Holiday rentals with a fire pit in Wintergreen Resort

Holiday home in Lovingston

4.97 out of 5 average rating, 258 reviews

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

5 out of 5 average rating, 241 reviews

Cottage in Afton

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

5 out of 5 average rating, 155 reviews

Cottage in Covesville

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.

4.96 out of 5 average rating, 758 reviews

The gravel pathway leads to a charming log cabin, framed by tall trees and surrounded by greenery. A sign reading 'COZY MOUNTAIN CABIN' is positioned near the path, inviting visitors to explore this secluded retreat in the Blue Ridge.

Cabin in Roseland

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

4.97 out of 5 average rating, 252 reviews

An outdoor seating area features several Adirondack chairs arranged on a stone patio overlooking a wooded landscape, with bare trees extending toward the mountains in the distance. The communal game room includes a foosball table and a television mounted on a stone wall.

Cabin in Roseland

Blue Ridge Cabin~Mtn View~Gameroom~SNP & Lake 5mi

The Blue Ridge Cabin is at the base of the mountain on the “151 Brewridge Trail”, just mins to wineries, breweries, hiking, skiing, golfing & lake fun. Experience a mountain vaca in this fun bear-themed cabin on 2 private acres, tucked away yet close to it all! Enjoy 12+ wineries & breweries within 15mins, 1/2 mi to Devils Backbone Brewery, 1 mi to Bold Rock Cider, 10 mins to Appalachian Trail, Shenandoah Nat. Park & Wintergreen Ski Resort! Charlottesville/Waynesboro 30mins. A perfect home base!

Villa in Wintergreen Resort

A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.

4.96 out of 5 average rating, 137 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!

4.98 out of 5 average rating, 121 reviews

Home in Roseland

Stargaze on 12 Acres: Hot Tub 55"TV Fire Pit Grill

Relax with the family on 12 private acres at our peaceful, brand new construction farmhouse. We're just 12 miles to Wintergreen Ski Resort and Stoney Creek Golf, breweries, and wineries. Sleeps 8: K, K, Q + daybed w/ trundle. ★Amazing mountain views ★Hot tub for 6 people ★Outdoor shower ★Rockers, Adirondacks chairs for idle stargazing ★Gas grill ★Teak dining table seats 6 ★Indoor/outdoor gas fireplaces ★View 55” TV from comfy leather sofa/kitchen ★Pack 'n Play/Bassinet/High chair ★Mud room

5 out of 5 average rating, 249 reviews

A quaint cottage is framed by a white picket fence, with a welcoming blue front door and vibrant flowers lining the walkway. Scenic mountains rise in the background, while lush trees and blooming dogwood add to the charming exterior.

Cottage in Roseland

Blue Ridge Cottage - 3 Miles to Wintergreen

Our little piece of Blue Ridge Heaven is ready to share! Cozy - 2 bedrooms (one king, one queen), 1 bath, 956 square feet - well appointed in a terrific location! Beautiful mountain view from the 360 square foot, partially covered deck; fiber optic TV and wi-fi; South Fork of the Rockfish River out back. 3 miles from Wintergreen Resort, 1 mile from Devil's Backbone; Close to great hiking/biking, and many wineries, breweries, cideries, and distilleries (if you're into that kind of thing!)!

4.97 out of 5 average rating, 144 reviews

The exterior view showcases a modern blue house set against a backdrop of lush green hills. A wooden deck extends from the home, providing access to outdoor space. The gravel driveway is lined with a rustic split-rail fence, enhancing the natural feel of the surroundings.

Home in Nellysford

Llama Loft | Fire Pit | Fenced Yard | Brew Trail

Escape to a spacious, colorful home off the Brew Ridge Trail with oversized windows, mountain views, and plenty of room for groups or couples. Cook in a stocked kitchen, then relax by the fire pit or grill out and unwind on the deck while the dogs enjoy the fenced in yard. Accessible bedrooms and bathrooms on the main floor make it easy for everyone to enjoy. Perfectly located near Wintergreen Resort, Skyline Drive, breweries, wineries, vineyards, hiking, biking, and golf.

4.99 out of 5 average rating, 371 reviews

Cabin in Vesuvius

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

An outdoor seating area features a sectional couch adorned with cushions, positioned around a fire table. The space is surrounded by trees, with a patterned area rug underneath. A small table holds a potted plant and a bottle, creating a relaxed ambiance.

