Lexington vacation rentals

Condo in Wintergreen Resort

A cozy living room features a comfortable seating arrangement with plush chairs and a sofa. Large windows allow natural light to fill the space, enhancing the view of the surrounding greenery. A coffee table is placed centrally, surrounded by decorative plants.

4.78 out of 5 average rating, 69 reviews

Wintergreen Best location,Arcades,king bed,2 room

Enjoy this beautifull newly renovated condo in the 18th hole of wintergreen resort entirely to yourself, cozy, centrally located dont miss this unique stay, within minutes of the slopes. Be pampered with a morning Coffee or hot cocoa in the new granite kitchen with new appliances and relax in the amazing view in the terrace peaceful, surrounded with trees and birds. Sleep really well with all new memory foam mattress, central a/c, heating, fully equipped, 2 Smart Tvs and 2 Arcades NBA and Pacman

Villa in Wintergreen Resort

4.96 out of 5 average rating, 78 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!

5 out of 5 average rating, 13 reviews

Home in Roseland

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.

4.86 out of 5 average rating, 101 reviews

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 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!

4.97 out of 5 average rating, 937 reviews

A private balcony is presented with a round table and two black chairs, overlooking lush greenery and distant buildings. Sunlight floods the space, highlighting the inviting outdoor setting and enhancing the serene atmosphere.

Loft in Buchanan

Edifice Rex

Edifice Rex, a 300 square foot studio apartment, is only one mile and less than 2 minutes from Interstate 81 yet offers a very bucolic, peaceful setting. Countless cultural, historical and recreational opportunities exist within a 30 mile radius. The James River and Appalachian Trail are but minutes away. The name, "Edifice Rex" is to honor the caretaker on the property, a German Shepard named Rex. You will not have to interact with him ( he wears a radio collar) but he welcomes attention.

4.97 out of 5 average rating, 202 reviews

Cabin in Afton

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.

Condo in Wintergreen Resort

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.

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!

4.84 out of 5 average rating, 239 reviews

The open living area features a large stone fireplace with a mounted television above it. Natural light floods through multiple windows, illuminating the wooden ceiling and floor. A cozy seating area is complemented by a decorative rug and a wooden coffee table.

Bungalow in Boones Mill

Starlight Falls Cottage

Built in the late fifties, this charming bungalow was rumored to be a gamblers cabin, although it was originally built as a guest cottage for Brookway Hideway, a large property next door. Large picture windows offer panoramic views of the creek boasting its own waterfall. This cottage is perfect for honeymooners, family getaways, or weekends away. Centrally air conditioned with a large stone fireplace to take the chill out of the air. Or to cozy up to on a cool evening.

Home in Wintergreen Resort

4.94 out of 5 average rating, 62 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.

Place to stay in Lexington

The exterior of a charming white house features a welcoming porch with several seating options. Lush greenery surrounds the property, with landscaped areas enhancing the view. A gravel driveway leads to the entrance, blending with the peaceful outdoor setting.

5 out of 5 average rating, 12 reviews

Sunset Farm - Rent the Whole House! WLU VMI VAHC

Sunset Farm is a beautifully restored feed store built in 1900s that's just minutes from downtown Lexington. Here, you'll be close to local shops, the Virginia Horse Center, restaurants, W&L, and VMI. Since it's also close to local wineries, breweries, and several wedding venues, Sunset Farm is a must stay! Whether you want a romantic weekend away, a trip to the mountains with your friends, or you just need to a little getaway, Sunset Farm is the perfect spot.

4.95 out of 5 average rating, 73 reviews

A charming white cottage is nestled beside a gently flowing stream, surrounded by lush greenery. A vibrant red tree offers a pop of color against the blue sky. Smooth stones line the stream, enhancing the serene natural setting.

Home in Hot Springs

Mountain View Cottage

Welcome to "Mountain View Cottage" a beautiful vacation rental that lives up to its name. This rental is nested in the quiet mountains of Hot Springs, VA and is the perfect spot for a beautiful mountain getaway. Mountain View is located within walking distance to the famous Omni Homestead resort, the Bacova Brewery, Sam Sneads Tavern and downtown Hot Springs. You will find hiking trails, the Warm Springs Pools, restaurants and Lake Moomaw nearby.

Treehouse in Stanardsville

A modern treehouse structure is perched above the ground, supported by stilts. Surrounding greenery adds to the natural ambiance. A pathway leads to a fire pit area, and multiple decks are visible, showcasing inviting outdoor spaces for relaxation.

5 out of 5 average rating, 29 reviews

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, recliner, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Lexington vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Lexington's top sights

Southern Inn Restaurant43 locals recommend

Virginia Military Institute41 locals recommend

Washington and Lee University40 locals recommend

TAPS27 locals recommend

Haywood's Restaurant25 locals recommend

Stonewall Jackson House23 locals recommend

Other great vacation rentals in Lexington

4.75 out of 5 average rating, 4 reviews

A modern cabin exterior features a sloped roof and wooden deck. Two seating areas are under the deck, with comfortable seating visible. The structure is surrounded by tall trees, offering a sense of privacy and tranquility.

Home in Stanardsville

Speckled Owl

5 out of 5 average rating, 25 reviews

Two green Adirondack chairs are positioned on a gravel area beside a gently flowing stream. Nearby, a black fire pit adds a cozy element to the outdoor space, surrounded by trees and fallen leaves.

Cabin in Montebello

Blue Ridge Cabin 5

5 out of 5 average rating, 20 reviews

A serene view of a lake surrounded by lush greenery, featuring a dock with boats and people enjoying the water. A grassy area leads to the water’s edge, offering space for relaxation. The scene conveys a peaceful outdoor atmosphere.

Home in Moneta

Stay Awhile @ Smith Mountain Lake

4.83 out of 5 average rating, 6 reviews

A dining area is highlighted by a round table surrounded by five modern white chairs with wooden legs. Two abstract art pieces in neutral tones are displayed on a textured brown wall, creating a stylish and inviting space.

Townhouse in Lynchburg

Low-key getaway

Condo in Wintergreen Resort

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.

4.88 out of 5 average rating, 163 reviews

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

4.97 out of 5 average rating, 63 reviews

The kitchen features stainless steel appliances and ample counter space, complemented by white cabinets. A doorway leads to a cozy sitting area with a comfortable chair. Natural light enters through multiple windows, creating a bright and functional cooking space.

Home in Buena Vista

Spacious Home in Buena Vista

4.89 out of 5 average rating, 190 reviews

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

C'Ville Barn Suite, Mountain View & Hot tub!