Vacation rentals with lake access in Wintergreen Resort

Condo in Wintergreen Resort

A spacious bed is dressed in plaid and textured bedding, accompanied by a decorative fern in a ceramic pot on a wooden nightstand. Soft lighting illuminates the serene atmosphere, enhancing the restful setting.

4.92 out of 5 average rating, 63 reviews

Views & Brews with 2 Floors

This unit is perfectly situated at The Ledges, just a quick five-minute drive to the Mountain Inn. Mountain Dreams is a newly designed, phenomenal condo that offers stunning 180-degree views of Charlottesville, Lake Monocan, the UVA observatory, and ski slopes. Located at the highest elevation, this two-story condo provides a prime location, only 8 miles from Devils Backbone Brewery, Bold Rock or Three Notch'd. Walk conveniently across the street for stone-fired pizza and beer at Fire and Frost.

Superhost

A spacious open living area features large windows offering natural light and views of the outdoors. The area includes a comfortable sofa, dining space with chairs, and a modern kitchen equipped with a stylish island and fixtures, enhancing the room's contemporary rustic feel.

4.79 out of 5 average rating, 104 reviews

Mntn View Hot Tub Pool Table Pool Tennis Golf

Sweeping views year round. Contemporary décor with rustic style. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and hiking. 5min drive to slopes. ★3,500sqft on 3 floors ★Hot tub for 8 people ★Sound system ★2-Story vaulted ceiling, gas fireplace, 55” TV ★Movie room: 65” TV, pool table, wet bar, wine fridge ★Dining table seats 10 ★Desk and FAST WiFi ★Roku TV in every bedroom ★Park 6 cars Seasonal outdoor pool/tennis. Resort access not included.

5 out of 5 average rating, 16 reviews

A warm and inviting living space features a stone fireplace with a fire glowing inside. A comfortable chair with patterned fabric sits beside a small glass coffee table. Natural light enters through large windows, creating a cozy atmosphere.

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.

4.96 out of 5 average rating, 216 reviews

The interior of the tiny house features an open kitchen layout with modern appliances and a central island. A geometric area rug extends across the floor, while light wood accents create a warm feel. Shelving holds books and decor, enhancing the cozy atmosphere.

Cabin in Nellysford

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Welcome to our luxurious tiny house nestled in the heart of Nelson County, Virginia. This enchanting retreat, surrounded by the majestic Blue Ridge Mountains, offers an unparalleled experience in a landscape dotted with wineries, breweries, distilleries, and sprawling farmland. This luxury tiny house was built in 2022 and is available for couples, solo travelers, or a small family wanting to explore this beautiful stretch of the Blue Ridge Mountains. FREE Electric Vehicle Charger on-site.

5 out of 5 average rating, 913 reviews

A serene landscape showcases rolling hills adorned with autumn foliage. In the foreground, tall grass and scattered trees lead to a cozy house perched on a hillside, surrounded by vibrant fall colors. The distant mountains create a peaceful backdrop.

Yurt in Afton

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

Cabin in Wintergreen Resort

A sweeping aerial view captures the snowy landscape of Wintergreen Resort at sunset, with vibrant colors illuminating the sky. Slopes are visible, lined with trees and softly lit by lights. The resort buildings are nestled below the mountains, framed by winter scenery.

4.88 out of 5 average rating, 128 reviews

The Bear Dance Cabin at Wintergreen Resort

Tucked back in the woods in the Wintergreen Resort, we're on the top of Wintergreen Mountain, elevation just under 4k, near all the resort's amenities. Our family built on Wintergreen Mountain after learning how unique and beautiful the seasons are here. The cabin quickly became a new member of the family and we can’t imagine not having her in our lives now. Ten years after building we decided to provide short term rental and the experience has been beyond what we had ever imagined. Enjoy!

4.96 out of 5 average rating, 141 reviews

A charming tiny house is positioned amidst lush greenery, featuring a welcoming front door with glass panels. Adjacent outdoor areas include a dining setup and a grill. Potted plants enhance the natural setting, creating a serene and inviting environment.

Tiny home in Crozet

CBD Hemp House Cottage

The Cottage is a warm, cozy, intimate tiny house space ideal for 1-2 peeps. Features full bed, smart tv, Wifi, AC/ Heat, & full rustic bth rm w/ tub, toilet, farm sink, hot/ cold h2o. Offering a unique experience, local "surprise" treats for guests & canna offerings (never a must, always avail.) Outdoor kitchen space is combined w/ an eatery bar, patio, fire pit, grill, smoker & pizza oven. We are nestled in the Blue Ridge just west of C’ville, VA @ the foot of Shen Nt'l Park. *NO animals*

A spacious deck is surrounded by greenery, featuring several black Adirondack chairs arranged around a firepit. The glass railing provides an unobstructed view of the outdoors, enhancing the inviting outdoor space.

