Title: Windsor County Vacation Home Rentals from CA $808: Search Top Private Vacation Homes for Rent | 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) ![Quechee Gorge- Vermont #autumn #colorful #roadtrip #weekendgetaway #travel #adventure #nature #vacation ](https://images.trvl-media.com/place/3000459649/7d354301-07a8-4d26-bfd8-54320ed05c30.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rachel Samanyi # Windsor County Vacation Rentals ## 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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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) In one month [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 two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-02-06&endDate=2026-02-08&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-Private-Vacation-Homes.d8496-aaPrivateVacationHomes.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-Private-Vacation-Homes.d10868-aaPrivateVacationHomes.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-Private-Vacation-Homes.d6294-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor-Private-Vacation-Homes.d7881-aaPrivateVacationHomes.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-Private-Vacation-Homes.d9580-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/6e1ce19989493034a8e8934b004054dd.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Norwich [](https://expedia.ca/Norwich-Private-Vacation-Homes.d184063-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Our top choices for Windsor County vacation homes ![Exterior](https://images.trvl-media.com/lodging/32000000/31430000/31429400/31429400/b3936866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/32000000/31430000/31429400/31429400/b0b7ad77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31430000/31429400/31429400/d701a57f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/32000000/31430000/31429400/31429400/3c4ba64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base [](https://www.expedia.ca/Ludlow-Hotels-Cozy-3br-Cabin-5-Minutes-From-Okemo-Mountain-Base.h31429400.Hotel-Information) Ludlow 9.6/10 Exceptional (55) "Great place! Warm and cozy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin C. [](https://www.expedia.ca/Ludlow-Hotels-Cozy-3br-Cabin-5-Minutes-From-Okemo-Mountain-Base.h31429400.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/5c4d09d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/50590f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/c05c5eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/7ff65ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable [](https://www.expedia.ca/Ludlow-Hotels-Classic-Ski-Home-With-Hot-Tub.h72131806.Hotel-Information) Ludlow 8.0/10 Very good (41) "Plenty of space and the two living rooms are great because the upstairs living room is very small." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brad H. [](https://www.expedia.ca/Ludlow-Hotels-Classic-Ski-Home-With-Hot-Tub.h72131806.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/73000000/72140000/72131800/72131736/73ed4359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131800/72131736/ceefcc91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131800/72131736/6a8a92cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72140000/72131800/72131736/be2ebd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rustic home with a private hot tub, fireplace, cable, & washer/dryer [](https://www.expedia.ca/Plymouth-Hotels-Rustic-Home-With-A-Hot-Tub.h72131736.Hotel-Information) Plymouth 9.6/10 Exceptional (63) "We were so happy with our stay. The house and surrounding area is beautiful and peaceful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela C. [](https://www.expedia.ca/Plymouth-Hotels-Rustic-Home-With-A-Hot-Tub.h72131736.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/dd998d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/a5bdbf23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/70722da7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/270-fc011965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo [](https://www.expedia.ca/Ludlow-Hotels-Traveling-With-Kids-Check-This-Secluded-Update-3-Bedroom-Home-Close-To-Okemo.h31137653.Hotel-Information) Ludlow 9.6/10 Exceptional (129) "Beautiful place! Enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cathy B. [](https://www.expedia.ca/Ludlow-Hotels-Traveling-With-Kids-Check-This-Secluded-Update-3-Bedroom-Home-Close-To-Okemo.h31137653.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/88000000/87720000/87714700/87714614/ffc672b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87720000/87714700/87714614/30f18a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/88000000/87720000/87714700/87714614/05b5add6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87720000/87714700/87714614/34863af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock [](https://www.expedia.ca/White-River-Junction-Hotels-Beautifully-Renovated-2BR-Townhome-With-Fireplace.h87714614.Hotel-Information) Hartford 10/10 Exceptional (131) "My sister and I stayed here while taking a two day class at King Arthur Baking School. The pictures don't even do it justice on how cute and well appointed the property is. The beds were very comfortable with nice linens and there were plenty of bath towels. The owners were always quick to respond to any question. We would definitely stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy S. [](https://www.expedia.ca/White-River-Junction-Hotels-Beautifully-Renovated-2BR-Townhome-With-Fireplace.h87714614.