Title: Holiday Rentals Wintergreen from £89: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Hotels in Wintergreen](https://expedia.co.uk/Wintergreen-Hotels.d10811.Travel-Guide-Hotels)[Wintergreen Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Wintergreen.d10811.Car-Hire-Guide)[Wintergreen Holidays](https://expedia.co.uk/Wintergreen.d10811.Holidays-City-Breaks) ![](https://mediaim.expedia.com/destination/2/30888d0dcbd6b56a6c3164112bdde6d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rebecca Brent # Search Holiday Rentals in Wintergreen ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [3 Oct - 5 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=10811&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=10811&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [14 Nov - 16 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=10811&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=10811&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Wintergreen ## Our top choices for Wintergreen holiday rentals ![Property grounds](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/74b5408b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/9e44df53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/3fa3435d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/ae868c04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite! Treeloft 10/10 Exceptional (60) "Great location, amenities and owner's willingness to address all our questions/issues." [](https://www.expedia.co.uk/Nellysford-Hotels-Modern-Luxe-Treetop-Retreat-WGas-Fire-Pit.h71969999.Hotel-Information) ![](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/f4cdee3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/6e5f684e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/c2b30482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/3ecd5830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes Roseland 10/10 Exceptional (327) "Great location to check out all that the Wintergreen area has to offer. The condo was cozy and well stocked for our long weekend adventure with our son and pup. We are regulars to the area and this was one of our favorite rentals. " [](https://www.expedia.co.uk/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111829500/111829485/a2e620f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table football](https://images.trvl-media.com/lodging/112000000/111830000/111829500/111829485/175b5594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table football](https://images.trvl-media.com/lodging/112000000/111830000/111829500/111829485/da0dc9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/112000000/111830000/111829500/111829485/6d5e7db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 6-bedroom cabin in Wintergreen Resort Wintergreen Resort 9.8/10 Exceptional (9) "Place was great we had a blast ! Only about a 5 min walk to the slopes!" [](https://www.expedia.co.uk/Nellysford-Hotels-Spacious-6-Bedroom-Cabin-In-Charming-Wintergreen-Resort.h111829485.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118930000/118927400/118927334/3fa11b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/119000000/118930000/118927400/118927334/e2418aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118930000/118927400/118927334/b35f53f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/119000000/118930000/118927400/118927334/b9c0b1ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-NEW-Warrens-Woods-Spacious-5-Bedroom-House-In-Fantastic-Wintergreen-Resort.h118927334.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/e57932c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/f81462f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/29fa29ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Modern Mountain Condo Wintergreen Resort 10/10 Exceptional (27) "Ideal location for skiing at Wintergreen. " £183 includes taxes & fees 21 Sept - 22 Sept [](https://www.expedia.co.uk/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/6703de10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/16dadee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/e2360eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/3eb2493c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Distinguished Squirrel Chalet walking distance Treeloft 9.8/10 Exceptional (6) "The house was beautiful and well stocked. The owner thought of everything and all the light switches were labeled which helped a lot. All of the appliances were top notch and the Keurig coffee maker had everything that was needed. Beds were very comfortable and each room had its own thermostat. Overall, excellent stay!" £305 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/Nellysford-Hotels-The-Distinguished-Squirrel-Chalet-Walking-Distance.h112532111.