Title: Windsor County Vacation Rentals from CA $263: Short-Term Rentals for 2025 | Expedia.ca [Windsor County Hotels](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Hotel-Destinations)[Windsor County Car Rentals](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Car-Rental-Destinations)[Windsor County Vacations](https://expedia.ca/Windsor-County.d553248635976432508.Destination-Travel-Guides) ![Weston showing interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93824-Central-Vermont.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Windsor County Vacation Rentals - ![](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 ## 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-Vacation-Rentals.d8496.Travel-Guide-VacationRentals) ![](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-Vacation-Rentals.d6294.Travel-Guide-VacationRentals) ![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-Vacation-Rentals.d9580.Travel-Guide-VacationRentals) ## Top Vacation Rentals in in Windsor County ![Beach](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/ad2f042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/36b6b61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/e717b065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/98873e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-friendly winter retreat in the woods near Okemo + Killington Plymouth 10/10 Exceptional (14) "Excellent week at a cozy property, convenient to Killington and Okemo. Easy check in and check out; highly responsive and helpful host. Would recommend to those looking for a great VT escape." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda L. CA $252 CA $631 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4a7f2bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4e43f1be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/5afbd4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/18611595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Addie's Place: A Quiet and Quirky Private Guesthouse Hartford 10/10 Exceptional (4) "Perfect size and location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyn H. CA $152 CA $286 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.Hotel-Information) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90120000/90115100/90115097/00eb8e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90120000/90115100/90115097/5b2f2adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90120000/90115100/90115097/2a7aeff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90120000/90115100/90115097/b2050abd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Queens | 10 Mins to the Mountains | Foliage Bridgewater 8.8/10 Excellent (5) "We really loved the location because we wanted to be close to Bridgewater Corners where our son just purchased a property. We loved the “Two Queens” unit and appreciated all the attention to detail with kitchen appliances, separate entrance, covered deck, available parking and very nicely landscaped side yard. Hoping to be able to stay there again this fall when we come back to VT to visit family and experience the VT fall season. Location made it so easy to go to many fun restaurants from the... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $112 CA $270 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Bridgewater-Hotels-NEW-Ski-VT-Suite-At-The-Bridgewater-Inn.h90115097.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/10b7883b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/c07b5f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/367c70d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/2f37dfc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit Cavendish 10/10 Exceptional (9) "Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas M. CA $246 CA $436 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Cavendish-Hotels-Luxury-Cabin-1-Hot-Tub.h107005892.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/7f99722e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/ce1e5a47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/3d411f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/57672945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-in/out mountainside condo close to everything with full kitchen - tranquil Clock Tower Base Area 9.0/10 Wonderful (73) "It was a perfect location and had everything we needed for a great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danna K. CA $105 CA $356 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Ludlow-Hotels-Ski-Inout-Mountainside-Condo-Close-To-Everything-With-Full-Kitchen-Tranquil.h21692155.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96390000/96381300/96381283/09218223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96390000/96381300/96381283/99e2bd8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/97000000/96390000/96381300/96381283/9974e428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/97000000/96390000/96381300/96381283/c863f86e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treehouse at Wise Pines- SoBo Woodstock 9.8/10 Exceptional (24) "The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Victoria M. CA $211 CA $263 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Treehouse-At-Wise-Pines-SoBo.h96381283.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102350000/102344700/102344670/c2860dca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102350000/102344700/102344670/5ed14255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102350000/102344700/102344670/4b80a3a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102350000/102344700/102344670/8705244b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area Clock Tower Base Area 9.8/10 Exceptional (10) "The place was great. Exactly like the listing described. Ski lift right off the rear of the building. Great location. Walking distance to some nightlife and food. And just a short drive for all other needs. Place was clean and nicely equipped kitchen. Will definitely be looking to stay again in the future." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ian w. CA $153 CA $494 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Ludlow-Hotels-Ski-Haven-1-Bed-Ski-Inout-Condo.h102344670.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83540000/83532200/83532143/1058a1f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/84000000/83540000/83532200/83532143/c630649f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83540000/83532200/83532143/d6466227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83540000/83532200/83532143/160cd324.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Let it Snow-Perfect Getaway! Cozy, Modern & convenience to everything! Ludlow 9.8/10 Exceptional (74) "This was a perfect spot for two to stay. Close walk to town and quick drive to Okemo. Had everything you would need to cook simple meals also." