Photo by Melissa Smestad

Find Family Hotels in Wintergreen, VA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Wintergreen Family Hotels

Tonight
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Top Wintergreen Family Hotels

Interior
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

2.0 star property
Wintergreen Resort
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space
10.0 out of 10, Exceptional, (24)
The price is AED 331
AED 1,072 total
includes taxes & fees
23 Nov - 24 Nov
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Fireplace
The Modern Mountain Condo

The Modern Mountain Condo

Wintergreen Resort
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
10.0 out of 10, Exceptional, (31)
The price is AED 368
AED 883 total
includes taxes & fees
23 Nov - 24 Nov
The Modern Mountain Condo
Outdoor spa tub
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Wintergreen Resort
  • Hot Tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
10.0 out of 10, Exceptional, (24)
The price is AED 397
AED 1,213 total
includes taxes & fees
3 Dec - 4 Dec
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Property grounds
Ready for Ski Season! Book NOW!

Ready for Ski Season! Book NOW!

Wintergreen Resort
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Fireplace
  • Microwave
9.8 out of 10, Exceptional, (25)
Ready for Ski Season! Book NOW!
Game room
4 BD Modern Cabin w/ Game Room + Golf Course View

4 BD Modern Cabin w/ Game Room + Golf Course View

Wintergreen Resort
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning
10.0 out of 10, Exceptional, (2)
The price is AED 878
AED 2,654 total
includes taxes & fees
24 Nov - 25 Nov
4 BD Modern Cabin w/ Game Room + Golf Course View
Pool
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Roseland
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
9.6 out of 10, Exceptional, (142)
The price is AED 404
AED 916 total
includes taxes & fees
1 Dec - 2 Dec
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Design-Lover’s Getaway • Game Room • Hot Tub

Design-Lover’s Getaway • Game Room • Hot Tub

Wintergreen Resort
  • Arcade/game room
9.8 out of 10, Exceptional, (6)
The price is AED 551
AED 2,095 total
includes taxes & fees
23 Nov - 24 Nov
Design-Lover’s Getaway • Game Room • Hot Tub
Exterior
Bide-a-Wee- Hike the Trails! Close to the slopes!

Bide-a-Wee- Hike the Trails! Close to the slopes!

Wintergreen Resort
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
9.4 out of 10, Exceptional, (11)
The price is AED 2,204
AED 3,772 total
includes taxes & fees
21 Dec - 22 Dec
Bide-a-Wee- Hike the Trails! Close to the slopes!
Terrace/patio
Cozy Cute Condo in Wintergreen Resort

Cozy Cute Condo in Wintergreen Resort

Roseland
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Fireplace
  • Lake view
10.0 out of 10, Exceptional, (2)
The price is AED 580
AED 1,204 total
includes taxes & fees
23 Nov - 24 Nov
Cozy Cute Condo in Wintergreen Resort
Property grounds
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking

Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking

Chestnut Springs
  • Arcade/game room
10.0 out of 10, Exceptional, (15)
The price is AED 590
AED 1,701 total
includes taxes & fees
24 Nov - 25 Nov
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now

Top Wintergreen Hotel Reviews

Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

10/10 Excellent
"Amazing location. Wonderful sunrise view from porch. Walk to restaurants. We had a great time in Wintergreen."
Nancy G. 1-night trip
Posted 2 months ago
Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

Explore a world of travel with Expedia

Frequently asked questions

What's Wintergreen like for family-friendly vacations?
The destination of Wintergreen is a good option if you've been considering a getaway with the kids. The excursions, recreation options, and mountain views are just a few things that make this an attractive family vacation spot. Arrange a flight into Weyers Cave, VA (SHD-Shenandoah Valley Regional), which is located 26.2 mi (42.1 km) from the city center.
When's the best time to book a family-friendly vacation in Wintergreen?
The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Wintergreen is 48 inches.
What's there to see and do with your family in Wintergreen?
While you are visiting Wintergreen, you might want to round up the kiddos and make time to see interesting attractions such as Wintergreen Resort, Rockfish Gap Entrance Shenandoah, and Walton's Mountain Museum. Make sure you have lots of time for activities like Pippin Hill Farm & Vineyards and Shenandoah Valley Art Center.