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Wintergreen Vacation Rentals

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Vacation Rentals in Wintergreen

Wintergreen Five Star Rated One Bedroom Condo at affordable prices.

Wintergreen Five Star Rated One Bedroom Condo at affordable prices.

Nellysford, VA
This family-friendly Wintergreen condo building is located in the mountains, just steps from George Washington National Forest and Wintergreen Resort. Sherando ...
4.9/5 Exceptional! (133 reviews)
Wonderful weekend
"Quiet, clean, cute, well taken care of property, perfect for a long weekend getaway of exploring the area. I can only imagine how convenient it would be for a ski weekend if we still skied! Great communication with the owner. I would definitely stay there again."

Reviewed on Nov 15, 2021

Wintergreen Five Star Rated One Bedroom Condo at affordable prices.
Comfy condo close to the Slopes, Main Lodge, shops, restaurants! Dog friendly.

Comfy condo close to the Slopes, Main Lodge, shops, restaurants! Dog friendly.

Nellysford, VA
This family-friendly Wintergreen condo building is located in the mountains, just steps from George Washington National Forest and Wintergreen Resort. Sherando ...
5/5 Exceptional! (38 reviews)
Just a great relaxing weekend
"I’ll be back"

Reviewed on Nov 29, 2021

Comfy condo close to the Slopes, Main Lodge, shops, restaurants! Dog friendly.
Comfy Mountain Retreat-Wintergreen Resort Lodge #2

Comfy Mountain Retreat-Wintergreen Resort Lodge #2

Nellysford, VA
Situated in the mountains, this condo building is steps from George Washington National Forest and Wintergreen Resort. Bold Rock Hard Cider Nellysford Cidery ...
4.7/5 Exceptional! (21 reviews)
Great location to hike
"Great stay and the owner was very helpful when I had an issue on arrival."

Reviewed on Nov 2, 2021

Comfy Mountain Retreat-Wintergreen Resort Lodge #2
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Best views on Mountain! Just remodeled!  Breathtaking 5 Star property! BOOK NOW!

Best views on Mountain! Just remodeled! Breathtaking 5 Star property! BOOK NOW!

Nellysford, VA
Situated in Wintergreen, this romantic condo building is 0.1 mi (0.1 km) from George Washington National Forest and 0.4 mi (0.6 km) from Bold Rock Hard Cider ...
4.9/5 Exceptional! (76 reviews)
Amazing view
"Beautiful condo with amazing views!"

Reviewed on Nov 23, 2021

Best views on Mountain! Just remodeled! Breathtaking 5 Star property! BOOK NOW!
A Loft For All Seasons Ski-in/Ski-out at the top of Wintergreen Mountain

A Loft For All Seasons Ski-in/Ski-out at the top of Wintergreen Mountain

Nellysford, VA
Situated in the mountains, this romantic condo building is steps from George Washington National Forest and Wintergreen Resort. Sherando Lake Recreation Area ...
4.7/5 Exceptional! (7 reviews)
Comfortable Bed!
"Great location, easy check in, clean and my favorite was the Bed and linens! Highly recommend!"

Reviewed on Nov 25, 2021

A Loft For All Seasons Ski-in/Ski-out at the top of Wintergreen Mountain
Cozy Condo in Wintergreen Resort/Walk to slopes

Cozy Condo in Wintergreen Resort/Walk to slopes

Nellysford, VA
The price is $270 per night from Dec 6 to Dec 6
Situated in Wintergreen, this ski condo building is steps from George Washington National Forest and Wintergreen Resort. Bold Rock Hard Cider Nellysford Cidery ...
4.5/5 Wonderful! (10 reviews)
GetAWay
"This hideaway condo is just beautifully decorated and comfy. We enjoyed our stay in the Mountains. Hope to return."

Reviewed on Aug 15, 2021

Cozy Condo in Wintergreen Resort/Walk to slopes
Ski-In Ski-Out Wintergreen Condo w/Balcony

Ski-In Ski-Out Wintergreen Condo w/Balcony

Nellysford, VA
Situated in Wintergreen, this ski condo building is steps from George Washington National Forest and Wintergreen Resort. Bold Rock Hard Cider Nellysford Cidery ...
4.7/5 Exceptional! (17 reviews)
Perfect getaway for two
"Everything was perfect. Enjoyed our stay very much. Perfect location. The fees are a bit high but I imagine nothing can be done about that. I disagree with using a sponge for dishes . I think dish-clothes would be more sanitary..I actually used paper towels. Overall, would rent this place again."

