Title: Top Guest Houses in Windsor County in 2026 | Expedia.ca [Windsor County Hotels](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Hotel-Destinations)[Vacation Rentals in Windsor County](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Vacation-Rental-Destinations)[Windsor County Car Rentals](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Car-Rental-Destinations)[Windsor County Vacations](https://expedia.ca/Windsor-County.d553248635976432508.Destination-Travel-Guides) ![Quechee Gorge- Vermont #autumn #colorful #roadtrip #weekendgetaway #travel #adventure #nature #vacation ](https://images.trvl-media.com/place/3000459649/7d354301-07a8-4d26-bfd8-54320ed05c30.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rachel Samanyi # Guest Houses in Windsor County ## Compare and save - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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 Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Windsor County ![Ludlow showing street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94298-Ludlow.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Ludlow [](https://expedia.ca/Ludlow-Guest-Houses.d8496-aaGuestHouses.Travel-Guide-Accommodation) ![Woodstock featuring a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94311-Woodstock.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Woodstock [](https://expedia.ca/Woodstock-Guest-Houses.d10868-aaGuestHouses.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/212ecbf3b606238229538e223f3f57eb.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### White River Junction [](https://expedia.ca/White-River-Junction-Guest-Houses.d6294-aaGuestHouses.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor-Guest-Houses.d7881-aaGuestHouses.Travel-Guide-Accommodation) ![Quechee featuring a river or creek, a bridge and tranquil scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93816-Central-Vermont.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Quechee [](https://expedia.ca/Quechee-Guest-Houses.d9580-aaGuestHouses.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/6e1ce19989493034a8e8934b004054dd.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Norwich [](https://expedia.ca/Norwich-Guest-Houses.d184063-aaGuestHouses.Travel-Guide-Accommodation) ## Our top choices for Windsor County guest houses ![Front of property](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/5fa05705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/cc3270b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/21c73f49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, steam room, deep-tissue massages, sports massages, facials](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/a66e865a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Weston [](https://www.expedia.ca/Weston-Hotels-The-Weston.h100702715.Hotel-Information) Weston 10/10 Exceptional (9) "Beautiful accommodations! You can't use enough flattering adjectives for this property and it's staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LISA CA $524 CA $572 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Weston-Hotels-The-Weston.h100702715.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/2000000/1800000/1791400/1791326/fc3e4c57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1800000/1791400/1791326/bd9fb058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Christina's Cottage, 1 King Bed, Private Bathroom, Hill View | Living area](https://images.trvl-media.com/lodging/2000000/1800000/1791400/1791326/2c3505a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1791400/1791326/57576b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Clearwater Pond (Quechee) [](https://www.expedia.ca/White-River-Junction-Hotels-Inn-At-Clearwater-Pond.h1791326.Hotel-Information) White River Junction 9.4/10 Exceptional (55) "AMAZING STAY AMAZING PLACE" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro [](https://www.expedia.ca/White-River-Junction-Hotels-Inn-At-Clearwater-Pond.h1791326.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/102000000/101140000/101137100/101137051/df7ec946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101140000/101137100/101137051/26f42a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/102000000/101140000/101137100/101137051/1055b96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101140000/101137100/101137051/1ccb1f8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly [](https://www.expedia.ca/Weston-Hotels-Mountain-Cabin-By-Skiing-With-Fireplaces-Well-Equipped-Kitchen-Dog-Friendly.h101137051.Hotel-Information) Weston 9.6/10 Exceptional (9) "Property was perfect for a weekend trip to nearby Okemo (20mins). Would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason N. [](https://www.expedia.ca/Weston-Hotels-Mountain-Cabin-By-Skiing-With-Fireplaces-Well-Equipped-Kitchen-Dog-Friendly.h101137051.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/6cbf7cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/bec38ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/13d01102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/3850e67e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! [](https://www.expedia.ca/Chester-Hotels-1868-Carriage-House-Quaint-Cozy-Perfect-Escape-20-MIN-TO-Okemo.h22120284.Hotel-Information) Chester Depot 9.4/10 Exceptional (39) "We enjoyed our stay at the Carriage House; it was clean and comfortable, and had everything we needed. Definitely would return!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie S. [](https://www.expedia.ca/Chester-Hotels-1868-Carriage-House-Quaint-Cozy-Perfect-Escape-20-MIN-TO-Okemo.h22120284.