Title: Windsor County Vacation Home Rentals from CA $369: 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 ![](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-05-29&endDate=2026-05-31&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://images.trvl-media.com/place/8496/505d08ac-b11f-4f25-a539-2958ea0722b2.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://images.trvl-media.com/place/10868/c2d6773f-8f3f-4c1a-b710-f2f2bceab647.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Woodstock [](https://expedia.ca/Woodstock-Private-Vacation-Homes.d10868-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![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=384&h=216&q=medium) #### White River Junction [](https://expedia.ca/White-River-Junction-Private-Vacation-Homes.d6294-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Quechee featuring a river or creek, a bridge and tranquil scenes](https://images.trvl-media.com/place/9580/a3d99a95-3156-473d-99ae-f796cac4afe4.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Quechee [](https://expedia.ca/Quechee-Private-Vacation-Homes.d9580-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Cornish-Windsor Covered Bridge](https://images.trvl-media.com/place/7881/cd323da6-a215-45d8-82e1-e1768184197a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor-Private-Vacation-Homes.d7881-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) ![Interior](https://images.trvl-media.com/lodging/32000000/31430000/31429400/31429400/d701a57f.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) ![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) ### 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 (58 reviews) "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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/f6b88b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/eb089c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131806/b3f0c7f8.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 8.2/10 Very good (44 reviews) "The ski cabin was exactly as described - the Jacuzzi hot tub, wood fireplace, and excellent cozy sleeping arrangements were the highlights of our stay. Moreover the cabin was just a mile from the Okemo Mountain skiing resort, which made it ideal. We loved everything about the ski cabin we rented. Can’t wait to be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bhavna [](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) ![Interior](https://images.trvl-media.com/lodging/73000000/72140000/72131800/72131736/be2ebd4c.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) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131800/72131736/4463a589.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 reviews) "Fireplace and hot tub great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise T. [](https://www.expedia.ca/Plymouth-Hotels-Rustic-Home-With-A-Hot-Tub.h72131736.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/5933bbde.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) ![Exterior](https://images.trvl-media.com/lodging/32000000/31140000/31137700/31137653/6914b0dc.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 (133 reviews) "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/88000000/87720000/87714700/87714614/1c700768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87720000/87714700/87714614/4ccdd3e6.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/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) ### 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 (137 reviews) "Beautiful condo, perfect for a girls trip or a romantic getaway! Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy F. [](https://www.expedia.ca/White-River-Junction-Hotels-Beautifully-Renovated-2BR-Townhome-With-Fireplace.h87714614.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/74000000/73080000/73076900/73076828/3dbaa916.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) ![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) ![Interior](https://images.trvl-media.com/lodging/74000000/73080000/73076900/73076828/ed4b66f2.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 (6 reviews) "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) ![TV, fireplace](https://images.trvl-media.com/lodging/62000000/61380000/61371000/61370917/c93d638c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/62000000/61380000/61371000/61370917/a57fedfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/62000000/61380000/61371000/61370917/9dd9e3d3.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 (42 reviews) "Very beautiful location Perfect view like photos on screen keep changing every morning and night, Spacious rooms, clean and comfortable lots of supplies Warm enough High speed WiFi Hot tub on the deck Fire pit outside under wonderful night sky Close by ski resorts and trails Are parts of charming you can experience here, in peace, far away from crowds We loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mohammad M. [](https://www.expedia.ca/Ludlow-Hotels-Mountain-View-Manor-Expansive-Views.h61370917.Hotel-Information) ![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/34000000/33970000/33961500/33961408/9a845e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33970000/33961500/33961408/c98d03f7.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 (229 reviews) "Great property well equipped and in a lovely location. Hidden away but easy to find and a short drive into Woodstock. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Stephen B. [](https://www.expedia.ca/Woodstock-Hotels-PRIVATE-AFFORDABLE-Charming-Custom-Ranch-In-S-Woodstock-WIFI-And-AC.h33961408.Hotel-Information) ![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) ![Dining](https://images.trvl-media.com/lodging/65000000/64540000/64536000/64535948/94141e6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/65000000/64540000/64536000/64535948/fcd4eaa4.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) ### 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 reviews) "Great weekend! Beautiful location !!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy V. [](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) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18764800/18764710/1370bf2f.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) ### 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 (102 reviews) "The house was perfect for our group." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt D. [](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) ![Interior](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376610/689329a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376610/5b785035.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) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/120000000/119380000/119376700/119376610/43d6975d.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 9.4/10 Exceptional (3 reviews) "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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110820000/110816700/110816634/bbce6d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110820000/110816700/110816634/5af1ee86.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 (12 reviews) "Vacationing with friends. The home was great; good location, lots of space, very clean and well kept. Would definitely stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda H. CA $671 CA $1,209 total includes taxes & fees Feb 4 - Feb 5 [](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/90000000/89410000/89405300/89405262/3bb19e15.