A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

Wintergreen Hotel Guide - Hotels with Pool in Wintergreen, Nellysford

  • 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 Hotels with Pool

Tonight
9 Sept - 10 Sept
Tomorrow
10 Sept - 11 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

Our top choices for Wintergreen hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by trees.
A modern kitchen with wooden cabinets, stainless steel appliances, granite countertops, and a built-in dishwasher.
A golf course with a sand bunker and a mountain backdrop.
A garden with a variety of flowers and trees at dusk.

1. 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
  • Mountain hideaway offers relaxation with sparkling pool and nearby hiking trails to explore.
€220
includes taxes & fees
10 Sept - 11 Sept
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.
A bedroom with a white bed, two bedside tables with lamps, a grey sofa, and a wall-mounted TV.
A compact kitchen with white cabinets, a black countertop, and two wooden chairs.
A wooden coffee table with playing cards and a lantern in a living room.

2. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
  • Secluded swimming in private fenced pool at modern mountain condo, steps from Wintergreen Resort slopes.
€170
includes taxes & fees
15 Sept - 16 Sept
Where the Trail Ends
A room with a wooden floor, a table with two stools, and a view through large windows with blinds.
A stone staircase leading up to a building surrounded by dense greenery.
A patio with a round table and four chairs, a decorative vase, and a door with a window.
A living room with a sofa, coffee table, and a dining area with a table and chairs. There is a ceiling fan, a kitchen area with a microwave and refrigerator, and large windows with blinds.

3. Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
€199
includes taxes & fees
14 Sept - 15 Sept
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.
A living room with two grey sofas, a wooden coffee table, a small wooden side table, and a floor lamp.
A bedroom with a bed, two bedside tables with lamps, a wall-mounted shelf with decorative items, and a window with blinds.
A living room with a fireplace, a dining area with a table and chairs, a kitchen with cabinets and a refrigerator, and a clock on the wall.

4. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
€232
includes taxes & fees
10 Sept - 11 Sept
Wintergreen Condo -Steps to Ski and restaurants
A rectangular swimming pool with a wooden deck surrounding it, equipped with lounge chairs and a small wooden building.
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.
A modern kitchen with a central island, bar stools, a refrigerator, and a microwave.
A wooden deck leading to a cabin surrounded by trees.

5. Three Little Bears

Three Little Bears
Nellysford
€237
includes taxes & fees
5 Oct - 6 Oct
Three Little Bears
A set of stone steps leading up to a house with a light-colored exterior.
A door with a wreath hanging on the wall beside it.
A wooden deck with a round table and chairs, overlooking a grassy area with trees.
A modern kitchen with granite countertops, a built-in oven, and a window.

6. Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
€227
includes taxes & fees
10 Sept - 11 Sept
Escape to the Blue Ridge Mountains at Wine-tergreen!
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.
A spacious living room with a fireplace, two sofas, a coffee table, and large windows offering a view.
A modern kitchen with white cabinets, a central island with bar stools, and a dining area with a wooden table and chairs.
A modern kitchen with white cabinetry, a granite countertop, and a built-in dishwasher.

7. Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
€314
includes taxes & fees
10 Sept - 11 Sept
Spacious + Serene Mtn Top Escape, 4 En Suites
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.
A sign reading "Vistas" with a flower bed in the foreground.
A kitchen with a coffee maker, a sink, and a framed black and white photo of a cityscape.
A modern kitchen with wooden cabinets, a black refrigerator, a stove, and a large window with a cityscape view.

8. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
€258
includes taxes & fees
10 Sept - 11 Sept
Panoramic Peak: Wintergreen Condo with Views
A two-story house with a stone foundation, a large front porch, and a chimney.
A living room with a sofa, a coffee table, a TV, and a fireplace.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dishwasher.
A kitchen with granite countertops, a stainless steel sink, wooden cabinets, a stone backsplash, a framed painting, and a bottle of hand soap.

9. Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
A bedroom with a large bed, a dresser, and a ceiling fan. There are two windows providing a view of the outdoors.
A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.
A modern living room with two grey sofas, a round coffee table, and a patterned rug.
A deck with outdoor seating and a view of the mountains.

10. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
€258
includes taxes & fees
10 Sept - 11 Sept
Mountain View Vista: Resort Condo w/ Views
View all properties

Choose what matters most at hotels with a pool in Wintergreen

Breakfast included
Hot tub
4 stars
5 stars
Spa

Hotels with pools and hot tubs in Wintergreen

A Mountain Inn sign with a stone base and colorful flowers.
A bedroom with a large bed, a desk, and a chair near a window.
A bedroom with a wooden ceiling, a bed with a patterned rug, a desk, and a chair.

Mountain Inn Studio 96 with Wintergreen Advantage

Mountain Inn Studio 96 with Wintergreen Advantage
Wintergreen
Mountain Inn Studio 96 with Wintergreen Advantage
A cozy living room with a stone fireplace, a mounted TV, and rustic decor.
A modern kitchen with stainless steel appliances, wooden cabinets, and a large island with a sink.

