Vacation 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 favorite

Cabin in Hedgesville

4.94 out of 5 average rating, 156 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 in Hedgesville

4.94 out of 5 average rating, 110 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 favorite

Cabin in Hedgesville

4.92 out of 5 average rating, 235 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 favorite

Guesthouse in Middletown

5 out of 5 average rating, 112 reviews

Cottage, Pool, & Breakfast on 100ac Horse Estate

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.

Guest favorite

Cabin in Frostburg

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 favorite

Cabin in Hedgesville

4.95 out of 5 average rating, 117 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 favorite

Chalet in Berkeley Springs

4.96 out of 5 average rating, 151 reviews

Christmas TREE up! Experience a Hallmark Christmas

WELCOME to BE STILL, our Flagship mountain getaway! Homegrown Hospitality is proud to share our cabin at BerkeleySpringsWVVacations where we are passionate about making our hospitality truly WV Homegrown. This top ranked cabin has 5 large bedrooms, 5 Full baths and one 1/2 bath on 2 wooded acres with private hot tub, pool table, games, 3 porches, campfire under the stars and the kiddos will LOVE our bunk room. ONLY 4 miles to downtown BERKELEY SPRINGS, WV. Americas #9 TOP Small town!

Guest favorite

Chalet in Tucker County

4.95 out of 5 average rating, 128 reviews

The Davis Ridge - Firewood, Mt Views, Skiing

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.

Superhost

Cabin in 1

4.93 out of 5 average rating, 232 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 favorite

Cottage in Harpers Ferry

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!

Superhost

Cabin in Hedgesville

4.9 out of 5 average rating, 163 reviews

Stocked Kitchen w Fireplace and Opt. Pool Access

The perfect getaway for small families or a friendly retreat! A well stocked kitchen, screened gazebo and spacious deck with a retractable gates and wide stairs leading to a fire pit area make this cozy home an outdoor lovers haven! Optional Resort access available to The Woods Resort with indoor and outdoor pools and sports courts, 36 holes of golf and only 10 minutes to public river access. All four seasons are sure to please with hiking and the beauty of West Virginia!

Guest favorite

Guest suite in Accident

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!