Holiday rentals with a pool in Winchester

4.95 out of 5 average rating, 318 reviews

Flat in Bluemont

A Great Getaway — Foxglove Retreat

Nestled in the Blue Ridge Mountains, "Foxglove Retreat" offers you complete privacy and beautiful vista views of the Shenandoah Valley. Equipped with all the necessities for a relaxed and luxurious experience, the "Foxglove Retreat" is sure to become one of your favorite destinations. "Foxglove Retreat" is ideally located near popular tourist destinations, restaurants and wineries. The Bears Den Trail Center is walking distance for those who would like to explore the beauty of the Blue Ridge Mountains on foot. For those who seek nearby shopping and sightseeing, the quaint village of Middleburg is to the southeast and has many antique shops and elegant boutiques nestled in its historic buildings. To the east is the town of Leesburg featuring the upscale Leesburg Corner Premium Outlets and the Leesburg Farmers’ Market. To the west is the Old Town of Winchester where you will discover charming shops, restaurants, galleries, centuries-old architecture, and historical landmarks.

4.95 out of 5 average rating, 410 reviews

A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.

Cottage in Hamilton

*Cottage @ Firefly Cellars* VA Wine Country escape

The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

Farm stay in Purcellville

A horse stands peacefully in a lush green pasture, surrounded by a black wooden fence. In the background, a well-maintained barn with a cupola is visible, complemented by a clear blue sky and scattered clouds.

4.98 out of 5 average rating, 210 reviews

The Hunt Box @ Tally Yo Farm

Residence above 5-stall horse barn. Two bedroom house with 2 bath, Juliette balcony, vaulted ceilings, fully appointed kitchen, laundry. Traditional English equestrian decor, with horse shows & fox hunts close by. Pool open 5/15-10/15. Extra guests $55/night. Pet fee $35 each. Please advise through Airbnb. Lovely antiques, equestrian art & decor, warm rugs. On site also~AirBnb: www.airbnb.com/rooms/826639006057875355?guests=1&adults=1&s=67&unique_share_id=4cdf4b76-3173-498a-9287-5ab54a38b4ee

4.95 out of 5 average rating, 167 reviews

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

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!

5 out of 5 average rating, 109 reviews

Farm stay in Bluemont

The Cottage at Nestled Inn

Nestled into the Blue Ridge mountains, practically walking distance from Bear Chase Brewery, Twin Oaks Tavern Winery & The Applachian Trail, our home offers you poolside views of our garden, hottub views of the stars, backyard views of our free range chickens & front yard views of our two horses as well as onsite massage therapy, cats & dogs. While being tucked away, we are still just 10minutes from Purcellville or Berryville & 30minutes from Leesburg, Middleburg, Winchester or Harper's Ferry.

4.99 out of 5 average rating, 595 reviews

An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.

Cabin in Bluemont

Rustic Blue Ridge Cabins

Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd of an Acre with access to wooded a trail featuring Cold Springs. Amenities-4 person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail,Shenandoah River, with restaurants, breweries, distilleries, and wineries close by! These are rustic not luxurious Cabins

4.94 out of 5 average rating, 180 reviews

A spacious great room features a large sectional sofa in rich orange, inviting relaxation. Tall windows allow natural light to fill the space, offering views of the surrounding forest. A decorative area rug anchors the seating area, complemented by a coffee table and thoughtfully arranged decor.

Chalet in Hedgesville

Starcatcher Chalet, The Woods Resort

Enjoy a fun, relaxing stay at our completely renovated chalet in The Woods Resort in beautiful Berkeley County, WV--a 90-minute drive from the Washington DC-Baltimore Metro Area. You'll be in the heart of the WV Eastern panhandle, close to Sleepy Creek, Berkeley Springs, Cacapon State Park, Antietam National Battlefield, and more. The Woods Resort amenities (fees apply) include a spa, restaurant, and two golf courses, three swimming pools, tennis, pickleball, fitness, and a playground.

5 out of 5 average rating, 102 reviews

A rustic outdoor seating area features log benches arranged around a circular fire pit. The red chalet with a flag is visible in the background, surrounded by trees shedding their leaves. A gravel pathway connects the seating area and the chalet.

Chalet in Hedgesville

Cherry Run Chalet

Kick back and relax in this peaceful, stylish chalet at The Woods community in wild and wonderful West Virginia. The 2-acre property backs up to the 23,000-acre Sleepy Creek State Wildlife Area, a hikers dream. The Woods offers 2 golf courses, indoor and outdoor pools, indoor hot tub, tennis, exercise gym and more. The Sports and Spa center is within walking distance from the chalet for self-care pampering. The Clubhouse Grille and Pub is a great option for dine in and carry out. Enjoy!

5 out of 5 average rating, 115 reviews

The living area features large two-story windows that offer views of the surrounding wooded landscape. A cozy leather sofa and armchair are complemented by a wooden dining table with seating for six. Warm lighting and natural textures enhance the inviting atmosphere.

