Title: Wintergreen Vacation Rentals from CA $161: Short-Term Rentals for 2025 | Expedia.ca [Hotels in Wintergreen](https://expedia.ca/Wintergreen-Hotels.d10811.Travel-Guide-Hotels)[Things to do in Wintergreen](https://expedia.ca/Things-To-Do-In-Wintergreen.d10811.Travel-Guide-Activities)[Wintergreen Car Rentals](https://expedia.ca/Car-Rentals-In-Wintergreen.d10811.Car-Rental-Guide)[Wintergreen Vacation Packages](https://expedia.ca/Wintergreen.d10811.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/30888d0dcbd6b56a6c3164112bdde6d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rebecca Brent # Wintergreen Vacation Rentals ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-13&endDate=2025-10-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-14&endDate=2025-10-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Wintergreen ![Property grounds](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/74b5408b.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) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/9e44df53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/6a324828.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 (63) "Loved our stay - the house, location, and amenities were perfect for us!" CA $560 CA $999 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/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) ![Interior](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/3ecd5830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/2cd4b400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes Roseland 10/10 Exceptional (329) "The property is nestled very nicely on the mountain and convenient to the main lodge, restaurants and other attractions. We really enjoyed our stay. The condo was plenty big for the two of us and our dog. It is well-appointed Kudos to the owner, Heather, for thinking of everything to make our stay great. " [](https://www.expedia.ca/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.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) ![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) ![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/w1273h849x4y3-b64d948a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Modern Mountain Condo Wintergreen Resort 10/10 Exceptional (29) "Ideal location for skiing at Wintergreen. " CA $140 CA $337 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.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/b9c0b1ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118927400/118927334/c85b5f78.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) ### NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort Wintergreen Resort 10/10 Exceptional (1) "We had a fabulous stay at Warren’s Woods! The location of the house is perfectly situated within Wintergreen, a short walk or drive to hiking and the main resort facilities. We enjoyed the hot tub and wood burning fireplace. The kitchen was very well stocked and the layout of the house was great for 2 families. We’ll be back! 5 stars! " [](https://www.expedia.ca/Nellysford-Hotels-NEW-Warrens-Woods-Spacious-5-Bedroom-House-In-Fantastic-Wintergreen-Resort.h118927334.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) ![Exterior](https://images.trvl-media.com/lodging/49000000/48630000/48629500/48629473/3089f54f.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) ![Interior](https://images.trvl-media.com/lodging/49000000/48630000/48629500/48629473/d20131c9.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.ca/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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33570000/33563300/33563291/w635h454x5y5-0adc8b55.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) "This was a beautiful place in the mountains. Much cooler than down below, and the deck is a nice place to be. We enjoyed the house, and the property manager was wonderful." [](https://www.expedia.ca/Nellysford-Hotels-Walk-To-SlopesLuxury-LivingSunset-Mountain-Views-And-Same-Day-Arrival-OK.h33563291.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, foosball](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, foosball](https://images.trvl-media.com/lodging/112000000/111830000/111829500/111829485/da0dc9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game 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.ca/Nellysford-Hotels-Spacious-6-Bedroom-Cabin-In-Charming-Wintergreen-Resort.h111829485.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) ![Exterior detail](https://images.trvl-media.com/lodging/75000000/74110000/74107700/74107687/d948503f.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) ![Interior](https://images.trvl-media.com/lodging/75000000/74110000/74107700/74107687/6ffaf395.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 (50) "House was great. We had friends with us for a wonderful birthday celebration. " [](https://www.expedia.ca/Nellysford-Hotels-New-Rental-Wintergreen-Ski-Golf-Resort-Hiking-Trails-Hot-Tub-Pet-Friendly.h74107687.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34160000/34151900/34151850/51dececb.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.ca/Nellysford-Hotels-Winter-Wonderland-Fantastic-Mountain-Valley-View-From-House.h34151850.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) ![Exterior](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/0a033000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/c029b4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game 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 (22) "The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. " CA $265 CA $639 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Nellysford-Hotels-Pine-Cottage-Hot-Tub-And-Central-To-Nelson-151.h78450238.Hotel-Information) ![Studio Suite | Private kitchen](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](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](https://images.trvl-media.com/lodging/49000000/48900000/48894400/48894364/7e8690a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Valley Extended Suites Fishersville 9.0/10 Wonderful (206) "Nice stay" CA $144 CA $161 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/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) ![Interior](https://images.trvl-media.com/lodging/89000000/88830000/88823700/88823641/d1523e5b.