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

Our Lovely Lake Retreat

Spacious 3 bedroom, 2.5 bath townhome with gorgeous views of Deep Creek Lake and WISP ski slopes. The newly updated townhome sleeps 8 comfortably. You will enjoy the air conditioning, fully equipped kitchen & grill, wood burning fireplace and 4 smart TV's. 15 steps up to entrance. Neighborhood amenities: indoor community pool, picnic tables, dock and a beach/sand area (kids will love). Level lakefront access right across the street. Min age to rent 25. Max 3 cars. HOA rule: no trailers/campers.

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.

Historic Farmhouse | Heated Plunge Pool, Billiards

Named a 2025 Silver Winner for Best Vacation Rental by WV Living magazine, this 1800s farmhouse is full of character and designed for comfort. The highlight is a heated saltwater plunge pool, open year-round, plus outdoor gathering spaces for summer and 3 fireplaces for cozy fall and winter stays. Guests rave about the incredibly comfortable beds! The Harpers Ferry area is a delight in every season, offering hiking, history, shopping, dining, river adventures, wineries and breweries.

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!

Ultimate Group Getaway5 Suites•HotTub•Fall Foliage

Be Still, our flagship #1 rated mountain retreat! 🌟8 person private Hot Tub 🌳Screened in porch+2 open Decks 🥾Direct access to hiking trails 👙Community Pool+Kiddie Pool+Jacuzzi (10 guests max per HOA) 🛋️3 Family Rooms 🪵Firepit+provided Firewood+Grill 🔥Cozy Propane Fireplace 🎲Pool Table+Shuffleboard table+Board Games+DVD Library 📺WIFI+two 65in TVs 🛏️5 comfy bedrooms 💆🏼‍♀️5 FULL Bathrooms+1/2 bath 🛍️5 min to downtown

Frog Hollow · A-Frame & Hot Tub · Stay With Branch

A-frame cabin in Berkeley Springs with private hot tub, cold plunge, and Big Green Egg grill set in the woods. Dedicated office with fast WiFi, fire pit, record player, and board games make it functional for groups or remote work. Access to shared outdoor pool and private backyard with hammock. Built for remote workers, families, and groups who want forest seclusion with full modern amenities.

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit

Hidden in the Valley sits on 30 private, wooded acres adjoining the George Washington National Forest. This remote property offers a pool, fire pit and foot trails throughout, perfect for your furry companions! If you’re looking for a true escape to nature, surrounded by Virginia’s best hiking trails, wildlife and clear, starry night skies, Hidden in the Valley is the getaway for you!

All Seasons Retreat - Screened Porch - Fire Pit

Be amongst the trees! All Seasons Retreat is nestled near the top of the mountain in The Woods. Come enjoy the mountain views and relax on the 50-foot deck surrounded by trees. If you love nature and the outdoors, this is the place for you. Create s’more memories in the most incredible fire pit village! You also have full access to all the resort amenities.