Title: Windsor County Cottages from CA $278 | 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 # Search Windsor County Cottage Rentals from CA $278 ## 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 [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Cottages.d8496-aaCottages.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-Cottages.d10868-aaCottages.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-Cottages.d6294-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor-Cottages.d7881-aaCottages.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-Cottages.d9580-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/6e1ce19989493034a8e8934b004054dd.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Norwich [](https://expedia.ca/Norwich-Cottages.d184063-aaCottages.Travel-Guide-Accommodation) ## Our top choices for Windsor County cottages ![Exterior](https://images.trvl-media.com/lodging/123000000/122120000/122116100/122116043/bc49c95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122120000/122116100/122116043/66c7225b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122120000/122116100/122116043/bc1682f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122120000/122116100/122116043/c758e302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Norwich [](https://www.expedia.ca/Norwich-Hotels-Peaceful-Riverview-Retreat-1-Mi-To-Dartmouth-College-4-Bd-3ba.h122116043.Hotel-Information) 10/10 Exceptional (1) "A great experience and stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cameron M. [](https://www.expedia.ca/Norwich-Hotels-Peaceful-Riverview-Retreat-1-Mi-To-Dartmouth-College-4-Bd-3ba.h122116043.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/99000000/98630000/98624200/98624120/1487350e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98630000/98624200/98624120/ffde0c18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/99000000/98630000/98624200/98624120/11fec3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98630000/98624200/98624120/29447a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Ludlow [](https://www.expedia.ca/Ludlow-Hotels-Renovated-Lakefront-Cottage-With-Deep-Water-Dock.h98624120.Hotel-Information) 9.6/10 Exceptional (20) "The house, its location, and dock are real nice. Would come here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy G. [](https://www.expedia.ca/Ludlow-Hotels-Renovated-Lakefront-Cottage-With-Deep-Water-Dock.h98624120.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4ccd0baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/18611595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4a7f2bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4e43f1be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Hartford [](https://www.expedia.ca/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.Hotel-Information) 10/10 Exceptional (4) "Perfect size and location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyn H. CA $148 CA $278 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34330000/34329400/34329330/15a9b459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34330000/34329400/34329330/w799h599x1y1-d72243d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34330000/34329400/34329330/5a13e6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34330000/34329400/34329330/469c25b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in West Windsor [](https://www.expedia.ca/Windsor-Hotels-Cozy-Historic-Hilltop-Cottage-With-Mount-Ascutney-View.h34329330.Hotel-Information) 9.6/10 Exceptional (84) "Beautiful country! Very laid back atmosphere!Easy to check in and out. Great experience!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul H. [](https://www.expedia.ca/Windsor-Hotels-Cozy-Historic-Hilltop-Cottage-With-Mount-Ascutney-View.h34329330.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/d3456560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/428535e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/0de3e860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/6f42cdc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Reading [](https://www.expedia.ca/Reading-Hotels-Cozy-Cottage-On-The-River.h100806959.Hotel-Information) 10/10 Exceptional (13) "What an adorable little place! The host was wonderful and we loved all the care put into every little detail from the decor to the outdoor area, this place had it all!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana V. [](https://www.expedia.ca/Reading-Hotels-Cozy-Cottage-On-The-River.h100806959.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/226bf513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/7ac968ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/a0f4cb13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/efc7ad5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Ludlow [](https://www.expedia.ca/Ludlow-Hotels-Lovely-Ludlow-Farmhouse-1-Mi-To-Town-Slopes.h104953935.Hotel-Information) 10/10 Exceptional (1) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mauro [](https://www.expedia.ca/Ludlow-Hotels-Lovely-Ludlow-Farmhouse-1-Mi-To-Town-Slopes.h104953935.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98555400/98555376/837e2e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98555400/98555376/a2fe346b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98555400/98555376/82047e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98555400/98555376/8127252b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Brownsville [](https://www.expedia.ca/Brownsville-Hotels-Luxury-Vermont-Vacation-Rental-Private-Hot-Tub.h98555376.Hotel-Information) [](https://www.expedia.ca/Brownsville-Hotels-Luxury-Vermont-Vacation-Rental-Private-Hot-Tub.h98555376.