Photo by Rebecca Brent

Find Hotels with a Pool in Wintergreen, VA

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

Check availability on Wintergreen Hotels with a Pool

Top Wintergreen Hotels with a Pool

Property grounds
The Modern Mountain Condo
The Modern Mountain Condo
10.0 out of 10, Exceptional, (30)
"Ideal location for skiing at Wintergreen. "
$213 nightly
The price is $239
Oct 20 - Oct 21
Total with taxes and fees
The Modern Mountain Condo
Smart TV, fireplace, books
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
9.8 out of 10, Exceptional, (25)
"Lovely condo. Perfect size for us. Highly recommend, perfect location to go and visit wineries and breweries. Then come back and make a delicious meal or enjoy a beverage on the deck. "
$210 nightly
The price is $236
Oct 23 - Oct 24
Total with taxes and fees
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
Terrace/patio
Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Condo -Steps to Ski and restaurants
9.8 out of 10, Exceptional, (25)
"We had a great time and the place was just right."
$236 nightly
The price is $265
Oct 20 - Oct 21
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Pool
Mountain Inn Studio 96 with Wintergreen Advantage
Mountain Inn Studio 96 with Wintergreen Advantage
10.0 out of 10, Exceptional, (1)
"A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. "
$240 nightly
The price is $269
Oct 26 - Oct 27
Total with taxes and fees
Mountain Inn Studio 96 with Wintergreen Advantage
Pool
Timbers Lodge 26 with Wintergreen Advantage
Timbers Lodge 26 with Wintergreen Advantage
2.0 star property
10.0 out of 10, Exceptional, (2)
"Love staying here! It’s so close to the slope and the staff is great."
$264 nightly
The price is $296
Oct 19 - Oct 20
Total with taxes and fees
Timbers Lodge 26 with Wintergreen Advantage
Pool
Timbers Studio 46 with Wintergreen Advantage
Timbers Studio 46 with Wintergreen Advantage
10.0 out of 10, Exceptional, (2)
"We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple...
$240 nightly
The price is $269
Oct 19 - Oct 20
Total with taxes and fees
Timbers Studio 46 with Wintergreen Advantage
Pool
Mountain Inn Lodge 78 with Wintergreen Advantage
Mountain Inn Lodge 78 with Wintergreen Advantage
10.0 out of 10, Exceptional, (2)
"Had so much fun! Perfect stay!"
$264 nightly
The price is $296
Oct 19 - Oct 20
Total with taxes and fees
Mountain Inn Lodge 78 with Wintergreen Advantage
Pool
Laurelwood Hollow: Walk to Ski & Swim
Laurelwood Hollow: Walk to Ski & Swim
$265 nightly
The price is $279
Oct 22 - Oct 23
Total with taxes and fees
Laurelwood Hollow: Walk to Ski & Swim
Pool
Timbers Lodge 54 with Wintergreen Advantage
Timbers Lodge 54 with Wintergreen Advantage
8.0 out of 10, Very Good, (1)
$264 nightly
The price is $296
Oct 19 - Oct 20
Total with taxes and fees
Timbers Lodge 54 with Wintergreen Advantage
Pool
Diamond Hill Studio 09 with Wintergreen Advantage
Diamond Hill Studio 09 with Wintergreen Advantage
$278 nightly
The price is $312
Oct 19 - Oct 20
Total with taxes and fees
Diamond Hill Studio 09 with Wintergreen Advantage
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

Top Wintergreen Hotel Reviews

Hotel 24 South

Hotel 24 South

10/10 Excellent
"Historic building. Nice accommodations."
Jane 4-night trip
Posted 3 days ago
Hotel 24 South

Frequently asked questions

What are some accommodations with pools in Wintergreen?
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes: Condo, 1-minute walk from Wintergreen Resort. Features an indoor pool, an outdoor pool, and a full-service spa. NEW! Warren's Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort: Condo, 1-minute walk from Wintergreen Resort. Offers complimentary wireless internet access, a communal pool, and kitchens. The Modern Mountain Condo: Condo, 1-minute walk from Wintergreen Resort. Features complimentary wireless internet access, a communal pool, and kitchens. Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!: Vacation home, 1-minute walk from Wintergreen Resort. Offers complimentary wireless internet access, a communal pool, and kitchens. Cozy 6-bedroom cabin in Wintergreen Resort: Vacation home, 1-minute walk from Wintergreen Resort. Offers kitchens, a communal pool, and televisions.
What is there to see and do in Wintergreen?
Spend some time experiencing the great outdoors at George Washington National Forest. Discover sights such as Wintergreen Resort during your stay. The mountain views and skiing are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Wintergreen?
You may want to consider a place to stay with an outdoor swimming pool if you're planning to visit Wintergreen in the warmest months of July, August, or June when the average temperature is 73°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 38°F.

Explore a world of travel with Expedia