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dominique P. CA $118 CA $330 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Ludlow-Hotels-Perfect-Getaway-Cozy.h83532143.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/8583048f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/ac902f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/fcd88235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/c8d6e7c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2nd-floor downtown Ludlow studio condo with kitchenette, streaming Ludlow 8.6/10 Excellent (4) "Clean room. Glad that the text responses are quick. We weren't initially provided a room number and then the door code we were given would not work. Host responded and was able to reset code from afar. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ana Maria C. CA $112 CA $329 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Ludlow-Hotels-2nd-Floor-Downtown-Ludlow-Studio-Condo-With-Kitchenette.h101332217.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/4e6773ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/cf58af9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/0d26f53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/dd9dbbe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whimsical Room & Private Bathroom in Historic Inn Chester Depot 8.8/10 Excellent (9) "The room was really cozy and the community area was quaint and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bethany CA $134 CA $229 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Chester-Hotels-Whimsical-Room-Private-Bathroom-In-Historic-Inn.h87135975.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/7a09fa49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Internet, bed sheets](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/781b4e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/be3d5210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/3d8cc946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Efficient condo near slopes with kitchenette & great location Ludlow 8.6/10 Excellent (32) "Stay was good. Couldn’t figure out the TV - Not sure if there was actually cable or not. Close to the main road so traffic was a bit loud. Other than that great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $110 CA $286 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Ludlow-Hotels-Efficient-Condo-Near-Slopes-With-Kitchenette-Great-Location.h66042213.Hotel-Information) ![Internet, bed sheets](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/023bb657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/b6513e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/a9f17f8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/68f24199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Studio Condo with Great Location, WiFi & Kitchenette Ludlow 8.6/10 Excellent (28) "Perfect spot to stay for a ski weekend at Okemo. It’s literally down the block. Can’t say enough great things about the room. Clean, comfortable, safe. It had everything I needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent CA $114 CA $304 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Ludlow-Hotels-Cozy-Studio-Condo-With-Great-Location.h74100124.Hotel-Information) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038655/811f5334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038655/ed39671f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038655/f304b3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/91000000/90040000/90038700/90038655/c93e4539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in the heart of town near skiing - less than a mile to Okemo Mountain Ludlow 9.0/10 Wonderful (14) "Great location and very comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard J. CA $114 CA $367 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Ludlow-Hotels-Light-Filled-Condo-In-The-Heart-Of-Town-Less-Than-A-Mile-To-Okemo-Mountain.h90038655.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/0a51ad2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/17915502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/f922de49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/c88e2df0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit Bridgewater 9.4/10 Exceptional (16) "It was a great location for what we were looking to do. Great size and we loved the hot tub. Very comfortable. We enjoyed our stay and would come again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley G. CA $192 CA $689 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-NEW-Blueberry-Hill-Escape-Pet-Friendly-King-Bed-Fire-Pit-Grill.h78342432.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 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 $139 CA $514 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-New-2021-Ski-House-2-Min-Drive-To-Killington-Gondola.h73076828.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/98a04e79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/c33b35a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/efdfd8b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/b2a8b57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gnome Home Mountain Ski Chalet w/Sauna Killington Stockbridge 10/10 Exceptional (4) "The Gnome Home was everything we hoped for and more. The hosts are so helpful with communication, especially when a hefty snow storm hit. The home is cozy, clean and very well stocked with everything you need." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leah S. CA $304 CA $699 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/7acc5bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/3ecbdb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/1d0d61a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/4ed0f838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street Ludlow 9.0/10 Wonderful (22) "This modest property was super clean and convenient to Okemo ski resort. Access was simple as the door codes were emailed. I do wish there was an interior deadbolt/chain-lock for security in addition to just the exterior access combo.This whole unit was freshly painted. The all purpose room was spacious. The kitchen corner was modestly equipped but offered the necessities. The couch was comfortable and the TV was average. The bathroom was spacious but had a dated floor and shower. The... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $112 CA $329 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Ludlow-Hotels-Downtown-Condo-W-Electric-Fireplace.h61636331.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/cb045568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/f3ef2aee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/f68608f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/78904746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails Ludlow 7.6/10 Good (53) "Property great location but needs interior renovations" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William D. CA $128 CA $441 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Ludlow-Hotels-Condo-With-Seasonal-Pool-Tennis-Courts-Walk-To-Ski-Trails.h21708413.