Reviewed on Nov 9, 2021

Ski-In Ski-Out Wintergreen Condo w/Balcony
COZY SKI COTTAGE--SKI IN SKI OUT

COZY SKI COTTAGE--SKI IN SKI OUT

Nellysford, VA
Located in Pedlars Edge, this family-friendly Wintergreen vacation home is steps from George Washington National Forest and Wintergreen Resort. Sherando Lake ...
4.8/5 Exceptional! (61 reviews)
Mountain Get-away
"Beautiful home on the mountainside with wonderful views. Extremely clean and nicely arranged. Enjoyed gorgeous sunsets in the area, fall foliage and abundant wildlife. The wood-burning fireplace was a real treat. The host, Bernie, was very attentive and responsive. Looking forward to coming back ..."

Reviewed on Nov 12, 2021

COZY SKI COTTAGE--SKI IN SKI OUT
Cozy Wintergreen Cabin Near Mountain Inn & Slopes!

Cozy Wintergreen Cabin Near Mountain Inn & Slopes!

Nellysford, VA
Situated in Wintergreen, this cabin is steps from George Washington National Forest and Wintergreen Resort. Bold Rock Hard Cider Nellysford Cidery and Reids ...
4.4/5 Excellent! (19 reviews)
Cozy Mountain Getaway
"Super cozy place! Loved the wood burning fireplace and the kitchen had everything we needed to cook!"

Reviewed on Jan 6, 2021

Cozy Wintergreen Cabin Near Mountain Inn & Slopes!
NEW! Cozy Couples Getaway: Ski-In, Ski-Out Condo!

NEW! Cozy Couples Getaway: Ski-In, Ski-Out Condo!

Nellysford, VA
Situated in Wintergreen, this ski condo building is steps from George Washington National Forest and Wintergreen Resort. Bold Rock Hard Cider Nellysford Cidery ...
4.7/5 Exceptional! (10 reviews)
Nice place
"Great v"

Reviewed on Oct 20, 2021

NEW! Cozy Couples Getaway: Ski-In, Ski-Out Condo!
NEW! Wintergreen Resort Cabin < Half Mile to Ski!

NEW! Wintergreen Resort Cabin < Half Mile to Ski!

Roseland, VA
This family-friendly Wintergreen cabin is steps from George Washington National Forest and Wintergreen Resort. Sherando Lake Recreation Area and Raven's Roost ...
1.5/5 (2 reviews)
Water issues
"After arriving at the house the water was turned off. So I contacted the property manager and was given instructions on how to turn it on. Then in the morning we went to take showers and found out there was no hot water. As you can imagine none of the guests were very happy. After contacting the ..."

Reviewed on Nov 8, 2021

NEW! Wintergreen Resort Cabin < Half Mile to Ski!
NEW! Cottage < 10 Mi to Wineries, Skiing & Hiking

NEW! Cottage < 10 Mi to Wineries, Skiing & Hiking

Nellysford, VA
Situated in Wintergreen, this cottage is 0.1 mi (0.1 km) from George Washington National Forest and 1.1 mi (1.8 km) from Bold Rock Hard Cider Nellysford Cidery. ...
5/5 Exceptional! (2 reviews)
Very cozy
"Very welcoming, cozy little cottage"

Reviewed on Nov 27, 2021

NEW! Cottage < 10 Mi to Wineries, Skiing & Hiking
NEW! Wintergreen Resort Condo; Pool, Skiing & More

NEW! Wintergreen Resort Condo; Pool, Skiing & More

Nellysford, VA
Situated in Wintergreen, this condo building is steps from George Washington National Forest and Wintergreen Resort. Bold Rock Hard Cider Nellysford Cidery and ...
5/5 Exceptional! (1 review)
Great spot for a mountain getaway
"The condo was very clean and had pretty much all of the kitchen supplies you might need. There's a well-stocked market a short walk away (including prepared food) and a number of trails within walking distance."

Reviewed on Nov 9, 2021

NEW! Wintergreen Resort Condo; Pool, Skiing & More
True Ski-in/out Condo! Step off the deck onto the beginner slopes!

True Ski-in/out Condo! Step off the deck onto the beginner slopes!

