Wintergreen Vacation Packages

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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.

Wintergreen Hotel Deals

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
Roseland
The price is CA $245 per night from Jun. 2 to Jun. 3
CA $245
CA $566 total
includes taxes & fees
Jun 2 - Jun 3
9.4/10 Exceptional! (216 reviews)
PhD Graduation weekend
"We had a great time. The house was comfortable and the area is beautiful! The only issues we had were a humming of the fan in the master bedroom upstairs, the door lock didn’t work for us (but the owners helped with this and all was well), and we had a hard time finding where to dump trash. The hot ..."

Reviewed on May 12, 2024

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
Wintergreen
10/10 Exceptional! (192 reviews)
Wintergreen getaway
"This is at least the third time we have stayed in this condo unit in the last two years. There is a reason we keep coming back; it is absolutely beautiful, both the accommodations and Mountain Views. I highly recommend!"

Reviewed on May 28, 2024

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Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Roseland
10/10 Exceptional! (269 reviews)
Anniversary getaway
"We thoroughly enjoyed our stay at this condo. Quiet neighborhood and very comfortable. Appreciated all the basics offered that other rentals do not such as soap, garbage bags, toilet paper. But the owners went above that and had lotions, specialty soaps, cleaning supplies etc. Well stocked kitchen ..."

Reviewed on May 20, 2024

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Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
See all 1,205 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Wintergreen vacation package cost?
Starting from a low , a package is your gateway to affordable travel. Put together your Wintergreen getaway by choosing from our extensive range of hotels, airfares and rental cars.
How do I get a cheap travel package to Wintergreen?
Bundling your flight and hotel with Expedia won’t just save valuable time — it’ll save you dollars too. A Wintergreen vacation package makes it simple to arrange the perfect trip. With more than 550 airlines across the world to pick from, finding convenient flights that fit your schedule will be no sweat. On top of that, we’ve got over 1,000,000 hotels globally to select from. Now that’s what you call choice. No matter who you are, Expedia puts the world within your reach.
Where should I stay in Wintergreen?
You’ll want to stay where the action is. Many people like to book hotels in the vicinity of popular attractions, such as Wintergreen Resort, Bold Rock Hard Cider Nellysford Cidery and Stoney Creek Golf Course.
What are the top hotels in Wintergreen?
Many people opt to stay at Wintergreen Five Star Rated One Bedroom Condo At Affordable Prices in Pedlars Edge. If it’s your first visit to Wintergreen, you’ll receive a warm welcome here.
How far in advance should I book my Wintergreen vacation?
Browse Expedia to compare flights as soon as you know your travel dates. You can usually purchase a ticket up to 12 months before departure. If it’s too early for your preferred air carrier, or you have to book last minute, don’t despair. Cheap fares to Wintergreen sometimes appear a few weeks before departure.
What does an Expedia Wintergreen travel package include?
Flights, car rentals and hotels — we connect you to the very best bargains. All you’ll have to do is decide on your preferred combination. Once you’ve made your booking, you can add on the exciting stuff like sightseeing activities. Our travel packages make it easy to customize an amazing Wintergreen vacation.
What should I know before booking a Wintergreen travel package?
You can look forward to saving with an Expedia travel package. Bundle your airfares, rental cars and hotels and unlock great discounts. Hotels aren’t your only choice, though. Book with us and choose from beach villas, rural cottages and everything in between!
Can I choose my airline with a Wintergreen Expedia vacation package?
Yes, the choice is yours. Expedia has access to more than 550 airlines globally, so you can customize your Wintergreen trip according to your travel needs.
If I'm not able to travel, can I cancel my Wintergreen vacation package?
Yes, you can. We totally understand that life happens, so we’re happy to help if you have to make changes to your Wintergreen vacation package. It may be possible to cancel or amend your itinerary at no cost if you’ve booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Wintergreen

Image for Wintergreen Resort

Wintergreen Resort

5/5(1 review)

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

Wintergreen Resort
Image for Bold Rock Hard Cider Nellysford Cidery

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.

Bold Rock Hard Cider Nellysford Cidery
Image for Stoney Creek Golf Course

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.

Stoney Creek Golf Course

What to do in Wintergreen

Image for Tesla Happy Hour & Dinner Tour - Charlottesville/Wintergreen

Tesla Happy Hour & Dinner Tour - Charlottesville/Wintergreen

CA $169
Per adult
Tesla Happy Hour & Dinner Tour - Charlottesville/Wintergreen
Image for Blue Ridge Parkway Tour: Self-Guided Drive

Blue Ridge Parkway Tour: Self-Guided Drive

CA $30
Per adult
94% of travellers recommend
Blue Ridge Parkway Tour: Self-Guided Drive
Image for East Coast USA: Self-Guided Driving & Walking Tour Bundle

East Coast USA: Self-Guided Driving & Walking Tour Bundle

CA $102
Per adult
East Coast USA: Self-Guided Driving & Walking Tour Bundle
See all activities in Wintergreen
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.