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/122000000/121860000/121855900/121855853/f743d1a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/122000000/121860000/121855900/121855853/b46c3163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121860000/121855900/121855853/01618d13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121860000/121855900/121855853/defccb39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 15 min to Killington & Okemo 4-bedroom Chalet w/ Private Sauna & Hot Tub Plymouth CA $377 CA $1,097 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Plymouth-Hotels-15-Min-To-Killington-Okemo-4-Bedroom-Chalet-W-Private-Sauna-Hot-Tub.h121855853.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/f1003380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/72aeb737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/c1d69bc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/aa44f0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrific 3-bedroom cottage with AC in charming Cavendish Cavendish CA $190 CA $692 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24®ionId=553248635976432508&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windsor-County.d553248635976432508.Vacation-Rental-Destinations)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windsor-County.d553248635976432508.Vacation-Rental-Destinations) ## Top Windsor County Hotel Reviews ![Align Inn Vermont](//images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Very clean and quiet property, comfortable bed. Slept very well!" [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Loved the casual, comfortable, easy atmosphere. Homey and welcoming but never overbearing. Staff were all wonderful and personable. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Great place to stay" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](//images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "We loved this hotel as everything was very clean. The staff was very friendly and helpful. They provided us with information as to other areas or places we could go with our family. They were very informative. And they do provide just about everything you need." [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Best Western Springfield Hotel](//images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480_y.jpg) ### Best Western Springfield Hotel 10/10 Excellent "Stayed for an overnight trip to visit family. Breakfast was good and the room was comfortable. " [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Hotel Coolidge](//images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "Charming place to stay! Very clean and easy access to restaurant and the highway. Highly recommend if you want to avoid a chain hotel. " [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information) ![On The River Inn](//images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b_y.jpg) ### On The River Inn 10/10 Excellent "The restaurant was very nice. Great service. Delicious food." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![The Vesper ](//images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64_y.jpg) ### The Vesper 10/10 Excellent "It was clean, the people were outstanding. I would stay again." [](https://expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) ## Find out more about Windsor County **Everything you need to know about** **Windsor County** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor County vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Windsor County vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Windsor County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor County vacation rentals we have selected for you start as low as CA $263 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Windsor County rentals** At Expedia, we put the best Windsor County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Windsor County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor County vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Popular Windsor County Cities - All accommodation types in Windsor County - [Ludlow Vacation Rentals](https://expedia.ca/Ludlow-Vacation-Rentals.d8496.Travel-Guide-VacationRentals) - [White River Junction Vacation Rentals](https://expedia.ca/White-River-Junction-Vacation-Rentals.d6294.Travel-Guide-VacationRentals) - [Quechee Vacation Rentals](https://expedia.ca/Quechee-Vacation-Rentals.d9580.Travel-Guide-VacationRentals) - [South Royalton Vacation Rentals](https://expedia.ca/South-Royalton-Vacation-Rentals.d3000459747.Travel-Guide-VacationRentals) - [Vacation Homes in Windsor County](https://expedia.ca/Windsor-County-Private-Vacation-Homes.d553248635976432508-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Condo Rentals in Windsor County](https://expedia.ca/Windsor-County-Condos.d553248635976432508-aaCondos.Travel-Guide-Accommodation) - [Apartments in Windsor County](https://expedia.ca/Windsor-County-Apartments.d553248635976432508-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Windsor County](https://expedia.ca/Windsor-County-Cabins.d553248635976432508-aaCabins.Travel-Guide-Accommodation) - [Cottages in Windsor County](https://expedia.ca/Windsor-County-Cottages.d553248635976432508-aaCottages.Travel-Guide-Accommodation) - [Chalets in Windsor County](https://expedia.ca/Windsor-County-Chalets.d553248635976432508-aaChalets.Travel-Guide-Accommodation) - [B&B in Windsor County](https://expedia.ca/Windsor-County-Bed-And-Breakfast.d553248635976432508-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Farmstay in Windsor County](https://expedia.ca/Windsor-County-Agritourism.d553248635976432508-aaAgritourism.Travel-Guide-Accommodation) - [Guest Houses in Windsor County](https://expedia.ca/Windsor-County-Guest-Houses.d553248635976432508-aaGuestHouses.Travel-Guide-Accommodation) - [Inns in Windsor County](https://expedia.ca/Windsor-County-Inns.d553248635976432508-aaInns.Travel-Guide-Accommodation) - [Motels in Windsor County](https://expedia.ca/Windsor-County-Motels.d553248635976432508-aaMotels.Travel-Guide-Accommodation) - [Aparthotels in Windsor County](https://expedia.ca/Windsor-County-Apart-Hotels.d553248635976432508-aaApartHotels.Travel-Guide-Accommodation) - [Resorts in Windsor County](https://expedia.ca/Windsor-County-Resort-Hotels.d553248635976432508-aaResortHotels.Travel-Guide-Accommodation) - [Lodges in Windsor County](https://expedia.ca/Windsor-County-Lodges.d553248635976432508-aaLodges.Travel-Guide-Accommodation) - [Villas in Windsor County](https://expedia.ca/Windsor-County-Villas.d553248635976432508-aaVillas.Travel-Guide-Accommodation) - [Treehouses in Windsor County](https://expedia.ca/Windsor-County-Treehouses.d553248635976432508-aaTreehouses.Travel-Guide-Accommodation)