Wintergreen Holidays from £803

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Your Wintergreen Holiday

When a break in the city is calling, answer it with a Wintergreen holiday package. The neighbourhood 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 holiday is only a few clicks away with Expedia.

Top Wintergreen Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Bluegreen Shenandoah Crossing, Ascend Resort Collection

Bluegreen Shenandoah Crossing, Ascend Resort Collection

2.5 out of 5
per person
18 Aug - 24 Aug
found 19 hours ago
Return flight included
London (LON) to Charlottesville (CHO)
8.2/10 Very Good! (788 reviews)
Extra charges for some things

Reviewed on 30 Mar 2025

Wintergreen Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Charlottesville-Albemarle Airport (CHO)
Population
170
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Bold Rock Hard Cider Nellysford Cidery, Hill Top Berry Farm & Winery and Stoney Creek Golf Course

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, VA
The price is £282 per night from 14 Jul to 15 Jul
£282
14 Jul - 15 Jul
includes taxes & fees
9.6/10 Exceptional! (258 reviews)
Summer Vacation
"The house was just as described. Scott was very quick to respond and always pleasant. The hot tub was very nice and the house is set in a beautiful wooded area close to pools and a convenience store. Would definitely rent the house again."

Reviewed on 29 Jun 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, VA
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!
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
Wintergreen Resort, VA
10/10 Exceptional! (56 reviews)
Clean and has everything you need
"We stayed for a week. The house is located in a peaceful area hidden in the trees. It was a perfect getaway to recharge."

Reviewed on 30 Jun 2025

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Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
See all 1,193 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Popular places to visit

Wintergreen Resort

Wintergreen Resort

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
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

What to do in Wintergreen

Blue Ridge Parkway GPS-Guided Audio Tour

Blue Ridge Parkway GPS-Guided Audio Tour (Roanoke to Afton)

£11
per traveller
Blue Ridge Parkway GPS-Guided Audio Tour (Roanoke to Afton)
Sharp Top Mountain

Blue Ridge Parkway Virginia Self-Guided Audio Tour

£10
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

£11
per traveller
Shenandoah National Park Self-Guided Audio Tour
See all activities in Wintergreen

Frequently asked questions

How much does a Wintergreen travel package cost?
We make it simple to explore the world, with Wintergreen travel packages starting from just £803. You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add a few tours and experiences to your travel itinerary?
If I'm not able to travel, can I cancel my Wintergreen travel package?
Your situation can change in the blink of an eye, so yes. You may be able to cancel or alter your Wintergreen travel package for free within 24 hours of booking. For bookings older than that, you can still cancel and rebook, but your hotel, car rental company or airline may charge additional fees. Looking for more information? Check out our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Wintergreen?
You'll save piles of cash if you combine your flights, car rentals and hotels into a Wintergreen travel package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1,000,000 hotels worldwide, which means you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even bigger discounts! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Wintergreen holidays?
We do. Expedia has teamed up with online lender Klarna to help you easily pay for your holiday in manageable instalments. Simply choose the payment plan that works for you during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying a little each month sounds right for you, pick this option at checkout.
  • Pay in instalments holidays: If you'd like to pay for your escape across multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you want to grab an amazing deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Wintergreen?
We recommend staying near the action. Many travellers like to book hotels around popular attractions, such as Bold Rock Hard Cider Nellysford Cidery, Hill Top Berry Farm & Winery and Stoney Creek Golf Course.
What are the top hotels in Wintergreen?
Many travellers like to stay at Wintergreen Five Star Rated One Bedroom Condo At Affordable Prices in Pedlars Edge. If it's your first time visiting Wintergreen, you'll receive a warm welcome here.
How far in advance should I book my Wintergreen holiday?
Be rewarded with the widest variety at the lowest prices by booking your holiday to Wintergreen nice and early. Airlines typically advertise tickets anywhere up to a year prior to departure, so reserve your spot as soon as you can. Having said that, Expedia is committed to giving you the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Wintergreen travel package include?
That depends on what you want. If you're travelling solo, you might decide to combine hotels and flights. Bringing the whole family to Wintergreen? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the freedom to build your own travel package.
What should I know before booking a Wintergreen travel package?
Tailor deals to match your budget with an Expedia package. Hotels, airfares, rental cars --- we have them all. You'll save loads just by combining your bookings. Whether you're embarking on an adventure in the snow or sipping cocktails on a beach, your dream holiday is only clicks away.
Can I choose my airline with a Wintergreen Expedia travel package?
Yes, and with over 550 airlines to pick from all over the world, you're spoiled for choice. Have a look through the available options and see which airline fits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.