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) ![Exterior](https://images.trvl-media.com/lodging/89000000/88830000/88823700/88823641/ec7a9bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table Shipman 10/10 Exceptional (15) "Family was in town for a baseball tournament. Was a great quiet place that was clean and well maintained. Pond was fun to fish in. Lots of nice areas to hang out outside or inside. Would definitely come back!" [](https://www.expedia.ca/Ridgetop-Cabin-Virginia.h88823641.Hotel-Information) ![](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/12a54ff8.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) ![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) ### 2br/2ba: Million Dollar View from Luxury Condo on the Ridge. Roseland 9.0/10 Wonderful (293) "Great view and very clean." CA $147 CA $340 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.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) ![Interior](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/1105ae93.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) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/c84e0b9e.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 (35) "Great property and host" CA $203 CA $318 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Montebello-Hotels-Beautiful-New-Cabins-Mile-Off-Blue-Ridge-Parkway-In-Montebello.h104258489.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/105000000/104790000/104787300/104787285/92db2d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104790000/104787300/104787285/08c83ebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104790000/104787300/104787285/48a73253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104790000/104787300/104787285/411a7c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries Montebello 9.8/10 Exceptional (14) "Cabin was clean and tidy. Everything i needed was there. I felt comfortable and safe. This is important because I was traveling alone. This feels like it will be my get away spot in the future. Host was polite and quick to respond" CA $203 CA $318 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Montebello-Hotels-5-Minutes-To-Blue-Ridge-Parkway.h104787285.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/091549e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/bd661df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/d4f21770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/6fa06431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape to the Blue Ridge Mountains at Wine-tergreen! Wintergreen Resort 9.8/10 Exceptional (120) "The condo was very nice . Had all the conveniences you need but, not really for over 60 years of age. Loved the area didn’t like the stairs. Would recommend it to anyone not old." CA $150 CA $345 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h43414813.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90700000/90696000/90695995/725e9324.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/91000000/90700000/90696000/90695995/82f8104a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90700000/90696000/90695995/1294fda2.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/91000000/90700000/90696000/90695995/f75a5953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes Wintergreen Resort 9.6/10 Exceptional (50) "Great place to stay for a relaxing weekend in the mountains to escape the heat. Greatly appreciated the fully stocked kitchen! It is truly fully stocked, unlike so many rental places which only claim to be. " [](https://www.expedia.ca/Nellysford-Hotels-Rosies-Retreat-Condo-In-Wintergreen-Resort-3BR3B.h90695995.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](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](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. " CA $299 CA $420 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Montebello-Hotels-Love-Ridge-Mountain-Lodging.h76366707.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/59000000/58990000/58985800/58985753/90-636eaa8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/59000000/58990000/58985800/58985753/90-7eeba939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/59000000/58990000/58985800/58985753/56d48ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/59000000/58990000/58985800/58985753/180-824892cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cabin with private HOT TUB! Nellysford 10/10 Exceptional (26) "This location was a nice place to relax and enjoy family time." [](https://www.expedia.ca/Nellysford-Hotels-Cozy-Cabin-With-Private-HOT-TUB.h58985753.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88860000/88859400/88859301/dc4c4d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/89000000/88860000/88859400/88859301/80faa0c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88860000/88859400/88859301/e8853be6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88860000/88859400/88859301/4a9a0bd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blair's Vintage Apartment Nestled in Wine Country Waynesboro 9.8/10 Exceptional (17) "Clean and vitage style type of apartment. Nice for a quiet stay." CA $137 CA $310 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Waynesboro-Hotels-Blairs-Vintage-Apartment-Nestled-In-Wine-Country.h88859301.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28®ionId=10811&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Vacation-Rentals.d10811.