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Holiday rentals with a pool in Western Maryland

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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

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!

4.95 out of 5 average rating, 188 reviews
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)

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

4.98 out of 5 average rating, 123 reviews
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

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.

5.0 out of 5 average rating, 109 reviews
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

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.

4.76 out of 5 average rating, 305 reviews
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

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.

4.99 out of 5 average rating, 138 reviews
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

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.

4.96 out of 5 average rating, 219 reviews
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

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!

5.0 out of 5 average rating, 127 reviews
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

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.

4.82 out of 5 average rating, 129 reviews
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

*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

4.92 out of 5 average rating, 293 reviews
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)

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

4.96 out of 5 average rating, 195 reviews
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)

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.

5.0 out of 5 average rating, 105 reviews
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

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!

4.98 out of 5 average rating, 143 reviews

Popular amenities for Western Maryland rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
Home in Front Royal

Windy Knoll Adventure | River Front | Hot Tub!

4.81 out of 5 average rating, 170 reviews
Top guest favourite
The ranch house is highlighted by a vibrant red roof, set against a backdrop of lush greenery. Large windows provide ample natural light, and a spacious patio with seating areas invites relaxation. The surrounding lawn is well-manicured, enhancing the property’s peaceful setting.
Home in Hyndman

Wills Mountain Ranch

4.98 out of 5 average rating, 173 reviews
Top guest favourite
A spacious mountain home is set against a backdrop of trees, with a gently sloping field leading to a small pond in the foreground. A wooden fence encircles the property, highlighting the serene outdoor environment that encompasses the house.
Home in Sabillasville

Stoney Spring Overlook

4.95 out of 5 average rating, 154 reviews
Top guest favourite
A spacious pool area features a heated in-ground pool and spa surrounded by lounge chairs. A well-maintained lawn and shaded seating areas complement the outdoor space, while a house is visible in the background, nestled among the trees.
Home in Marshall

Clean 5BR w Heated Pool, Spa - Horse, Wine Country

4.94 out of 5 average rating, 147 reviews
Guest favourite
A spacious outdoor area features a large in-ground pool surrounded by a patio. Lounge chairs in a bright blue color are arranged along the edge. A picnic area with tables and chairs is also visible, along with a children's play area nearby.
Home in Lovettsville

COZY3500sf Private-10acres Pool-PickleBall-Hot Tub

4.87 out of 5 average rating, 142 reviews
Guest favourite
Home in Oakland

Amazing Views! | 4BD/4.5BA | Dock, WISP, Hot Tub

4.96 out of 5 average rating, 299 reviews
Top guest favourite
A spacious solarium features large windows allowing plenty of natural light to fill the room, with views of the surrounding greenery. A comfortable seating area is arranged with a mix of sofas and chairs, complemented by various plants adding a touch of nature. The heated concrete floor enhances comfort in this inviting gathering space.
Home in Knoxville

An Escape Bordering National Park land 1 mi to C&O

5.0 out of 5 average rating, 109 reviews
Top guest favourite
A spacious living area features a large leather sectional sofa arranged around a wooden coffee table. A stone fireplace with a fire is highlighted, while a flat-screen TV hangs above it. Large windows allow for natural light, and a dining space is visible in the background.
Home in Champion

5BR Seven Springs Home on Resort, Hot Tub, Shuttle

4.94 out of 5 average rating, 111 reviews

Apartment rentals with a pool

Top guest favourite
An inviting living area features a large, comfortable sofa with warm-toned cushions, situated near a stone fireplace. Exposed wooden beams adorn the ceiling, while natural light streams through doors leading to an outdoor space. A dining table and rustic decor complement the cozy ambiance.
Apartment in Champion

Sleeps 6, 2BR, 3BED, FREE Shuttle, POOL, Hot Tub

4.99 out of 5 average rating, 146 reviews
Top guest favourite
A two-story condo building is shown against a clear blue sky, surrounded by well-maintained greenery. The parking area in front features designated spaces, with vehicles parked nearby. Trees provide shade, enhancing the inviting atmosphere of the community.
Apartment in McHenry