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/74000000/73080000/73076900/73076828/a33a0cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/74000000/73080000/73076900/73076828/1d650f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/74000000/73080000/73076900/73076828/62168f7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73080000/73076900/73076828/0d07615f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola [](https://www.expedia.ca/Bridgewater-Corners-Hotels-New-2021-Ski-House-2-Min-Drive-To-Killington-Gondola.h73076828.Hotel-Information) Bridgewater Corners 10/10 Exceptional (3) "Very clean, cozy, & had exactly what we needed for the last leg of our vacation. Bed was comfy, & nice to have the hot tub, we appreciated that after all the driving. We had just stayed at a vrbo that was not clean, so it was a great contrast! Thanks Russ & family for sharing your cute little cottage with us! Mark & Sherry" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherry M. CA $369 CA $808 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-New-2021-Ski-House-2-Min-Drive-To-Killington-Gondola.h73076828.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/62000000/61380000/61371000/61370917/741acc65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/62000000/61380000/61371000/61370917/75ea71fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/62000000/61380000/61371000/61370917/95b6ccbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/62000000/61380000/61371000/61370917/5d0ed62a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes! [](https://www.expedia.ca/Ludlow-Hotels-Mountain-View-Manor-Expansive-Views.h61370917.Hotel-Information) Ludlow 9.8/10 Exceptional (41) "Had a great and comfortable stay with family. House is clean and had all the amenities and supplies needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aruna G. [](https://www.expedia.ca/Ludlow-Hotels-Mountain-View-Manor-Expansive-Views.h61370917.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33961500/33961408/3825f7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/34000000/33970000/33961500/33961408/83fb1dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33970000/33961500/33961408/bd63a0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/34000000/33970000/33961500/33961408/c40494bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC. [](https://www.expedia.ca/Woodstock-Hotels-PRIVATE-AFFORDABLE-Charming-Custom-Ranch-In-S-Woodstock-WIFI-And-AC.h33961408.Hotel-Information) Woodstock 9.8/10 Exceptional (228) "Lovely property. Peaceful and beautiful surroundings." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen G. [](https://www.expedia.ca/Woodstock-Hotels-PRIVATE-AFFORDABLE-Charming-Custom-Ranch-In-S-Woodstock-WIFI-And-AC.h33961408.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/65000000/64540000/64536000/64535948/daeecc36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64540000/64536000/64535948/c1911294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/65000000/64540000/64536000/64535948/5df48a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64540000/64536000/64535948/4351db05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront house with skiing nearby, dock, and amazing views - dog-friendly [](https://www.expedia.ca/Ludlow-Hotels-Stylish-Cabin-On-The-Lake-W-A-Scenic-Deck.h64535948.Hotel-Information) Ludlow 9.4/10 Exceptional (41) "Lovely property and great location to outdoor activities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen C. [](https://www.expedia.ca/Ludlow-Hotels-Stylish-Cabin-On-The-Lake-W-A-Scenic-Deck.h64535948.Hotel-Information) ![Smart TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/19000000/18770000/18764800/18764710/db1cc71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18764800/18764710/13d05abf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18764800/18764710/81cd03f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/19000000/18770000/18764800/18764710/72e1b0dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE [](https://www.expedia.ca/Ludlow-Hotels-Private-Home-On-Okemo-W-HOT-Tub-Walk-To-Ski-Trail-Or-Drive-2-Min-To-Base-Lodge.h18764710.Hotel-Information) Ludlow 10/10 Exceptional (101) "perfect for us" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) scott h. [](https://www.expedia.ca/Ludlow-Hotels-Private-Home-On-Okemo-W-HOT-Tub-Walk-To-Ski-Trail-Or-Drive-2-Min-To-Base-Lodge.h18764710.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376610/4a27625d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376610/cc3bad1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376610/bf337fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376610/86ecd5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Trails & Village +Pets - Highland Cabin [](https://www.expedia.ca/Woodstock-Hotels-Mt-Peg-Hiking.h119376610.Hotel-Information) Woodstock 10/10 Exceptional (1) "Loved this cabin! The attention to details inside is amazing. Close to everything in Woodstock. The jar of dog treats and Nespresso pods were a fantastic bonus. Very cozy! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne L. [](https://www.expedia.ca/Woodstock-Hotels-Mt-Peg-Hiking.h119376610.