Nellysford, VA
This family-friendly Wintergreen condo building is steps from George Washington National Forest and Wintergreen Resort. Sherando Lake Recreation Area and Bold ...
4.9/5 Exceptional! (47 reviews)
Enjoyable Thanksgiving!
"This cozy cabin was perfect for our Thanksgiving getaway. Location right on the slopes and close to everything, great space for 2 adults and 2 kiddos and kitchen made a full Thanksgiving dinner! Bob was wonderful to communicate with and we can’t wait to come back!"

Reviewed on Nov 27, 2021

True Ski-in/out Condo! Step off the deck onto the beginner slopes!
Mountain Escape: < 1 Mi Walk to Wintergreen Resort

Mountain Escape: < 1 Mi Walk to Wintergreen Resort

Nellysford, VA
This family-friendly Wintergreen vacation home is located in the mountains, just steps from George Washington National Forest and Wintergreen Resort. Sherando ...
4.7/5 Exceptional! (3 reviews)
Nice
"Needs AC"

Reviewed on Aug 3, 2021

Mountain Escape: < 1 Mi Walk to Wintergreen Resort
Fireside Retreat at Wintergreen Resort

Fireside Retreat at Wintergreen Resort

Roseland, VA
Situated in the mountains, this condo building is steps from George Washington National Forest and Wintergreen Resort. Bold Rock Hard Cider Nellysford Cidery ...
Fireside Retreat at Wintergreen Resort
Blue Ridge Mountain Retreat at Wintergreen

Blue Ridge Mountain Retreat at Wintergreen

Roseland, VA
This family-friendly Wintergreen vacation home is located in the mountains, just steps from George Washington National Forest and Wintergreen Resort. Sherando ...
4.5/5 Wonderful! (28 reviews)
Great place for a retreat!
"We needed a big space with everyone having separate beds for our 10 person retreat - this place was marvelous!"

Reviewed on Oct 4, 2021

Blue Ridge Mountain Retreat at Wintergreen
A-Frame Cabin w/Grill, Steps to Wintergreen Slopes

A-Frame Cabin w/Grill, Steps to Wintergreen Slopes

Nellysford, VA
Situated in Wintergreen, this cabin is steps from George Washington National Forest and Wintergreen Resort. Bold Rock Hard Cider Nellysford Cidery and Reids ...
4.7/5 Exceptional! (6 reviews)
It was beautiful my family and I enjoy our stay
"My family and I enjoy our stay. That weekend was mother's day weekend and my husband and I anniversary the home was beautiful and relaxing."

Reviewed on Jun 14, 2021

A-Frame Cabin w/Grill, Steps to Wintergreen Slopes
Wintergreen Resort Mountain Condo w/ Pool Access!

Wintergreen Resort Mountain Condo w/ Pool Access!

Nellysford, VA
This family-friendly Wintergreen condo building is steps from George Washington National Forest and Wintergreen Resort. Sherando Lake Recreation Area and Raven's ...
4.8/5 Exceptional! (33 reviews)
Great weekend vacation!
"This condo was wonderful! It was perfect for our family of four. It is so close to the market to get snacks and even pizza, sandwiches etc. Very clean and has everything you need. We really enjoyed our time here and will be coming back!"

Reviewed on Nov 26, 2021

Wintergreen Resort Mountain Condo w/ Pool Access!
PERFECT & COZY Mountain Getaway! (Walk to the Shops)

PERFECT & COZY Mountain Getaway! (Walk to the Shops)

Nellysford, VA
Situated in Wintergreen, this condo building is steps from George Washington National Forest and Wintergreen Resort. Bold Rock Hard Cider Nellysford Cidery and ...
4.4/5 Wonderful! (30 reviews)
Perfect Weekend
"Beautiful condo with everything we needed. Quick response from owner when questions came up. Very clean. Highly recommend!"

Reviewed on Nov 12, 2021

PERFECT & COZY Mountain Getaway! (Walk to the Shops)
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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.

Large Group Cabins Wintergreen

NEW! Wintergreen Resort Cabin < Half Mile to Ski!

NEW! Wintergreen Resort Cabin < Half Mile to Ski!

Roseland, VA
NEW! Wintergreen Resort Cabin < Half Mile to Ski!
A-Frame Cabin w/Grill, Steps to Wintergreen Slopes

A-Frame Cabin w/Grill, Steps to Wintergreen Slopes

Nellysford, VA
A-Frame Cabin w/Grill, Steps to Wintergreen Slopes
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.

Everything you need to know about Wintergreen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on … and on. 

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wintergreen vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wintergreen. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Wintergreen vacation rentals range between $270 per night and $270 per night.

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wintergreen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wintergreen vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wintergreen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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