Diamond Hill Studio 09 with Wintergreen Advantage

Diamond Hill Studio 09 with Wintergreen Advantage
Wintergreen
Diamond Hill Studio 09 with Wintergreen Advantage
A living room with a brown leather armchair, a beige sofa, and a wooden coffee table. There is a painting on the wall, a clock, and a plant on a shelf.
A cozy living room with a wooden ceiling, a sofa with green cushions, a coffee table, and a TV stand.

Mountain Inn Lodge 55 with Wintergreen Advantage

Mountain Inn Lodge 55 with Wintergreen Advantage
Wintergreen
Mountain Inn Lodge 55 with Wintergreen Advantage
A bedroom with a large bed, a nightstand with a lamp, a dresser, a chair, and a window with curtains.

Timbers Studio 14 with Wintergreen Advantage

Timbers Studio 14 with Wintergreen Advantage
Wintergreen
Timbers Studio 14 with Wintergreen Advantage
An aerial view of a residential area with multiple houses surrounded by dense forest, featuring a central building with a prominent roof and a well-lit driveway.
A spacious living area with a dining table, wooden chairs, a dark wooden cabinet, and a kitchen with wooden cabinets and a microwave.
A spacious living room with a wooden staircase, a dining area with wooden furniture, and a kitchen with modern appliances.
A sign for Mountain Inn with a stone base and colorful flowers.

Mountain Inn Lodge 77 with Wintergreen Advantage

Mountain Inn Lodge 77 with Wintergreen Advantage
Wintergreen
Mountain Inn Lodge 77 with Wintergreen Advantage
An aerial view of a residential area with multiple houses surrounded by dense forest, featuring a central building with a prominent roof and a well-lit driveway.
A modern kitchen with stainless steel appliances, white cabinetry, and a green-tiled backsplash.
A living room with a blue sofa, a wooden side table, and a view through a glass door to an outdoor deck.
A bedroom with a bed, a nightstand, a TV mounted on the wall, and a window.

Northridge 07 With Wintergreen Advantage

Northridge 07 With Wintergreen Advantage
Wintergreen
Northridge 07 With Wintergreen Advantage
A cabin with a deck, outdoor seating, and a fire pit.
A modern kitchen with a large island, bar stools, a stove, and a microwave.
A room with two leather armchairs, a small table with a potted plant, a wicker basket, and a framed poster on the wall.
A bedroom with a bed, a wooden dresser, a television, a ceiling fan, and a window with curtains.

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Chestnut Springs
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
A spacious room with a leather armchair, a sofa, and a large sliding glass door leading to a balcony.
A bedroom with a large window, a bed with white bedding, two bedside tables with lamps, and framed certificates on the wall.

Vistas 71 with Wintergreen Advantage

Vistas 71 with Wintergreen Advantage
Wintergreen
Vistas 71 with Wintergreen Advantage
A multi-story wooden cabin surrounded by dense forest, featuring multiple decks and a chimney.
A spacious living room with a high ceiling, large windows, a fireplace, and a cozy seating area.
A kitchen with a large island, bar stools, and a view of the Blue Ridge Parkway.
A modern living room with leather sofas, a stone fireplace, and large windows.

Blue Ridge Cabin · 3 Levels · 3 Scenic Decks · Music Game Room · Hot Tub· Arcade

Blue Ridge Cabin · 3 Levels · 3 Scenic Decks · Music Game Room · Hot Tub· Arcade
Wintergreen Resort
Blue Ridge Cabin · 3 Levels · 3 Scenic Decks · Music Game Room · Hot Tub· Arcade
A multi-story building with balconies and a pathway leading to the entrance.

Timbers Lodge 49 with Wintergreen Advantage

Timbers Lodge 49 with Wintergreen Advantage
Wintergreen
Timbers Lodge 49 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

Frequently asked questions

What are some accommodation options with pools in Wintergreen?
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes: Condo, 1-minute walk from Wintergreen Resort. Features complimentary wireless Internet access, a communal pool and kitchens. Highlands Condo Views for days! Tons of details listed ⬇️☺️: Condo, 1-minute walk from Wintergreen Resort. Offers complimentary wireless Internet access, a pool and kitchens. New Build! Log Cabin with Hot Tub in Wintergreen: Cabin, 1-minute walk from Wintergreen Resort. Provides complimentary wireless Internet access, a communal pool and kitchens. Endless Mountain Top Views from All The Way Up!: Condo, 1-minute walk from Wintergreen Resort. Features kitchens, a communal pool and Smart televisions. Large and Luxurious Exec 5BR Chalet: Holiday home, 1-minute walk from Wintergreen Resort. Offers kitchens, a communal pool and LED 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 Bold Rock Hard Cider Nellysford Cidery, Wintergreen Resort and Raven's Roost Overlook 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 that has an outdoor pool if you'll be visiting Wintergreen in the warmest months of July, August or June, when the average temperature is 23°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temperature is 4°C.