Holiday rentals with a pool in Western Maryland

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, 1-gig fiber

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

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 acre with access to wooded a trail leads to 5 small 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

*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!

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.

Luxe Cottage, Pool, & Breakfast on MD Horse Farm

Enjoy the unique opportunity to spend time on a stunning Maryland horse farm and estate with private access to the Appalachian Trail in Maryland's Blue Ridge mountains. Located in historic Middletown, the farm is just 60 miles from downtown DC and 20 minutes west of Frederick. Our lovingly renovated 1900 guest cottage sits above an active mountain spring and beside the estate's main residence. You'll encounter chickens, cattle, horses and abundant wildlife as you hike and explore the property.

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!

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.

Heated Pool I Hot Tub I View I Bedford Heights

Welcome to the best view in Bedford County! Our updated 1940s home offers the perfect getaway with ample space for the whole family. Enjoy a hot tub, heated pool (open mid-May through mid-Sept), and a playground. Just a few short miles from downtown Bedford and the Omni Bedford Springs, you'll be close to dining, shopping, and local attractions. Whether you're seeking adventure or relaxation, our home is the perfect place to make lasting memories. We'd love to host your next vacation!

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

Wizards and Humans are invited to experience the magic of Wizard's Escape. A magical home with an escape room twist as you immerse yourself in 2 thrilling themed escape rooms. Perfect for large family gatherings, bachelorette/bachelor/birthdays. Spend hours on our magical scavenger hunt throughout the castle to find the 7 cruxes. Weddings/Events/Pool additional cost. Follow us on Insta for more videos. Book your favorite Gamekeeper's Hut next door for larger parties.

Windy Knoll Adventure | River Front | Hot Tub!

Discover our Black Modern Charm Home, a private retreat atop 35 acres with sweeping mountain and Shenandoah River views. Relax in the hot tub overlooking the river, fish or kayak below, and unwind by the campfire in this peaceful woodland setting. 🌲♨️ Designed for comfort and escape, this modern retreat is perfect for unplugging, reconnecting, and enjoying nature at its finest. Book now for a true mountaintop getaway. ✨

Mountain Retreat-Stunning View/Hot tub/Pool

Pool open from May 31st - Sep 30. Our secluded 5 acre mountain retreat in Lost City s a perfect space for couples, families (with older kids), and groups looking to get away from urban life and unplug. Plenty of outdoor excursions nearby, or just come to relax, unwind and enjoy the breathtaking views. Modern amenities and fiber optic internet ideal for remote work Hot tub with mountain views.