Title: Holiday Rentals Wintergreen from £183: 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) ![Overlook near Wintergreen Ski Resort](https://images.trvl-media.com/place/10811/f7c97680-28b4-457d-9bcc-051a2160b6d3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rebecca Brent # Search Holiday Rentals in Wintergreen - ![](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 ## Check prices for these dates Tonight [28 Dec - 29 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=10811&startDate=2025-12-28&endDate=2025-12-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [29 Dec - 30 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=10811&startDate=2025-12-29&endDate=2025-12-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [2 Jan - 4 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=10811&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [9 Jan - 11 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=10811&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Wintergreen holiday rentals ![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/81343878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/3c52de65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/2c4c7806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/w1003h683x0y0-5eec0b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information) 10/10 Exceptional (2) "We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander H. £210 includes taxes & fees 13 Jan - 14 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/ef5206ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/eab7e1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/e60e6023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/10d4b392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-First-Floor-Slopeside-Ski-In-Ski-Out-At-Wintergreen.h122831616.Hotel-Information) 10/10 Exceptional (2) "Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lloyd F. £201 includes taxes & fees 12 Jan - 13 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-First-Floor-Slopeside-Ski-In-Ski-Out-At-Wintergreen.h122831616.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) ![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/29fa29ea.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) ### Condo in Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) 10/10 Exceptional (37) "Quiet, one-night stay while in the area for an event. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie M. £205 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/3c2ad4b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/319b2ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/b384df8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/48c0e694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort [](https://www.expedia.co.uk/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) 10/10 Exceptional (95) "Fantastic stay again! Condo is perfect for a get away! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenna M. £263 includes taxes & fees 11 Jan - 12 Jan 2026 [](https://www.expedia.co.uk/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.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) ![2 bedrooms, desk, iron/ironing board, Internet](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/abde4226.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) ### Cottage in Nellysford [](https://www.expedia.co.uk/Nellysford-Hotels-Pine-Cottage-Hot-Tub-And-Central-To-Nelson-151.h78450238.Hotel-Information) 10/10 Exceptional (23) "The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jody W. £355 includes taxes & fees 13 Jan - 14 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Pine-Cottage-Hot-Tub-And-Central-To-Nelson-151.h78450238.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/93f9d9bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/d176c035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/b003bae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/68a8e7c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.Hotel-Information) 10/10 Exceptional (25) "The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cassie H. £282 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123220000/123217600/123217549/3cc1f40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123220000/123217600/123217549/502be393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/124000000/123220000/123217600/123217549/6f9b9681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123220000/123217600/123217549/dce794be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-Cozy-Studio-In-The-Fantastic-Wintergreen-Resort.h123217549.Hotel-Information) £154 includes taxes & fees 27 Jan - 28 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Cozy-Studio-In-The-Fantastic-Wintergreen-Resort.h123217549.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/a870a931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/bc03c18d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/90-e785bc8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/093de133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Roseland [](https://www.expedia.co.uk/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information) 9.6/10 Exceptional (142) "Great stay in Wintergreen!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pete K. £202 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/8b86069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/b8f83d57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/e7802cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/6989a232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Nellysford [](https://www.expedia.co.uk/Nellysford-Hotels-Bear-Tracks-Cottage-NEW-HOT-TUB-FIRE-PIT.h107854723.Hotel-Information) 10/10 Exceptional (30) "Great location, beautiful home and so much to do nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jordan D. £328 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Bear-Tracks-Cottage-NEW-HOT-TUB-FIRE-PIT.h107854723.