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/75000000/74110000/74107700/74107687/2669b133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74110000/74107700/74107687/6ffaf395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74110000/74107700/74107687/608dd305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74110000/74107700/74107687/c670d883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!! Pedlars Edge 10/10 Exceptional (48) "House was great. We had friends with us for a wonderful birthday celebration. " [](https://www.expedia.co.uk/Nellysford-Hotels-New-Rental-Wintergreen-Ski-Golf-Resort-Hiking-Trails-Hot-Tub-Pet-Friendly.h74107687.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/f8a3b378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/c029b4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/0a033000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/1d0451ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Cottage: Hot Tub, 2 mins to Bold Rock! Nellysford 10/10 Exceptional (21) "The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. " £341 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/Nellysford-Hotels-Pine-Cottage-Hot-Tub-And-Central-To-Nelson-151.h78450238.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34160000/34151900/34151850/21552524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34160000/34151900/34151850/d8ca69d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34160000/34151900/34151850/a04aa380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/35000000/34160000/34151900/34151850/bde57962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort! Roseland 9.8/10 Exceptional (175) "Nice property and views. " [](https://www.expedia.co.uk/Nellysford-Hotels-Fantastic-Mountain-Valley-Views-Top-Of-The-Mountain-Close-To-The-Resort.h34151850.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48630000/48629500/48629473/b54553f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48630000/48629500/48629473/d20131c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48630000/48629500/48629473/e2c6cbb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48630000/48629500/48629473/82369e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large and Luxurious Exec 5BR Chalet Pedlars Edge 10/10 Exceptional (249) "Perfect location for family ski trip" [](https://www.expedia.co.uk/Nellysford-Hotels-Large-And-Luxurious-Exec-5BR-Chalet.h48629473.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/34000000/33570000/33563300/33563291/6d4cf049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33563300/33563291/3bc6132a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33563300/33563291/4fd7871a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33570000/33563300/33563291/w634h458x6y5-d1d06fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK Roseland 9.4/10 Exceptional (88) "Wonderful stay" [](https://www.expedia.co.uk/Nellysford-Hotels-Walk-To-SlopesLuxury-LivingSunset-Mountain-Views-And-Same-Day-Arrival-OK.h33563291.Hotel-Information) ![Studio Suite | Private kitchen | Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48900000/48894400/48894364/66a9e021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Suite | Living area | 43-inch flat-screen TV with satellite channels, TV, Netflix](https://images.trvl-media.com/lodging/49000000/48900000/48894400/48894364/dfd2f559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Street view](https://images.trvl-media.com/lodging/49000000/48900000/48894400/48894364/5f37fc68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Suite | Living area | 43-inch flat-screen TV with satellite channels, TV, Netflix](https://images.trvl-media.com/lodging/49000000/48900000/48894400/48894364/40c602e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Valley Extended Suites Fishersville 9.0/10 Wonderful (198) "Nice stay" £89 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Staunton-Hotels-Valley-Extended-Suites.h48894364.