4.91 out of 5 average rating, 105 reviews

Modern Cabin with Hot tub and Sauna

Welcome to Blue Ridge Hollow! This designer-decorated cabin in the heart of Wintergreen has one of the best outdoor spaces in the area. Relax in the hot tub or cedar barrel sauna, then enjoy a meal at the oversized outdoor table or sip wine around the firepit. The updated kitchen is fully stocked and open to the living room and sun-drenched dining room. 3 bedrooms are masters, the others share a bathroom, and the downstairs game room can be a 6th bedroom. Plus, pet friendly!

A spacious living area features vaulted ceilings, large windows that invite natural light, and a stone fireplace as a focal point. Comfortable seating includes two armchairs and a dark sofa adorned with decorative pillows. A dining table is visible with a backdrop of green trees.

4.99 out of 5 average rating, 109 reviews

Cozy Mountain Retreat- Walk to trails-EV charger

Escape to a bright, spacious mountain retreat just minutes from the slopes and walkable to scenic trails. Perfect for families and groups, this open concept, light-filled home features a cozy fireplace, stocked kitchen, and screened porch for relaxing after adventure-filled days. EV charger available to guests during your stay. Sleeps comfortably with 2 king ensuites, a queen bedroom, and a fun bunk room - ideal for skiing, hiking, and wine country getaways.

Popular amenities for Wintergreen Resort Holiday Accommodation with Fire Pit

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fire pit

4.94 out of 5 average rating, 158 reviews

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

Three Springs with EV charging station

An inviting outdoor space features a hot tub surrounded by a spacious deck, with mountain views in the background. A large dining table with wooden chairs is positioned indoors, complemented by a fully-equipped kitchen visible in the adjacent area. A cozy fire pit with adirondack chairs provides a warm setting.

4.99 out of 5 average rating, 146 reviews

Hot Tub, Firepit, Mtn Views, Walk to Coffee & Park

4.98 out of 5 average rating, 113 reviews

A wooden deck is adorned with hanging lights, providing a warm atmosphere. The scene captures a captivating sunrise over a range of mountains, with soft pastel colors illuminating the sky and the landscape below, showcasing the natural beauty of the surrounding area.

Home in Roseland

Fire pit with MTN views! Summer fun! Nelson 151.

A vast expanse of green grass stretches across the foreground, framed by lush orchard trees. Rolling hills covered with foliage rise in the background, under a clear blue sky dotted with soft white clouds, creating a serene rural atmosphere.

4.97 out of 5 average rating, 117 reviews

Perfect getaway among the orchards of Batesville

A spacious living room features a prominent stone fireplace adorned with wildlife sculptures. Large windows allow natural light to fill the space, illuminating comfortable seating. An inviting sectional couch and wooden coffee table create a cozy gathering area, while art pieces enhance the room's character.

4.96 out of 5 average rating, 379 reviews

FLASH SALE: Blue Ridge Estate Wine, Beer, & Skiing

Superhost

A hot tub is positioned on a wooden deck, surrounded by lush greenery and trees. The serene view of the mountains is visible in the distance, complementing the tranquil setting. Steps lead to the hot tub, creating easy access.

Home in Wintergreen Resort

4.81 out of 5 average rating, 164 reviews

Misty Mountain Cabin w/spa

The two-story house features a white exterior with dark shutters and a welcoming front porch. A gently sloped lawn surrounds the home, leading to mature trees and a scenic backdrop. The roof is accented with three gabled dormer windows, adding character to the facade.

4.98 out of 5 average rating, 185 reviews

Clean family-friendly 5br for wine country getaway

The exterior of the two-story house is illuminated at dusk, showcasing a welcoming aesthetic. A circular stone fire pit is situated in the foreground, surrounded by landscaped gravel and rocks. A pair of chairs sits nearby, inviting relaxation by the fire.

4.98 out of 5 average rating, 138 reviews

Afton Home on 25 Acre Ridgetop with Amazing Views

Apartment rentals with a fire pit

5 out of 5 average rating, 6 reviews

The exterior of the garage apartment is visible, showcasing a rustic wooden facade and a metal roof. A gravel driveway leads to the structure, which features multiple doors and windows. Surrounding greenery includes trees, with a colorful seating area to the side.

