Holiday rentals with a pool in Shenandoah Valley

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Top-rated rentals with a pool in Shenandoah Valley

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Guest favourite
An aerial view captures a vibrant ski in/out complex at dusk, with lights illuminating the slopes and buildings. The lower section showcases a cozy studio featuring a bunk bed and seating area, complemented by a spacious counter and scenic window.
Apartment in Snowshoe
4.97 out of 5 average rating, 148 reviews

Renovated Ski in/out, pool/hot tub, slps 6, #1105

Renovated Ski In/Out Poolside/View This studio has been re-designed to maximize space. LVP flooring, granite counters, and lots of storage innovations. Queens size bed has drawers & extra stg., a Queen Sleepr & a bunk. Ideal for 2-4 adults or 2 adults & 2-4 kids. Silver Creek has day/night skiing, pool, & tubing. Your season pass is good for ALL slopes at Snowshoe, Western Territory(all black diamonds), & Silvercreek. Take the free shuttle to the Village & Western Territory (little over 2 miles)

Top guest favourite
A gravel area features several rustic wooden chairs arranged around a stone fire pit, with a gentle fire burning. Soft string lights illuminate the space, enhancing the cozy atmosphere. The exterior of the cabin is visible in the background, surrounded by trees.
Cabin in Hedgesville
4.95 out of 5 average rating, 165 reviews

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

Experience the epitome of luxury in our breathtaking A-frame cabin, nestled amidst the serene woods. This modern retreat offers lavish amenities and a stunning open living space with floor-to-ceiling windows, immersing you in nature's beauty. Indulge in the private hot tub, relax by the fire pit, and unleash your culinary skills in our fully equipped kitchen. The large screened porch provides a tranquil oasis, while nearby hiking trails, golf courses, and a spa offer an unforgettable getaway!

Top guest favourite
A private rear deck is visible, featuring a spacious hot tub nestled among trees. A table and chairs sit nearby, illuminated by string lights that create a cozy ambiance. The cabin's green exterior blends harmoniously with the surrounding natural landscape.
Cabin in Berkeley Springs
4.98 out of 5 average rating, 111 reviews

Romantic, hot tub, king bed, private, pet-friendly

Uniquely spacious escape for couple, small family, or solo traveler. 30-foot great room, wall of windows facing large deck, oak floors NEW HOT TUB in private setting. King bedroom with en suite bath; loft has twin bed. Modern with touches of mcm & vintage create a magical retreat for you in the treetops. On 2 acres. Hike to top of Cacapon Mountain from back door. Quick drive (3 mins) to private community pool/hot tub/tot pool (summer only). 10 minutes to Berkeley Springs with Roman Baths, arts s

Guest favourite
A premium saltwater hot tub is illuminated with soft blue and green lights, creating a calming ambiance. Two lanterns sit on side tables, and ambient string lights are visible in the background, enhancing the relaxing outdoor space.
Cabin in Basye
4.85 out of 5 average rating, 113 reviews

Mountain & Lake Retreat: 2x Queen, saltH2O Hottub

The Tortoise and the Bear B&B: Where Relaxation Meets Adventure Features: - 6-person premium saltwater hot tub - 1 Gbps fiber internet for seamless remote work/streaming - Two bedrooms with Sleep Number dual-side queen beds - Fully stocked kitchen - Multiple outdoor dining/seating areas Location: - 10-minute walk to Lake Laura with a 3-mile path - 5-minute drive to Bryce mountain skiing, biking, and golf Our home features a spiral staircase which may not be suitable for very young children

Top guest favourite
A round green yurt stands surrounded by a grassy area, accented by a flower bed of daffodils in bloom. A wooden deck leads to the entrance, while a fire pit with log seating is positioned nearby. Bare trees provide a serene mountain backdrop.
Yurt in Stanardsville
4.96 out of 5 average rating, 1,251 reviews

Yurt fireplace*FARM*horses*goats*woods*STARS*Hotub

Come experience living in a round structure filled with amenities-fully equipped kitchen, deep tub, heating and AC, hot tub and in-ground pool. Great for couples, friends, and families. A 10 minute hike gets you into Shenandoah National Park, explore our 58 acres on numerous walking trails, visit Charlottesville, historical sites, caves, or play in rivers. Child friendly- no pets.( PRIVATE hot tub Nov 20- March 1.) Check out Cair Paravel Farmstead on FB/the web to see all we have to offer.

Top guest favourite
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.
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 163 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

Top guest favourite
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.
Flat in Rockfish
4.98 out of 5 average rating, 213 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 favourite
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.

Guest favourite
Mountains are visible in the distance, showcasing gentle slopes and a partially snow-covered landscape. Wispy clouds stretch across the sky, with soft sunlight breaking through, highlighting the tranquil beauty of the natural surroundings.
Chalet in Tucker County
4.93 out of 5 average rating, 191 reviews

The Davis Ridge - Mt Views, Fireplace, Balcony

This beautiful property is centrally located close to Davis, Thomas and Canaan Valley's most famous attractions. Witness the sunrises and sunsets over the mountains from the balcony, take a dip in the heated seasonal pool, get cozy and warm next to the wood fireplace (free firewood included), cook a delicious meal on the outdoor grill, and end the day toasting from the balcony and cuddled by the fire. You're only a few minutes from all the major sites and attractions in the area.

Top guest favourite
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.
Flat in Wintergreen Resort
4.97 out of 5 average rating, 114 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.

Guest favourite
Apartment in Wintergreen Resort
4.96 out of 5 average rating, 158 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 favourite
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 122 reviews

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!

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