Wintergreen Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Wintergreen Vacation

When a break in the city is calling, answer it with a Wintergreen vacation package. The neighborhood of Laurel Ridge, which is good for skiing, adventure sports and mountain biking, makes a fantastic base for your adventures. Fill your days with visits to Bold Rock Hard Cider Nellysford Cidery, Stoney Creek Golf Course and Hill Top Berry Farm & Winery, some of the things you simply have to see during a trip to Wintergreen. Don't delay exploring this city any longer. Your dream Wintergreen vacation is only a few clicks away with Expedia.

Where to stay in Wintergreen

Find the best Wintergreen areas and neighborhoods for the activities you enjoy most. Learn more about Wintergreen
A person taking a photo of a mountainous landscape with a wooden fence in the foreground.

Treeloft

When in Treeloft, you can plan a visit to Wintergreen Resort and Raven's Roost Overlook, some noteworthy sights in the nearby area.

Find hotels in Treeloft

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Wintergreen Hotel 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
The price is CA $133 per night from Nov 18 to Nov 19
CA $133
CA $339 total
Nov 18 - Nov 19
includes taxes & fees
9/10 Wonderful! (339 reviews)
"My wife Teresa and I have been renting this condo for 12 yrs in a row. For the money, its the best rental in Wintergreen! Already booked and paid for for next year's visit. Accessibility is another plus with this condo that no one ever mentions. we are both 60 yrs old so this is important and if ..."

Reviewed on Oct 24, 2026

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Cozy Cabin with private HOT TUB!

Cozy Cabin with private HOT TUB!

Nellysford VA
10/10 Exceptional! (54 reviews)
"Beautiful location. Private. Hosts were great!!"

Reviewed on Oct 27, 2026

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Cozy Cabin with private HOT TUB!
Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

Wintergreen Resort VA
9.8/10 Exceptional! (9 reviews)
"We had a lovely experience staying at this property. We stayed two nights with our 3 kids (ages 5, 7, 9) and we all thoroughly enjoyed the hot tub, Pac Mac console and enjoyed making a fire and roasting s'mores. The house was very clean, beds were comfortable and communication was prompt. We did ..."

Reviewed on Oct 20, 2026

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Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard
See all 654 properties in Wintergreen
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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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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What to do in Wintergreen

Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

CA $24
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

CA $34
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

CA $18
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
See all activities in Wintergreen

Frequently asked questions

How much does a Wintergreen vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Wintergreen costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Wintergreen?
March, April and August are great times to search for cheap Wintergreen vacation packages. Choosing to travel in less busy periods means you can generally find better prices on flights and accommodations.
How many days is enough for Wintergreen?
Wintergreen vacations can be as short or long as you like, but to get a real feel for this destination, we'd say 3 days is a good ballpark. In this timeframe, you can fit in headline attractions like Stoney Creek Golf Course and Hill Top Berry Farm & Winery and seek out some underrated gems. Don't forget to visit neighbourhoods such as Chestnut Springs and Treeloft either. If you plan wisely, you can even allow for a day trip outside of Wintergreen too.
How to find the best Wintergreen package deals?
Use Expedia's filters to find some unbeatable Wintergreen package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Wintergreen package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Wintergreen vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the freedom to create a customized Wintergreen vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Wintergreen?
Land fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Wintergreen getaway.
How to plan a trip to Wintergreen?

  1. Choose when to get away: Check your schedule and get packing. Your favourite time of year and the type of activities on offer will also help you decide when to escape to Wintergreen.
  2. Figure out your budget: Make sure you have enough money to cover everything from food and transportation to flights and activities. Your accommodations will likely be the biggest expense during your trip to Wintergreen.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Wintergreen. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the ideal Wintergreen vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.