Vacation rentals with outdoor seating in Wintergreen Resort

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Top-rated outdoor seating rentals in Wintergreen Resort

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A charming cottage is nestled among lush green grass and surrounded by trees. Its metal roof and white siding are complemented by well-maintained shrubbery. Dappled sunlight filters through the tree branches, creating a serene outdoor ambiance.

Cottage in Covesville

5 out of 5 average rating, 118 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 favorite

An elevated back deck features a dining table with four black mesh chairs, overlooking verdant hills and mountains. Double sliding doors offer a view into the inviting living area with a cozy blue armchair and a flat-screen television.

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.

Superhost

A rustic cabin constructed of timber sits amidst a wooded area, showcasing a wraparound porch with steps leading up. Large windows provide glimpses of the surrounding trees, while gravel paths lead to the entrance, enhancing the natural setting.

Cabin in Crozet

4.86 out of 5 average rating, 101 reviews

#4 Cabin Near Wineries, Breweries, UVA, & Hiking

The #4 Loblolly Cottage is an eco-friendly cabin overlooking a lake. Small 450 sq ft, cottage has a queen size bed in the primary bedroom, bunk beds in the second bedroom and a full size futon in living room. Kitchenette equipped with modern appliances and breakfast table. Bathroom and shower. Wi-Fi. Private porch. Pets are welcome for an additional fee. Hike, canoe, fish and bike onsite on a 129 acres. Close by wineries, 15 min to Shenandoah National Park. This cabin is ideal for families!

Top guest favorite

Yurt in Afton

5 out of 5 average rating, 901 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!

Superhost

A spacious living area features a large sectional sofa adorned with colorful throw pillows. High, wooden ceilings are complemented by large windows that bring in natural light. A dining table and rustic décor are visible, creating a comfortable gathering space.

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 favorite

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 favorite

Cabin in Afton

4.97 out of 5 average rating, 202 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 favorite

A covered porch area features a comfortable seating arrangement adorned with a yellow throw blanket, surrounded by greenery. Natural stone landscaping and wooden elements provide a warm, rustic charm, inviting relaxation in a serene outdoor setting.

Guesthouse in Schuyler

4.91 out of 5 average rating, 387 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!

Guest favorite

Chalet in Vesuvius

4.94 out of 5 average rating, 218 reviews

Luxury Mountain Lodge w/ Hot Tub & Stunning Views!

Welcome to Harvest Moon Lodge & Retreat, where adventure and serenity meet. Nestled high on 9.2 acres in the heart of the Blue Ridge Mountains, this one-of-a-kind getaway offers breathtaking panoramic views and a perfect blend of luxury, comfort, and entertainment. Whether you’re unwinding on one of the two massive wraparound porches, soaking in the seven-person hot tub, or gathering around the fire pit under a star-filled sky, your mountain retreat awaits.

Guest favorite

A rustic exterior of the camp is shown, featuring wooden siding and a sloped roof blanketed in snow. Snow rests on the overhang, while a set of wind chimes hangs near the window, overlooking the distant DePriest Mountains, partially veiled by a winter mist.

Tiny home in Roseland

4.92 out of 5 average rating, 253 reviews

The Humble Abode Camp

The Humble Abode is a secluded CAMP & offers a scenic view of DePriest Mountains range and is the perfect place to un-plug & disconnect to reconnect!! Our private and secluded camp provides with spectacular mountain views and a NEW OUTDOOR Shower!! with pressurized ambient water temperature, spacious deck, covered porch, double bed, hammock, yard to play croquet/corn hole, private port-a-potty, charcoal grill, and a solo stove firewood pit.

Guest favorite

A neutral-toned bedroom features a spacious bed with crisp white linens and decorative pillows. A ceiling fan circulates air above, while a mirrored closet reflects light. A nightstand with a lamp and a decorative wall piece add subtle charm, creating a relaxed atmosphere.

Barn in North Garden

4.89 out of 5 average rating, 187 reviews

C'Ville Barn - King Suite, Mountain View & Hot tub

Beautiful views off route 29, approximately 10 minutes to UVA, nestled near the area's BEST wineries and attractions. This barndominium has 1 bedroom, 1 bathroom, open living area with a pull-out sofa bed and cot for additional guests. Relax and enjoy the breathtaking scenery and sunsets outside on the patio complete with a hot tub, firepit, and lounge chairs. This cozy barn has all you need and more for a great quality stay.

Guest favorite

Bungalow in Waynesboro

4.91 out of 5 average rating, 264 reviews

Cheerful 2 bd bungalow with HOT TUB! Pet friendly!

