Holiday rentals with a pool in Western Maryland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Western Maryland

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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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, 188 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 Bath (Berkeley Springs)

4.98 out of 5 average rating, 123 reviews

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

Top guest favourite

An inviting open-concept living space is highlighted by vaulted ceilings and ample natural light. The kitchen features modern stainless steel appliances and a spacious island. A comfortable seating area with a leather couch and stylish decor is situated nearby, enhancing the home's welcoming ambiance.

Townhouse in McHenry

5.0 out of 5 average rating, 109 reviews

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.

Guest favourite

An aerial view captures the 1930 stone house set against vibrant autumn foliage and rolling mountains. The home features large windows reflecting the warm colors of nature. A swimming pool is visible in the backyard, surrounded by trees, with ample space for outdoor activities.

Home in Strasburg

4.76 out of 5 average rating, 305 reviews

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 early April to early October usually. Hot tub is ready year round.

Top guest favourite

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

4.99 out of 5 average rating, 138 reviews

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.

Guest favourite

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

4.96 out of 5 average rating, 219 reviews

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.

Top guest favourite

A fire pit surrounded by smooth stones emits warmth and light, set on a stone patio. Comfortable seating is provided by dark wicker chairs. The scenic landscape of rolling hills and valleys is visible in the background, showcasing a range of autumn colors beneath a clear sky.

Home in Bedford

5.0 out of 5 average rating, 127 reviews

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!

Guest favourite

A wooden deck extends from the cabin, surrounded by lush green trees. A striped awning provides shade over a picnic table, creating a space for outdoor dining or relaxation. The natural ambiance enhances the secluded feel of the property.

Cabin in Keedysville

4.82 out of 5 average rating, 129 reviews

Quiet Antietam Cabin

This quiet cabin is located between Boonsboro and Sharpsburg in Keedysville, MD. It is surrounded by tall oaks and pines. A wide path leads to Antietam Creek, popular for fishing, kayaking, and tubing. 45-min drive to Whitetail Ski Resort (30 miles); 1-hr to Gettysburg, PA; Close to Antietam Battlefield, Shepherdstown, Harpers Ferry, Hagerstown, Frederick, Washington, D.C., C&O canal bike trail and Appalachian Trail. Minimum age to rent is 25 yrs. Families with children are welcome.

Top guest favourite

A rustic cottage is showcased within a wooded setting, featuring a welcoming front porch with wooden railings. An American flag hangs beside the door, while decorative skis are mounted on the facade. A gravel driveway leads to a nearby garage.

Cottage in Swanton

4.92 out of 5 average rating, 293 reviews

*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit

Deep Retreat Cottage is 10 minutes from Wisp resort and most Lake activities! Boat Slip, Fire Place, Hot tub, fire pit, wifi and Streaming smart hdtv's. Awesome outdoor area with corn hole and horse shoes. The Cottage is Comfy, Cozy and ready for your Deep Creek Lake getaway. 2 Bedroom, 2 bath with loft sleeps 8 adults comfortably with amenities including Fire Place, Hot Tub, Fire Pit, WIFI and Gas and Charcoal Grills. Minimum Rental Age - 25

Top guest favourite

A stone patio surrounded by Adirondack chairs encircles a fire pit, with flames dancing at the center. The cabin is set against a backdrop of lush green trees, and a hot tub is positioned nearby, offering a serene outdoor gathering space.

Chalet in Bath (Berkeley Springs)

4.96 out of 5 average rating, 195 reviews

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

Top guest favourite

A modern A-Frame cabin is nestled among trees, featuring large windows that enhance the open design. The inviting deck leads to a fire pit area surrounded by Adirondack chairs, creating a perfect space for gathering and enjoying nature.

Cabin in Bath (Berkeley Springs)

5.0 out of 5 average rating, 105 reviews

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.

Top guest favourite

A log cabin is nestled among the trees, featuring a fenced inground pool in the foreground. The pool area is surrounded by a textured patio, complemented by several wooden chairs positioned nearby. The cabin is situated on a gravel driveway, highlighting its private setting.

Cabin in Fort Valley

4.98 out of 5 average rating, 143 reviews

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!