Photo by Rebecca Brent

Search Vacation Homes in Wintergreen

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Homes in Wintergreen

Aftonshire Cottage - Heart of Afton's Wine Region

10.0 out of 10, Exceptional, (4)
"Place was nice an quite and had a good view of the horses outback. The location was great and close to restaurants and wineries. "
Aftonshire Cottage - Heart of Afton's Wine Region

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

10.0 out of 10, Exceptional, (33)
"Loved the home! Was a perfect experience for us."
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

The Firefly Springhouse

10.0 out of 10, Exceptional, (32)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is SAR 311
SAR 429 total
includes taxes & fees
31 Aug - 1 Sep
The Firefly Springhouse

White Rock Cabin

10.0 out of 10, Exceptional, (210)
"Above and beyond on everything highly recommend staying here"
White Rock Cabin

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

10.0 out of 10, Exceptional, (135)
"Excellent house close to the slopes"
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

Farmhouse at the foot of the Blue Ridge Mountains

10.0 out of 10, Exceptional, (27)
"We loved the farm atmosphere. Everything was beautiful"
The price is SAR 692
SAR 950 total
includes taxes & fees
8 Sep - 9 Sep
Farmhouse at the foot of the Blue Ridge Mountains

House / hot tub/pet friendly

9.8 out of 10, Exceptional, (63)
"Great mountain get-away. Owner was very quick to respond to questions. Good location for hiking and relaxation."
The price is SAR 694
SAR 1,155 total
includes taxes & fees
26 Sep - 27 Sep
House / hot tub/pet friendly

3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

10.0 out of 10, Exceptional, (60)
"House was very nice. Great set up for family."
3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

NEW! Secluded Farmhouse + Solar Heated Pool + Firepit

10.0 out of 10, Exceptional, (25)
"We had a great time. Very pretty house in a very pretty setting!"
NEW! Secluded Farmhouse + Solar Heated Pool + Firepit

The red house

9.6 out of 10, Exceptional, (18)
"Great location when visiting JMU. House was very clean and well equipped. Owners were excellent and responded very quickly to any inquiries and provided great recommendations for area restaurants."
The red house

Newtown Retreat: Award-Winning Renovation + Ideal Location

10.0 out of 10, Exceptional, (29)
"This was a great place with a great location! 10/10 would stay here again."
Newtown Retreat: Award-Winning Renovation + Ideal Location

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (60)
"Great location, amenities and owner's willingness to address all our questions/issues."
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Thrilling Views HotTub Sauna Gym EV Charger DogOK

10.0 out of 10, Exceptional, (2)
"Beautiful place! Amazing views! Great hospitality! Has everything you need! Plenty of amenities. Host provided everything we needed. "
Thrilling Views HotTub Sauna Gym EV Charger DogOK

The newest and largest edition to the Wintergreen Retreat portfolio!

9.6 out of 10, Exceptional, (44)
"We had a lovely time in this lovely house. "
The newest and largest edition to the Wintergreen Retreat portfolio!

Rockfish River Retreat

2.0 star property
10.0 out of 10, Exceptional, (11)
"Everything was perfect for us. Beautiful area!"
Rockfish River Retreat

Come and enjoy a beautiful view and relaxing time at Windy Knoll....

10.0 out of 10, Exceptional, (207)
"Very relaxing getaway. "
Come and enjoy a beautiful view and relaxing time at Windy Knoll....

Charming 3-bedroom house, breweries! hiking! wineries! scenic routes! Fishing!

10.0 out of 10, Exceptional, (2)
"We traveled to VA from NY. Check in was easy and simple. As was checkout. It was conveniently located to a lot of places. Would stay again "
Charming 3-bedroom house, breweries! hiking! wineries! scenic routes! Fishing!

Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV

9.4 out of 10, Exceptional, (3)
"The property was well stocked and the location was excellent. There was plenty of firewood for the fireplace and the hot tub was perfect after a long day of skiing at the resort. "
Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV

Updated Mtn House 2 Mins to Resort: 3King Beds, HotTub, Game room, Family & Pets

Updated Mtn House 2 Mins to Resort: 3King Beds, HotTub, Game room, Family & Pets

Peaceful Mountain Get Away

10.0 out of 10, Exceptional, (71)
"This is a lovely property, had everything we needed and Laurie was great to work with. Looking forward to our next stay!"
Peaceful Mountain Get Away
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Wintergreen Hotel Reviews