Title: 20 Best B&B in Windsor, VT - Bed and Breakfast from $145 | 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 [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 two weeks [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) In one month [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=7881&startDate=2026-05-22&endDate=2026-05-24&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) ![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) ![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) ### Harvest Barn Inn [](https://www.expedia.com/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.Hotel-Information) Bellows Falls 9.8/10 Exceptional (255 reviews) "Staff were wonderful, food was excellent, environment was peaceful, everything was clean and in decent condition." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles $139 nightly $152 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.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 (116 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 Apr 6 - Apr 7 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/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) ![Exterior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/676cb54e.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 $131 nightly $145 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-The-Vesper.h103415437.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) ![Exterior](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/97b53e6b.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) ![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 $228 nightly $251 total Mar 29 - Mar 30 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) ![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) ![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 $263 nightly $285 total Mar 28 - Mar 29 Total with taxes and fees [](https://www.expedia.com/Sunapee-Hotels-Dexters-Inn.h2042604.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/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) ![Exterior](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/b9dbfee0.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 29 - Mar 30 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/104000000/103190000/103188700/103188664/d7baa23b.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) ![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 (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 [](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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/832ba4c3.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) ![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 (391 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) ![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) ![Garden](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/594556d7.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 $210 nightly $229 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) ![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) ![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 $318 nightly $350 total Apr 3 - Apr 4 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=2026-04-10&endDate=2026-04-11®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 ![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 2/10 Terrible "The check-in started with a parking fee that is not advertised as front facing when you check out and Expedia indicates this is what you will pay. The parking fee is included on Expedia, but you have to dig to find it. Further the fee is a ridiculous money grab, nickel and dime, classless fee. There is no garage, no parking attendant, no patrol, and I am certain that if anything happens to your vehicle the hotel does not take responsibility. It serves no purpose. The room was fine enough. The tub had multiple large chunks missing with with clear rusting and what appeared to be blood in a second spot. So was it cleaned prior? Who knows. I’d honestly find anywhere else on the mountain, or even head out toward awesome little Woodstock and stay before I stays here again. It is beyond deaf ears to add purposeless fees to check in given the current economy. " [](https://expedia.com/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/fae277d0_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Nice quiet Clean rooms and plenty of parking. " [](https://expedia.com/Killington-Hotels-Mountain-Sports-Inn.h1339833.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 8/10 Good "Room was clean. Shower needed a remodel. Water pressure not great and tub a bit worn. Beds were not super comfortable but not awful. Room on road side had a bit of traffic noise." [](https://expedia.com/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.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 "Everything was great no complaints on this side. I will be returning again next winter season." [](https://expedia.com/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.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 "Well maintained, nicely decorated and ticked all of our boxes. I highly recommend staying here." [](https://expedia.com/Newbury-Hotels-Hideaway-Inn-Mt-Snow.h120341253.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 "There's a cute little town nearby with a great coffee shop. " [](https://expedia.com/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 4/10 Poor "I’ve stayed in budget hotels before, but this was on another level entirely. The room clearly hadn’t been properly cleaned in a long time. The floor was full of crumbs, and there was literally a pile of Cheerios sitting under the door to the connecting room. That alone should have been a red flag. It didn’t get better from there. The shower mat looked like something had chewed a hole straight through it. honestly, it looked like a mouse had been at it. Not exactly what you want to see in a place you’re supposed to relax. The sheets were just as bad; old, rough, and so worn they felt like you were sleeping on sandpaper. To top it all off, I got an automated text at 6:01 a.m. asking how my stay was. Who sends that kind of message that early? If anything, it just highlighted how out of touch the place is with basic guest experience. The only positive is the location—it’s convenient. But that’s not nearly enough to make up for everything else. I wouldn’t stay here again under any circumstances. " [](https://expedia.com/Lebanon-Hotels-Best-Western-West-Lebanon-Hanover-Hotel.h1200405.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 " Very cozy. Lovely breakfast. Fun smores" [](https://expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Turn of River Lodge](https://images.trvl-media.com/lodging/19000000/18550000/18540700/18540657/4273b3c6_y.jpg) ### Turn of River Lodge 10/10 Excellent "Great location, quaint atmosphere and good for families. " [](https://expedia.com/Killington-Hotels-Turn-Of-River-Lodge.h18540657.Hotel-Information) ## Find out more about Windsor ## Windsor B&B information | Number of reviews | 1,265 | | ----------------- | ------ | | Accommodation | 26 B&B | | Lowest Price | $145 | | Highest Price | $350 | ## 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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