Find Hotels with a Pool in Wintergreen, VA

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Check availability on Wintergreen Hotels with a Pool

Our top choices for Wintergreen hotels with a pool

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

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (152 reviews)
  • cleanliness
    Mountain hideaway offers relaxation with sparkling pool and nearby hiking trails to explore.
"Perfect size condo for a couple and one pet. Ideally situated for many activities: hiking, golf, tennis, pickleball, swimming, etc. Very close to multiple restaurants. The only downside was the noise from the unit above (the TV and personal conversations are easily heard through the ceiling)."
United States
Jason E.
The price is AED 404
AED 899 total
includes taxes & fees
11 May - 12 May
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (56 reviews)
"We had a fun visit to the mountains of VA on our annual family vacation. The property was clean and had plenty of space for our crew. The long dining table had room enough for all 8 of us to enjoy meals and games together. The kitchen was equipped with the basics and there were ample dishes and glasses for us to have a day of meals before having to run the dishwasher. A pool is a little over a mile away and there is a bocce court and corn hole boxes just across from the property which we used....
United States
Becky M.
Spacious + Serene Mtn Top Escape, 4 En Suites

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (49 reviews)
  • cleanliness
    Secluded swimming in private fenced pool at modern mountain condo, steps from Wintergreen Resort slopes.
"The property was just as described and the communication was a breeze. The view from the unit’s deck was beautiful. "
United States
Susan
The price is AED 346
AED 851 total
includes taxes & fees
11 May - 12 May
Where the Trail Ends

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (34 reviews)
"Well set up and comfortable "
United States
Rena L.
The price is AED 419
AED 973 total
includes taxes & fees
11 May - 12 May
Wintergreen Condo -Steps to Ski and restaurants

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"Clean and accommodating. The host took care of all the details. Loved the game closet. It’s the little things that make a big difference. "
United States
Shalonda
The price is AED 349
AED 1,025 total
includes taxes & fees
11 May - 12 May
Laurelwood Hollow: Walk to Ski & Swim

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (14 reviews)
"From location, to comfort, to ease, this condo was perfect for our weekend getaway at wintergreen!!!"
United States
Emily R.
The price is AED 496
AED 1,188 total
includes taxes & fees
11 May - 12 May
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (103 reviews)
"The community pool was awesome too!"
United States
Roberta R.
The price is AED 275
AED 853 total
includes taxes & fees
11 May - 12 May
Endless Mountain Top Views from All The Way Up!

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (111 reviews)
"My husband and I and another couple stayed for a long weekend in this beautiful condo. Everything from booking to checking out went well. We arrived to the condo after a long day to a complimentary bottle of wine, a nice welcome note and a beautiful sunset. The condo is very nicely decorated, has 2 very comfortable king bedrooms with nice linens, has a nice balcony with comfy chairs with new cushions and a heat lamp, and the kitchen is well stocked with supplies and coffee and tea and spices and...
United States
Judy C.
The price is AED 612
AED 1,194 total
includes taxes & fees
11 May - 12 May
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (127 reviews)
"Host gave us an early check-in after our Crabtree Falls hike was rained out. We were grateful to not have to wait it out in the car with eager children. Condo was clean and well equipped. Much better in person then the pictures. The kids called it "posh". Many critters to be seen from the deck. Our favorite part was the fireplace. The property management does not keep wood stocked as promised so it's wise to pick some up. Mattress in master is very comfortable. Kids enjoyed the use of indoor...
United States
Orion L.
The price is AED 426
AED 949 total
includes taxes & fees
11 May - 12 May
Escape to the Blue Ridge Mountains at Wine-tergreen!

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (13 reviews)
"This was a wonderful place for family and friends. The host was very responsive, the kitchen was well stocked and the beds and linens were very comfortable! The location was perfect and close to the slopes. A fantastic stay in a fantastic cabin! "
United States
Stacy M.
The price is AED 424
AED 1,391 total
includes taxes & fees
11 May - 12 May
Serenity Cabin-Woodland Retreat
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.

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Frequently asked questions

What are some accommodations with pools in Wintergreen?
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.: Features kitchens, a communal pool, and televisions. Cozy Cabin with private HOT TUB!: Offers kitchens, a communal pool, and Smart TVs. Best views on Mountain! Breathtaking 5 Star condo! Book Summer and Fall now!: Provides kitchens, a communal pool, and Smart TVs. New Build! Log Cabin with Hot Tub in Wintergreen: Offers complimentary wireless internet access, a communal pool, and kitchens. Endless Mountain Top Views from All The Way Up!: Features kitchens, a communal pool, and Smart TVs.
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 Bold Rock Hard Cider Nellysford Cidery, Stoney Creek Golf Course, and 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.