Deals on vacations and trips to Wintergreen
Save when you book Wintergreen package deals
Wintergreen flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Charlottesville-Univ Area by IHG
The Meadows
per person
Oct 5 - Oct 9
found 22 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Charlottesville (CHO)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a picnic area are also offered.
Omni Charlottesville Hotel
North Downtown
per person
Oct 5 - Oct 9
found 22 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Charlottesville (CHO)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and valet parking. Enjoy the gym and perks like free self parking.
Dinsmore Boutique Inn
Venable
per person
Oct 5 - Oct 9
found 22 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Charlottesville (CHO)
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free cooked-to-order breakfast each morning. A terrace and wedding services are also provided.
Graduate by Hilton Charlottesville
Venable
per person
Oct 5 - Oct 9
found 22 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Charlottesville (CHO)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.
Kimpton The Forum Hotel by IHG
UVA
per person
Oct 5 - Oct 9
found 22 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Charlottesville (CHO)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 10 conference rooms on site, along with the valet parking and WiFi in public areas. A garden, a communal living room, and luggage storage are also on offer.
Top Wintergreen hotels deals
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
This condo features an outdoor pool and an indoor pool. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
Ski-in/ski-out access and a hot tub are featured at this smoke-free vacation home. There's a gym on site, and laundry facilities and barbecue grills are also offered.
Hot Tub
Kitchen
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
$414 nightly
The price is $465 total per night
$465 total
Jul 28 - Jul 29
Total includes taxes and fees
A hot tub is featured at this cottage, along with laundry facilities.
Hot Tub
Kitchen
Sleep Inn Staunton
222 Jefferson Hwy, Staunton, VA
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $104 total per night
$104 total
Aug 3 - Aug 4
Total includes taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Luggage storage and a safe deposit box are also provided.
Breakfast included
Pet friendly
Hotel 24 South
24 South Market Street, Staunton, VA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $123 total per night
$123 total
Aug 11 - Aug 12
Total includes taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, a 24-hour business center, and a lobby fireplace are also offered.
Pool
Pet friendly
Howard Johnson by Wyndham Staunton
268 N Central Ave, Staunton, VA
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $79 total per night
$79 total
Jul 29 - Jul 30
Total includes taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. The front desk is staffed around-the-clock and free newspapers are on offer.
Pool
Breakfast included
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.
Popular places to visit
Wintergreen Resort
4.5/5(79 reviews)
Hit the slopes in Nellysford with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area.
Bold Rock Hard Cider Nellysford Cidery
4.5/5(6 reviews)
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.
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.
Frequently asked questions
Photos of local treasures
Browse Wintergreen vacation photos for more inspiration
Top all inclusive vacation packages with airfare
Book a vacation to Wintergreen
Most popular
Hotels
Flights
Cars
Activities