn Mt.Sunapee 10/10 Excellent "Staff were super friendly. Rooms were cozy. Our dog was welcome. A great experience!" [](https://expedia.com/Newbury-Hotels-Hideaway-Inn-Mt-Snow.h120341253.Hotel-Information) ## Find out more about Windsor ## Windsor B&B information | Number of reviews | 1,436 | | ----------------- | ------ | | Accommodation | 26 B&B | | Lowest Price | $124 | | Highest Price | $345 | ## 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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