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111460000/111452000/111451911/6421312c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111460000/111452000/111451911/def44751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111460000/111452000/111451911/78f359e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111460000/111452000/111451911/9fbc2e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Wintergreen Resort [](https://www.expedia.co.uk/Roseland-Hotels-Close-To-The-Slopes-2min-Large-Private-Hot-Tub.h111451911.Hotel-Information) 9.8/10 Exceptional (6) "Peaceful family trip. The cabin was beautiful, lots of space, and very clean. The cabin had everything we needed. The game room, board games and puzzles were a hit with our kids. Hot tub was huge, clean had its own separate gated area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria R. £476 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Roseland-Hotels-Close-To-The-Slopes-2min-Large-Private-Hot-Tub.h111451911.Hotel-Information) ![](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/4641225d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/b70b419a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/26d64274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Roseland [](https://www.expedia.co.uk/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) 9.0/10 Wonderful (305) "Great view!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne W. £183 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/604129c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/e1d8c140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/200109ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/d40343ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Roseland [](https://www.expedia.co.uk/Nellysford-Hotels-Cozy-1-Bedroom-Condo-Off-12th-Hole-At-Devils-Knob-Golf-Course.h95269237.Hotel-Information) 9.8/10 Exceptional (22) "Great communication from the startReturn texts the same day on any questionsGreat location for our tripVery cleanViews around property are greatNice restaurant A plus for what we neededDog friendly Thanks againHope to be back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phil P. £191 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Cozy-1-Bedroom-Condo-Off-12th-Hole-At-Devils-Knob-Golf-Course.h95269237.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/b49906d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/0c4a4ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/f29177b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/629cabeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Nellysford [](https://www.expedia.co.uk/Nellysford-Hotels-Glass-Pine-Home-Close-To-Bold-Rock-Vineyards.h112394246.Hotel-Information) 10/10 Exceptional (2) "We only stayed one night but wished we could have stayed longer! The place was super clean and the views were beautiful once the rain finally stopped! Close to our favorite brewery and cidery. There were issues with TV reception (buffering) which may just be the area. Not much time for TV watching anyway with all the beautiful things to explore. We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert H. £327 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Glass-Pine-Home-Close-To-Bold-Rock-Vineyards.h112394246.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/711d6b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/cc117128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/aabdc1d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/c893d39d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.Hotel-Information) 10/10 Exceptional (24) "Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Courtney S. £307 includes taxes & fees 13 Jan - 14 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/5164314f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/66529dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/a4f9ddda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/a1aab594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-Serenity-Cabin-3-Bedroom-Woodland-Retreat-In-Wintergreen.h109542556.Hotel-Information) 10/10 Exceptional (3) "Great house and great host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe B. £403 includes taxes & fees 8 Jan - 9 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Serenity-Cabin-3-Bedroom-Woodland-Retreat-In-Wintergreen.h109542556.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106850000/106847400/106847377/15dbaac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106850000/106847400/106847377/88db804a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106850000/106847400/106847377/b71ab38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106850000/106847400/106847377/9a1fe697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Chestnut Springs [](https://www.expedia.co.uk/Nellysford-Hotels-Blue-Ridge-Bliss-9BR6BA-2-Homes-Across-The-Street-From-Each-Other-Sleeps-24.h106847377.Hotel-Information) 10/10 Exceptional (1) £1,583 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Blue-Ridge-Bliss-9BR6BA-2-Homes-Across-The-Street-From-Each-Other-Sleeps-24.h106847377.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/78744a11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/85dceb55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/a54a7818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/ddfb8915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-NEW-Mountain-View-Vista-Resort-Condo-W-Views.h111307828.Hotel-Information) 9.4/10 Exceptional (8) "Beautiful view!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Serge L. £229 includes taxes & fees 13 Jan - 14 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-NEW-Mountain-View-Vista-Resort-Condo-W-Views.h111307828.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/f2101dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/faaf96bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/40009d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/29dbadf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Treeloft [](https://www.expedia.co.uk/Nellysford-Hotels-Lofty-Pursuits-Spectacular-View-EV-Charger.h119238386.Hotel-Information) 10/10 Exceptional (4) "Will definitely stay at this location again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard W. £303 includes taxes & fees 14 Jan - 15 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Lofty-Pursuits-Spectacular-View-EV-Charger.h119238386.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/42c89d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/cf3b06c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/6f8277a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/974f0f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort [](https://www.expedia.co.uk/Nellysford-Hotels-Overlook-180-Degree-Views-WPeloton.h114150295.Hotel-Information) 9.4/10 Exceptional (3) "Excellent stay. Thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly B. £282 includes taxes & fees 13 Jan - 14 Jan 2026 [](https://www.expedia.co.uk/Nellysford-Hotels-Overlook-180-Degree-Views-WPeloton.h114150295.