Title: Holiday Rentals Windsor County from £142: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Windsor County Hotels](https://expedia.co.uk/Destinations-In-Windsor-County.d553248635976432508.Hotel-Destinations)[Windsor County Car Hire](https://expedia.co.uk/Destinations-In-Windsor-County.d553248635976432508.Car-Hire-Destinations)[Windsor County Holidays](https://expedia.co.uk/Windsor-County.d553248635976432508.Holidays-City-Breaks) ![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 # Search Holiday Rentals in Windsor County - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Windsor County Accommodation: Most Popular Cities to Stay ![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.co.uk/Windsor-Holiday-Rentals.d7881.Travel-Guide-HolidayRentals) ![](https://mediaim.expedia.com/destination/2/6e1ce19989493034a8e8934b004054dd.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Norwich [](https://expedia.co.uk/Norwich-Holiday-Rentals.d184063.Travel-Guide-HolidayRentals) ## Our top choices for Windsor County holiday rentals ![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/107000000/106160000/106157400/106157385/79181b11.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) ![Marina](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/0df9f82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington [](https://www.expedia.co.uk/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information) Plymouth 10/10 Exceptional (14) "Really enjoyed the setup at the location and the owners were very responsive to any queries!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ed N. £439 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/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) ![Exterior](https://images.trvl-media.com/lodging/117000000/116350000/116341300/116341257/4ccd0baf.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 [](https://www.expedia.co.uk/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.Hotel-Information) Hartford 10/10 Exceptional (4) "Perfect size and location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyn H. £154 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Wilder-Hotels-Addies-Place-A-Quiet-And-Quirky-Private-Guesthouse.h116341257.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) ![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) ![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) ### Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit [](https://www.expedia.co.uk/Cavendish-Hotels-Luxury-Cabin-1-Hot-Tub.h107005892.Hotel-Information) Cavendish 10/10 Exceptional (11) "Super easy check in, beautiful and peaceful. Will def be back " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler S. £295 includes taxes & fees 20 Jan - 21 Jan 2026 [](https://www.expedia.co.uk/Cavendish-Hotels-Luxury-Cabin-1-Hot-Tub.h107005892.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) ![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) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/97000000/96390000/96381300/96381283/w2439h1625x0y0-7dca8401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treehouse at Wise Pines- SoBo [](https://www.expedia.co.uk/Treehouse-At-Wise-Pines-SoBo.h96381283.Hotel-Information) Woodstock 9.8/10 Exceptional (24) "I was on an adventure with my young daughter and was looking for something unique. This was perfect. The common building was beautiful and had a great bathroom and other amenities if needed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) scott b. £142 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/Treehouse-At-Wise-Pines-SoBo.h96381283.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/4db62919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/66bd663f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/ede6bd11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119700000/119697100/119697097/75f1fd44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape to this private and peaceful tiny home with hot tub in Sharon, VT! [](https://www.expedia.co.uk/South-Royalton-Hotels-Escape-To-This-Private-And-Peaceful-Tiny-Home-With-Hot-Tub-In-Sharon.h119697097.Hotel-Information) Sharon 10/10 Exceptional (3) "Very welcoming, awesome weekend getaway." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zachary B. £214 includes taxes & fees 13 Jan - 14 Jan 2026 [](https://www.expedia.co.uk/South-Royalton-Hotels-Escape-To-This-Private-And-Peaceful-Tiny-Home-With-Hot-Tub-In-Sharon.h119697097.Hotel-Information) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90120000/90115200/90115101/5eb0592b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90120000/90115200/90115101/60c82c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90120000/90115200/90115101/dda6c75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90120000/90115200/90115101/249fcf43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Studio | 10 Min to Killington [](https://www.expedia.co.uk/Bridgewater-Hotels-NEW-Woodstock-Suite-The-Bridgewater-Inn.h90115101.Hotel-Information) Bridgewater 10/10 Exceptional (5) "We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosie L. £200 includes taxes & fees 12 Jan - 13 Jan 2026 [](https://www.expedia.co.uk/Bridgewater-Hotels-NEW-Woodstock-Suite-The-Bridgewater-Inn.h90115101.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) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/3d411f82.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) ![TV, DVD player](https://images.trvl-media.com/lodging/22000000/21700000/21692200/21692155/fadced98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-in/out mountainside condo close to everything with full kitchen - tranquil [](https://www.expedia.co.uk/Ludlow-Hotels-Ski-Inout-Mountainside-Condo-Close-To-Everything-With-Full-Kitchen-Tranquil.h21692155.Hotel-Information) Clock Tower Base Area 9.0/10 Wonderful (74) "Perfect location for a quick ski trip. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael D. £254 includes taxes & fees 11 Jan - 12 Jan 2026 [](https://www.expedia.co.uk/Ludlow-Hotels-Ski-Inout-Mountainside-Condo-Close-To-Everything-With-Full-Kitchen-Tranquil.h21692155.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) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/1f2d7230.