Lake Access/2BR/2Bath/kitchen/pool/5m to Wisp

4.95 out of 5 average rating, 173 reviews
Guest favourite
Apartment in Champion

Stay 2+Nights, Get 1 Free @ 7 Springs w/ Hot Tub

4.86 out of 5 average rating, 180 reviews
Guest favourite
A cozy living area features a dark blue sofa, a coffee table with decorative plants, and a dining table visible in the background. A ladder leads to a loft area with additional sleeping space. Large windows allow natural light to brighten the space.
Apartment in Somerset County

Beautiful, 2 bedroom condo

4.93 out of 5 average rating, 311 reviews
Guest favourite
The spacious living area features wood-paneled walls and a cozy arrangement of seating, including a dark sofa and two armchairs. A coffee table is placed at the center, with a stone fireplace serving as a focal point. Light enters through large windows, enhancing the warm atmosphere.
Apartment in Champion

Seven Springs Adventure Condominium

4.91 out of 5 average rating, 254 reviews
Guest favourite
A newly renovated kitchen features wooden cabinetry and granite countertops. Two pendant lights hang above a large island with seating for four. Stainless steel appliances, including a refrigerator and microwave, are visible, while ample cabinet space contributes to a functional layout.
Apartment in Champion

Seven Springs 2 Bedroom Condo

4.97 out of 5 average rating, 135 reviews
Superhost
A modern living area features a light-colored sectional sofa adorned with a patterned throw. A kitchen with a wood countertop and seating area can be seen in the background, complemented by pendant lighting. Mirrored walls enhance the sense of space, reflecting the inviting atmosphere.
Apartment in Mount Jackson

Bike,Hike,Relax in Lux! at Bryce Resort

4.85 out of 5 average rating, 114 reviews
Guest favourite
Apartment in Jefferson Township

Walk to the Pool, Pet-friendly

4.86 out of 5 average rating, 111 reviews

Other holiday rentals with a pool

Top guest favourite
A rustic outdoor seating area features log benches arranged around a circular fire pit. The red chalet with a flag is visible in the background, surrounded by trees shedding their leaves. A gravel pathway connects the seating area and the chalet.
Chalet in Hedgesville

Cherry Run Chalet

5.0 out of 5 average rating, 110 reviews
Top guest favourite
An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.
Cabin in Bluemont

Rustic Blue Ridge Cabins

4.99 out of 5 average rating, 635 reviews
Top guest favourite
A cabin exterior is shown, featuring a wooden facade and a star accent above the entrance. A spacious deck extends around the front, surrounded by well-maintained landscaping. A gravel driveway leads to the home, framed by trees and gentle rolling hills in the background.
Cabin in Edinburg

Cozy Log Home, (szn)Heated Pool/6 Bedrooms

5.0 out of 5 average rating, 108 reviews
Guest favourite
A spacious great room features a large sectional sofa in rich orange, inviting relaxation. Tall windows allow natural light to fill the space, offering views of the surrounding forest. A decorative area rug anchors the seating area, complemented by a coffee table and thoughtfully arranged decor.
Chalet in Hedgesville

Starcatcher Chalet, The Woods Resort

4.94 out of 5 average rating, 200 reviews
Top guest favourite
A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.
Cottage in Hamilton

*Cottage @ Firefly Cellars* VA Wine Country escape

4.95 out of 5 average rating, 426 reviews
Top guest favourite
A charming outdoor seating area features red wooden chairs and a fire pit, surrounded by lush greenery and pavers. The Cottage, with its welcoming facade and gray metal roof, is visible in the background, offering a cozy retreat in a natural setting.
Cottage in Bluemont

Cottage on Horse Farm: Wineries/Breweries, Horses!

4.95 out of 5 average rating, 288 reviews
Top guest favourite
Home in Harpers Ferry

3BR Chalet | Sauna · Plunge · Hot Tub | Views

4.97 out of 5 average rating, 64 reviews
Top guest favourite
A serene lagoon is depicted, with two individuals quietly floating in the calm water, surrounded by lush greenery and rocky cliffs. The surface mirrors the tranquil sky, while the soft colors of the setting sun enhance the peaceful atmosphere.
Villa in Harpers Ferry

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

4.99 out of 5 average rating, 92 reviews

Destinations to explore