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) ![Must stop while in Vermont #autumn #fall #roadtrip #travel #adventure #colorful #vermont ](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rachel Samanyi ![](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [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) In two weeks [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Windsor County ![Ludlow showing street scenes](https://images.trvl-media.com/place/8496/505d08ac-b11f-4f25-a539-2958ea0722b2.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://images.trvl-media.com/place/10868/c2d6773f-8f3f-4c1a-b710-f2f2bceab647.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Woodstock [](https://expedia.ca/Woodstock-Guest-Houses.d10868-aaGuestHouses.Travel-Guide-Accommodation) ![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=384&h=216&q=medium) #### White River Junction [](https://expedia.ca/White-River-Junction-Guest-Houses.d6294-aaGuestHouses.Travel-Guide-Accommodation) ![Quechee featuring a river or creek, a bridge and tranquil scenes](https://images.trvl-media.com/place/9580/a3d99a95-3156-473d-99ae-f796cac4afe4.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Quechee [](https://expedia.ca/Quechee-Guest-Houses.d9580-aaGuestHouses.Travel-Guide-Accommodation) ![Autumn Scenery - Plymouth Notch, Vermont](https://images.trvl-media.com/place/146918/76664a38-b8fd-4f62-bcc0-686770b64c70.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Plymouth [](https://expedia.ca/Plymouth-Guest-Houses.d146918-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) ![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) ![Room 4, Not Pet-friendly](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/8b3fdb1b.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) ### The Weston [](https://www.expedia.ca/Weston-Hotels-The-Weston.h100702715.Hotel-Information) Weston 10/10 Exceptional (9 reviews) "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 $526 CA $574 total includes taxes & fees Feb 22 - Feb 23 [](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) ![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) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1800000/1791400/1791326/0aa59e3c.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) ### 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 (56 reviews) "Beautiful place, nice clean and comfortable rooms. Great for a quick weekend getaway." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph [](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) ![Exterior detail](https://images.trvl-media.com/lodging/102000000/101140000/101137100/101137051/1055b96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101140000/101137100/101137051/5c3ceb31.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) ### 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 9.8/10 Exceptional (11 reviews) "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) ![Smart TV](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/3850e67e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/4f3a85b6.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) ### 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 (42 reviews) "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) ![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) ![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) ![TV](https://images.trvl-media.com/lodging/88000000/87590000/87589900/87589843/afdd7c38.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 reviews) "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) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22130000/22125500/22125463/ceff38ca.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) ![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22125500/22125463/09e5c7ec.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 reviews) "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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1787800/1787707/64d6171c.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) ### Salt Ash Inn [](https://www.expedia.ca/Plymouth-Hotels-Salt-Ash-Inn.h1787707.Hotel-Information) Plymouth 6.0/10 (126 reviews) "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=2026-02-19&endDate=2026-02-20®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 ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Everything from the manager to the staff to the room and food. 5 stars" [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Clean room, nice breakfast, nice restaurant next door" [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.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 "Staff was very Courteous, Clean rooms and great stay. Breakfast was decent with a waffle machine and kids enjoyed it. " [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.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 "Clean room! Great food!" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Comfort Inn White River Junction](https://images.trvl-media.com/lodging/1000000/10000/8900/8850/a720acb3_y.jpg) ### Comfort Inn White River Junction 10/10 Excellent "Very nice staff, clean rooms. " [](https://expedia.ca/White-River-Junction-Hotels-Comfort-Inn.h8850.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 "The room was so comfortable and the staff here is top notch. The included breakfast is one of the best I’ve ever had when it was included with your stay. This place is a hidden jewel!" [](https://expedia.ca/Weston-Hotels-The-Colonial-House-Inn-And-Motor-Lodge.h104395732.Hotel-Information) ![Norwich Inn](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519573/30ba8066_y.jpg) ### Norwich Inn 10/10 Excellent "Spectacular place and great service !! " [](https://expedia.ca/Norwich-Hotels-Norwich-Inn.h2519573.Hotel-Information) ![The Quechee Inn at Marshland Farm](https://images.trvl-media.com/lodging/2000000/1930000/1924800/1924710/c8372335_y.jpg) ### The Quechee Inn at Marshland Farm 10/10 Excellent "Had a great Stay. Food was Very Good" [](https://expedia.ca/Quechee-Hotels-The-Quechee-Inn-At-Marshland-Farm.h1924710.Hotel-Information) ## Find out more about Windsor County ## Windsor County Guest Houses information | Number of reviews | 157 | | ----------------- | -------------- | | Accommodation | 7 Guest Houses | | Lowest Price | CA $574 | | Highest Price | CA $574 | ## 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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