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) ### Whimsical Room & Private Bathroom in Historic Inn [](https://www.expedia.co.uk/Chester-Hotels-Whimsical-Room-Private-Bathroom-In-Historic-Inn.h87135975.Hotel-Information) Chester Depot 8.8/10 Excellent (9) "After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul S. £153 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Chester-Hotels-Whimsical-Room-Private-Bathroom-In-Historic-Inn.h87135975.Hotel-Information) ![TV, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/9a087dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/0429cb18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/77b10ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/17514ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-In/Out condo with patio, mountain views, washer/dryer, & cable [](https://www.expedia.co.uk/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information) Clock Tower Base Area 9.2/10 Wonderful (26) "Loved the location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven W. £269 includes taxes & fees 8 Jan - 9 Jan 2026 [](https://www.expedia.co.uk/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.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/a20acb9d.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) ### Gnome Home Mountain Ski Chalet w/Sauna Killington [](https://www.expedia.co.uk/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information) Stockbridge 10/10 Exceptional (4) "Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald S. £428 includes taxes & fees 12 Jan - 13 Jan 2026 [](https://www.expedia.co.uk/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.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) ![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) ![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) ### Condo in the heart of town near skiing - less than a mile to Okemo Mountain [](https://www.expedia.co.uk/Ludlow-Hotels-Light-Filled-Condo-In-The-Heart-Of-Town-Less-Than-A-Mile-To-Okemo-Mountain.h90038655.Hotel-Information) 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. £279 includes taxes & fees 12 Jan - 13 Jan 2026 [](https://www.expedia.co.uk/Ludlow-Hotels-Light-Filled-Condo-In-The-Heart-Of-Town-Less-Than-A-Mile-To-Okemo-Mountain.h90038655.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78370000/78365400/78365390/4efa5e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78370000/78365400/78365390/15d900fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78370000/78365400/78365390/f0af7662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/79000000/78370000/78365400/78365390/086927c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi [](https://www.expedia.co.uk/Ludlow-Hotels-Ski-Inout-Mountainside-Condo-With-Balcony.h78365390.Hotel-Information) Clock Tower Base Area 8.6/10 Excellent (14) "Excellent Location.. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juan Carlos L. £356 includes taxes & fees 19 Jan - 20 Jan 2026 [](https://www.expedia.co.uk/Ludlow-Hotels-Ski-Inout-Mountainside-Condo-With-Balcony.h78365390.Hotel-Information) ![Golf](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/39b8fc78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/f4ee1a7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/ff9fa2e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Internet, bed sheets](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/21079c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Efficient condo near slopes with kitchenette & great location [](https://www.expedia.co.uk/Ludlow-Hotels-Efficient-Condo-Near-Slopes-With-Kitchenette-Great-Location.h66042213.Hotel-Information) Ludlow 8.6/10 Excellent (32) "Nice place close to mountain easy in easy out" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron B. £202 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/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) ![Towels](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/a8fc6b6d.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) ![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) ### Cozy Studio Condo with Great Location, WiFi & Kitchenette [](https://www.expedia.co.uk/Ludlow-Hotels-Cozy-Studio-Condo-With-Great-Location.h74100124.Hotel-Information) Ludlow 8.8/10 Excellent (29) "Great location and great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda G. £209 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Ludlow-Hotels-Cozy-Studio-Condo-With-Great-Location.h74100124.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) ![TV](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/1cf3d726.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) ![Interior](https://images.trvl-media.com/lodging/102000000/101340000/101332300/101332217/ac902f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2nd-floor downtown Ludlow studio condo with kitchenette, streaming [](https://www.expedia.co.uk/Ludlow-Hotels-2nd-Floor-Downtown-Ludlow-Studio-Condo-With-Kitchenette.h101332217.Hotel-Information) Ludlow 8.6/10 Excellent (4) "Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin C. £236 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Ludlow-Hotels-2nd-Floor-Downtown-Ludlow-Studio-Condo-With-Kitchenette.h101332217.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/7e86ce1f.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/e40e49c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/8fb11d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/809fbf0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit [](https://www.expedia.co.uk/Bridgewater-Corners-Hotels-NEW-Blueberry-Hill-Escape-Pet-Friendly-King-Bed-Fire-Pit-Grill.h78342432.Hotel-Information) Bridgewater 9.6/10 Exceptional (17) "Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerri B. £432 includes taxes & fees 13 Jan - 14 Jan 2026 [](https://www.expedia.co.uk/Bridgewater-Corners-Hotels-NEW-Blueberry-Hill-Escape-Pet-Friendly-King-Bed-Fire-Pit-Grill.h78342432.