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Vacation-Rentals.d10811.Travel-Guide-VacationRentals) ## Top Wintergreen Hotel Reviews ![Sleep Inn Staunton](//images.trvl-media.com/lodging/1000000/170000/168400/168389/f334eca9_y.jpg) ### Sleep Inn Staunton 10/10 Excellent "Breakfast was very minimal. Clean room. " [](https://expedia.ca/Staunton-Hotels-Sleep-Inn-Staunton.h168389.Hotel-Information) ![Best Western Staunton Inn](//images.trvl-media.com/lodging/1000000/20000/18500/18431/5e29fbfa_y.jpg) ### Best Western Staunton Inn 10/10 Excellent "Very nice room. Breakfast was good as well" [](https://expedia.ca/Staunton-Hotels-Best-Western-Staunton-Inn.h18431.Hotel-Information) ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "Awesome" [](https://expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ![Holiday Inn Staunton Conference Center by IHG](//images.trvl-media.com/lodging/1000000/20000/19200/19125/c184cf6d_y.jpg) ### Holiday Inn Staunton Conference Center by IHG 10/10 Excellent "Clean Property, excellent check-in super staff, especially in the hotel restaurant lounge area. Staff seems to be a little over work, but works completely as a team which makes that issue not issue for the customer you can tell they’re tired. Rooms are very clean. Parking is great close to the interstate. The only thing I would have to say is the hotel is a little worn out. Needs to update. We would stay there again " [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Staunton-Conference-Center.h19125.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 "Great, parked outside of the room…very well lit parking area. Staff was friendly. Room clean. " [](https://expedia.ca/Staunton-Hotels-Motel-6-Staunton.h8977.Hotel-Information) ![Holiday Inn Express & Suites Staunton by IHG](//images.trvl-media.com/lodging/47000000/46550000/46550000/46549911/8e95e8a0_y.jpg) ### Holiday Inn Express & Suites Staunton by IHG 10/10 Excellent "Clean and friendly. " [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Express-And-Suites-Staunton.h46549911.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 "Comfortable clean and quiet place to stay during the beginning of October." [](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.Hotel-Information) ![Comfort Inn](//images.trvl-media.com/lodging/1000000/70000/64100/64084/2a69aac3_y.jpg) ### Comfort Inn 10/10 Excellent "Good place" [](https://expedia.ca/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 "Everything was top notch " [](https://expedia.ca/Waynesboro-Hotels-Holiday-Inn-Express-And-Suites-Waynesboro-East.h96545978.Hotel-Information) ## Find out more about Wintergreen **Everything you need to know about** **Wintergreen** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Wintergreen vacation 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 vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wintergreen vacation rentals we have selected for you start as low as CA $161 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 vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top 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 vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around 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.ca - All accommodation types in Wintergreen ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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[Penticton Vacation Rentals](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Vacation Homes in Wintergreen](https://expedia.ca/Wintergreen-Private-Vacation-Homes.d10811-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Condo Rentals in Wintergreen](https://expedia.ca/Wintergreen-Condos.d10811-aaCondos.Travel-Guide-Accommodation) - [Apartments in Wintergreen](https://expedia.ca/Wintergreen-Apartments.d10811-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Wintergreen](https://expedia.ca/Wintergreen-Cabins.d10811-aaCabins.Travel-Guide-Accommodation) - [Cottages in Wintergreen](https://expedia.ca/Wintergreen-Cottages.d10811-aaCottages.Travel-Guide-Accommodation) - [B&B in Wintergreen](https://expedia.ca/Wintergreen-Bed-And-Breakfast.d10811-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Wintergreen](https://expedia.ca/Wintergreen-Chalets.d10811-aaChalets.Travel-Guide-Accommodation) - [Farmstay in Wintergreen](https://expedia.ca/Wintergreen-Agritourism.d10811-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Wintergreen](https://expedia.ca/Wintergreen-Apart-Hotels.d10811-aaApartHotels.Travel-Guide-Accommodation) - [Motels in Wintergreen](https://expedia.ca/Wintergreen-Motels.d10811-aaMotels.Travel-Guide-Accommodation) - [Guest Houses in Wintergreen](https://expedia.ca/Wintergreen-Guest-Houses.d10811-aaGuestHouses.Travel-Guide-Accommodation) - [RV Parks in Wintergreen](https://expedia.ca/Wintergreen-RV-Parks.d10811-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Wintergreen](https://expedia.ca/Wintergreen-Resort-Hotels.d10811-aaResortHotels.Travel-Guide-Accommodation) - [Lodges in Wintergreen](https://expedia.ca/Wintergreen-Lodges.d10811-aaLodges.Travel-Guide-Accommodation) - [Townhomes in Wintergreen](https://expedia.ca/Wintergreen-Townhomes.d10811-aaTownhomes.Travel-Guide-Accommodation) - [Villas in Wintergreen](https://expedia.ca/Wintergreen-Villas.d10811-aaVillas.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find vacation rentals in Wintergreen? > Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip. ### What are some of the best vacation rentals that Wintergreen has to offer? > [Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!](https://www.expedia.ca/Nellysford-Hotels-Modern-Luxe-Treetop-Retreat-WGas-Fire-Pit.h71969999.Hotel-Information): Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Wintergreen are [NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort](https://www.expedia.ca/Nellysford-Hotels-NEW-Warrens-Woods-Spacious-5-Bedroom-House-In-Fantastic-Wintergreen-Resort.h118927334.Hotel-Information) and [Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK](https://www.expedia.ca/Nellysford-Hotels-Walk-To-SlopesLuxury-LivingSunset-Mountain-Views-And-Same-Day-Arrival-OK.h33563291.Hotel-Information). ### How many vacation rentals are there in Wintergreen? > Choose from 53 Expedia vacation rentals in Wintergreen for a memorable vacation. ### 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 larger area. ### What’s a vacation rental in Wintergreen like? > A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on 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,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)