Cabin in Hedgesville

Cozy Secluded A-Frame Cabin Retreat

Visit us on IG @almostheavenwvcabin for the latest photos and cabin moments! Welcome to Almost Heaven Cabin, our beloved A-frame escape tucked away on a private, wooded acre in the heart of the Sleepy Creek Wildlife Management area. Surrounded by 23,000 acres of protected wilderness, this cabin was created as a peaceful family retreat from city life-yet it's just a scenic 1.5-hour drive from DC and Baltimore. Expect quiet mornings, fresh mountain air, and a true West Virginia getaway.

4.76 out of 5 average rating, 292 reviews

An aerial view showcases the nine-acre estate featuring a charming stone house, surrounded by vibrant fall foliage. The swimming pool is visible adjacent to a patio area, with a gazebo nearby. The spacious driveway accommodates several vehicles, enhancing accessibility.

Home in Strasburg

Cedar Creek Wayside Castle

1930 Stone House 'Mini Castle' on 9 private acres near Strasburg Virginia bordering Cedar Creek Battlefield and Belle Grove Plantation National Park. Home was built by Otis Elevator company in 1930 for their daughter. You have nature trails and fire pit, swimming pool (opened April 15th), deer and wildlife too. Short walk to historic Ceder Creek. Full estate is yours to play and relax. No dogs in pool. Pool is open into early October usually. Hot tub is ready year round.

4.88 out of 5 average rating, 123 reviews

An indoor saltwater pool area features a large, tranquil pool surrounded by multiple windows allowing natural light. Lounge chairs line one side, with red and white striped towels neatly arranged. The ceiling is accented with skylights, enhancing the spacious feel.

Home in Luray

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

The home features spacious and tastefully decorated interiors, providing ample space for relaxation and enjoyment. With its 20ft by 40ft heated up to 84 degrees indoor salt water pool you and your family can indulge in refreshing swims and soak up the sun in complete privacy. Whether you're seeking a rejuvenating getaway or quality time with your friends our home rental is the perfect choice for a memorable and enjoyable vacation. New level 2 EV charger installed Feb 18, 2026!

4.87 out of 5 average rating, 174 reviews

A relaxing outdoor area features a private hot tub beside a fire table and lounge chairs. Market lights illuminate the space as the sun sets over rolling hills and distant mountains, creating a warm ambiance. The swimming pool is visible in the background.

Home in Woodstock

Sunset Ranch: Hot Tub! Mountain Views! Pool

If you want to bask in the beauty of the Shenandoah Valley, this is the perfect spot! Dip in the pool and watch the sun dip behind the mountains for some of the most gorgeous sunsets you will ever see! Soak in your own private hot tub. Dine on the patio underneath the market lights. Enjoy the scenery of the rolling hills with awesome mountain views. Inside this updated farmhouse has everything you need to relax and refresh. Venture out to the caverns, hiking, and wineries.

Popular amenities for Winchester rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 219 reviews

A spacious backyard is surrounded by a wooden fence, showcasing a patio area with multiple seating options. A hot tub is visible, along with a fire pit and several Adirondack chairs arranged for gathering. Lush green grass and mature trees enhance the outdoor setting.

Home in Harpers Ferry

The Historic Booth House at the Harpers Ferry KOA

5 out of 5 average rating, 117 reviews

A circular fire pit is surrounded by six gray Adirondack chairs, set on gravel. Beyond, a spacious wooden deck is visible, featuring a covered area and a picnic table. The yard is fenced with trees providing a natural backdrop.

Home in Hedgesville

4BR: Chef’s Kitchen, Wood Stove, Resort Access

4.94 out of 5 average rating, 104 reviews

A wooden deck is illuminated by string lights, featuring a hot tub with blue lighting and a gas grill nearby. Seating is provided with several chairs around a small fire pit, surrounded by lush foliage for a private setting.

Home in McGaheysville

Makin' Mountain Memories Jacuzzi, Game room, Dogs!

4.96 out of 5 average rating, 209 reviews

The exterior of the farmhouse is showcased at dusk, highlighting the blend of historic and modern architecture. A stone path leads to the welcoming entry, framed by glowing flower pots. The wraparound porch features multiple illuminated windows, reflecting a cozy and inviting ambiance.

Home in Harpers Ferry

Historic Farmhouse w/ Heated Pool, Harpers Ferry

5 out of 5 average rating, 291 reviews

A historic stone farmhouse from 1861 is set on a well-maintained lawn, surrounded by green shrubbery and trees. The two-story structure features red shutters on the windows and a welcoming front porch that invites relaxation.

Home in Gettysburg

Civil War Farm House w/Heated (seasonal) Pool

4.94 out of 5 average rating, 142 reviews

Home in Adamstown

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

5 out of 5 average rating, 100 reviews

A spacious solarium features large windows allowing plenty of natural light to fill the room, with views of the surrounding greenery. A comfortable seating area is arranged with a mix of sofas and chairs, complemented by various plants adding a touch of nature. The heated concrete floor enhances comfort in this inviting gathering space.