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/8d3a3825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/b4ab3fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/8eaccf48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/f33dbcd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Ludlow [](https://www.expedia.ca/Ludlow-Hotels-8-Mi-To-Okemo-Mountain-Resort-Mtn-View-Retreat.h118040302.Hotel-Information) [](https://www.expedia.ca/Ludlow-Hotels-8-Mi-To-Okemo-Mountain-Resort-Mtn-View-Retreat.h118040302.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/c1d69bc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/72aeb737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/aa44f0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/82ebadba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Cavendish [](https://www.expedia.ca/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) CA $308 CA $824 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/438fcc97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/573416c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/a5748b5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/811848ec_edited_9b37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Woodstock [](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Village-Carriage-House.h20157543.Hotel-Information) 9.8/10 Exceptional (102) "Clean, friendly host, quiet. Perfect location to everything in town" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mia M. [](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Village-Carriage-House.h20157543.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/a6ff177b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/0f7235da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/915d9041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/d9fba77b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Chester [](https://www.expedia.ca/Chester-Hotels-Peaceful-Brookside-Getaway-10-Mi-To-Okemo-Slopes.h108315854.Hotel-Information) 10/10 Exceptional (1) "The property was lovely, peaceful, and quiet, surrounded by trees on a quiet country drive. It was the perfect weekend getaway and we really enjoyed sitting on the porch and out under the string lights, watching the sun go down through the trees. The house itself is lovely, cozy, and comfortable. Our hosts were very sweet, everything was very thoughtfully laid out and clean and easy to access. We also loved meeting the goats, Ozzy and Coco, and the chickens! This was such a pleasant stay, I... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela [](https://www.expedia.ca/Chester-Hotels-Peaceful-Brookside-Getaway-10-Mi-To-Okemo-Slopes.h108315854.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93590000/93587000/93586992/d0fc1919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93590000/93587000/93586992/d67c14e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93590000/93587000/93586992/555e634a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93590000/93587000/93586992/3d468dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Brownsville [](https://www.expedia.ca/Brownsville-Hotels-Inviting-Vermont-Cabin-On-Mount-Ascutney.h93586992.Hotel-Information) [](https://www.expedia.ca/Brownsville-Hotels-Inviting-Vermont-Cabin-On-Mount-Ascutney.h93586992.Hotel-Information) ![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353127/6deb0bff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353127/e45bf1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (6 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353127/baab8466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353127/7c229706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Bridgewater Corners [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Picture-Perfect-Vermont-Mtn-Cabin-W-Hot-Tub.h94353127.Hotel-Information) [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Picture-Perfect-Vermont-Mtn-Cabin-W-Hot-Tub.h94353127.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100010000/100000700/100000677/ff7a99a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100010000/100000700/100000677/30d97aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100010000/100000700/100000677/25ab4db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100010000/100000700/100000677/b94f2668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Weston [](https://www.expedia.ca/Weston-Hotels-Weston-Vacation-Rental-Close-To-Ski-Resorts.h100000677.Hotel-Information) [](https://www.expedia.ca/Weston-Hotels-Weston-Vacation-Rental-Close-To-Ski-Resorts.h100000677.Hotel-Information) ![House (5 Bedrooms) | Property grounds](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/c1e4cd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/50c3a6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/28858758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/b2722f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Chester [](https://www.expedia.ca/Chester-Hotels-Chester-Farmhouse-On-100-Acres.h94321966.Hotel-Information) [](https://www.expedia.ca/Chester-Hotels-Chester-Farmhouse-On-100-Acres.h94321966.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110930000/110920400/110920350/4717ae92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110930000/110920400/110920350/93825cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110930000/110920400/110920350/2266a97c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110930000/110920400/110920350/3b1a5bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Springfield [](https://www.expedia.ca/Springfield-Hotels-18-Mi-To-Skiing-Colorful-Home-In-Springfield.h110920350.Hotel-Information) [](https://www.expedia.ca/Springfield-Hotels-18-Mi-To-Skiing-Colorful-Home-In-Springfield.h110920350.