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110820000/110816700/110816634/95b37058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/111000000/110820000/110816700/110816634/2fd46b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/111000000/110820000/110816700/110816634/a093b323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110820000/110816700/110816634/6045d79d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Ludlow Village Home with Stunning Okemo Mountain View [](https://www.expedia.ca/Ludlow-Hotels-New-Ludlow-Village-Home-With-Stunning-Okemo-Mountain-View.h110816634.Hotel-Information) Ludlow 10/10 Exceptional (8) "Beautiful and clean place near Okemo with everything you need. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rob M. CA $617 CA $1,144 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Ludlow-Hotels-New-Ludlow-Village-Home-With-Stunning-Okemo-Mountain-View.h110816634.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89410000/89405300/89405262/aa30a9f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books](https://images.trvl-media.com/lodging/90000000/89410000/89405300/89405262/6bafda7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89410000/89405300/89405262/c03e57a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89410000/89405300/89405262/9b202377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Minutes to Skiing/Hot Tub/Arcades [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Minutes-To-SkiingHot-TubArcades.h89405262.Hotel-Information) Bridgewater Corners 10/10 Exceptional (5) "Jamie was a great host. Provided a detailed overview on the house and made our stay very easy. Jamie was very responsive to any questions and answered all questions extremely quick. Would definitely recommend the vacation rental to friends when visiting Killington. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris S. [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Minutes-To-SkiingHot-TubArcades.h89405262.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84360000/84354300/84354224/4aab6481.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/85000000/84360000/84354300/84354224/c348ebfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84354300/84354224/d7f67db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/85000000/84360000/84354300/84354224/f0a976f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog-friendly cabin with forest setting, woodstove & deck - near Killington [](https://www.expedia.ca/Plymouth-Hotels-Dog-Friendly-Cabin-With-Forest-Setting.h84354224.Hotel-Information) Plymouth 8.4/10 Very good (30) "Quarry across the street added floating noise from 8am to 4pm. Otherwise very tranquil. Ageing property needs TLC. Overall a good value in the cash cow vrbo business. Appreciate able to bring dog. Beautiful thunder falls down the street." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt A. [](https://www.expedia.ca/Plymouth-Hotels-Dog-Friendly-Cabin-With-Forest-Setting.h84354224.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83370000/83366700/83366622/a6c30c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83370000/83366700/83366622/69ebcb00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83370000/83366700/83366622/18e82374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83370000/83366700/83366622/8323dea2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BRIDGEWATER RETREAT [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Luxurious-Country-Retreat-In-The-Mountains.h83366622.Hotel-Information) Bridgewater 10/10 Exceptional (11) "A true gem." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mckenzie L. [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Luxurious-Country-Retreat-In-The-Mountains.h83366622.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87600000/87590100/87590031/abe07057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/88000000/87600000/87590100/87590031/57a5323f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87600000/87590100/87590031/b35d5195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/88000000/87600000/87590100/87590031/ae4c6248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saltbox townhome with AC, fireplace & deck - near Quechee Club, golf & ski [](https://www.expedia.ca/Quechee-Hotels-Saltbox-Townhome-With-AC.h87590031.Hotel-Information) Quechee 9.2/10 Wonderful (21) "Great house to stay in the area. Quiet and clean! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle P. [](https://www.expedia.ca/Quechee-Hotels-Saltbox-Townhome-With-AC.h87590031.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/ad0c9f1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/6ae2121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/24cd6b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/7f96a731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Townhome with patio & on-site pool, hot tub, sauna & tennis access [](https://www.expedia.ca/Cavendish-Hotels-Townhome-With-Fireplace.h99947943.Hotel-Information) Cavendish 9.4/10 Exceptional (9) "Had a great stay, I highly recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey M. [](https://www.expedia.ca/Cavendish-Hotels-Townhome-With-Fireplace.h99947943.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19520000/19512900/19512838/244fcf22_edited_6b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/20000000/19520000/19512900/19512838/a684d1f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/20000000/19520000/19512900/19512838/8acb247f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/20000000/19520000/19512900/19512838/20fae85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A1 Solitude.4 BDRM, ski in/out to main Solitude lift, pool/gym access. Parking! [](https://www.expedia.ca/Ludlow-Hotels-SOLITUDE-4-Bdrm-Ski-Inski-Out-Walk-To-Heated-Pool-And-Epic-Plenty-Of-Parking.h19512838.Hotel-Information) Ludlow 10/10 Exceptional (21) "We loved our stay and the place is llarge and comfortable for everyone!