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/448c50fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table football](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/4e7f6a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/8c44b91f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table football](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/52e5512c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Chestnut Springs [](https://www.expedia.co.uk/Roseland-Hotels-Wintergreen-Retreat-Cozy-Cabin-With-Hot-Tub.h101916242.Hotel-Information) 10/10 Exceptional (15) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl P. £380 includes taxes & fees 13 Jan - 14 Jan 2026 [](https://www.expedia.co.uk/Roseland-Hotels-Wintergreen-Retreat-Cozy-Cabin-With-Hot-Tub.h101916242.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=2026-01-12&endDate=2026-01-13®ionId=10811&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=CABIN) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=APARTMENT) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=CHALET) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=VACATION_HOME) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=COTTAGE) ![](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 ![Wintergreen. Sunset Vista Villa - Sea of Mountains](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/3c2ad4b6_y.jpg) ### Wintergreen. Sunset Vista Villa - Sea of Mountains 10/10 Excellent "The host is very welcoming. Rooms were nice and clean. We really enjoyed the view of the mountains!" [](https://expedia.co.uk/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) ![The Modern Mountain Condo ](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131_y.jpg) ### The Modern Mountain Condo 10/10 Excellent "I have been coming to Wintergreen since 1999 and this is by far the best condo I’ve ever stayed in! Absolutely loved it! So clean, well apportioned, cozy, comfortable, absolutely adorable, and Keith was an extremely responsive, kind host. Can’t wait to book our next trip back to this exceptional condo!" [](https://expedia.co.uk/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS](https://images.trvl-media.com/lodging/49000000/48840000/48830800/48830715/2a174ad4_y.jpg) ### WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS 10/10 Excellent "Such a fun Christmas/mountain vibe! Loved the location and the host was super easy to work with! " [](https://expedia.co.uk/Charlottesville-Hotels-Wintergreen-Resort-Home-With-Blue-Ridge-Views.h48830715.Hotel-Information) ![Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort](https://images.trvl-media.com/lodging/117000000/116730000/116728200/116728114/552218fd_y.jpg) ### Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort 10/10 Excellent "What a wonderful place. The views breath taking. It was comfortable and clean. Check in easy and very attentive. Highly recommended. " [](https://expedia.co.uk/Nellysford-Hotels-Breathtaking-Mountain-Views-In-A-2-Bedroom-Condo-At-Wintergreen-Resort.h116728114.Hotel-Information) ![Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026! ](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/922abceb_y.jpg) ### Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026! 10/10 Excellent "We absolutely loved this condo, and especially the outstanding views.....a front row seat to gorgeous winter sunrises in your pjs! It was well equipped with everything one needs and was super cozy with a wood burning fireplace to boot. This 2 bedroom was perfect for 2 couples on a birthday weekend....an ideal spot for watching lots of football with beautiful views at every angle in the backdrop. The location is perfect, right across the street from the golf course, seconds from the Wintergarden, and just a few minutes from best sunset spot, Three Ridges Overlook on Devils Knob. We look forward to coming back. Maureen, our host, was wonderful and always available to answer any questions." [](https://expedia.co.uk/Nellysford-Hotels-Best-Views-On-Mountain-Breathtaking-5-Star-Available-August-26-31-BOOK-NOW.h30501528.Hotel-Information) ![Stylish-Updated-Central -Walk to Slopes-Dogs OK!](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/b73ebb05_y.jpg) ### Stylish-Updated-Central -Walk to Slopes-Dogs OK! 10/10 Excellent "Host was great. Great price and location. " [](https://expedia.co.uk/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information) ![Endless Mountain Top Views from All The Way Up!](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/b0ffcdf7_y.jpg) ### Endless Mountain Top Views from All The Way Up! 10/10 Excellent "Well appointed, beautiful condo! " [](https://expedia.co.uk/Nellysford-Hotels-Endless-Mountain-Top-Views-From-All-The-Way-Up.h90087205.Hotel-Information) ![2br/2ba: Million Dollar View from Luxury Condo on the Ridge. ](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2_y.jpg) ### 2br/2ba: Million Dollar View from Luxury Condo on the Ridge. 10/10 Excellent "Gorgeous view. Our fourth time here, and still a lovely place. " [](https://expedia.co.uk/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) ![Unbeatable Views Atop Wintergreen Resort](https://images.trvl-media.com/lodging/56000000/55570000/55560400/55560333/bbf04c4d_y.jpg) ### Unbeatable Views Atop Wintergreen Resort 10/10 Excellent "Everything about Blue Ridge Heaven was wonderful. The hosts provided everything, including the things that you think won’t be there.We have been to many places, both mountain and seaside, but have never experienced such breathtaking sunrises. A beautiful place, clean well-maintained and in a great location." [](https://expedia.co.uk/Charlottesville-Hotels-Newly-Renovated-5-Br-Home-With-Unbeatable-Views-At-The-Top-Of-Wintergreen.h55560333.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 £183 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? ### What are some of the best holiday rentals that Wintergreen has to offer? ### How many holiday rentals are there in Wintergreen? ### What can I see and do in Wintergreen? ### What’s a holiday rental in Wintergreen like? ![](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. 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