
House vacation rentals in Wintergreen Resort
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Top-rated house rentals in Wintergreen Resort
Guests agree: these houses are highly rated for location, cleanliness, and more.

Close to skiing! | King Beds | Fireplace | Hot Tub
Welcome to Blackrock Escape! Dog friendly, 2BR/2.5BA mountain home in prime location at Wintergreen Resort. 3-min drive to the Mountain Inn. Walk to hiking trails–the Plunge Trail/Blackrock Park is only a 2-min walk. Two BRs on first floor - both with King-size Helix mattresses, smart TVs, and en suite bathrooms. Wood burning fireplace, games, puzzles, 65” smart TV in living room. Two decks w/gas grill and hot tub. Keurig K-Duo coffee maker and dishwasher in kitchen. Full-sized washer and dryer.

“Small" House/Peaceful/Brewery/Hike/Winery/River
The Small House is anything but small when it comes to comfort and relaxation. Located in the heart of Nellysford near a local grocery store and restaurants. Close to many hikes, the Blue Ridge Parkway, the AT, wineries, cideries, and breweries! The property includes a deck, outdoor fire pit, grill, and 11 acres to explore. At the very back of the property is 600 feet of private river/creek access. The perfect spot to fish, picnic, and/or let the kids and pups cool off and play! Come and stay!

Hottub Ski InOut Renovated Chalet Lower Tyro Slope
Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.

Mountain Mama- Amazing Views! + Hot Tub!
MOUNTAIN MAMA - The home for gorgeous Blue Ridge Mountain views : ) Situated on a graceful 26 acres minutes off Rt. 151, our mountainside home is nestled within the beautiful Rockfish Valley and offers incredible views from every window in a truly unique and newly renovated home. Enjoy sunsets over 3600’ Humpback Mountain due west and sunrises lighting up the valley ridges. If you need time to be inspired by nature’s beauty, this home offers a rare breath of fresh air! Book your stay today!

Bear's Mountain Escape
Dog friendly, 3 BR, 2 BA, loft style condo located in the heart of the Wintergreen Resort. Ski check-in, restaurants, the mountaintop market, & The Mountain Inn are all right across the street! 2-story unit with a main floor primary BR & hall bath. Main floor bonus room with single & trundle. The loft contains 2 twin beds and the 2nd full bath. Parking, pool, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps up to six.

Saltbox at Wintergreen, a Modern Mountain Escape
Your mountain adventure awaits at Saltbox, an inviting, eclectic home at Wintergreen Resort in the Blue Ridge Mountains. Combining modern and vintage decor, plus original art, Saltbox was designed to provide escape, inspiration and fun. Nestled at the end of a quiet cul-de-sac drive, with beautiful woods to explore, it's just seconds from the Resort (skiing, tubing, hiking, dining, spa, outdoor movies and more)! Saltbox is the perfect home base for your next getaway, any time of year!

Cliffs Edge -A Contemporary Mountain Home
An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

The Branch at Afton Mountain Retreat
Welcome to The Branch at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. Located 1/8th mile from Veritas Vineyard. It is within 10 minutes to every brewery, vineyard, distillery and cidery along Route 151 & Crozet, 1 mile from the newly opened Blue Ridge Tunnel and 20 minutes to Wintergreen Resort for winter fun! Completely remodeled and ready to spoil the best guests who simply want to unwind.

Cozy Mountain Home Nestled in Nature!
4 bedroom/2.5 bath home nestled in the Blue Ridge Mountains at Wintergreen Resort. This will be your favorite home away from home. Enjoy all the creature comforts while basking in all that nature has to offer. First floor master bedroom w/ private bathroom featuring a whirlpool tub . Two bedrooms upstairs with shared bathroom. Common space with large wood burning fireplace, full kitchen amenities, and high capacity washer/dryer. Outdoor deck with table and gas grill!

Afton Home on 25 Acre Ridgetop with Amazing Views
Architect-designed 2,900 sf home sits on a high ridge. Main living space optimizes dramatic views of Humpback Mountain. Covered porch wraps around entire second floor. Situated on 25 private acres within the George Washington National Forest. House is only 1 paved mile to Rockfish Valley Road, Rt. 151 (aka the Red, White and Brew Trail). 30 minutes from Charlottesville, Va. Close to breweries, wineries, hiking & excellent restaurants.

