Wintergreen Holidays

Photo by Rebecca Brent

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Top hotels in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Roseland
The price is €371 per night from 7 Aug to 8 Aug
€371
7 Aug - 8 Aug
includes taxes & fees
9.6/10 Exceptional! (260 reviews)
"Great spot for a summer weekend mountain getaway."

Reviewed on 14 Jul 2025

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

Wintergreen
9.8/10 Exceptional! (220 reviews)
Mother/daughter getaway
"Beautiful, clean, comfortable, spectacular views. The property was exactly as advertised and pictures were accurate. Kitchen had everything you need if you decide to cook-in. Pots and pans in great shape. This was the best of any rental that we have stayed in. It is a lovely property. Highly recommend ..."

Reviewed on 20 May 2025

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Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Nellysford
The price is €408 per night from 22 Jul to 23 Jul
€408
22 Jul - 23 Jul
includes taxes & fees
9.8/10 Exceptional! (19 reviews)
Perfect location
"We had such a great girls weekend!! The Cottage was so cute, fun, clean and beds were super comfy. The house was in the perfect location for everything. Can’t wait to go back."

Reviewed on 10 Mar 2025

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
See all 1,194 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.

What to do in Wintergreen

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

€20
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Sharp Top Mountain

Blue Ridge Parkway Virginia Self-Guided Audio Tour

€11
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

€14
per traveller
Shenandoah National Park Self-Guided Audio Tour
See all activities in Wintergreen

Frequently asked questions

How much does a Wintergreen holiday package cost?
You'll find cheap prices on Expedia for your Wintergreen break. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Wintergreen costs.
What are the cheapest months to go to Wintergreen?
If you'd like to score a cheap Wintergreen holiday package, consider travelling in March, April and August. You'll generally find better rates on flights and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Wintergreen?
The ideal duration of your Wintergreen holiday depends on what you'd like to see. Generally, a handful of days to a week will give you plenty of time to check out all the top sights and explore some hidden gems along the way.
How to find the best Wintergreen package deals?
Begin your search for a Wintergreen package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Wintergreen package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Wintergreen adventure off to a flying start.
Is it cheaper to book a Wintergreen holiday as a package?
You can enjoy significant savings on your next Wintergreen break by booking a customised holiday package. Check the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Wintergreen?
If you've got your Wintergreen travel dates locked in, book early to snap up some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Wintergreen?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Wintergreen.
  2. Work out your budget: Ensure you have enough money to pay for everything from meals and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Wintergreen.
  3. Decide how long to go for: Now that you're more familiar with Wintergreen, you can figure out the ideal length of your holiday. Put together a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Wintergreen holiday package that brings all your bookings together.

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