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    Check prices for these dates, 12 – 13 December 2026

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    Our top choices for Wintergreen holiday rentals

    1. New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

    A garden with a variety of flowers and trees at dusk.

    2. 2 minutes from the shops and activities; Cozy 1 bedroom end unit.

    A two-story house with a front porch, a mailbox, and a wooden fence.

    3. Updated! Cozy and clean two bedroom condo.

    A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

    4. Escape to the Blue Ridge Mountains at Wine-tergreen!

    A set of stone steps leading up to a house with a light-colored exterior.

    5. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

    A balcony with a table and chairs, offering a view of a mountainous landscape.

    6. Three Little Bears

    A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

    7. Walk to Market/Private community outdoor pool!

    A two-story wooden cabin with a wooden deck and a small porch.

    8. Panoramic Peak: Wintergreen Condo with Views

    A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

    9. Mountain Inn Studio 96 with Wintergreen Advantage

    Exterior

    10. Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

    A hallway with a dark carpet, wooden flooring, and white doors with black handles.

    11. Wintergreen Condo -Steps to Ski and restaurants

    A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

    12. Spacious + Serene Mtn Top Escape, 4 En Suites

    A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

    13. Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace

    A two-story house with a stone foundation, a large front porch, and a chimney.

    14. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

    Private kitchen

    15. Timbers Studio 46 with Wintergreen Advantage

    Exterior

    16. Mountain View Vista

    A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

    17. Mountain Inn Lodge 77 with Wintergreen Advantage

    An aerial view of a residential area with multiple houses surrounded by dense forest, featuring a central building with a prominent roof and a well-lit driveway.

    18. Mountain Inn Lodge 78 with Wintergreen Advantage

    Exterior

    19. Luxury Condo in the Sky! Finest in Wintergreen!

    A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

    20. Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails

    Gather around the stone fireplace after a day on the mountain, with a large-screen TV above and the deck just steps away.

    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.

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    Top Wintergreen Hotel Reviews

    Holiday Inn Express & Suites Waynesboro East by IHG

    A modern hotel with a flat roof, large windows, and a covered entrance area with stone pillars.

    Best Western Plus Waynesboro Inn & Suites Conference Center

    A Best Western Plus hotel with a covered entrance, multiple floors, and a landscaped area with trees.

    The Farmhouse at Veritas

    A wooden porch with two rocking chairs and a white fence.

    Village Inn

    A covered outdoor seating area with benches and a sheltered entrance to a building.

    Holiday Inn Express & Suites Staunton by IHG

    A hotel lobby with a reception desk, seating area, and a large window.

    Hampton Inn Waynesboro/Stuarts Draft

    A swimming pool area with four lounge chairs and large windows offering a view of trees.

    Fairfield Inn & Suites by Marriott Staunton

    A clean, modern reception area with a wooden reception desk, a refrigerated display case, and shelves stocked with snacks.

    Avid Hotel Staunton

    A swimming pool with four lounge chairs and a view of trees through large windows.

    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, cottages, apart-hotels, 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 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 £163 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.

    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?

    Wintergreen cabin, hot tub, sauna, walk to trails: This highly rated holiday home rental in Wintergreen is located in the mountains, and has a fireplace, a balcony 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 Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 and Remodeled 3BR/2BA Ski Chalet off Tyro Slope.

    How many holiday rentals are there in Wintergreen?

    Choose from 232 Expedia holiday rentals in Wintergreen for a memorable holiday.

    What can I see and do in Wintergreen?

    While you're exploring the area, George Washington National Forest and Humpback Rocks are a couple of picturesque spots to get outside and enjoy nature. While here, Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort are other places worth a visit.

    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.

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