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88830000/88823700/88823641/0add693b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/89000000/88830000/88823700/88823641/ec7a9bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/89000000/88830000/88823700/88823641/2e2cf95b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88830000/88823700/88823641/c0ea455e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area Shipman 10/10 Exceptional (15) "Nice time exploring the area" [](https://www.expedia.co.uk/Ridgetop-Cabin-Virginia.h88823641.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/73239ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/c84e0b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/3ef8ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/33c95369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA Montebello 10/10 Exceptional (32) "Great property and host" £173 includes taxes & fees 21 Sept - 22 Sept [](https://www.expedia.co.uk/Montebello-Hotels-Beautiful-New-Cabins-Mile-Off-Blue-Ridge-Parkway-In-Montebello.h104258489.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112620000/112613800/112613786/893db66c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112620000/112613800/112613786/09b8fb80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112620000/112613800/112613786/2ce56f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112620000/112613800/112613786/07707045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wow! What A View! Wintergreen Resort 9.4/10 Exceptional (16) "Découverte de la corse pour la 1ère fois. Proche de tous, plage, équitation mer montagne, spécialités, petit port avec restau,rando, village et super point de vue." [](https://www.expedia.co.uk/Nellysford-Hotels-Youll-Say-Wow-Over-This-View.h112613786.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/922abceb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/f17119a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/2a856bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/acbf5d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026! Wintergreen 10/10 Exceptional (240) "Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. " [](https://www.expedia.co.uk/Nellysford-Hotels-Best-Views-On-Mountain-Breathtaking-5-Star-Available-August-26-31-BOOK-NOW.h30501528.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91330000/91328100/91328004/w906h683x59y0-b9465527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91330000/91328100/91328004/w527h683x257y0-c2472cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, travel cot, free WiFi](https://images.trvl-media.com/lodging/92000000/91330000/91328100/91328004/w508h683x258y0-9a2415f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91330000/91328100/91328004/w906h683x59y0-44f9ac7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ivy Rose Cottage nestled b/t Cville & Vineyards Charlottesville 10/10 Exceptional (59) "Loved staying here!" £261 includes taxes & fees 23 Sept - 24 Sept [](https://www.expedia.co.uk/Charlottesville-Hotels-Ivy-Rose-Cottage-Nestled-Bt-Cville-Vineyards.h91328004.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/84000000/83600000/83596100/83596018/dca9a905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83600000/83596100/83596018/05d7d899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83600000/83596100/83596018/3cc2c133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83600000/83596100/83596018/b2eab8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes Laurel Ridge 10/10 Exceptional (62) "House was very nice. Great set up for family." [](https://www.expedia.co.uk/Roseland-Hotels-Stunning-Mountain-Views-In-Renovated-Home-2-Mins-From-The-Ski-Slopes.h83596018.Hotel-Information) ![Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/77000000/76370000/76366800/76366707/7dba8e3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/77000000/76370000/76366800/76366707/f06ddae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Private kitchen | Microwave, stovetop, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/77000000/76370000/76366800/76366707/84d8b7d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![High Meadows Cabin, 1 King Bed, Deep Soaking Tub, Mountain View | Living area | 30-inch LED TV with digital channels, TV, DVD player](https://images.trvl-media.com/lodging/77000000/76370000/76366800/76366707/4701c701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Love Ridge Mountain Lodging Montebello 10/10 Exceptional (12) "Amazing stay I had, very peaceful and very quiet. " £207 includes taxes & fees 24 Sept - 25 Sept [](https://www.expedia.co.uk/Montebello-Hotels-Love-Ridge-Mountain-Lodging.h76366707.