
Holiday rentals with a pool in Western Maryland
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Top-rated rentals with a pool in Western Maryland
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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.

*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!

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!

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

Bear Pines Retreat ~ Game Room ~ Screened Porch
Come enjoy this 3 bedroom/2 bath A frame cabin in The Woods. Bear Pines Retreat features 2 bedrooms on the lower level with 4 beds and full bathroom. The Master Suite loft has a queen bed with mountain spa bathroom. You can connect to the built in Bluetooth speaker and play some relaxing music while looking out the skylight above. The living area has plenty of seating with wood burning fireplace and 55” TV mounted above. You can enjoy over 100 cable channels, music and streaming services.

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

The Davis Ridge - Mt Views, Fireplace, Balcony
This is a beautiful property and 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.

Five Oaks Cabin at The Woods Resort
Get away without going far at our cozy, colorful, family-friendly cabin. Watch the sunset over the woods from the deck, stargaze by the A-frame window, or play ping-pong in our games room. Do some work in our office space overlooking the trees. Enjoy golf, pools, the spa, hiking and fishing, or explore the beautiful countryside of rural West Virginia. Best of all, our cabin is less than two-hours drive from D.C. and Baltimore, so you can feel like you're far away without a long drive.

Harmony Lodge nestled in wooded tranquility!
Tranquil lodge nestled on 3 wooded acres in Myersville, MD. Relax by the heated pool, enjoy the warmth of the fire pit, or receive a massage in the studio. Minutes away from downtown Frederick and Middletown restaurants, shops, and parks. Visit the local wineries and festivals. Tour historic battlefields. Go antiquing. Take in a round of golf, bike the C&O canal, hike the Appalachian trail, boat on the Potomac River, or go skiing. Bring your fur baby with you to enjoy the activities!

Peak season! Coffee bar, fish, fire-pit, stargaze!
PET FRIENDLY Come experience Reel and Relax!! Hike, explore the trails, fish, float, go rafting, read, enjoy a fire, grill, shop/eat in super cute country towns... Whether its the river, the rolling mountains, the whispering breeze or the cozy cottage, this property offers all of the feels you are searching for without ever leaving! Every season is magical and offers its own reason to visit!!! "This place is amazing; you have literally thought of EVERYTHING! -past guest.

New! The Butterfly Suite at Enchanted Table Meadow
Minutes from Wisp Ski Resort & Deep Creek Lake! Come as you are & take a seat at nature’s table under the canopy of stars. Embrace the wooded ambiance and meadow views from our 825 sq. ft suite as you melt your cares away in front of the fireplace. Located between I-68 and Deep Creek Lake/Wisp. Our hope is to provide a serene landscape where you can find peace and rest through nature. Our setup works well for business travelers & as a couple's romantic escape!

Tiny Cabin Retreat 1 @ Camp Shenandoah Meadows
The Cabin sits on 40 acres in the heart of Fort Valley with views of the blue ridge mountains Across the property. The Cabin is part of the larger Shenandoah Meadows Camp with great amenities as the summer camps only operates June-August. Within a short drive there are hiking, biking, rock climbing, and many local attractions like Luray Caverns, Skyline Drive, vineyards and breweries. Firewood is included! *Pet Fee of $20.00
Popular amenities for Western Maryland rentals with a pool
House rentals with a pool

Stoney Spring Overlook

Spacious & Charming! Large deck+Game shed+Firepit

Clean 5BR w Heated Pool/Spa - Horse & Wine Country

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

Cedar Creek Wayside Castle

Walnut Lane

Lake View Home w/Fire Pit, Indoor Pool, Dogs OK!

Potomac Overlook Farms: 6 BR, 10 Acre River Estate
Apartment rentals with a pool

Beautiful, 2 bedroom condo

Fall Special - Book 2 Nights Get a 3rd FREE

Lake Access/2BR/2Bath/kitchen/pool/5m to Wisp

Ski-in and Ski-out Condo at Seven Springs Resort

A Cozy, Quiet Getaway

Bike,Hike,Relax in Lux! at Bryce Resort

Seven Springs *Ski-in/Ski-out Condo 1 Bed, 1 Bath

1-Bedroom Condo 4701 Swiss Mountain Seven Springs
Other holiday rentals with a pool

Serene Mountaintop Cabin - Pool, Hot Tub, Sauna

Frog Hollow A Frame by Stay With Branch | Hot Tub

Cozy Chalet w Hot Tub ~EV~Gym~Pool~Fire pit

Romantic Cabin Retreat | King Bed, Pet-Friendly

Private Indoor Pool~WiFi~ Arcade~Fire Pit~Views

Dreamcatcher Cabin ~Scenic views with BIG sky hues

Starcatcher Chalet, The Woods Resort

Relaxing Romantic Cabin*HotTub*Pets*Walk To Lake
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- Rentals with pools United States
- Fallingwater
- Seven Springs Mountain Resort
- Timberline Mountain
- Wisp Resort
- Idlewild & SoakZone
- Ohiopyle State Park
- Blackwater Falls State Park
- Shawnee State Park
- Hidden Valley Resort
- Canaan Valley Resort & Conference Center
- Lakeview Golf Resort
- Bella Terra Vineyards
- White Grass
- Pikewood National Golf Club
- Canaan Valley Ski Resort
- Laurel Mountain Ski Resort
- Lodestone Golf Course
- Warden Lake
- Forks of Cheat Winery
- Mountain Dragon Mazery Fine Honey Wine
- West Whitehill Winery
- Winter Experiences at The Peak