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/54a5f76c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/b0da744f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/1662100f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/cc4de1c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route [](https://www.expedia.co.uk/Central-Vermont-Killington-Hotels-2-Bed-Fireplace-Condo-In-The-Heart-Of-Town-On-Shuttle-Route-1-Mile-To-Okemo.h45708952.Hotel-Information) Ludlow 10/10 Exceptional (102) "Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew L. £269 includes taxes & fees 12 Jan - 13 Jan 2026 [](https://www.expedia.co.uk/Central-Vermont-Killington-Hotels-2-Bed-Fireplace-Condo-In-The-Heart-Of-Town-On-Shuttle-Route-1-Mile-To-Okemo.h45708952.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/9fc41d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/fb8c05d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/7b016615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/dffaa55c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chester Farmhouse Ski Retreat near Slopes [](https://www.expedia.co.uk/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) Chester Depot 9.6/10 Exceptional (17) "This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori N. £253 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73760000/73756200/73756146/447741a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/74000000/73760000/73756200/73756146/7ab5ab3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73760000/73756200/73756146/2aac0c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73760000/73756200/73756146/a1762c1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ground Floor ski-in/out condo, full kitchen & high-speed WiFi [](https://www.expedia.co.uk/Ludlow-Hotels-Ski-InSki-Out-Condo-With-Fireplace.h73756146.Hotel-Information) Clock Tower Base Area 9.4/10 Exceptional (21) "Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan G. £334 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Ludlow-Hotels-Ski-InSki-Out-Condo-With-Fireplace.h73756146.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) ![Exterior](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/1aed61ad.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) ![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 [](https://www.expedia.co.uk/Ludlow-Hotels-Downtown-Condo-W-Electric-Fireplace.h61636331.Hotel-Information) Ludlow 9.0/10 Wonderful (22) "Great rate for a place with all the basics!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Macgregor £236 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Ludlow-Hotels-Downtown-Condo-W-Electric-Fireplace.h61636331.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.co.uk/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08®ionId=553248635976432508&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=APARTMENT) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CABIN) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CONDO) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=VACATION_HOME) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=COTTAGE) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CHALET) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor+County%2C+Vermont%2C+United+States+of+America®ionId=553248635976432508&latLong=43.624765%2C-72.518979&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windsor-County.d553248635976432508.Holiday-Rental-Destinations)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windsor-County.d553248635976432508.Holiday-Rental-Destinations) ## Top Windsor County Hotel Reviews ![Hotel Coolidge](https://images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "No breakfast and parking was ok" [](https://expedia.co.uk/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "A very clean and comfortable room. Nice facility, the continental breakfast was great." [](https://expedia.co.uk/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Luxurious and friendly resort! Loved it" [](https://expedia.co.uk/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.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 "Super responsive staff, great accomodations " [](https://expedia.co.uk/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Norwich Inn](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519573/30ba8066_y.jpg) ### Norwich Inn 10/10 Excellent "I wanted a White Christmas inn in Vermont and I got it. The inn was decorated for Christmas, had a roaring fire and even a holiday puzzle to complete. The rooms were great, ours had a fireplace, and the beds were comfortable. The staff were great (willing to open the bar for a hot toddy if needed ;-)), were helpful, and easy to contact. Not much in town, but close to other attractions." [](https://expedia.co.uk/Norwich-Hotels-Norwich-Inn.h2519573.Hotel-Information) ![The Vesper ](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64_y.jpg) ### The Vesper 10/10 Excellent "Clean, very comfortable & spacious room (SOTO). Very friendly, welcoming host & staff. Our jacuzzi tub's jets were not working. We would have appreciated knowing that in advance." [](https://expedia.co.uk/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.co.uk/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.co.uk/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing." [](https://expedia.co.uk/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ## Find out more about Windsor County **Everything you need to know about** **Windsor County** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor County holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. **Windsor County holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Windsor County holiday rentals we have selected for you start as low as £142 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 holiday 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 holiday. 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 - [Plymouth Holiday Rentals ](https://expedia.co.uk/Plymouth-Holiday-Rentals.d146918.Travel-Guide-HolidayRentals) - [Norwich Holiday Rentals ](https://expedia.co.uk/Norwich-Holiday-Rentals.d184063.Travel-Guide-HolidayRentals) - [Windsor Holiday Rentals ](https://expedia.co.uk/Windsor-Holiday-Rentals.d7881.Travel-Guide-HolidayRentals) - [Hartland Holiday Rentals ](https://expedia.co.uk/Hartland-Holiday-Rentals.d6052375.Travel-Guide-HolidayRentals) - [Stockbridge Holiday Rentals ](https://expedia.co.uk/Stockbridge-Holiday-Rentals.d6357893.Travel-Guide-HolidayRentals) - [Reading Holiday Rentals ](https://expedia.co.uk/Reading-Holiday-Rentals.d177836.Travel-Guide-HolidayRentals)