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111820000/111816400/111816333/3f9e513c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111820000/111816400/111816333/04766930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111820000/111816400/111816333/fbd9f8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111820000/111816400/111816333/ad98fd24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aftonshire Cottage - Heart of Afton's Wine Region Afton 9.8/10 Exceptional (9) "Better than advertised. Kitchen has everything needed. Perfect for two couples. Comfy firm beds. Beautiful views- enjoyed watching the horses out back and the roaming deer. The brewery across the street has a fantastic scratch kitchen food truck - and great staff. Would love to book again in the near future. " [](https://www.expedia.co.uk/Afton-Hotels-Aftonshire-Cottage-In-The-Heart-Of-Aftons-Wine-Region.h111816333.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=2025-10-04&endDate=2025-10-05®ionId=10811&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Holiday-Rentals.d10811.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Holiday-Rentals.d10811.Travel-Guide-HolidayRentals) ## Top Wintergreen Hotel Reviews ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "Historical. Beautiful own just off Hwy I81. " [](https://expedia.co.uk/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ![Motel 6 Staunton, VA](//images.trvl-media.com/lodging/1000000/10000/9000/8977/e2fd1c0e_y.jpg) ### Motel 6 Staunton, VA 10/10 Excellent "The front desk clerk that rides the motorcycle is absolutely amazing, very sweet and understanding individual. I had to stay 3 weeks and she was amazing" [](https://expedia.co.uk/Staunton-Hotels-Motel-6-Staunton.h8977.Hotel-Information) ![Comfort Inn](//images.trvl-media.com/lodging/1000000/70000/64100/64084/2a69aac3_y.jpg) ### Comfort Inn 10/10 Excellent "i stay here when I have an appointment at UVA. Reasonably priced and very clean. Staff is very friendly. Conveniently located." [](https://expedia.co.uk/Staunton-Hotels-Comfort-Inn.h64084.Hotel-Information) ![Holiday Inn Express & Suites Waynesboro East by IHG](//images.trvl-media.com/lodging/97000000/96550000/96546000/96545978/22c5f5c1_y.jpg) ### Holiday Inn Express & Suites Waynesboro East by IHG 10/10 Excellent "Great Property!" [](https://expedia.co.uk/Holiday-Inn-Express-And-Suites-Waynesboro-East.h96545978.Hotel-Information) ![Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes](//images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/f4cdee3d_y.jpg) ### Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes 10/10 Excellent "Wonderful location. Clean place and updated. Owner was excellent at communication! " [](https://expedia.co.uk/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.Hotel-Information) ![Comfort Inn & Suites Staunton](//images.trvl-media.com/lodging/1000000/10000/4300/4272/f4b37015_y.jpg) ### Comfort Inn & Suites Staunton 10/10 Excellent "Pet friendly. " [](https://expedia.co.uk/Staunton-Hotels-Comfort-Inn-Suites.h4272.Hotel-Information) ![Sleep Inn Staunton](//images.trvl-media.com/lodging/1000000/170000/168400/168389/f334eca9_y.jpg) ### Sleep Inn Staunton 10/10 Excellent "Amazing clean with friendly staff worth the value. " [](https://expedia.co.uk/Staunton-Hotels-Sleep-Inn-Staunton.h168389.Hotel-Information) ![Clarion Pointe Staunton East](//images.trvl-media.com/lodging/1000000/330000/328900/328834/150e95df_y.jpg) ### Clarion Pointe Staunton East 10/10 Excellent "Staff was super helpful. Would definitely stay again." [](https://expedia.co.uk/Staunton-Hotels-Quality-Inn-Suites.h328834.Hotel-Information) ![The Blackburn Inn and Conference Center](//images.trvl-media.com/lodging/23000000/22460000/22455000/22454998/5e926ba4_y.jpg) ### The Blackburn Inn and Conference Center 10/10 Excellent "What a gem. A beautiful historic building close to downtown shopping & dining and loved my room’s high ceiling & wood floors. Great wi fi connection. Very quiet!" [](https://expedia.co.uk/Staunton-Hotels-The-Blackburn-Inn-And-Conference-Center.h22454998.Hotel-Information) ## Find out more about Wintergreen **Everything you need to know about** **Wintergreen** **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 Wintergreen 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 Wintergreen holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Wintergreen holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Wintergreen. 