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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Guest favourite

Apartment in Bluemont

4.95 out of 5 average rating, 303 reviews

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.

Guest favourite

Cabin in Hedgesville

4.94 out of 5 average rating, 119 reviews

Dog-friendly, boutique & chic + fireplace

A cool, retro, dog-friendly, Mid-Century modern A-frame cabin in a woodsy, secluded setting near DC and Baltimore! Free firewood! Sleeps 10 in SUPER COMFY beds w/high-quality sheets + a pull out cushy sofa bed in LR + futon in loft. Lux pillows & towels. Deck w/Grill & free propane. Modern ultra-stocked kitchen. High speed wifi + work space. Screened-in porch. Generator w/transfer switch. Basic supplies provided. Hike + golf + swim + ski+ fish + spa + shopping + breweries + farm markets nearby.

Guest favourite

Cabin in Hedgesville

4.94 out of 5 average rating, 121 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!

Guest favourite

Cabin in Woodstock

4.92 out of 5 average rating, 103 reviews

Luxury Cabin: Pool, Hot Tub, Romance & Family Fun

Escape to a romantic retreat featured in The Washingtonian as a top DC-area getaway. This enchanting three-bedroom cabin in the Shenandoah Valley offers everything you need for a perfect stay. Surrounded by lush woods with stunning mountain views and a short walk to the peaceful river, you'll experience nature at its best. Relax in king-size beds, swim in the indoor pool, or unwind in the hot tub. Savor the fire pit with a glass of wine under the starry sky. Book your unforgettable escape today!

Top Guest favourite

Home in Hyndman

4.99 out of 5 average rating, 148 reviews

Wills Mountain Ranch

Lovely, private home overlooking our beautiful valley with breathtaking views of Wills Mountain. It is the perfect setting for a family retreat/reunion. The ranch house has a red roof in the pictures. My husband & I live in the 3 story. We have a in-ground pool on property (heated from Mid-May to early September), a gas grill, and fire pit on the large scenic patio for your enjoyment. The large windows & patio offer a spectacular view of Wills Mt. The ranch house offers a quiet getaway retreat.

Top Guest favourite

Cabin in Bluemont

4.99 out of 5 average rating, 542 reviews

Rustic Blue Ridge Cabin

A quaint rustic cabin nested at the top of the Blue Ridge Mountains, with a detached 150 ft² bedroom, 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- 4person 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!This is a rustic not luxurious cabin!

Guest favourite

Cabin in Hedgesville

4.92 out of 5 average rating, 264 reviews

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.

Guest favourite

Cabin in Hedgesville

4.94 out of 5 average rating, 143 reviews

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.

Guest favourite

Chalet in Tucker County

4.93 out of 5 average rating, 158 reviews

The Davis Ridge - Heated Pool, Mt Views, Location!

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.

Guest favourite

Cabin in Hedgesville

4.94 out of 5 average rating, 183 reviews

Hot Tub, Dog Friendly Boho Cabin in The Woods

Unwind at our secluded A-frame cabin in The Woods! Feel transported into the trees as you enjoy coffee on the screened-in porch, roast marshmallows by the fire pit, relax in the hot tub, or simply look out the expansive windows. Furry friends will feel at home with a built-in dog bowl station and two-acres for exploring. Just under two hours from the D.C./Baltimore area with a ChargePoint EV station in the driveway, it's the perfect all-seasons getaway for families and groups of friends.

Top Guest favourite

Guesthouse in Monrovia

4.97 out of 5 average rating, 150 reviews

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

Guest favourite

Cabin in Hedgesville

4.88 out of 5 average rating, 115 reviews

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.