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93545900/93545845/449fbfcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93545900/93545845/47c3c64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93545900/93545845/f0eb7aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93545900/93545845/edfe5f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Stockbridge [](https://www.expedia.ca/Stockbridge-Hotels-Killington-Area-Escape-W-Deck-Private-Hot-Tub.h93545845.Hotel-Information) [](https://www.expedia.ca/Stockbridge-Hotels-Killington-Area-Escape-W-Deck-Private-Hot-Tub.h93545845.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/8df9a704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/6d64ba8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/ae7a4439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/4ca5a9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Weston [](https://www.expedia.ca/Weston-Hotels-4bdrm-Cottage-Central-To-Year-Round-Fun-Wfireplace.h76855859.Hotel-Information) [](https://www.expedia.ca/Weston-Hotels-4bdrm-Cottage-Central-To-Year-Round-Fun-Wfireplace.h76855859.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94327900/94327824/7b160391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94327900/94327824/12e558f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94327900/94327824/8787a401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94327900/94327824/074e02cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Chester [](https://www.expedia.ca/Chester-Hotels-Private-Chester-Home-W-Deck.h94327824.Hotel-Information) [](https://www.expedia.ca/Chester-Hotels-Private-Chester-Home-W-Deck.h94327824.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121198900/121198871/58e3633e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121198900/121198871/046234a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121198900/121198871/793663a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121198900/121198871/6b053334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Bridgewater Corners [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Riverfront-Home-W-Hot-Tub-Near-Killington-Resort.h121198871.Hotel-Information) [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Riverfront-Home-W-Hot-Tub-Near-Killington-Resort.h121198871.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=2026-01-08&endDate=2026-01-09®ionId=553248635976432508&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Cottages.d553248635976432508-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-County-Cottages.d553248635976432508-aaCottages.Travel-Guide-Accommodation) ## Top Windsor County Hotel Reviews ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Wonderful stay. Staff were very kind. Room was clean. " [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.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 "Staff are exceptionally friendly and helpful " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "Everything about this place is amazing, the homey feel, the cleanliness, and friendly atmosphere ran by people who put love and care into their inn, people who care about their guests and provides top notch hospitality. We were able to check in 2 hours early, Ally gave us all the perfect recommendations around town. They had a small menu with light bites and wine available for purchase. Super convenient when you can text their number for any requests, with quick response time. They brought our light bites and wine up to our room, there’s also free coffee, tea, and games in their warm and nicely holiday decorated guest living room. Cherry on top, breakfast was included in our stay with a wide spread of eggs, bacon, juices, bagels, yogurt… etc Excellent choice of stay for our short weekend ski trip. Cozy and welcoming definitely coming back. " [](https://expedia.ca/Weston-Hotels-The-Colonial-House-Inn-And-Motor-Lodge.h104395732.Hotel-Information) ![Hotel Coolidge](https://images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "No breakfast and parking was ok" [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.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 "The greeting from staff was lovely. My room was neat and well stocked with toiletries. " [](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 "Luxurious and friendly resort! Loved it" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.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 "Super responsive staff, great accomodations " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Norwich Inn](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519573/30ba8066_y.jpg) ### Norwich Inn 10/10 Excellent "I wanted a White Christmas inn in Vermont and I got it. The inn was decorated for Christmas, had a roaring fire and even a holiday puzzle to complete. The rooms were great, ours had a fireplace, and the beds were comfortable. The staff were great (willing to open the bar for a hot toddy if needed ;-)), were helpful, and easy to contact. Not much in town, but close to other attractions." [](https://expedia.ca/Norwich-Hotels-Norwich-Inn.h2519573.Hotel-Information) ![The Vesper ](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64_y.jpg) ### The Vesper 10/10 Excellent "Clean, very comfortable & spacious room (SOTO). Very friendly, welcoming host & staff. Our jacuzzi tub's jets were not working. We would have appreciated knowing that in advance." [](https://expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) ## Find out more about Windsor County ## Windsor County Cottages information | Number of reviews | 191 | | ----------------- | ----------- | | Accommodation | 52 Cottages | | Lowest Price | CA $278 | | Highest Price | CA $824 | ## 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) - [Hostels in Bridgewater ](https://www.expedia.ca/Bridgewater-Hostels.d553248635975851833-aaHostels.Travel-Guide-Accommodation) - 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