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 Wintergreen 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 Wintergreen holiday rentals we have selected for you start as low as £89 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Wintergreen rentals** At Expedia, we put the best Wintergreen 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 Wintergreen 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 Wintergreen 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 Wintergreen. 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 - Trending destinations on Expedia.co.uk ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) ## Frequently asked questions ### Can I find holiday rentals in Wintergreen? > Yes, there are holiday rentals close to the most popular sights in Wintergreen, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffee shops during your trip. ### What are some of the best holiday rentals that Wintergreen has to offer? > [Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!](https://www.expedia.co.uk/Nellysford-Hotels-Modern-Luxe-Treetop-Retreat-WGas-Fire-Pit.h71969999.Hotel-Information): This highly rated holiday home rental in Wintergreen is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Some other top choices in Wintergreen are [NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort](https://www.expedia.co.uk/Nellysford-Hotels-NEW-Warrens-Woods-Spacious-5-Bedroom-House-In-Fantastic-Wintergreen-Resort.h118927334.Hotel-Information) and [The Distinguished Squirrel Chalet walking distance](https://www.expedia.co.uk/Nellysford-Hotels-The-Distinguished-Squirrel-Chalet-Walking-Distance.h112532111.Hotel-Information). ### How many holiday rentals are there in Wintergreen? > Choose from 50 Expedia holiday rentals in Wintergreen for a memorable holiday. ### What can I see and do in Wintergreen? > While exploring the area, visit family-friendly sights like War Fields, or get outside and enjoy nature at George Washington National Forest. Wintergreen Resort and Bold Rock Hard Cider Nellysford Cidery are a couple of places you'll find in the wider area. ### What’s a holiday rental in Wintergreen like? > Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wintergreen. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFNUlEQVR4Xu3bMXIbORBAUbAcMPQR5ihzNPBoPMocYUMFLMHuRqOBwcAqd+ANqP8Tkk0AbzJI8m4q/0NpHvyLQEKBhAIJBRIKJBRIKJBQIKFAQoGEAgkFEgokFEgokFAgoUBCgYQCCQUSCiQUSCiQUCChQEKBhAIJBRJqQF5paqujn+XTBsOqWynPYVUu/9kaL/eTQUBAQGogtdxPBgHRtT3Zrun2vY37ifPo1j63kQeyGIFoyxMXIxBteeJiBKItT1yMQLTliYsRiLY8cTH6e0S3p3SvSF/7lKktfKR+x5dyyIshOjpvlEBAQOQFBCSBgFhfI0VO/Okr5JsfFWmBSCB1CKLJNyAWiLyAgKQo8qqfkv0+fd7+rKvULSAgICAWSAEBCSM9WVvOd7xc6D/qHd9O9G8U8UA0EA+kBrLJCwhIATkj57a6Vrfbhf7VaCr3k0EWo6ncTwZZjKZyPxlkMZrK/WSQxWgq95NBFqOp3E8GWYymcj95QBaZe7OPfuKYXvtfB9ID8UCmQHogHsjU2yMfcvYm7x7VOaf/w9M+rCqra98DARkDATmdboGcA/leyCPpha5rS9Hb+5H0L9xPOc9G84m6UV3NV3kgIAVEN4KAgIDUBuRli6S+XU5McqHL4jYq9UR9FM2QXd7LNyCyGKS/BZFAQEBAWjNiaz9OV3XbbtmJjkwbQUAsEBCQeSMIiPVnxNY+6jsbbXWV/SJu9VWanZX7ySAgICAgmp2V+8kgIPqF/u26yIn9C+mZ7qfPn37iIcj8izgIiEz6WxAQkF3egYBY01l1raVr5drXPurQTryZK6suG22VBwKigYCA+CoPBORV7/hWKYe85KIX+l7X6EhqiG2UR2nXviUbLRAQEBAJpCUbLRCQMvw5W75JW3Nv8vlDvjmPzjVknoOAaCAaCMgUCEgRRK/qXU48fVEM0QRpj1LK8ceRB3I5cTHyQC4nLkYeyOXExcgDuZy4GHkglxMXIw/kcuJi5F0RTU/c6nvdntL99+JT+iiS/Tm7PZ3/JOCBJBAQEBAQkFyn0hmR2tpSjra9yJ+zLR11V1aleuJnW9JWeSAaCEjd6IGM20E8kO+GvHyJIin5Va3bLyfufav+cNCQYWyBgIBIICAgIK0zkov+0/GzrVVXt++6+Ler9Tt+MboGAgIyj66BgIDMo2tvjpThjhekuHvUozT/ScDqj/L1r9ggGggIiLwDAUkgFdHufVzdp0wF6dufddU4Gp8u9yFIAQEBAQEByX14RuZs+6d99BP1UXZ5Zyd649N5IAlkWGuBTIEkkGGtBTL1lsii13DtJ0H8Udq1b+W6/tkQ3eiBgCwCAZFsJIEsAvkOiG3vbTJ9JP0HZs2XqrvLO/tGHmV07YcDCySBtBWtTaYgYyAJpK1obTIFGXtXJPdPRRB19R+Yxx5J7/jFn7NBQMZAQEBAJJC/QPT2TulekSIn6h2/txN1pPlIH8W6y4JD3mU/GEQCAemBgPjBIBLIAil1tOvi08hP/OGPYiM7ywMBAQEBAQEJIbJd+6h/4X7VBTf7fdp3azY65CX3MQgIyJCNDnnJfQwCAjJko0Nech+/L9IzpFR3F0RGhrSRLX4kdfVRfKMHAgIigYCAgLTOyLlNpnLHf8qJsriPilzod3k5ZGku+t93GZLkt+4hkAIynK9tMgUZAykgw/naJlOQsbdE/l0goUBCgYQCCQUSCiQUSCiQUCChQEKBhAIJBRIKJBRIKJBQIKFAQoGEAgkFEgokFEgokFAgoUBCgYQCCfU+yC/S1VsFai8HggAAAABJRU5ErkJggg==)