Enjoy the entire home to yourself, including a relaxing backyard retreat with hot tub. Perfect for singles or couples who want to stay home and relax or visit the sites then come home to enjoy the hot tub under the stars. 10 min drive to shopping; 10 min to Blue Ridge Parkway & Skyline Drive; 15 min to 151 Breweries. kayaking/canoeing/hiking/fishing on the beautiful South River.

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What guests are saying

Crabtree Falls Mountain Hollow Guesthouse

4.97 out of 5 average rating, 35 reviews2 weeks ago

Beverly is a fantastic hostess. Not only is the cabin immaculately clean and cozy, it truly feels like it’s your own space. Plenty of fun toys, games, and books to keep kids and adults entertained when spending time in the cabin, though you likely won’t! Her property offers so much outdoor activity. Walks around the property, time spent next to the river and pond, plenty of flowers to admire, and friendly dogs that come and say “hello.” We were lucky and her goats just had kids! Beverly willingly took our child to pet and hold the babies. We loved our stay. Thank you, Beverly!

Apartment in Tyro

What guests are saying

Blue Ridge Treehouse

4.92 out of 5 average rating, 60 reviews2 weeks ago

The treehouse was exactly what we were looking for in a weekend getaway. The house was private, tranquil, and peaceful. The views were absolutely incredible from every spot in the house. You could move just a few feet to either side and find a new mountain peak to look at on the range. The home was perfect for a weekend of unplugging and recovering from the hustle and bustle of everyday life. I am sure people say this after every stay, but this has been one of our favorite listings so far. There were several hikes within a five minute drive and the house was right off the parkway which provided a scenic start and end to the weekend. We are looking forward to visiting this home again in the winter when there is snow on the ground so we can take advantage of the woodstove and all the comfort this house has to offer.

Treehouse in Roseland

What guests are saying

Adventure Outpost w/ EV Outlet

5 out of 5 average rating, 18 reviews2 months ago

Our stay was perfect! Check in was so easy and smooth - the house was even better than the pictures showed! Richard had everything you could think about needing for a trip. Located on wintergreen resort mountain and only a 5 minute drive from the driveway to the front of ticket sales at the slopes. Anytime we had questions Richard responded in 5 minutes. He also has n amazing set up in the garage with ski racks and boot/glove dryers/warmers. We couldn’t have thought of a Better place to stay and definitely will be returning. Richard also was very accommodating and gave us a late check out! This place was amazing!

Townhouse in Wintergreen Resort

What guests are saying

Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV

4.93 out of 5 average rating, 61 reviews6 days ago

The house was nothing short of amazing, it truly surpassed our expectations! The view was absolutely breathtaking. The house itself was impeccably clean and stocked with all the utensils we could possibly need, making it feel like a home away from home. The location is beautiful and tranquil, ideal for unwinding, yet offers plenty of outdoor activities for those looking to explore and stay active. The host was incredibly responsive and friendly, providing clear instructions and fantastic tips for local attractions and activities, which added an extra layer of ease and enjoyment to our trip. We couldn't have asked for a better place to stay. Highly recommend!

Home in Wintergreen Resort

What guests are saying

Luxury|Outdoor Lounge|Hot Tub|Fire Pit|Family&Pets

5 out of 5 average rating, 22 reviews1 week ago

We had an amazing stay at Sundown Sanctuary in Wintergreen! It was the perfect spot for our two families, with plenty of space for all the kids to spread out and have fun. The layout was super family-friendly, and everything was clean, comfortable, and thoughtfully stocked. The backyard was definitely a highlight—we spent so much time out there! The kids especially loved the hot tub and outdoor TV, which kept them entertained while the adults relaxed and enjoyed the space. From morning coffee on the patio to the beautiful fire pit, it really added something special to our trip. The host was also fantastic—great communication from start to finish, which made everything easy and stress-free. Highly recommend Sundown Sanctuary for anyone traveling with a big group or multiple families—it’s a gem!

Home in Wintergreen Resort

What guests are saying

Farmette! On River by Wintergreen & Blue Ridge Pkw

4.96 out of 5 average rating, 52 reviews3 months ago

We absolutely loved our stay for a family Christmas trip! The house was perfect!! It had a great amount of space to fit everyone. The bathrooms especially were so nice and it was great that everyone has their own. We loved the property with the fire pit and stream. It was so close to skiing, wineries, and restaurants. We had such a great time and definitely recommend staying here!

Home in Roseland

What guests are saying

The Peony Cottage in Charlottesville - Brand New!

5 out of 5 average rating, 31 reviews1 week ago

The Peony Cottage was better than what the pictures portrayed. The hosts were very friendly, the beds and linens were nice and comfortable, and the kitchen was well equipped. The cottage was extremely clean, had a thoughtful layout, was in a quiet setting, and had plenty of wood for the outdoor fire pit. The hosts thought of every nice amenity including fresh tulips on the kitchen table! Highly recommend!

Cottage in Charlottesville