4.99 out of 5 average rating, 138 reviews

151Escape | 5☆ Group Fun! Game Room/Bar/Deck/4kTVs

Enjoy mountain adventures with friends & family at this beautiful & newly renovated 5 bedroom mountain house ideally located in Virginia Wine Country at Wintergreen Resort’s Stoney Creek valley area. This amazing home features: - 75” & 55” 4k TVs - Fully equipped, live edge wet bar & bar countertop - Professional Ping Pong table - Deck with views, firepit & grill Just minutes from skiing, golf, hiking, wineries, breweries, apple-picking and other adventures the area offers all year long!

Guesthouse in Massies Mill

Lush green grass stretches across the foreground, leading to a scenic vista dominated by rolling hills and misty mountains. The trees display varying shades of green, indicating the freshness of spring, with a backdrop of soft clouds partially covering the peaks.

4.99 out of 5 average rating, 82 reviews

Solar-powered Guesthouse at Peak Time Property

This cozy guesthouse is a perfect getaway. It has SPECTACULAR views of the Priest and Three Ridges. Located in Massies Mill, it is a 20-30 minute drive to the Appalachian Trail, Wintergreen, breweries, wineries, and distilleries. It is also practically around the corner from Pharsalia Events. There are several convenience stores close by, but the closest grocery store is an 18 minute drive. Situated on 26 acres, there is more than a mile of marked trails available to walk as you wish.

Condo in Wintergreen Resort

The spacious living area features a stone fireplace and large windows that allow natural light. A comfortable sofa faces the cozy seating area, while a dining table accommodates several guests. An artwork piece complements the warm decor, enhancing the inviting space.

4.97 out of 5 average rating, 35 reviews

WonderfulViews/WalktoResort&WTGMusicFest

Welcome to Sample’s Summit! Ski In/Ski Out… slope side! It doesn’t get better! This two story, mountain condo is situated right on Eagle’s Swoop and within walking distance to some of the best hiking trails and lookouts on the mountain! Enjoy gorgeous views of the mountains, wake up early & catch an amazing sunrise! We are centrally located and just a short walk to the Mountain Inn, ski check in, the Market, restaurants, shops and entertainment. *WTG is now part of the Indy Ski Pass!

Condo in Wintergreen Resort

A glass of white wine is positioned in the foreground, capturing the warm hues of a sunset. The sun's golden rays reflect off the wine, while silhouettes of trees and distant mountains create a tranquil backdrop in the evening sky.

5 out of 5 average rating, 236 reviews

Sunset Vista (Mountain Views) “Skies for Miles”

Welcome to Sunset Vista Villa, where you enjoy, “Skies for Miles.” This beautiful, 2 bedroom, 2 bath, first-floor-unit with second story views, is near all amenities the Wintergreen Resort has to offer. It comfortably sleeps five and with its western vistas, sunsets are a thing to behold! Whether you spend your days hiking, skiing or enjoying the wineries and breweries, SVV will enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

A home surrounded by lush greenery features a spacious outdoor area with bright red chairs arranged around a fire pit. The structure has large windows and a deck that extends into the natural setting, inviting relaxation and outdoor gatherings.

5 out of 5 average rating, 11 reviews

FamilyFriendly-Pets-HotTub Gameroom-Firepits-Grill

Bring the whole family to this warm mountain home! Welcome to Whitetail Lodge, a well designed home in the heart of Wintergreen. A perfect spot for groups or families, with tons of games, record player, kids teepee tent area, two fire pits, lots of areas to spread out, and multiple outdoor seating areas. With 5 bedrooms total, a full loft, plus a downstairs living room, bunk room, and game room, there is plenty of room for up to 14 guests and it is pet friendly!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Wintergreen Resort lake access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake access house rentals

A spacious home is set among tall trees with a covered porch featuring a wooden deck and steps leading to the entrance. The exterior displays a neutral color palette, with ample windows reflecting natural light, providing a serene sense of privacy.

Home in Roseland

4.75 out of 5 average rating, 4 reviews

5 mi to slopes+ Wintergreen Mt getaway+Luxury

AmandaRating, 5 stars4 months ago

Rhonda and Tim’s house was perfect for our families on our ski weekend! The location was great and close to ski facilities and great restaurants. We loved the open floor plan on the second floor because it allowed us to all hang out together while we were cooking, eating and playing games. We used the back deck and the grill and everything we needed for cooking our meals was there in the kitchen. The sun room was perfect for morning coffee and watching the sun come up. We got snow while we were there and there was plenty of room in the yard for the kids to play and build a snowman. We would love to come back in the summer! Rhonda and Tim were very responsive and every time we reached out with a question they got right back to us the info we needed. Thanks so much for allowing us to stay in your beautiful home!!!