Mountain Bauhaus | Sleeps 8 | Amenities | Grill
Welcome to your newly decorated and upgraded home in the Blue Ridge Mountains at Wintergreen Resort! A bright and welcoming feel will let you settle in and relax in no time. This space is perfect for families, groups, couples, and adventurous souls who want to explore the mountains or take in the beautiful mountain scenery. Please be sure the read below for Wintergreen Resort Amenities rules and accessibility during your stay.

Updated 5Bd home wineries/breweries/hiking/golf
Welcome to Stoney Creek Sanctuary, a 4,200 sq ft luxury retreat located in the highly sought-after Wintergreen Stoney Creek community, just minutes from the iconic 151 Brew & Wine Trail. Overlooking the lush fairways of Stoney Creek Golf Course and steps from Lake Monocan, this spacious home is designed for unforgettable group getaways — girls’ weekends, guys’ trips, family gatherings, and multi-family vacations.
Popular amenities for Wintergreen Resort house rentals
House rentals with a hot tub

Hot Tub! Wintergreen Resort!

Wren Time

The Inn at Blue Mountain Brewery

Hot Tub, Firepit, Mtn Views, Walk to Coffee & Park

White Wolf Chalet at Wintergreen

4 min to Ski: Whispering Creek Hot Tub King Beds

Perfect getaway among the orchards of Batesville

Ski season is coming! Time to book your trip! SNOW
House rentals with a pool

Stunning Views, Hot Tub, Impeccable Design

Cozy 5-bedroom home for large gatherings.

Private Pool Opens April 1 - All Year Hot Tub

Farmhouse on Working Vineyard

Perfect House

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

5 min toSki! Mntn View HotTub Pool Table MovieRoom

Ski & Stay at Wintergreen | Hike, Hot Tub, Firepit
Weekly house rentals

Welcome to Winterhaven! 5BR/4BA .5mi from lodge!

Summit Serenity - Walk To Slopes and Restaurants

Panorama Peak Lodge-4 bedroom with sweeping views

Privacy and Views in Wintergreen

Beech Grove Cottage: 151, Firepit, EV Charger

Charming Wintergreen resort home

Mountaintop Home, Walk to Lifts

Mountain Overlook House - Blue Ridge Parkway
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,230 | ﺩ.ﺇ1,197 | ﺩ.ﺇ922 | ﺩ.ﺇ881 | ﺩ.ﺇ959 | ﺩ.ﺇ881 | ﺩ.ﺇ984 | ﺩ.ﺇ973 | ﺩ.ﺇ859 | ﺩ.ﺇ1,102 | ﺩ.ﺇ1,083 | ﺩ.ﺇ1,282 |
| Avg. temp | 2°C | 4°C | 8°C | 14°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 9°C | 4°C |
Quick stats about house rentals in Wintergreen Resort

Total vacation rentals
Explore 240 vacation rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort vacation rentals start at ﺩ.ﺇ477 per night before taxes and fees

Verified guest reviews
Over 9,140 verified reviews to help you choose

Family-friendly vacation rentals
240 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Vacation rentals with a pool
130 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wi-Fi availability
240 of Wintergreen Resort vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wintergreen Resort rentals

4.9 Average rating
Wintergreen Resort stays are highly rated by guests—averaging 4.9 out of 5!
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- Shenandoah National Park
- Early Mountain Winery
- Downtown Mall
- James Monroe's Highland
- Wintergreen Resort
- Frontier Culture Museum
- Homestead Ski Slopes
- Blenheim Vineyards
- Amazement Square
- Devils Backbone Brewing Co Basecamp
- Cardinal Point Winery
- Liberty Mountain Snowflex Centre
- John Paul Jones Arena
- Glass House Winery
- Monticello
- University of Virginia
- Virginia Horse Center
- James Madison University
- The Rotunda
- Grand Caverns
- White Lotus Eco Spa Retreat
- IX Art Park
- James Madison's Montpelier
- James River State Park




