Holiday rentals in Wintergreen Resort

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.

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

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!

#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!

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.

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.

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.

5-star Luxury 4BR/4BA Lodge w/ HotTub!

Rustic, 5-star lodge great for a Guys or Gals weekend, weddings and family gatherings. Well-appointed with 4 cozy bedrooms each with their own private en suite bathroom. Unleash your inner chef in the gourmet kitchen w/ sun-filled dining area. Spread out in the 2-story family room with gas fireplace. Head outside to the expansive deck overlooking the 14th hole on Devils Knob golf course and enjoy the hot tub and firepit.

Super Comfy Mtn Escape w/ 4 Bedrooms & Hot Tub

Bring the whole family or group of friends to this awesome, comfortable home with lots of room for fun; a brand new hot-tub and huge patio; plenty of parking/two-car garage; and central location for epic views, hikes, and skiing. Two master bedrooms on each end with king size beds. One bedroom with a queen and another with two twin beds and a crib make it a perfect place for multiple families.