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason C. [](https://www.expedia.ca/Ludlow-Hotels-SOLITUDE-4-Bdrm-Ski-Inski-Out-Walk-To-Heated-Pool-And-Epic-Plenty-Of-Parking.h19512838.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/42000000/41050000/41048500/41048437/648fb275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/42000000/41050000/41048500/41048437/9375cae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/42000000/41050000/41048500/41048437/1730d455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/42000000/41050000/41048500/41048437/38d3e2fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths [](https://www.expedia.ca/Bethel-Hotels-King-Size-Master-With-Attached-Bath.h41048437.Hotel-Information) Bethel 10/10 Exceptional (64) "Very cozy, warm and inviting. Beds were all comfortable. House is big enough to have your own space yet intimate enough for pool, and family game night. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine F. [](https://www.expedia.ca/Bethel-Hotels-King-Size-Master-With-Attached-Bath.h41048437.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106970000/106960800/106960716/fc88ee58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106970000/106960800/106960716/505ca36a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/107000000/106970000/106960800/106960716/a7e932fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/107000000/106970000/106960800/106960716/a6059d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CHRISTMAS/NYE AVAILABLE -8 BR, 4 Bth, 1/2 mi to Okemo, Hot Tub, on Shuttle, King [](https://www.expedia.ca/Ludlow-Hotels-BRAND-NEW-8-Bedroom-HouseOn-Shuttle-RouteWalk-To-Downtown-Minutes-To-Okemo.h106960716.Hotel-Information) Ludlow 10/10 Exceptional (3) "This home was an amazing find. The house was equipped with everything we would need and the owners made sure the property was well taken care of. I would love to go back next year. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorie J. [](https://www.expedia.ca/Ludlow-Hotels-BRAND-NEW-8-Bedroom-HouseOn-Shuttle-RouteWalk-To-Downtown-Minutes-To-Okemo.h106960716.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=2025-12-28&endDate=2025-12-29®ionId=553248635976432508&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=APARTMENT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CONDO) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=VILLA) ![](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-Private-Vacation-Homes.d553248635976432508-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-County-Private-Vacation-Homes.d553248635976432508-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Windsor County Hotel Reviews ![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 "Yea" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "Clean room, very nice staff, everything was excellent! " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.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 "I stayed at here on a whim in December ‘25 on an early ski trip to Stratton & Killington, looking for a spot that wouldn’t break the bank. Got a whole lot more than I bargained for! Eggs & bacon for breakfast, super cozy cabin, great hospitality, and good recommendations. New owners Ali & Lane are hard at work investing more and more into the place and I can’t wait to go back in the summer. Highly recommend for anyone seeking an unfussy stay with rustic charm and super-welcoming owner/operators." [](https://expedia.ca/Weston-Hotels-The-Colonial-House-Inn-And-Motor-Lodge.h104395732.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "So kind and accommodating " [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "After reading reviews I was pleasantly surprised of the high quality of our room. We had a premium king room in the river house. Was large and bathroom was also large with a jacuzzi tub, shared balcony overlooking the river. Walking distance to town, shops and restaurants. Only stayed one night for a wedding in town but overall had a very good experience!" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Excellent place to stay anytime of the year." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Sleep Woodstock Motel](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11_y.jpg) ### Sleep Woodstock Motel 10/10 Excellent "The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. " [](https://expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Jackson Gore Village](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "Great location, pool, hot tub, game room, staff." [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Friend of mine and I stayed overnight just to check out Vermont (I had always wanted to go there). We both LOVED this place. Very charming, lovely decor, and great food--especially at dinner. The staff were very friendly and accomodating. Would definitely recommend this place and return again in the future. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ## Find out more about Windsor County ## Windsor County Vacation Homes information | Number of reviews | 865 | | ----------------- | ------------------ | | Accommodation | 444 Vacation Homes | | Lowest Price | CA $808 | | Highest Price | CA $1,144 | ## 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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