Title: Top Guest Houses in Windsor County in 2025 | 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) ![Weston showing interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93824-Central-Vermont.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## Featured Guest Houses in Windsor County ![Gazebo](https://images.trvl-media.com/lodging/2000000/1800000/1791400/1791326/574cf180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1800000/1791400/1791326/c2df15a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/2000000/1800000/1791400/1791326/5fc2d51f.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) White River Junction 9.4/10 Exceptional (55) "Lovely stay at Tina’s place - very welcoming and homely with beautiful grounds . We even got see the hot air balloon take off from the garden for sunset. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Steve [](https://www.expedia.ca/White-River-Junction-Hotels-Inn-At-Clearwater-Pond.h1791326.Hotel-Information) ![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) ![Restaurant](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/b5317610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/8f6b12a1.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) ### The Weston 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 $521 CA $568 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Weston-Hotels-The-Weston.h100702715.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101140000/101137100/101137051/7e4bc6f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101140000/101137100/101137051/5f9f967f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101140000/101137100/101137051/df7ec946.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/f7d748cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly 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) ![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/w5261h3503x5y5-a5207a7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/72352b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/2c112eb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/0092519b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! Chester Depot 9.4/10 Exceptional (39) "This space was more than expected. The beds were super comfy and everything we needed was at our fingertips whether it be coffee making supplies, dish soap or Kleenex. Hosts use environmentally friendly products that are also allergen friendly. they provided lots of local information which helped us plan our stay. Loved this spot! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Narda C. [](https://www.expedia.ca/Chester-Hotels-1868-Carriage-House-Quaint-Cozy-Perfect-Escape-20-MIN-TO-Okemo.h22120284.Hotel-Information) ![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) ![TV](https://images.trvl-media.com/lodging/88000000/87590000/87589900/87589843/afdd7c38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87590000/87589900/87589843/035ba6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts Woodstock 9.4/10 Exceptional (36) "This space was very clean and a beautiful spot in nature. We loved all of the birds and wildlife and fireflies at night. It is very close to a little General Store to get coffee and snacks. Its only a 10 minute drive to get to the Woodstock main street. Neighborhood is quiet and the fire pit was lovely to sit around at night and enjoy the quiet. There was also a cute little Farmer's Market in the ski parking lot that was only a 5 minute walk to on Sunday. Overall a great little space for a... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katee R. [](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) ![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22125500/22125463/09e5c7ec.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) ![Smart TV](https://images.trvl-media.com/lodging/23000000/22130000/22125500/22125463/18daf7ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants Ludlow 9.8/10 Exceptional (42) "We had a great time staying in VT, and were blessed to stay in this cozy home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David R. [](https://www.expedia.ca/Ludlow-Hotels-Ludlow-Village-Guest-House-Prime-Location-On-Ski-Shuttle.h22125463.Hotel-Information) ![Billiards](https://images.trvl-media.com/lodging/2000000/1790000/1787800/1787707/aecd81af.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) ![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1790000/1787800/1787707/09218158.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) ### Salt Ash Inn 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=2025-11-14&endDate=2025-11-15®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 ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "Great swimming pools.. Also enjoyed the hot chocolate at the complimentary wending machine.. Rooms were cosy too.." [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![Best Western Springfield Hotel](//images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480_y.jpg) ### Best Western Springfield Hotel 10/10 Excellent "Nice clean place to stay!" [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Align Inn Vermont](//images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Cute property in a great location. It was less expensive to stay in Quechee than Woodstock so we chose to stay here. It’s walking distance to the Quechee gorge which was beautiful. Room is clean, AC works well, good water pressure, has some food options near by but we chose to drive to Woodstock to eat. Breakfast is simple, hotel is cozy, and the area is beautiful during Fall when we went. Definitely would stay again" [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Nice view , great location " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![On The River Inn](//images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b_y.jpg) ### On The River Inn 10/10 Excellent "My family and I stayed Friday through Sunday. The room was spacious and we had a cute little balcony that overlooked the river and the property. It was the perfect getaway. The room had all the necessary toiletries, plenty of towels, and blankets. The best part was that the pool was very clean and we enjoyed it a lot. There was also a toddler room with some toys that kept my kids entertained. The Bistro in the Inn was amazing because we didn’t need to leave to get dinner. Our stay included a continental breakfast and it did not disappoint at all. We love our stay. " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "This was our ideal hotel! Charmingly decorated, functional, and a walking distance to the town. We appreciated the complimentary champagne on our arrival, it was a wonderful place to spend our honeymoon." [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Sleep Woodstock Motel](//images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11_y.jpg) ### Sleep Woodstock Motel 10/10 Excellent "Easy check in, very clean. Close to Woodstock shopping and dining areas. Staff very informative. Great little ice cream/breakfast place right next door. " [](https://expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Room clean and comfy, well stocked." [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](//images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Very nice place a room. We were disappointed that both restaurants at the place were closed. Had to drive to another small town as there was nothing in this remote area within 10 miles. The recommended nearby deli that was recommended by staff had closed early on a Tuesday afternoon @4pm." [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ## Find out more about Windsor County ## Windsor County Guest Houses information | Number of reviews | 154 | | --- | --- | | Accommodation | 7 Guest Houses | | Lowest Price | CA $568 | | Highest Price | CA $568 | ## 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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[Visit Woodstock](https://www.expedia.ca/Woodstock.dx10868) - [Car rentals near Red Wagon Toy Company](https://www.expedia.ca/Car-Rentals-In-Red-Wagon-Toy-Company.d553248621532667633.Car-Rental-Guide) - [Car rental Woodstock](https://www.expedia.ca/Car-Rentals-In-Woodstock.d10868.Car-Rental-Guide) - [Hertz Rental Cars in Woodstock](https://www.expedia.ca/Hertz-Car-Rentals-In-Woodstock.d10868-c40.Car-Rental-Guide-Suppliers) - [Quechee Vacation Rentals](https://www.expedia.ca/Quechee-Vacation-Rentals.d9580.Travel-Guide-VacationRentals) - [Things to do in Woodstock](https://www.expedia.ca/Things-To-Do-In-Woodstock.d10868.Travel-Guide-Activities) - [Book Guest Houses in Windsor County on Expedia.com](https://www.expedia.com/Windsor-County-Guest-Houses.d553248635976432508-aaGuestHouses.Travel-Guide-Accommodation)