Vacation 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.

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Top guest favorite
The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.
Condo in Wintergreen Resort
4.96 out of 5 average rating, 337 reviews

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.

Top guest favorite
A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.
Condo in Wintergreen Resort
4.97 out of 5 average rating, 160 reviews

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

Guest favorite
A spacious living area features a brick fireplace as a focal point, surrounded by natural light from windows. Comfortable sofas are arranged for conversation, with soft cushions added for support. A wooden floor complements the neutral tones, creating a cozy and inviting space.
Cabin in McGaheysville
4.96 out of 5 average rating, 123 reviews

Cozy Cabin in Massanutten Resort, Private Yard

Your family will be close to everything when you stay at this centrally-located home. 5 minutes from several attractions located in Massanutten Resort (slopes, water park, outdoor pool, golf, bike trails, and way more). Downtown Harrisonburg and James Madison University are 15 miles away. Many shops, restaurants, and tourist activities. Explore the fantastic restaurants, museums and shops downtown. The Shenandoah Valley offers many attractions including caverns, wineries and breweries.

Guest favorite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 170 reviews

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.

Top guest favorite
A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.
Apartment in Rockfish
4.98 out of 5 average rating, 211 reviews

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.

Top guest favorite
A spacious yurt is surrounded by lush greenery, with trees framing its exterior. The entrance is marked by a set of steps leading up to the door. Natural stone borders the well-maintained pathway, enhancing the connection to the countryside.
Yurt in Afton
4.96 out of 5 average rating, 106 reviews

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.

Top guest favorite
A table set for two features a bottle of sparkling beverage and two glasses, accompanied by an elegant plate of appetizers. The backdrop showcases expansive mountain views under a bright sky, enhancing the serene atmosphere of the outdoor dining area.
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 109 reviews

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.

Top guest favorite
Double doors framed by potted plants and embellished with decorative wreaths welcome guests into the home. The brick exterior and pathway provide a warm entryway, hinting at the charm within.
Guest suite in Penn Laird
5 out of 5 average rating, 157 reviews

An Escape to 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!

Guest favorite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 152 reviews

Ski-In Ski-Out ~ Mtn Views ~ King Suite

Just steps from Wintergreen Resort’s slopes, Slope Side Gem offers the perfect mountain escape! Located in the heart of Mountain Village next to the Mountain Inn, you’re just a short walk to Starbucks, The Market, shops, and three restaurants and bars. Whether you’re skiing, hiking, golfing, or enjoying a local brewery or winery, adventure is at your doorstep. After an exciting day, unwind on the private balcony and take in the breathtaking mountain views!

Top guest favorite
A private hot tub is set on a wooden deck, surrounded by trees with autumn foliage. Two reclining lounge chairs and a small table with two chairs are nearby, creating a serene space to relax and enjoy the tranquil nature views.
Farm stay in Stanardsville
4.97 out of 5 average rating, 636 reviews

GreeneHouse*PvtHotTub*Fireplace* MTN*Hiking*farm

The Greene House Apartment is a private, adults-only (18+) retreat on the ground floor of our farmhouse with stunning Piedmont Valley views. Relax in your private hot tub or take a dip in the shared pool. Perfect for couples or up to four friends! Hike right into Shenandoah National Park from the property or explore nearby Swift Run Gap. Enjoy walking trails, peaceful views, and high-speed WiFi. Find more about us at Cair Paravel Farmstead on the web.

Top guest favorite
Condo in Wintergreen Resort
4.97 out of 5 average rating, 121 reviews

Mountain View Condo at Wintergreen, Fireplace

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!

Guest favorite
A wooden staircase is flanked by trees, leading to a brown wooden building with a triangular roof. Large windows allow natural light to enter, surrounded by a peaceful forested area.
Condo in Wintergreen Resort
4.78 out of 5 average rating, 102 reviews

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

Quick stats about vacation rentals with a pool in Staunton

  • Total vacation rentals

    Explore 10 vacation rentals in Staunton

  • Nightly prices starting at

    Staunton vacation rentals start at € 69 per night before taxes and fees

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  • Pet-friendly vacation rentals

    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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