Title: Windsor County Cottages from CA $307 | 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) # Search Windsor County Cottage Rentals from CA $307 ## 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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Cottages in Windsor County ![Exterior](https://images.trvl-media.com/lodging/99000000/98630000/98624200/98624120/1487350e.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) ![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/99000000/98630000/98624200/98624120/21287767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit Ludlow 9.6/10 Exceptional (18) "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/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/aa44f0f1.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/f1003380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrific 3-bedroom cottage with AC in charming Cavendish Cavendish CA $189 CA $690 total includes taxes & fees Oct 28 - Oct 29 [](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) ![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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/5d9eaf9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Village Carriage House Woodstock 9.8/10 Exceptional (100) "We had a very nice stay at the property. Great home and great central location. Close to town, Billings farm and hiking trails. We would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George S. [](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) | Front of property](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/4070a40e.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) ### Peaceful Brookside Getaway ~10 Mi to Okemo Slopes! Chester 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) ![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/101000000/100810000/100807000/100806959/0de3e860.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) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/cf09c2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy cottage on the river, minutes from skiing, horse events, and so much more! Reading 10/10 Exceptional (11) "very good cozy location. enjoyed the privacy during our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harminder [](https://www.expedia.ca/Reading-Hotels-Cozy-Cottage-On-The-River.h100806959.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/5afbd4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Addie's Place: A Quiet and Quirky Private Guesthouse Hartford 10/10 Exceptional (3) "Perfect size and location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyn H. CA $168 CA $307 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.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/efc7ad5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/23b8f87a.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) ### Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes! Ludlow 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/99000000/98560000/98555400/98555376/82047e63.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) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98555400/98555376/f51309a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Vermont Vacation Rental: Private Hot Tub! Brownsville [](https://www.expedia.ca/Brownsville-Hotels-Luxury-Vermont-Vacation-Rental-Private-Hot-Tub.h98555376.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/c52cc6b2.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/bf1c03ce.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) ### Inviting Vermont Home On Mount Ascutney! Brownsville [](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) | 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/e45bf1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353127/6e2b204c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Picture-perfect Vermont Mtn Cabin w/ Hot Tub! Bridgewater Corners [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Picture-Perfect-Vermont-Mtn-Cabin-W-Hot-Tub.h94353127.Hotel-Information) ![House (5 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/a05c05f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/22309641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/6daf08f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94322000/94321966/8876af3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chester Farmhouse on 100 Acres, 15 Min to Okemo! Chester [](https://www.expedia.ca/Chester-Hotels-Chester-Farmhouse-On-100-Acres.h94321966.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) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/35000000/34330000/34329400/34329330/bc28e3c3.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) ### Cozy Historic Hilltop Cottage with Mount Ascutney View West Windsor 9.6/10 Exceptional (83) "Great location for our vacation. Owner was bery quick to respond to questionsz" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin C. [](https://www.expedia.ca/Windsor-Hotels-Cozy-Historic-Hilltop-Cottage-With-Mount-Ascutney-View.h34329330.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/ab774371.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) ### 18 Mi to Skiing: Colorful Home in Springfield! Springfield [](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/94000000/93550000/93545900/93545845/0d517a22.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/94000000/93550000/93545900/93545845/47c3c64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Killington Area Escape w/ Deck, Views & Hot Tub! Stockbridge [](https://www.expedia.ca/Stockbridge-Hotels-Killington-Area-Escape-W-Deck-Private-Hot-Tub.h93545845.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96900000/96895900/96895881/e019fe28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/97000000/96900000/96895900/96895881/b64a02af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96900000/96895900/96895881/3515f141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/97000000/96900000/96895900/96895881/cfdd327a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spruce Moose Cottage | Tiny House on 65 private acres Hartland [](https://www.expedia.ca/Hartland-Hotels-Spruce-Moose-Cottage-Tiny-House-On-65-Private-Acres.h96895881.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/101000000/100010000/100000700/100000677/4bf96103.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) ![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) ### Weston Vacation Rental - Close to Ski Resorts! Weston [](https://www.expedia.ca/Weston-Hotels-Weston-Vacation-Rental-Close-To-Ski-Resorts.h100000677.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) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/af57ac2b.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) ### 4bdrm Cottage central to year round fun w/fireplace Weston [](https://www.expedia.ca/Weston-Hotels-4bdrm-Cottage-Central-To-Year-Round-Fun-Wfireplace.h76855859.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/f33dbcd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/07caf31e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 Mi to Okemo Mountain Resort: Mtn-view Retreat! Ludlow [](https://www.expedia.ca/Ludlow-Hotels-8-Mi-To-Okemo-Mountain-Resort-Mtn-View-Retreat.h118040302.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113570000/113569600/113569511/b3e4761f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113570000/113569600/113569511/0f5f29d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113570000/113569600/113569511/75673fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113570000/113569600/113569511/9737f0d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hike, Ski & Unwind: Cabin w/ Deck in Chester! Chester [](https://www.expedia.ca/Chester-Hotels-Hike.h113569511.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/102000000/101550000/101545100/101545089/2149d165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/102000000/101550000/101545100/101545089/12cf5032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/102000000/101550000/101545100/101545089/74b90a6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/102000000/101550000/101545100/101545089/18e498c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Cavendish Retreat w/ Hot Tub & Fireplace! Cavendish [](https://www.expedia.ca/Cavendish-Hotels-Peaceful-Cavendish-Retreat-W-Hot-Tub-Fireplace.h101545089.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=2025-11-10&endDate=2025-11-11®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](//images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Great value-clean, quiet, safe and good price. Breakfast was basic." [](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 "Beautiful view from the waterside " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.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) ![COHO Inn & Motor Lodge](//images.trvl-media.com/lodging/105000000/104400000/104395800/104395732/3f7fd5fb_y.jpg) ### COHO Inn & Motor Lodge 10/10 Excellent "Charming lodge and rooms in a nicely curated vintage vibe. The hosts, Ali and Lane, were friendly and accommodating of our every request and question. Location very convenient to hiking and sightseeing in nearby towns." [](https://expedia.ca/Weston-Hotels-The-Colonial-House-Inn-And-Motor-Lodge.h104395732.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 "Relaxing, clean, staff was nice" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "Property is great for kids. It is not within walking to any bars or restaurants, other than what they have on site. Staff are friendly, but they don't have daily housekeeping if that is important to you." [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![The Vesper ](//images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64_y.jpg) ### The Vesper 10/10 Excellent "Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!" [](https://expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) ![Hotel Coolidge](//images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "Front row, parking, super friendly staff, and the bed was the most comfortable bed I’ve ever slept in in any hotel!" [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information) ![Fullerton Inn](//images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab_y.jpg) ### Fullerton Inn 10/10 Excellent "Manager was very helpful . We enjoyed the lunch during our stay. " [](https://expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ## Find out more about Windsor County ## Windsor County Cottages information | Number of reviews | 180 | | --- | --- | | Accommodation | 47 Cottages | | Lowest Price | CA $307 | | Highest Price | CA $690 | ## 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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