Title: 20 Best B&B in Windsor, VT - Bed and Breakfast from $158 | 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) ![Exterior](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/0ee737a0.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) ### Harvest Barn Inn [](https://www.expedia.com/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.Hotel-Information) Bellows Falls 9.8/10 Exceptional (253 reviews) "Harvest Barn Inn was the perfect place to stay warm on a freezing Vermont winter weekend. We absolutely loved the cozy atmosphere - homemade cookies, endless tea, plenty of books, and beautiful views. The three-course weekend breakfast was the highlight of our stay. Blessing and Kaelan were very communicative and friendly hosts. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah $144 nightly $158 total Mar 29 - Mar 30 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) ![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) ![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) ### 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 $159 nightly $175 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) ![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 9.6/10 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) ![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/7060d495.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) ![Porch](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/450d23d8.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 $195 nightly $213 total Apr 20 - Apr 21 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) ![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) ![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) ![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) ### 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 $256 nightly $278 total Mar 28 - Mar 29 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) ![Interior](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/abd58cfe.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) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/b1b23979.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 Apr 5 - Apr 6 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) ![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) ![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) ### 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) ![Golf](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/8b78ee8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/bc79e27c.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 (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) ![Garden](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/594556d7.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) ![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) ### 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 $221 nightly $241 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) ![Interior detail](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/447cd0b4.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) ![Individually decorated, individually furnished, soundproofing](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/ff272214.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 $296 nightly $325 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=2026-04-04&endDate=2026-04-05®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 ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/fae277d0_y.jpg) ### Mountain Sports Inn 8/10 Good "Clean, great breakfast, room is a little small" [](https://expedia.com/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![White River Inn and Suites](https://images.trvl-media.com/lodging/1000000/30000/28000/27933/ba27b41f_y.jpg) ### White River Inn and Suites 10/10 Excellent "Clean room " [](https://expedia.com/White-River-Junction-Hotels-White-River-Inn-And-Suites.h27933.Hotel-Information) ![Best Western West Lebanon-Hanover Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1200500/1200405/911e9465_y.jpg) ### Best Western West Lebanon-Hanover Hotel 10/10 Excellent "Staff was great clean room " [](https://expedia.com/Lebanon-Hotels-Best-Western-West-Lebanon-Hanover-Hotel.h1200405.Hotel-Information) ![Hideaway Inn Mt.Sunapee](https://images.trvl-media.com/lodging/121000000/120350000/120341300/120341253/7f350a77_y.jpg) ### Hideaway Inn Mt.Sunapee 6/10 Okay "The rooms were clean but the walls are paper thin. We were able to hear EVERYTHING from the room next door. Things I would’ve rather not hear." [](https://expedia.com/Newbury-Hotels-Hideaway-Inn-Mt-Snow.h120341253.Hotel-Information) ![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) ## Find out more about Windsor ## Windsor B&B information | Number of reviews | 1,261 | | ----------------- | ------ | | Accommodation | 26 B&B | | Lowest Price | $158 | | Highest Price | $325 | ## 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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