Title: Windsor County Vacation Home Rentals from CA $1,144: 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) ![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 # 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 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 two weeks [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 one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-02-13&endDate=2026-02-15&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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31430000/31429400/31429400/ea02c384.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) ### 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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/f6b88b6d.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) ![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) ![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) ### 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 (64) "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) ![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) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/c707b887.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) ### 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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87720000/87714700/87714614/30f18a35.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) ![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) ![Dining](https://images.trvl-media.com/lodging/74000000/73080000/73076900/73076828/1d650f62.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. [](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) ![Dining](https://images.trvl-media.com/lodging/62000000/61380000/61371000/61370917/5d0ed62a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61380000/61371000/61370917/77557170.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) ### 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) ![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) ![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) ### 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) ![TV, fireplace, books](https://images.trvl-media.com/lodging/65000000/64540000/64536000/64535948/4a5f32be.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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18764800/18764710/1370bf2f.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) ![Exterior](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376610/86ecd5cc.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) ![TV, offices](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376610/d7d8c22e.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) ![Dining](https://images.trvl-media.com/lodging/111000000/110820000/110816700/110816634/4b29929d.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) ![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) ### 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 17 - Dec 18 [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89410000/89405300/89405262/e4327375.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) ![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) ![TV, fireplace](https://images.trvl-media.com/lodging/85000000/84360000/84354300/84354224/74d01a13.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) ![Interior](https://images.trvl-media.com/lodging/84000000/83370000/83366700/83366622/8323dea2.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) ### 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/f854b494.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) ![Exterior](https://images.trvl-media.com/lodging/88000000/87600000/87590100/87590031/b35d5195.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) "We had a wonderful time staying at this townhome. It was very convenient and easy to get to things. Great tranquil place for family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy D. [](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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/ecfe02cc.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) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/20000000/19520000/19512900/19512838/c65836cf.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) ![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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106970000/106960800/106960716/84a5f894.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=2025-12-30&endDate=2025-12-31®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-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 ![The Vesper ](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64_y.jpg) ### The Vesper 10/10 Excellent "We were in town for Wassail Weekend. The Vesper was a great place to stay. The location was so close to all of the fun activities and restaurants. Jessica was very accommodating and friendly. Would recommend! " [](https://expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.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 "Clean rooms, front desk personal could use people skill update, not young lady there this am, she was great. Guys in restaurant were the best. " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.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 "All very good. " [](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 "I stay at Woodstock Inn every December and it never disappoints. The rooms are comfortable and well-appointed, but it's hard to decide whether to enjoy the comforts of the room or sitting in front if the fire in the lobby. I look forward to the next visit." [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.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 "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) ![Hotel Coolidge](https://images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "Spacious, quirky and historical accommodations. Staff was great, amenities were just as described. Room was actually better than I had anticipated " [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.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) ## Find out more about Windsor County ## Windsor County Vacation Homes information | Number of reviews | 868 | | ----------------- | ------------------ | | Accommodation | 444 Vacation Homes | | Lowest Price | CA $1,144 | | 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) - 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