Deals on vacations and trips to Wintergreen

Save when you book Wintergreen package deals

Choose two or more items and save on your trip:

Wintergreen flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3 out of 5
The Meadows
Price was $619, price is now $533 per person
$533
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Charlottesville (CHO)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $1,008, price is now $803 per person
$803
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Charlottesville (CHO)
This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A terrace, concierge services, and wedding services are also on offer.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $715, price is now $574 per person
$574
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Charlottesville (CHO)
This hotel features a restaurant, free WiFi in public areas, and a picnic area. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Express check-in and express check-out are also provided.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $731, price is now $593 per person
$593
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Charlottesville (CHO)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the sauna and conveniences like a 24-hour front desk and concierge services.
Boar's Head Resort

Boar's Head Resort

4 out of 5
Ednam
Price was $762, price is now $634 per person
$634
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Charlottesville (CHO)
This luxury hotel features a golf course, a full-service spa, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 3 outdoor pools and perks like free self parking and free WiFi.

Top Wintergreen hotels deals

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

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

Roseland VA
$216 nightly
The price is $242 total per night
$242 total
Oct 6 - Oct 7
Total with taxes and fees
A hot tub is featured at this condo, along with laundry facilities.
Pool
Hot Tub
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Roseland VA
Get rates
This condo features laundry facilities.
Kitchen
Washer
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 VA
$220 nightly
The price is $247 total per night
$247 total
Nov 1 - Nov 2
Total with taxes and fees
This condo features laundry facilities.
Pool
Kitchen
Cozy Cabin with private HOT TUB!

Cozy Cabin with private HOT TUB!

Nellysford VA
Get rates
A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Large and Luxurious Exec 5BR Chalet

Large and Luxurious Exec 5BR Chalet

Wintergreen Resort VA
Get rates
This vacation home features ski-in/ski-out access, laundry facilities, and barbecue grills.
Kitchen
Washer
Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Resort VA
$227 nightly
The price is $255 total per night
$255 total
Oct 5 - Oct 6
Total with taxes and fees
This condo features laundry facilities.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Wintergreen
View all properties
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.

Stay near popular Wintergreen attractions

A waterfall in a forest with autumn leaves.

Wintergreen Resort

8.8/10 (140 reviews)
Hit the slopes in Wintergreen with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area.
See properties

Frequently asked questions

How much are vacation packages to Wintergreen?
With a Travelocity vacation package, you could be living it up in Wintergreen for a mere $533. Flights, tours and hotels — we've got you. You'll save a bunch just by bundling together your bookings. With everything taken care of before you leave, you can sit back, relax and enjoy the adventure.
How long should my Wintergreen vacation be?
Many travelers pack their bags and vacation in Wintergreen for around 3 nights. That gives you a rough guide, but don't let it restrict you. Whether you stay for a day or two to see the big attractions or hang around to experience this place like a local, an unforgettable adventure awaits.
Where can I get the best vacation package deals for Wintergreen?
Travelocity can help you snag a terrific Wintergreen package deal. With no less than 400 airlines and 1,000,000 properties across the world, you're sure to find the perfect mix.
Why should I book my Wintergreen vacation bundle with Travelocity?
Because you'll never roam alone if you book through us, and we offer 24/7 customer support and first-rate service to boot. Add to that our Price Match Guarantee and countless experiences and destinations to select from. We're here to help you have the trip of a lifetime.
Can I save on my Wintergreen car rental if I bundle it with a hotel or flight?
Combining your hotel, flight and car into a Wintergreen vacation package is the easiest way to land the best deal. Plus, having your own rental car gives you absolute freedom to get to all those big-name sights you want to check out. Situated 120 mi from Wintergreen, White House is one place that should feature on your itinerary. Load up the car and make a day trip of it.
Which airport is best for Wintergreen?
Charlottesville-Albemarle Airport (CHO) (30 mi away from the city center), Lynchburg Regional Airport (LYH) (40 mi away from central Wintergreen) and Shenandoah Valley Regional Airport (SHD) (25 mi away from central Wintergreen) are the best options for Wintergreen.
Where should I stay when visiting Wintergreen?
If you're searching for somewhere to lay your head, consider the Mountain Inn Lodge 70 with Wintergreen Advantage. It's the top pick for many visitors.

Photos of local treasures

Browse Wintergreen vacation photos for more inspiration

A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.
A mountainous landscape with lush green hills and a clear blue sky with contrails.
A snow-covered mountain landscape with a ski resort and a clear blue sky.
A mountainous landscape with dense forests and a valley.
A stone tunnel with moss-covered walls and a rocky hillside.

Explore More Ways to Travel with Travelocity