
Holiday rentals with a pool in Staunton
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Top-rated rentals with a pool in Staunton
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Mountain Cottage, Swimming Pool, Views, Nelson 151
Wake to gorgeous Mountain views & rolling green meadows bordering the Rockfish River on our family estate. Private attached unit with built in pool (mid April-mid Sept)in the Blue Ridge mountains of Nelson County Virginia on the center of the 151 Brew Ridge Trail. Much preparation has gone into making your stay beautiful, convenient and comfy. No need to physically interact if that’s your desire. Enjoy swimming, hiking, kayaking, horse back riding, skiing, snowboarding, and more! 3 nite minimum

Five Minute Walk to Everything!
**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

The Modern Mountain Condo
Conveniently located within the 4-season Wintergreen Resort, this recently renovated condo offers a quiet and cozy stay while you take in the mountain views and enjoy endless outdoor activities, wineries, breweries, restaurants, and antique shops. Rest and recharge while you enjoy the light-filled, open floor plan with a wood-burning fireplace, a kitchen with plenty of cabinet space, and full-sized appliances for cooking. Private patio and community pool access are located outside the unit.

2-min drive to slopes, stair-free/free firewood!
Peaceful, recently renovated mountain-top retreat. Relax or work from home. End your day with a hike or spa treatment around the corner—linger with a glass of wine at sunset. It’s all only a 2 minute walk from the front door. Welcome to our mountain home! 2-3 min drive from ski lifts/resort, hiking Free firewood (seasonal) Family games & smart TVs (no cable) for movie night (must sign into your own subscriptions) Smartlock entry Stair-free entry *outdoor HOA pools CLOSED for season

Eight Minute Walk to Everything
This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

1 bedroom condo, walk to the slopes !
Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

Blue Ridge Bliss - For family & friends to enjoy!
Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

Mountain View Getaway Yurt
Come enjoy country living in beautiful western Albemarle county. Our yurt is on a 13 acre property on a quiet country road. (My husband and I also have our home about 200 ft away from yurt). The yurt features a relaxing outdoor claw foot tub/shower with beautiful country views. The private bathroom is situated on the deck of the yurt. The pool is a shared space directly behind our home. The wooded part of the property is private with a beautiful walking trail for you to enjoy.

Mountain View Nest
From the moment you walk in, this condo offers endless opportunities to relax and retreat. The sweeping mountain views over the back deck provide the ideal setting for a romantic getaway, a girls weekend, or much needed time to recharge. This one bedroom/bathroom unit with a king sized bed, fully stocked kitchen, and artistic decor is located on the third floor of the Ledges. It is the perfect location for those who ski, hike, golf, or taste the flavors from local wineries.

On Cottonwood Pond
A beautiful country setting just minutes from Harrisonburg and JMU, winter snow sports (skiing/tubing/ice skating) at Massanutten Resort, Shenandoah National Park, hiking, other local universities and countless Shenandoah Valley attractions! You won't want to miss the new features in this home with a full kitchen, updated fixtures, plush accommodations and thoughtful touches throughout. Enjoy a quaint getaway in this meticulously designed home away from home!

Mountaintop Overlook – Updated 2BR w/ Deck & Views
Breathe in the crisp mountain air, cozy up by the fireplace, and soak in sweeping views of the Blue Ridge Mountains. This clean, comfortable 2-bedroom condo at Wintergreen Resort features two king beds, two full bathrooms, and a sleeper sofa—perfect for up to 6 guests. Enjoy panoramic windows overlooking the mountains,, a fully stocked kitchen, in-unit washer/dryer, central heat/AC, and free parking. The shuttle to the ski lodge is just steps away!

Cozy Condo - Sleeps 4
A wonderful weekend escape no matter the time of year. Condo has been completely renovated in the heart of Wintergreen Resort. Fully equipped condo for guests to come and enjoy the slopes. Within walking distance to the ski lift and all the amenities that the area has to offer. We are the only condo complex that also has a pool it's own pool for condo owners only. **the pool is for the condo complex and is shared with the other units.
Popular amenities for Staunton rentals with a pool
House rentals with a pool

Luxury Retreat~Hot Tub~Sauna~Game Rm~2 King Suites

Makin' Mountain Memories Jacuzzi, Fireplace!

Top 1% Shenandoah Family Retreat | 4BR w/ 2 Kings

Charming Carrie's Cottage at Fairhill Farm

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

Indoor Heated Pool~EV- Arcade~Fire Pit-WIFI-VIEWS!

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Mountain Bauhaus | Sleeps 8 | Amenities | Grill
Condo rentals with a pool

Panoramic Peak: Wintergreen Condo with Views

Massanutten Woodstone 2-BR, 2 Bath

Bike,Hike,Relax in Lux! at Bryce Resort

New Construction! 1 Bed/2 Bath, pet friendly

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

Cozy Comfort with a View - Wintergreen Resort

Sunset Vista Villa, Mountain Views-Close to Slopes
Other holiday rentals with a pool

Mountain Valley Luxury with Pool and Hot Tub

The Pool House: 30+ Day Stays & 15 mins downtown

Private Apt on Quiet Cul-de-sac

Lakeside Retreat, Coffee bar, firepit, swim, relax

Resort Feel & Mountain Views!

Peaceful rural retreat with pool and spa

Hot Tub, Heated Pool 180-Mt View Pvt Retreat

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10
Quick stats about holiday rentals with a pool in Staunton

Total holiday rentals
Explore 10 holiday rentals in Staunton

Nightly prices starting at
Staunton holiday rentals start at $112 AUD per night before taxes and fees

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Over 90 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Staunton rentals

4.9 Average rating
Staunton stays are highly rated by guests—averaging 4.9 out of 5!
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- Shenandoah National Park
- Luray Caverns
- Bryce Resort
- Early Mountain Winery
- Downtown Mall
- James Monroe's Highland
- Wintergreen Resort
- Frontier Culture Museum
- Blenheim Vineyards
- Homestead Ski Slopes
- John Paul Jones Arena
- Cardinal Point Winery
- Glass House Winery
- Devils Backbone Brewing Co Basecamp
- University of Virginia
- Monticello
- Virginia Horse Center
- James Madison University
- Cooter's Place
- White Lotus Eco Spa Retreat
- The Rotunda
- Grand Caverns
- IX Art Park
- Cass Scenic Railroad State Park




