Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

Top rated by guests
Main upstairs living area (wide screen lens was used to show entire space)
Dining area and kitchen.
Kitchen with plenty of cooking supplies
Kitchen has coffee, hot water pot, Keurig coffee machine (not pictured)
View from stairway, overlooking back deck
review stars
10Outstanding
(6 Ratings)
"Host was very responsive and anything that came up they were super helpful and got it addressed very quickly. Not too far from the lodge and the slopes. Very cozy but plenty of room. "
Johanna F.
Don't miss out! Price and availability may change
10 / 10
Outstanding(6 Ratings)

House in Massies Mill, VA

10 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Escape to this cozy four-season mountain retreat tucked away on a private wooded lot in the heart of Wintergreen Resort. Perfect for families, friends, girls’ weekends, reunions, and couples’ getaways, this traditional mountain home combines comfort, adventure, and relaxation.

Walk to Wintergreen Resort dining, market, spa, and slopes — then return home to unwind by the wood-burning fireplace or soak in your private hot tub surrounded by serene woods.

Highlights
★ Private 4-person hot tub overlooking the forest

★ Walk to Wintergreen Resort - lodge, restaurants, market, spa & lifts (This is a 10-min walk, but if you have ski gear we recommend the 2 minute drive & free parking at the lodge)

★ Hiking trails accessible directly from the backyard

★ Two separate living spaces — ideal for multiple families

★ Game room with 70” HDTV, indoor basketball, mini Pac-Man, Atari, games & puzzles

★ Fast WiFi + AC

★ Two decks overlooking a private wooded setting, with new propane grill
★ Wood-burning fireplace, exposed beams & vaulted ceilings

★ Newly renovated bathrooms completed June 2026!

The Space
This mountain-style home sits on a private ½-acre wooded lot with a small creek and trails right outside the door. The home features two separate levels, each with bedrooms, a bathroom, and its own living area — giving families and groups room to spread out.

Sleeping arrangements include:
2 king bedrooms
1 queen bedroom
1 bunk bed with trundle

The home comfortably sleeps up to 9 guests in designated sleeping areas. We allow up to 10 guests for families with babies or young children. A Pack ’n Play is available.

After a day of skiing, hiking, or exploring, gather around the fireplace, watch a movie, play games, or relax under the stars in the hot tub.

Outdoor Adventures:
Step out into the backyard and connect with Wintergreen’s trail system - the Laurel Ridge Loop is right off the property, and can be used to walk to the market. The resort boasts miles of scenic mountain trails. Enjoy morning coffee on the deck, listen to the creek, or simply relax in the quiet of the woods.

Resort Amenities:
★ Chestnut Springs Pool and Rhodes Farm Pool (6 guests max; guest hours 2 PM–close)
★ Rhodes Farm tennis and pickleball courts
★ Lake Monocan - sandy beach, water slide and trampoline, beach volleyball, kayak/paddle board rentals, and a snack bar (closed Tuesdays and Saturdays)*
★ WinterGarden Spa*
★ Discovery Ridge Adventure: kids rock climbing, mini-golf, summer tubing, gem mining, adventure course, etc. *
★ Stoney Creek Golf Course & driving range*
*fee for service

Wintergreen Resort offers year-round activities including skiing, snowboarding, tubing, scenic chairlift rides, festivals, hiking, mountain biking, and summer concerts.

Wintergreen in Every Season:

Winter:
Ski, snowboard, or tube at Wintergreen Resort, then return to your own cozy cabin for hot chocolate by the fire, a relaxing soak in the hot tub, or cuddle up for a family movie night.

Spring:
Hike from your backyard, explore waterfalls, enjoy mountain biking, kayaking, fishing, and local dining.

Summer:
Enjoy pools, lake days, hiking, biking, breweries, wineries, outdoor concerts, stargazing from the deck, and long evenings relaxing on the decks. Walk to the slopes to catch the sunset.

Fall:
Experience breathtaking Virginia foliage, scenic drives along the Blue Ridge Parkway, hiking trails, wineries, and crisp mountain evenings by the fire.

Explore the Area:
Wintergreen is surrounded by some of Virginia’s best outdoor and cultural destinations. Enjoy nearby wineries, breweries, cideries, restaurants, orchards, historic sites, Charlottesville, the University of Virginia, Monticello, and the Blue Ridge Parkway. Sherando Lake is a short drive away.

A peaceful mountain escape awaits — whether your perfect day includes adventure, relaxation, or simply enjoying time together.

Amenities at Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

Non-smoking

Map of Massies Mill, VA


Ratings and reviews

10 / 10
Outstanding(6 Ratings)
10 / 10Outstanding·Feb 2026
Host was very responsive and anything that came up they were super helpful and got it addressed very quickly. Not too far from the lodge and the slopes. Very cozy but plenty of room.
10 / 10Outstanding·Jan 2026
Great host! Was very helpful as we were dealing with some weather back home.
10 / 10Outstanding·Jan 2026
Accommodations were great. It was a cozy and comfortable stay close to the slopes. We had a great time! Any questions that we had were answered right away. We would definitely stay here again. Thank you!!
10 / 10Outstanding·Dec 2025
We had such a great stay here! The host did such a beautiful and wonderful job decorating! The host did a terrific job making this house feel like a home. Beyond that, the location was perfect! Within a minute of the slopes and top of the mountain. This allowed for my family to be able to ski in and out and grab a bite to eat without hassle! Overall such a great experience would recommend to anyone!

$$$$
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard?

We found 1 amenities for this rental. This includes , and non-smoking.