House vacation rentals in Wintergreen

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Top-rated house rentals in Wintergreen

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Top guest favorite

A charming three-bedroom home is surrounded by lush gardens filled with colorful flowers and vibrant greenery. Towering hills rise in the background, while a variety of trees and shrubs add to the scenic landscape of the property.

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 available for $20/night.

Superhost

Home in Roseland

4.88 out of 5 average rating, 142 reviews

Hikers, Spring has sprung & ready for you to come!

Wintergreen mountain house located yards from the Blue Ridge Parkway & Appalachian Trail! The house is 3 stories with several porches, 3 of them are private. It has a lighted circular driveway. The top floor has two bedrooms & one large bathroom. The main living area is on the second floor with a master bedroom. The bottom floor has another master bedroom, & additional bunk room. The kitchen has a 10-seat kitchen table. After a long day enjoying the outdoors, relax by the fireplace or hot-tub!

Guest favorite

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.

Guest favorite

A charming two-story house is depicted, featuring a light blue exterior with white trim. A welcoming front porch with stairs leads to a yellow door. Lush greenery and colorful flowers adorn the surroundings, enhancing the inviting entryway.

Home in Charlottesville

4.99 out of 5 average rating, 142 reviews

Belleview Retreat | 5 Bedroom Home Near Downtown

Charming 5 bedroom house in Charlottesville located just 1.6 miles from downtown. The Rivanna River Trail is only a five minute walk away. Amazing shopping and dining is close by. The house comes with two kayaks and two bikes for your enjoyment! Use this space as your starting point for vineyard/brewery tours. Whether you're visiting the area for a weekend getaway, a wedding, graduation, UVA event, or anything else, the Belleview Retreat is the perfect place to stay to experience our area!

Top guest favorite

A brick house is framed by a well-maintained lawn and leafy trees. A stone pathway leads to the front door, surrounded by greenery. The overall setting conveys a peaceful ambiance, enhanced by the dappled sunlight filtering through the branches.

Home in Charlottesville

4.97 out of 5 average rating, 130 reviews

Wakefield Ct | Private Parking spots | Fast WiFi

BRAND NEW LISITING! Cozy stay in an updated colonial style house on a quiet street. Short drive from great local spots along Downtown Cville, UVA Corner, Monticello, Blue Ridge Parkway, The Appalachian Trail, breweries and local wineries. An excellent choice for hosting small gathering with good yard space and pouch. A wonderful stay if you like to be close to all the attractions Cville has to offer, but still far enough to enjoy peace and quiet. Thank you, for your time and consideration.

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.

Superhost

This tranquil bedroom features a spacious bed with a tufted headboard, flanked by large windows allowing natural light. A mirrored dresser and a cozy accent chair add functionality. Warm beige walls complement the soft area rug, creating a relaxing atmosphere for restful nights.

Home in Charlottesville

4.86 out of 5 average rating, 129 reviews

Close to UVA/Downtown - for Large Groups

Specious house in one of the nicest neighborhoods in Charlottesville close to Stonefield Shopping Center, Whole Foods and Trader Joe's and 5 min drive from UVA and Downtown. You can enjoy the gorgeous view from all floors. The house has a lot of space for large groups and includes DeLonghi Espresso Machine, K-Cup and Regular Coffee Makers, Air Hockey, Oculus VR, Netflix, HBO Max, Disney Plus, Hulu, ESPN+, Prime Video and 245+ channels. The house is well equipped for families with kids.

Top guest favorite

A living area features a rustic slate fireplace prominently set against a neutral wall. The inviting seating arrangement is centered around the fireplace, with a light-colored sofa and a modern floor lamp nearby. Natural light flows through the front door, illuminating the wooden floors.

Home in Schuyler

4.93 out of 5 average rating, 180 reviews

HeartRock Home Stay or Retreat

Welcome to HeartRock. Enjoy our ready made late 21st century rustic homestead. The space is old and humble yet full of life! Surrounded by edible, medicinal, and floral gardens will have you catching the breath you’ve been waiting for. No kidding! Plus the quite afternoon atmosphere tends to hold sunsets and starry nights where by chance your pace has simply slowed down. Lastly we are anywhere from 15-30 mins away from vineyards breweries hiking and the Rockfish River.

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Home in Crozet

4.9 out of 5 average rating, 101 reviews

Beauchamp House 2 BD Fishing Hiking Lake

The Beauchamp House is in the Blue Ridge Mountains of Virginia, near the Shenandoah National Park and Charlottesville, Va. Ideal for couples, friends and families. One pet welcome with additional $100 fee. Enjoy 129 acres with hiking trails, small lake, free mountain bikes, canoes, fishing. Wineries and fine dining nearby. Includes high speed internet and Roku TV. House has a separate basement apartment with a separate entrance and driveway.

Guest favorite

A modern kitchen is presented with sleek dark countertops and white cabinetry. An archway provides a view into a well-lit living area. Various kitchen appliances are neatly arranged, with fresh fruit displayed in a decorative bowl. Natural light enhances the bright ambiance.

Home in Charlottesville

4.93 out of 5 average rating, 110 reviews

Greenleaf Grove

Charming 1947 Cape Cod Style home with three bedrooms and two updated bathrooms. The upstairs is big attic space with double bed and private bathroom. Modern kitchen with all new amenities. The home is 1.7 miles from UVA Rotunda and walking distance to parks, restaurants and downtown mall. Open to inquiries about any dates that do not appear open on calendar and price reduction for visits greater than 7 days

Superhost

Home in Charlottesville

4.95 out of 5 average rating, 130 reviews

Scenic Private Farm House Great for Large Groups

CHURCH FIELD HOUSE. Large 5 bedroom, 4 bath house with sweeping 360 degree views featuring beautiful pastoral and mountain landscapes on a 250 year old family farm in the Southern Albemarle Historic District. Enjoy large windows in almost every room with unobstructed western views. Large outdoor deck and a separate fire pit area are favorite places to view spectacular sunsets over the Blue Ridge Mountains.

Guest favorite

Home in Afton

4.93 out of 5 average rating, 106 reviews

Sycamore Shade: 151 House, HOT TUB, Mountain Views

Newly renovated home inviting Appalachian adventure and craft exploration with ample gathering space for friends and family to create lasting memories. Sycamore Shade features 3 bedrooms, a new modern kitchen, 2 full baths, bright dining room, and gorgeous mountain views from a spacious deck with a 6 person hot tub. The house has been completely renovated with all the MCM feels and eco friendly thrifts.