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

Cabin

4.94 out of 5 average rating, 161 reviews

Hot Tub, Dog Friendly Boho Cabin in The Woods

Get cozy at our secluded A-frame cabin in The Woods! Feel transported into the trees as you enjoy coffee on the screened-in porch, cuddle next to the wood burning fire, relax in the hot tub, or simply look out the expansive windows. Furry friends will feel at home with a custom-built 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.

Superhost

Cabin

4.94 out of 5 average rating, 111 reviews

NEW! Boutique-Chic w/fireplace @ The Woods

A cool, retro, dog-friendly, Mid-Century modern A-frame cabin in a woodsy, secluded setting near DC and Baltimore! 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. Free firewood. Basic supplies provided. Hike + golf + swim + ski+ fish + spa + shopping + breweries + farm markets nearby.

Guest favourite

Cabin

4.92 out of 5 average rating, 237 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

4.92 out of 5 average rating, 140 reviews

Big Savage Guest Cabin

Nestled on 10 acres near the summit of Big Savage Mountain is our home site which includes our guest cabin. Warm summer days and cool evenings make for a great vacation spot. In the country but just 1 mile from down town. Your retreat is just 3 minutes from dining, biking, hiking, swimming, and live music. Fall brings beautiful foliage and winter plenty of snow. There is something for fans of all seasons. We are only 5 minutes from Frostburg State University & 30 minutes from Deep Creek Lake.

Guest favourite

Cabin

4.95 out of 5 average rating, 118 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

Home

4.97 out of 5 average rating, 181 reviews

Harpers Ferry Farmhouse, Heated Year Round Pool

Nestled in the Blue Ridge Mountains of West Virginia, this lovingly restored 1800s farmhouse and barn studio is the perfect blend of historic charm and modern convenience. Relax in our year-round heated saltwater plunge pool. Ideal for groups, the farmhouse is just minutes from hiking trails, vineyards, and breweries. Conveniently located only an hour from Baltimore and DC, and within easy reach of Philadelphia and NYC. Follow @perennialstays for exclusive details and behind-the-scenes.

Superhost

Cabin

4.93 out of 5 average rating, 233 reviews

Cozy Modern Private Cabin with Hot Tub in Coolfont

Welcome to our private ,modern and cozy chalet located in exclusive Coolfont Mountainside . We have two large bedrooms and bathrooms , screened in porch , two decks , woodstove , hot tub and a one of a kind custom light fixture that sets the mood for the perfect escape to the mountains . Aptly named " Ode to Joy " you will find much needed joy should you choose to stay at our one of a kind retreat nestled in the Cacapon Mountains in Berkeley Springs . Please reach out with any questions !

Guest favourite

Cottage

4.95 out of 5 average rating, 220 reviews

Harper's Ferry Tree House/ hot tub / nature/ trees

Cozy cabin in a private community minutes away from downtown Harper's Ferry. This cottage in the trees is situated on a private wooded road and has parking for 5 vehicles. You'll enjoy a large deck, inflatable hot tub, outdoor fire pit, and gated access to a beautiful picnic area with canoe/kayak/swim spot on east side of Shenandoah River. If you are interested in fishing/boating/tubing/swimming this spot cannot be beat . Ride the commuter train to DC to take in the sites. Enjoy!

Guest favourite

Chalet

4.96 out of 5 average rating, 152 reviews

Exclusive Mountain Lodge and Unmatched Hospitality

Welcome to Be Still, our flagship mountain retreat! Nestled on 2 private wooded acres, this top-rated cabin features 5 spacious bedrooms, 5 full baths, 1 half bath. Relax in the private hot tub, enjoy the pool table and games, or unwind on one of 3 porches. Kids will love the custom bunk room, and evenings are perfect for a campfire under the stars. Just 4 miles from charming downtown Berkeley Springs, WV—ranked one of America’s Top 9 Small Towns—this is the ultimate getaway!

Guest favourite

Guest suite

4.98 out of 5 average rating, 249 reviews

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!

Superhost

Cabin

4.87 out of 5 average rating, 174 reviews

Stylish Retreat with Pool Access and Fire Pit

Experience a peaceful getaway at The Woods Resort. With an outdoor screened porch, a fire pit and a wood burning fireplace, you can comfortably enjoy this retreat in any season! With an additional fee you can enjoy access to two outdoor pools, an indoor pool with hot tub, tennis and pickle ball courts, a gym, and 36 holes of golf. Close to the Sleepy Creek WMA, public river access, Berkeley Springs and tons of hiking - enjoy the indoors or outdoors in any season.

Superhost

Cabin

4.84 out of 5 average rating, 164 reviews

Cabin Getaway: Hot Tub/Game Room/Berkeley Springs

Welcome to this beautifully furnished 3 bedroom, 2 bath cabin with gleaming hardwood floors, a cozy wood stove, a beautiful screened patio, and a front deck for relaxing. It's centrally located to Berkeley Springs, Cacapon State Park, and a variety of hiking, fishing, restaurants, and shopping. Enjoy the local attractions and breweries year round! Whether it's site-seeing or solitude, this unique cabin is a great retreat for your next getaway!