Title: Windsor County Cottages from CA $265 | 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 $265 ## 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 In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=COTTAGE&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) ![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/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor-Cottages.d7881-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) ## 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) ![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) ![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) ### Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit Ludlow 9.6/10 Exceptional (19) "We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen R. [](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) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/82ebadba.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) ### Terrific 3-bedroom cottage with AC in charming Cavendish Cavendish CA $191 CA $695 total includes taxes & fees Nov 9 - Nov 10 [](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/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) ![Property grounds](https://images.trvl-media.com/lodging/21000000/20160000/20157600/20157543/573416c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Village Carriage House Woodstock 9.8/10 Exceptional (101) "A very pleasant experience all around. The house is great and the town is charming. Thank you! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent C. [](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) | 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) ![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) ### 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) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100810000/100807000/100806959/cf09c2e6.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) ![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) ### Cozy cottage on the river, minutes from skiing, horse events, and so much more! Reading 10/10 Exceptional (12) "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) ![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) ![Interior](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4a7f2bad.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 (4) "Perfect size and location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyn H. CA $135 CA $265 total includes taxes & fees Nov 9 - Nov 10 [](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/105000000/104960000/104954000/104953935/7ac968ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104960000/104954000/104953935/23b8f87a.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/a0f4cb13.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/f51309a4.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) ### 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/94000000/93590000/93587000/93586992/555e634a.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) ![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) ### 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/95000000/94360000/94353200/94353127/7c229706.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/95000000/94330000/94322000/94321966/27b4d6ae.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/d36edeba.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) ![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) ![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) ### 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/94000000/93550000/93545900/93545845/47c3c64d.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) ### 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) ![TV](https://images.trvl-media.com/lodging/97000000/96900000/96895900/96895881/a4519e31.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) ![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) ### 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/101000000/100010000/100000700/100000677/30d97aef.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/b94f2668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100010000/100000700/100000677/25ab4db4.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) ![Interior](https://images.trvl-media.com/lodging/77000000/76860000/76855900/76855859/6d64ba8c.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/119000000/118050000/118040400/118040302/8eaccf48.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/b4ab3fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/119000000/118050000/118040400/118040302/07caf31e.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/114000000/113570000/113569600/113569511/75673fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113570000/113569600/113569511/4b17a586.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) ### 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/102000000/101550000/101545100/101545089/18e498c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/102000000/101550000/101545100/101545089/30cd9b17.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=2025-11-22&endDate=2025-11-23®ionId=553248635976432508&adults=2&lodging=COTTAGE&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-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 "Very clean and quiet property, comfortable bed. Slept very well!" [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Loved the casual, comfortable, easy atmosphere. Homey and welcoming but never overbearing. Staff were all wonderful and personable. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Great place to stay" [](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 "We loved this hotel as everything was very clean. The staff was very friendly and helpful. They provided us with information as to other areas or places we could go with our family. They were very informative. And they do provide just about everything you need." [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.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 "Stayed for an overnight trip to visit family. Breakfast was good and the room was comfortable. " [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Hotel Coolidge](//images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "Charming place to stay! Very clean and easy access to restaurant and the highway. Highly recommend if you want to avoid a chain hotel. " [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.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 "The restaurant was very nice. Great service. Delicious food." [](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 "The staff were so welcoming and friendly! When we got engaged they all cheered for us and were so sweet!" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![The Vesper ](//images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64_y.jpg) ### The Vesper 10/10 Excellent "It was clean, the people were outstanding. I would stay again." [](https://expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) ## Find out more about Windsor County ## Windsor County Cottages information | Number of reviews | 184 | | --- | --- | | Accommodation | 47 Cottages | | Lowest Price | CA $265 | | Highest Price | CA $695 | ## 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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