Holiday rentals with outdoor seating in Wintergreen Resort

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Wintergreen Resort

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite

Holiday home in Lovingston

4.97 out of 5 average rating, 189 reviews

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

Guest favourite

Home in Lovingston

4.93 out of 5 average rating, 150 reviews

Three Springs with EV charging station

Beautiful 3-bedroom home outfitted to accommodate a variety of visitors with high-speed internet, 2 large screen TVs, whirlpool tub, hiking, wildlife, and a huge deck. Nestled in a quiet cove in the beautiful Blue Ridge Mountains. Located on Nelson's Craft Beverage Trail and a short drive to Charlottesville, Lynchburg, Staunton, Wintergreen, and Skyline Drive. Close to Oak Ridge for music festivals/events. Larger parties, see the Three Springs Plus listing. EV charging is available for $10/day.

Top Guest favourite

Cottage in Covesville

5 out of 5 average rating, 119 reviews

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

Guest favourite

Home in Afton

4.99 out of 5 average rating, 153 reviews

Clean family-friendly 5br for wine country getaway

Come to Sunnyside! A new 5 bedroom home with game room, hot tub, and space for 12 people on 4 acres on a private farm road. Just off the infamous Route 151, or "Brew Ridge Trail", you are RIGHT in the middle of the action: 7 minutes to 10 wineries / breweries, 5 minutes to the nearest family farm or golf course, 10 minutes to Skyline Drive with PLENTY of places to hike, and 25 minutes to skiing at Wintergreen. You are surrounded by jaw-dropping mountain views/sunsets that surprise every guest.

Top Guest favourite

Yurt in Afton

5 out of 5 average rating, 904 reviews

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

Top Guest favourite

Cottage in Tyro

5 out of 5 average rating, 246 reviews

Bear Creek Inn

You will be renting the 2 bedroom cottage, optional 3rd bedroom, very large, fenced yard for your pet. Relax at this quiet, peaceful place with year round trout stream. Minutes from the breweries and wineries on Nelson 151. Plenty of outdoor activities to enjoy. The George Washington National Forest is across the street for exploring, hiking and hunting. The house is only 4 miles from Crabtree Falls and several minutes from the Appalachian Trail access. Wintergreen Resort is 12 miles away.

Superhost

Home in Wintergreen Resort

4.86 out of 5 average rating, 107 reviews

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool table Seasonal pool/tennis. Resort access not included. Pet fee $150. 8min walk or 3min drive to ski.

Top Guest favourite

Home in Wintergreen Resort

4.96 out of 5 average rating, 103 reviews

Cliffs Edge Memorial Weekend & Summer Camp

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.

Guest favourite

Cabin in Afton

4.97 out of 5 average rating, 203 reviews

Inn at the Woods: Updated Cabin w/Mountain Views

Fall in love with the charm of this recently updated ‘Hansel & Gretel’ style cabin located on Castle Rock Mountain. This cabin has 3 bedrooms + a loft, with a total of 4 queen beds. Hike and explore the 20+ acres or relax on the large multi-tiered deck and fire-pit area while soaking in the mountain sunsets. Enjoy nearby dining, breweries, or wineries, the historical town of Charlottesville, or spa, golf, tennis, and skiing at the Wintergreen Resort - both just a short drive away.

Guest favourite

Barn in North Garden

4.88 out of 5 average rating, 193 reviews

Barn Suite, Mountain View's & Hot tub! Pets OK

Beautiful views just off Route 29, only 10 minutes from UVA, and tucked near the area’s finest wineries and top attractions. This intimate, luxury barn suite offers a private setting with 1 king bedroom, 1 bathroom, and an open-concept living room and kitchen featuring a cozy fireplace, queen pullout sofa bed, and single cot for extra guests. Unwind and relax on the back patio with breathtaking sunsets, hot tub, grill and a firepit — all fully yours to enjoy during your stay.

Top Guest favourite

Home in Nellysford

4.97 out of 5 average rating, 114 reviews

Llama Loft | No Service Fee | Fire Pit

Save money on fees and enjoy our open-concept home a mile off Brew Ridge Trail and close to Wintergreen Resort for skiing, Skyline Drive, hiking, biking, golfing, and local eats/breweries/wineries and vineyards. Oversized windows bring amazing mountain views and sunrise in, the deck provides a spot to relax, and the modern interior is a fun place to gather. Our spacious and colorful home is perfect for large groups of families or friends or an intimate couples' retreat.

Guest favourite

Guesthouse in Schuyler

4.91 out of 5 average rating, 388 reviews

Homestead at HeartRock

Welcome to HeartRock Homestead. Our sweet spot offers rustic charm and modern comfort. Come for a private grownup nature camp! A getaway for couples, friends and families. Really, there is something for everyone. AND we have great check in and check out times to maximize your stay! Have you ever heard the whippoorwill sing while watching the stars or grazed organic cut flowers amongst the morning dew or felt a seasoned sunset kiss your heart? We hope to see you soon!