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87590000/87589900/87589843/035ba6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/88000000/87590000/87589900/87589843/f5f2fce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Internet, bed sheets](https://images.trvl-media.com/lodging/88000000/87590000/87589900/87589843/a39baed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87590000/87589900/87589843/e33c8394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts [](https://www.expedia.ca/South-Pomfret-Hotels-Updated-Guesthouse-With-Mountain-Views-Firepit-Walk-To-Saskadena-Six-Lifts.h87589843.Hotel-Information) Woodstock 9.4/10 Exceptional (36) "Amazingly quaint, quiet and cozy cottage type location. Gorgeous views, relaxing atmosphere and very comfortable. The little market across the street and small town vibe made my stay very enjoyable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin T. [](https://www.expedia.ca/South-Pomfret-Hotels-Updated-Guesthouse-With-Mountain-Views-Firepit-Walk-To-Saskadena-Six-Lifts.h87589843.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22125500/22125463/88e0aea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/23000000/22130000/22125500/22125463/18daf7ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/23000000/22130000/22125500/22125463/41c7b117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22130000/22125500/22125463/ceff38ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants [](https://www.expedia.ca/Ludlow-Hotels-Ludlow-Village-Guest-House-Prime-Location-On-Ski-Shuttle.h22125463.Hotel-Information) Ludlow 9.8/10 Exceptional (42) "Perfect location and very clean!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Ludlow-Hotels-Ludlow-Village-Guest-House-Prime-Location-On-Ski-Shuttle.h22125463.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1790000/1787800/1787707/4668bf1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1790000/1787800/1787707/98205ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1787800/1787707/1419db5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/2000000/1790000/1787800/1787707/ff69585c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salt Ash Inn [](https://www.expedia.ca/Plymouth-Hotels-Salt-Ash-Inn.h1787707.Hotel-Information) Plymouth 6.0/10 (126) "Great place, close proximity to Killington. Clean & quiet...Recommend this location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kingston F. [](https://www.expedia.ca/Plymouth-Hotels-Salt-Ash-Inn.h1787707.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.ca/Hotel-Search?startDate=2025-12-31&endDate=2026-01-01®ionId=553248635976432508&adults=2&lodging=GUEST_HOUSE&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-County-Guest-Houses.d553248635976432508-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-County-Guest-Houses.d553248635976432508-aaGuestHouses.Travel-Guide-Accommodation) ## Top Windsor County Hotel Reviews ![The Vesper ](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64_y.jpg) ### The Vesper 10/10 Excellent "We were in town for Wassail Weekend. The Vesper was a great place to stay. The location was so close to all of the fun activities and restaurants. Jessica was very accommodating and friendly. Would recommend! " [](https://expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.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 "Clean rooms, front desk personal could use people skill update, not young lady there this am, she was great. Guys in restaurant were the best. " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Best Western Springfield Hotel](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480_y.jpg) ### Best Western Springfield Hotel 10/10 Excellent "All very good. " [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "I stay at Woodstock Inn every December and it never disappoints. The rooms are comfortable and well-appointed, but it's hard to decide whether to enjoy the comforts of the room or sitting in front if the fire in the lobby. I look forward to the next visit." [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "The staff was super nice and flexible! Location was great " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![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 "Yea" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "Clean room, very nice staff, everything was excellent! " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Hotel Coolidge](https://images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "Spacious, quirky and historical accommodations. Staff was great, amenities were just as described. Room was actually better than I had anticipated " [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information) ![COHO Inn & Motor Lodge](https://images.trvl-media.com/lodging/105000000/104400000/104395800/104395732/3f7fd5fb_y.jpg) ### COHO Inn & Motor Lodge 10/10 Excellent "I stayed at here on a whim in December ‘25 on an early ski trip to Stratton & Killington, looking for a spot that wouldn’t break the bank. Got a whole lot more than I bargained for! Eggs & bacon for breakfast, super cozy cabin, great hospitality, and good recommendations. New owners Ali & Lane are hard at work investing more and more into the place and I can’t wait to go back in the summer. Highly recommend for anyone seeking an unfussy stay with rustic charm and super-welcoming owner/operators." [](https://expedia.ca/Weston-Hotels-The-Colonial-House-Inn-And-Motor-Lodge.h104395732.Hotel-Information) ## Find out more about Windsor County ## Windsor County Guest Houses information | Number of reviews | 154 | | ----------------- | -------------- | | Accommodation | 7 Guest Houses | | Lowest Price | CA $572 | | Highest Price | CA $572 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Billings Farm and Museum ](https://www.expedia.ca/Billings-Farm-And-Museum-Hotels.0-l6175222-0.Travel-Guide-Filter-Hotels) - [Farmstay in Bridgewater ](https://www.expedia.ca/Bridgewater-Agritourism.d553248635975851833-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Bridgewater ](https://www.expedia.ca/Bridgewater-Bed-And-Breakfast.d553248635975851833-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Bridgewater ](https://www.expedia.ca/Bridgewater-Guest-Houses.d553248635975851833-aaGuestHouses.Travel-Guide-Accommodation) - 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