Apartment in Crozet

Sugar Hollow Outpost on the Moormans River

4.9 out of 5 average rating, 154 reviews

A wooden deck is elevated and features a vibrant red umbrella. Surrounding the deck are leafy green plants and a small seating area with pink chairs. A lattice design is present under the deck, adding texture to the space.

Apartment in Lovingston

Lovingston Get-Away Lovingston, VA

4.96 out of 5 average rating, 57 reviews

A craftsman-built apartment is nestled among lush greenery, surrounded by mountain forests. Vibrant flowers frame the foreground, leading to the wooden structure with a metal roof. The natural landscape features rolling hills and a clear blue sky, creating an inviting outdoor setting.

Apartment in Tyro

Crabtree Falls Mountain Hollow Guesthouse

Superhost

The green exterior of a spacious house is surrounded by trees and gently rolling hills, showcasing a panoramic view of the Blue Ridge Mountains in the background. A well-maintained yard is visible, with landscaped gardens and a gravel driveway leading to the entrance.

Apartment in Afton

Luxury Guest Quarters w/Blue Ridge Mountain Views

4.79 out of 5 average rating, 108 reviews

A warm and cozy bedroom is visible, featuring a spacious bed with yellow pillows and a neutral quilt. A bedside table holds a ceramic cup and a small lamp with a textured shade. Soft lighting enhances the inviting atmosphere against wooden accents and a colorful area rug.

Apartment in Afton

Earth Room Suite | Peaceful Blue Ridge Retreat

An open living and dining area is visible, featuring a comfortable gray sofa and a wooden dining table with multiple chairs. Light hardwood flooring extends throughout. A modern kitchen is partially seen in the background, with contemporary appliances and a small unobtrusive rug underfoot.

Apartment in Stuarts Draft

4.06 out of 5 average rating, 16 reviews

Sandstone Lodge

Apartment in Wintergreen Resort

4.92 out of 5 average rating, 13 reviews

Eagles Court Ski In/Out Condo

Apartment in Fishersville

4.93 out of 5 average rating, 14 reviews

Valley Oasis: Luxury Fishersville Apartment

Cabin rentals with a fire pit

Superhost

An open-concept living area features high vaulted ceilings with exposed wooden beams. A cozy seating arrangement is positioned around a fireplace, with a contemporary dining table nearby. Large windows allow natural light to fill the space, showcasing views of the surrounding outdoor landscape.

Cabin in Faber

4.93 out of 5 average rating, 250 reviews

Modern cabin, hot tub, mtn views, fireplace

4.88 out of 5 average rating, 57 reviews

Bide-a-Wee- Hike the Trails! Close to the slopes!

A two-story home nestled among autumn-colored trees features a welcoming front entrance. A covered porch with steps leads to the door. Leaves carpet the driveway, and the building's exterior showcases a blend of warm tones and large windows that invite natural light.

4.91 out of 5 average rating, 134 reviews

Stylish 7BR/16 pp Wintergreen Resort Home Ski/Hike

4.97 out of 5 average rating, 155 reviews

A rustic log cabin is featured with a green metal roof. An outdoor fire pit surrounded by stones provides a warm glow in front of the cabin. Comfortable chairs are positioned nearby, inviting relaxation. A gas grill is seen to the side, enhancing the outdoor experience.

Cabin in Lyndhurst

Cozy Log Cabin

4.95 out of 5 average rating, 170 reviews

The exterior of a lakeside log cabin showcases a large, sloped roof with wooden beams and expansive windows. A spacious deck is visible, featuring various seating options. The structure combines natural stone and wood elements, reflecting a rustic yet modern aesthetic.

Cabin in Faber

Lakefront Cabin w Stunning Curated Decor & Hot Tub

The cabin features a warm wooden exterior with a red metal roof, set against a backdrop of lush greenery. A spacious front porch is presented, supported by wooden columns and adorned by wooden railing, inviting guests to enjoy the surrounding nature.

4.89 out of 5 average rating, 141 reviews

The Bear Dance Cabin at Wintergreen Resort

4.96 out of 5 average rating, 235 reviews

A two-story cabin features a light-colored exterior with a steep roof and large windows. A wraparound deck includes wooden railings draped with soft outdoor lighting. A walkway leads from the deck to the landscaped area, surrounded by lush greenery.

Cabin in Afton

Inn at the Woods: Updated Cabin w/Mountain Views