Wintergreen Vacations

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    Save up to SAR 390 when you book a flight and hotel together*
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    Plan, book, and manage your trip all in one place

Find the Best Wintergreen Vacation Packages

Wintergreen Hotel Deals

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
9.6/10 Exceptional! (245 reviews)
134 Gumtree Dr, Roseland VA
"Excellent"

Reviewed on 6 March 2025

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!
Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!
Wintergreen
9.8/10 Exceptional! (216 reviews)
Wintergreen
"Clean, well maintained, phenomenal views. Comfy beds, lots of blankets, and pillows. We will definitely book again!"

Reviewed on 2 March 2025

Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Roseland
10/10 Exceptional! (306 reviews)
Family Favorite!
"I’ve stayed here a few times now with various members of my family and all of us love this place! The accommodations are great, the place is well stocked with careful attention to detail, and we always look forward to returning. Thanks again for a great stay!"

Reviewed on 10 March 2025

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

Frequently asked questions

How much does a Wintergreen vacation 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 vacation to Wintergreen costs.
What are the cheapest months to go to Wintergreen?
If you’d like to score a cheap Wintergreen vacation package, consider traveling in March, April and August. You’ll generally find better rates on flights and hotels during these months — ideal for budget-conscious travelers.
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 vacation as a package?
You can enjoy significant savings on your next Wintergreen break by booking a customized vacation 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 vacation 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 vacation. 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 vacation package that brings all your bookings together.

Discover the most popular places to visit in Wintergreen