A bright game room features a blue pool table at the forefront, surrounded by a variety of games like foosball and air hockey. Comfortable seating is arranged near large windows, allowing natural light to fill the space. Tall bar stools add extra seating options.

5 out of 5 average rating, 72 reviews

Game Room & Hot Tub Near Wineries + Breweries

TiffanyRating, 5 stars1 month ago

If you're looking for a nice, clean getaway for some R&R this is the place. Accommodations are immaculate with lots to do on the property. Game room, board games, outdoor games and quiet sitting room. Plenty of room and all the amenities you may need.

4.99 out of 5 average rating, 81 reviews

Spacious, Ensuite BRs, Pet Friendly, Hot Tub!

HeatherRating, 5 stars4 months ago

Amazing stay! The home was stocked with towels, coffee pods, dishes, cookware, etc. The hot tub was lovely and the location was perfect for our weekend ski trip. We hope to be back soon!

Superhost

The vacation rental home is nestled among trees, featuring a light-colored exterior and a spacious front deck. A pathway leads to the entrance, while a stack of firewood is visible next to the house. The surrounding foliage displays autumnal hues.

DianaRating, 5 stars9 months ago

Briarpatch @ Wintergreen Resort

Everything about the house, our host and the area was truly great! This is not a knock against this property at all, I simply wish we had more of a view of the open mountain scenery. I was looking forward to sitting on the porch drinking my coffee and seeing the views but the location wasn't perfect for that. Also, looked to be more of a Wintergreen issue as none of the properties had much open land for the kids to run and play.

The living area features a spacious sectional sofa arranged around a wooden coffee table. Large windows allow natural light to fill the space, and skylights are visible above. The neutral color palette of the walls complements the cozy atmosphere, leading to an adjoining kitchen area.

5 out of 5 average rating, 5 reviews

4 Bedroom 3 Full Bath - Foxwood at Stoney Creek

TammyRating, 5 stars1 month ago

Wow - Huge thank to Jason & Stephanie! We loved staying at your home - so beautiful, very homey & extremely peaceful! Easily accommodated all nine of us who flew in from Oregon for a graduation at Liberty University! Stephanie was very helpful prior to arriving by quickly answering questions, providing great recommendations to try the local coffee shop (so good!), a bakery for graduation desserts (YUM - PB pie was the best!) and spot for dinner (Iron & Ale). All recommendations were spot on! The dinner was so good & Lindsey was the best server! Thank you for helping make this a special weekend for our daughter! If we are ever back in the area we will stay here again! It felt like home when we arrived with the welcoming lights wrapped throughout the outdoor walkway🩷

The living room features a stone fireplace, providing a central focal point. Large windows allow natural light to brighten the space, while a comfortable sofa invites relaxation. A wooden shelf displays decorative items, and a smart TV is mounted on the wall for entertainment.

4.83 out of 5 average rating, 24 reviews

The Hideaway at the Waterfall

AlysonRating, 5 stars3 months ago

100 Stars!!! ⭐️ We reached out to Jessica (owner) and Cindy (host) about booking a stay on very short notice after losing heat at a separate Airbnb - in the middle of some very cold winter weather. They were immediately responsive, kind and so welcoming of our family of 4 and senior pup. They happily accommodated our short notice. Cindy arrived ahead of us to get the place warm and toasty while her husband cleared the snow from the driveway - and even had welcome goodies upon our arrival to-boot. The home itself was spotless. I have stayed in many wonderful airbnbs, but this one was by far the cleanest. We felt right at home and spoiled with the beautiful views of the fresh snowfall and creek in the backyard. So much heart and attention to detail - our son loved the touch of bean bags in his room! Could not recommend enough and we hope to come back for another wonderful vacation!

Superhost

A wooden deck features several Adirondack chairs arranged around a fire pit, providing a cozy setting for relaxation. Expansive views of the surrounding mountains and valleys are visible beyond the railing, with a mix of trees and rolling hills extending into the distance.

4.87 out of 5 average rating, 71 reviews

Luxury Lodge: Stunning All-Season Views! Sleeps 14

KatieRating, 5 stars2 weeks ago

This place was the perfect fit for a weekend getaway with the girls. The views from the deck were amazing and so peaceful. Wineries and breweries within a 15 minute drive. There was plenty of space for all of us to feel at home. I would highly recommend this place to anyone looking to stay in the area.