Holiday Rentals in Wintergreen

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Our top choices for Wintergreen holiday rentals

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (105 reviews)
"Great stay with a fabulous view! Very cozy and comfortable! We had a wonderful little getaway!"
United States
Vicki E.
The price is €232
includes taxes & fees
29 Mar - 30 Mar
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is €215
includes taxes & fees
30 Mar - 31 Mar
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (13 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is €189
includes taxes & fees
26 Mar - 27 Mar
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Little Mountain Haven. True ski-in, ski-out. First floor!

Little Mountain Haven. True ski-in, ski-out. First floor!
Wintergreen Resort
10.0 out of 10, Exceptional, (9 reviews)
"Great little ski and ski out Property"
United States
Richard
The price is €167
includes taxes & fees
26 Mar - 27 Mar
Little Mountain Haven. True ski-in, ski-out. First floor!

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
The price is €244
includes taxes & fees
26 Mar - 27 Mar
Laurelwood Hollow: Walk to Ski & Swim

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (46 reviews)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is €201
includes taxes & fees
29 Mar - 30 Mar
The Modern Mountain Condo

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (32 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is €227
includes taxes & fees
27 Mar - 28 Mar
Wintergreen Condo -Steps to Ski and restaurants

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (316 reviews)
"Gorgeous view. Our fourth time here, and still a lovely place. "
United States
Elaine B.
The price is €219
includes taxes & fees
29 Mar - 30 Mar
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (36 reviews)
"Great"
United States
Daniel W.
The price is €342
includes taxes & fees
30 Mar - 31 Mar
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (40 reviews)
"Our host were great communicators and everything was very pleasant! A great stay and would do it again in a heartbeat :-)"
United States
william M.
The price is €252
includes taxes & fees
26 Mar - 27 Mar
Panoramic Peak: Wintergreen Condo with Views

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (30 reviews)
"Great condo and n the Wintergreen area. Absolutely beautiful with the fall foliage colors. Close to so many breweries and wineries."
United States
Anna D.
The price is €216
includes taxes & fees
30 Mar - 31 Mar
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (99 reviews)
"Highly recommend staying at this beautiful condo! The kitchen has everything you need, the views are breath-taking, the condo is very clean, and the hosts are very communicative and helpful. Will definitely stay here again the next time we travel to the area!"
United States
Allison N.
The price is €221
includes taxes & fees
26 Mar - 27 Mar
Endless Mountain Top Views from All The Way Up!

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (126 reviews)
"Everything was as is listed, we were off season so hiking and scenic views is what there was to do, relaxing. Host was accessible on phone, place was clean. "
United States
David L.
The price is €222
includes taxes & fees
30 Mar - 31 Mar
Escape to the Blue Ridge Mountains at Wine-tergreen!

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful view!"
United States
Serge L.
Mountain View Vista: Resort Condo w/ Views

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (34 reviews)
"The home was clean and in a great location to explore the Wintergreen area. Host was welcoming and responsive."
United States
Rob M.
The price is €280
includes taxes & fees
26 Mar - 27 Mar
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Wintergreen Resort Condo Available Now!!

Wintergreen Resort Condo Available Now!!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
The price is €276
includes taxes & fees
26 Mar - 27 Mar
Wintergreen Resort Condo Available Now!!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (28 reviews)
"Well stocked house with great layout for families or two couples. Great kitchen setup with everything you’ll need. Close to the resort and skiing. Close to hiking trails. "
United States
Jeremiah H.
The price is €283
includes taxes & fees
16 Apr - 17 Apr
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is €298
includes taxes & fees
8 Apr - 9 Apr
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Mountain Inn Studio 96 with Wintergreen Advantage

Mountain Inn Studio 96 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. "
United States
Lana
Mountain Inn Studio 96 with Wintergreen Advantage

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is €312
includes taxes & fees
26 Mar - 27 Mar
Blackwood Chalet
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.
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Top Wintergreen Hotel Reviews

Find out more about Wintergreen

Everything you need to know about Wintergreen holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wintergreen holiday 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 and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wintergreen holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wintergreen holiday rentals we have selected for you start as low as €201 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Wintergreen?

Yes, there are holiday rentals close to the most popular sights in Wintergreen, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffee shops during your trip.

What are some of the best holiday rentals that Wintergreen has to offer?

4 BR cabin mins to trails & breweries pets welcome: This highly rated holiday home rental in Wintergreen offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Some other top choices in Wintergreen are Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope and Upscale and Family-Friendly in Wintergreen.

How many holiday rentals are there in Wintergreen?

Choose from 223 Expedia holiday rentals in Wintergreen for a memorable holiday.

What can I see and do in Wintergreen?

While exploring the area, visit family-friendly sights like War Fields, or get outside and enjoy nature at George Washington National Forest. While here, Bold Rock Hard Cider Nellysford Cidery and Stoney Creek Golf Course are other places worth a visit.

What’s a holiday rental in Wintergreen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wintergreen. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway.