Wintergreen Vacation Packages 2025/2026 from $908

Wintergreen flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Little Mod Hotel at the University

Venable

$908

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

The Doyle Hotel

Starr Hill

$1,134

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. A coffee shop, a terrace, and a picnic area are also on offer.

Kimpton The Forum Hotel by IHG

UVA

$1,086

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 10 conference rooms on site, along with the valet parking and WiFi in public areas. A garden, a communal living room, and luggage storage are also on offer.

Oasis Near Charlottesville With Pool Grill

Save 100% on your flight

$3,836

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

This vacation home features free WiFi in public areas, a garden, and barbecue grills.

Oakhurst Inn at the University

Jefferson Park Avenue

$998

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottesville (CHO)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Self parking, a coffee shop, and a terrace are also offered.

Top Wintergreen hotels deals

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

Get rates

A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.

Hot Tub

Washer

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

Get rates

Ski-in/ski-out access and a hot tub are featured at this smoke-free vacation home. There's a gym on site, and laundry facilities and barbecue grills are also offered.

Hot Tub

Kitchen

The Modern Mountain Condo

$213 nightly

$239 total

Sep 24 - Sep 25

Total with taxes and fees

This condo features laundry facilities.

Pool

Kitchen

The Distinguished Squirrel Chalet walking distance

$361 nightly

$406 total

Sep 24 - Sep 25

Total with taxes and fees

This vacation home features ski-in/ski-out access, laundry facilities, and barbecue grills.

Kitchen

Washer

Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

Get rates

A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.

Pool

Hot Tub

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

Get rates

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.

Popular places to visit

Wintergreen Resort

Hit the slopes in Nellysford with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area.

Bold Rock Hard Cider Nellysford Cidery

You can take time to visit Bold Rock Hard Cider Nellysford Cidery during your travels to Nellysford. Discover the mountain views in this family-friendly area.

Stoney Creek Golf Course

Enjoy a round of golf in Nellysford at Stoney Creek Golf Course. Discover the mountain views and top-notch restaurants in this vibrant area.

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 $908. 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.