Home in Knoxville

An Escape Bordering National Park land 1 mi to C&O

4.97 out of 5 average rating, 113 reviews

The exterior of the house is framed by mature trees and lush grass, capturing the early morning light. A sunbeam emerges from behind the hills, illuminating the front façade of the home, which features multiple windows and a welcoming entrance.

Home in Luray

Walnut Lane

Apartment rentals with a pool

A large, dark green sign displays 'Northern Lights Village' in bold white letters. The sign is situated amidst snow-covered ground, with leafless trees and distant buildings in the background, conveying a winter landscape.

4.97 out of 5 average rating, 37 reviews

SlopeSide

A spacious room is highlighted by a king-sized bed with a checkered blanket and a bedside lamp. A small dining table with two chairs is situated near the entrance, while the walls are painted in a calming blue tone, complemented by soft lighting.

4.95 out of 5 average rating, 22 reviews

Rockwell Suite #104 at the Inns of Whitetail

A covered outdoor patio is presented, featuring a small round table surrounded by two chairs. Decorative string lights are hung above, and a view of snow-capped hills is visible in the background, providing a scenic backdrop for outdoor relaxation.

4.85 out of 5 average rating, 85 reviews

Fabulous Ski In & Out Mountain-view Condo

Apartment in McGaheysville

A series of ski gondolas are seen ascending a mountain, suspended from overhead cables. Snow-covered slopes can be observed below, with a bright blue sky providing a clear backdrop. The gondolas feature large windows, allowing views of the winter landscape.

4.84 out of 5 average rating, 146 reviews

Massanutten Woodstone 2-BR, 2 Bath

The illuminated sign of Whitetail Resort is showcased against a winter backdrop, surrounded by snow-covered ground and barren trees. Stone pillars frame the sign, creating a welcoming entrance to the resort.

4.93 out of 5 average rating, 56 reviews

Whitetail Resort Ski-in/Ski-out slope side condo.

Apartment in West Springfield

A welcoming living room features a gray sofa adorned with colorful throw pillows, flanked by two yellow armchairs. A light wood coffee table sits atop a textured area rug, with a serene wall art piece above. Natural light is provided by nearby windows.

4.84 out of 5 average rating, 249 reviews

Beautiful 2BR/1BA Renovated Condo near DC

Apartment in Mount Jackson

A modern living area features a light-colored sectional sofa adorned with a patterned throw. A kitchen with a wood countertop and seating area can be seen in the background, complemented by pendant lighting. Mirrored walls enhance the sense of space, reflecting the inviting atmosphere.

4.87 out of 5 average rating, 110 reviews

Bike,Hike,Relax in Lux! at Bryce Resort

Apartment in Mount Jackson

A comfortable living area features a stone fireplace adorned with greenery. A brown sectional sofa is positioned around a small wooden coffee table. A television is mounted on the wall, and ski equipment is visible nearby, enhancing the cozy ambiance.

4.9 out of 5 average rating, 83 reviews

Cozy condo at Bryce Resort

Other holiday rentals with a pool

Guest suite in Myersville

A heated pool is surrounded by a stone wall and lush greenery, offering a serene atmosphere. The lodge features large windows and a balcony overlooking the pool area, seamlessly connecting indoor and outdoor spaces.

4.91 out of 5 average rating, 335 reviews

Harmony Lodge nestled in wooded tranquility!

4.98 out of 5 average rating, 91 reviews

The cabin's exterior features a dark wooden facade, surrounded by lush greenery and colorful shrubs. A large wraparound deck offers ample space for outdoor relaxation, while a soft sunset casts a warm glow over the landscape.

Cabin in Gore

Serene Mountaintop Cabin - Pool, Hot Tub, Sauna

Chalet in Berkeley Springs

A spacious interior features vaulted wooden ceilings and large windows, allowing natural light to fill the room. A wooden dining table is surrounded by several chairs. A comfortable seating area includes an armchair and a rocking chair, offering views of the outdoors.

4.87 out of 5 average rating, 261 reviews

The Mountain House

4.85 out of 5 average rating, 122 reviews

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

Mountain & Lake Retreat: 2x Queen, saltH2O Hottub

5 out of 5 average rating, 10 reviews

A spacious green lawn is enclosed by a wire fence, providing a sense of privacy. In the background, a variety of trees display autumn colors, while two houses are visible among the greenery. A clear blue sky complements the scenery.

Home in Winchester

Winchester farm

4.77 out of 5 average rating, 114 reviews

An aerial view of a log cabin nestled among lush greenery on a mountainside, featuring a rectangular pool adjacent to the cabin. The expansive landscape offers rolling hills and valleys, with a clear view of the horizon in the distance.

Cabin in Rileyville

Log Cabin, *Pool, Hot Tub* Views, Views, Log Fires

4.94 out of 5 average rating, 128 reviews

Aerial view showcases a cabin nestled amid a vast expanse of lush green forest. The treetops create a vibrant, uninterrupted canopy, with distant mountain peaks visible under a clear sky, emphasizing the cabin's serene and secluded location.

Cabin in Hedgesville

The Cabin on the Run