Places to stay near Wintergreen Resort

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Top-rated vacation rentals near Wintergreen Resort

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Top guest favorite

An outdoor deck features a wooden surface with a dining table and six chairs. A hot tub is enclosed with a cover, positioned alongside a grassy area and tall trees. In the background, a fire pit area can be seen, surrounded by natural greenery.

Home in Afton

4.98 out of 5 average rating, 101 reviews

Hot Tub, Firepit, Foosball, Walk to Coffee & Park!

Welcome to Creekside! Just minutes from the best wineries and breweries, it’s the perfect getaway to explore the 151 Brew Trail, Wintergreen Resort and the Blue Ridge Parkway. Enjoy mountain views and privacy in the hot tub. Roast marshmallows around the huge fire pit. Cozy up on the large sectional sofa in front of the 65" 4K TV. Cooks will enjoy the spacious and fully equipped kitchen! All beds have new memory foam mattresses. Fast Wi-Fi for remote work! Level 2 EV charger located in driveway.

Top guest favorite

A charming cottage is framed by lush green lawns, with two prominent stone chimneys rising from its exterior. The landscape is complemented by mature trees and distant mountains under a bright blue sky, creating a serene rural atmosphere.

Cottage in Covesville

5 out of 5 average rating, 116 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

A hot tub is positioned in the foreground, showcasing bubbling water. In the background, a vibrant pink tree stands against a clear blue sky, surrounded by green grass and blooming shrubs. String lights are suspended above, enhancing the outdoor space.

Barn in North Garden

4.89 out of 5 average rating, 186 reviews

BARN SUITE, Mountain View's & Hot tub! Pets OK

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. You can upgrade your space at anytime to include the downstairs suites

Top guest favorite

Villa in Wintergreen Resort

4.96 out of 5 average rating, 76 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

Guest favorite

Home in Roseland

5 out of 5 average rating, 13 reviews

Hot Tub! Wintergreen Resort!

Check out our 5 star reviews on VRBO and "cozy cabin at wintergreen dot com". Prepare to escape and relax at our three bedroom, two bath cabin, nestled atop the Blue Ridge mountains, a short walk (5 Houses) to the Devils Knob Overlook. This luxury resort retreat is perfect for couples getaway, wedding, family vacation or girls weekend. Spend the day brewery hopping down the famous Route 151, where you have over twelve wineries and breweries to visit. Or enjoy hiking, skiing, spa & golfing.

Superhost

A private porch is shown with wooden flooring and a rustic wooden ceiling. Several outdoor chairs are arranged around a small table. Trees are visible in the background, providing a 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!

Guest favorite

A spacious wooden deck is highlighted by a black metal table surrounded by four chairs, all shaded by a large green umbrella. An Adirondack chair is positioned nearby, offering a relaxing spot to enjoy views of the surrounding trees.

Townhouse in Wintergreen Resort

4.89 out of 5 average rating, 37 reviews

Chic Getaway w/ Private Hot Tub and Walk to Lodge

Welcome to Eagle's Landing, a modern oasis just a 5-min walk from the main ski lodge. Unwind in the private hot tub after a day on the slopes or cozy up by the fireplace after a vineyard tour. With sleek cozy decor & amenities, our home offers the perfect blend of comfort and style. Enjoy seasonal mountain views from the balcony, and explore nearby hiking trails and charming wineries & breweries. Your mountain adventure begins here to experience the ultimate retreat in the heart of nature!

Superhost

The kitchen showcases a blend of rustic and modern design, featuring a farmhouse sink under large windows that invite natural light. A dark refrigerator is positioned adjacent to the sink, with wood accents enhancing the inviting atmosphere. Copper pendant lights provide additional warm illumination.

Condo in Wintergreen Resort

4.88 out of 5 average rating, 163 reviews

Wander Lodge: Golf, Spa, Wine, or just a getaway

Comfortable 3-BR, 2-bath condo on Devil's Knob Golf Course. Comfortably sleeps 6-7, 2 Queen beds, 1 full bed, futon, & comfy couch. Woodburning fireplace; balcony, small newly renovated kitchen w/stove, dishwasher, microwave, Keurig, tea kettle,coffee maker, crockpot; Smart TV w/ Streaming apps(free only); Walking distance to hiking trails, nature center, DeVine Wine & Coffee shop, tennis facilities, & the lovely wintergreen spa; less than 1 mile from Mountain Inn & restaurants & shops.

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 spacious outdoor deck features a round dining table surrounded by tall chairs, complemented by a striped couch with soft cushions. An umbrella provides shade, while the scenic mountain views extend into the distance, above a layer of mist.

Condo in Wintergreen Resort

4.94 out of 5 average rating, 132 reviews

BlueRidge Getaway- Dog Friendly

Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

Guest favorite

A clean, inviting swimming pool is surrounded by lush greenery and tall trees. Comfortable lounge chairs are positioned nearby, and sunlight reflects off the water, creating a serene atmosphere. The pool area is enclosed with a wooden railing for safety.

Condo in Wintergreen Resort

4.98 out of 5 average rating, 130 reviews

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

Guest favorite

Home in Wintergreen Resort

4.93 out of 5 average rating, 61 reviews

Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV

Impressive 3-story mountain estate. Ideal for family retreats and adventurous getaways. Features HOT TUB. Wineries, breweries, farmers market, and walk to hiking trails. 4min dive to slopes! ★Comfortably sleeps 10: K, K, Full, Twin bunk beds, Sleeper sofa in loft ★Great room with stone fireplace ★Dining table for 8 ★FAST Wi-Fi ★Two 52" HDTVs ★Wrap around decks ★Fire Pit ★Hot Tub ★Plenty of parking Seasonal outdoor pool/tennis access. Resort access not included.