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 (6 reviews) "This house was in the perfect location! It is exactly as pictured and perfect for multiple families. The owners are very responsive and answered all questions before asking!! We would stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Minutes-To-SkiingHot-TubArcades.h89405262.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/85000000/84360000/84354300/84354224/3c28d76b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/85000000/84360000/84354300/84354224/b22e4326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84354300/84354224/97208723.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) ### 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 (31 reviews) "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) ![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/84000000/83370000/83366700/83366622/1628e4bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83370000/83366700/83366622/9d36259d.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 reviews) "We had a terrific stay at the Bridgewater Retreat. The house was just as we imagined it to be and we would love to return!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul L. [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Luxurious-Country-Retreat-In-The-Mountains.h83366622.Hotel-Information) ![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) ![TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/88000000/87600000/87590100/87590031/8a64e1a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87600000/87590100/87590031/0d0fb83e.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 9.0/10 Wonderful (22 reviews) "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) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/003cdb7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/aad30b8f.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) ![Interior](https://images.trvl-media.com/lodging/100000000/99950000/99948000/99947943/ad0c9f1b.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 reviews) "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) ![Smart TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/20000000/19520000/19512900/19512838/20682972.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/fed39b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/20000000/19520000/19512900/19512838/78e38b2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19520000/19512900/19512838/0d4ceb81.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 (24 reviews) "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) ![Interior](https://images.trvl-media.com/lodging/42000000/41050000/41048500/41048437/c2fb5654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/42000000/41050000/41048500/41048437/732ce36d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/42000000/41050000/41048500/41048437/acc3dc35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/42000000/41050000/41048500/41048437/1520d62a.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 (66 reviews) "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. CA $220 CA $369 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Bethel-Hotels-King-Size-Master-With-Attached-Bath.h41048437.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106970000/106960800/106960716/cf636054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/107000000/106970000/106960800/106960716/80246597.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) ### PRESIDENT WK 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 (4 reviews) "This home was the perfect ski house for our family. It is cozy, warm, bedding is extremely comfortable and the kitchen is equipped with anything you might need during your stay. We loved the proximity to Okemo, less than a five minute drive. We thoroughly enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda D. [](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=2026-02-17&endDate=2026-02-18®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=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&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=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=VACATION_HOME) 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=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=COTTAGE) 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=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=APARTMENT) 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=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=CHALET) 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=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=CONDO) 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=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=APART_HOTEL) 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=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&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 ![Best Western Springfield Hotel](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480_y.jpg) ### Best Western Springfield Hotel 10/10 Excellent "Staff was very Courteous, Clean rooms and great stay. Breakfast was decent with a waffle machine and kids enjoyed it. " [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Comfort Inn White River Junction](https://images.trvl-media.com/lodging/1000000/10000/8900/8850/a720acb3_y.jpg) ### Comfort Inn White River Junction 10/10 Excellent "Very nice staff, clean rooms. " [](https://expedia.ca/White-River-Junction-Hotels-Comfort-Inn.h8850.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 "Friendly staff, clean rooms. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Very polite staff and very clean rooms." [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.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 "Everything was great from the room to the staff making everything as convenient as possible." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.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 "The room was so comfortable and the staff here is top notch. The included breakfast is one of the best I’ve ever had when it was included with your stay. This place is a hidden jewel!" [](https://expedia.ca/Weston-Hotels-The-Colonial-House-Inn-And-Motor-Lodge.h104395732.Hotel-Information) ![Norwich Inn](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519573/30ba8066_y.jpg) ### Norwich Inn 10/10 Excellent "Spectacular place and great service !! " [](https://expedia.ca/Norwich-Hotels-Norwich-Inn.h2519573.Hotel-Information) ![The Quechee Inn at Marshland Farm](https://images.trvl-media.com/lodging/2000000/1930000/1924800/1924710/c8372335_y.jpg) ### The Quechee Inn at Marshland Farm 10/10 Excellent "Had a great Stay. Food was Very Good" [](https://expedia.ca/Quechee-Hotels-The-Quechee-Inn-At-Marshland-Farm.h1924710.Hotel-Information) ## Find out more about Windsor County ## Windsor County Vacation Homes information | Number of reviews | 899 | | ----------------- | ------------------ | | Accommodation | 444 Vacation Homes | | Lowest Price | CA $369 | | Highest Price | CA $1,209 | ## 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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