Photo by Rebecca Brent

Find Family Hotels in Wintergreen, VA

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Wintergreen Family Hotels

This weekend
Next weekend

Top Wintergreen Family Hotels

Clarion Pointe Staunton East

2.5 star property
8.6 out of 10, Excellent, (1017)
"Very nice hotel with great sunrise view"
The price is AED 283
AED 317 total
includes taxes & fees
27 Oct - 28 Oct
Clarion Pointe Staunton East

avid hotel Staunton by IHG

2.5 star property
9.0 out of 10, Wonderful, (1000)
"The location of the hotel was great, a short walk to restaurants."
The price is AED 334
AED 372 total
includes taxes & fees
19 Oct - 20 Oct
avid hotel Staunton by IHG

Comfort Inn & Suites Raphine - Lexington near I-81 and I-64

2.5 star property
7.8 out of 10, Good, (523)
"Very convenient to hwy"
The price is AED 336
AED 388 total
includes taxes & fees
5 Oct - 6 Oct
Comfort Inn & Suites Raphine - Lexington near I-81 and I-64

Retreat @ 3 Ridges / 2min->Slopes / Walk to Dining

2.0 star property
10.0 out of 10, Exceptional, (21)
"Loved our short stay at the property. Everything was as described. Would stay again."
The price is AED 294
AED 1,023 total
includes taxes & fees
5 Oct - 6 Oct
Retreat @ 3 Ridges / 2min->Slopes / Walk to Dining

The Modern Mountain Condo

10.0 out of 10, Exceptional, (28)
"Ideal location for skiing at Wintergreen. "
The price is AED 368
AED 891 total
includes taxes & fees
2 Oct - 3 Oct
The Modern Mountain Condo

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

10.0 out of 10, Exceptional, (23)
"The bed was very comfortable and the hot tub was perfect. Enjoyed the views"
The price is AED 598
AED 1,455 total
includes taxes & fees
20 Oct - 21 Oct
Cozy chalet w/ king beds, fireplace, and hot tub. Dog-friendly! Close to hiking.

4BR Near Slopes • Mid-Century Vibes • Hot Tub • Game Room • Family Friendly

9.4 out of 10, Exceptional, (3)
"Peaceful family trip. The cabin was beautiful, lots of space, and very clean. The cabin had everything we needed. The game room, board games and puzzles were a hit with our kids. Hot tub was huge, clean had its own separate gated area. "
The price is AED 680
AED 1,992 total
includes taxes & fees
7 Oct - 8 Oct
4BR Near Slopes • Mid-Century Vibes • Hot Tub • Game Room • Family Friendly

The Distinguished Squirrel Chalet walking distance

9.8 out of 10, Exceptional, (6)
"The house was beautiful and well stocked. The owner thought of everything and all the light switches were labeled which helped a lot. All of the appliances were top notch and the Keurig coffee maker had everything that was needed. Beds were very comfortable and each room had its own thermostat. Overall, excellent stay!"
The price is AED 716
AED 1,634 total
includes taxes & fees
2 Oct - 3 Oct
The Distinguished Squirrel Chalet walking distance

Spacious 5 bedroom modern home with mountain views galore. Sauna + EV charger.

10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay! The home was amazing and very well appointed. We enjoyed local breweries and hiking!"
The price is AED 1,308
AED 3,147 total
includes taxes & fees
28 Oct - 29 Oct
Spacious 5 bedroom modern home with mountain views galore. Sauna + EV charger.

Spacious and Updated Home in Wintergreen

10.0 out of 10, Exceptional, (4)
"Family bonding time with husband, son, daughter-in-law and two grand boys. The home was spotless - open with wonderful views. Everything we needed was at our fingertips - even pencils for games and flashlights throughout the house. Location is great - close to the slopes and snow tubing. We will return to try the snow tubing! Perfect winter break!"
Spacious and Updated Home 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.

Top Wintergreen Hotel Reviews

Explore a world of travel with Expedia

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.