Wintergreen Vacation Packages 2026 from $589

Wintergreen flight + hotel vacation packages

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

Oakhurst Inn at the University

Jefferson Park Avenue

$589

per person

Sep 23 - Sep 25

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 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.

The Doyle Hotel

Starr Hill

$845

per person

Sep 23 - Sep 25

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.

Sonesta ES Suites Charlottesville University

Barracks Road

$985

per person

Oct 6 - Oct 11

found 1 day ago

Roundtrip flight included

Phoenix (PHX) to Charlottesville (CHO)

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Little Mod Hotel at the University

Venable

$870

per person

Sep 4 - Sep 7

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.

Dinsmore Boutique Inn

Venable

$973

per person

Sep 27 - Oct 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Top Wintergreen hotels deals

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

Roseland VA

$224 nightly

$251 total

Aug 18 - Aug 19

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

Roseland VA

Get rates

This condo features laundry facilities.

Kitchen

Washer

Endless Mountain Top Views from All The Way Up!

Wintergreen Resort VA

$282 nightly

$317 total

Aug 23 - Aug 24

Total with taxes and fees

This condo features laundry facilities.

Pool

Kitchen

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

Roseland VA

$195 nightly

$218 total

Aug 6 - Aug 7

Total with taxes and fees

An outdoor pool is featured at this condo, along with laundry facilities.

Pool

Kitchen

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA

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

Pool

Hot Tub

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Wintergreen Resort VA

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Ski-in/ski-out access and an outdoor pool are featured at this smoke-free condo. Laundry facilities are provided for your convenience.

Pool

Kitchen

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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.

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.

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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 $589. 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.