Holiday rentals with a pool in Berkeley County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Berkeley County

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, 186 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!

ValueFamilyBiking

Top Guest favourite

The cabin features a contemporary A-frame design with large windows that reflect surrounding trees. A spacious deck wraps around the structure, providing outdoor seating options. Natural light streams through the windows, inviting a connection with the outdoors.

Cabin in Hedgesville

4.93 out of 5 average rating, 316 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.

LocationFamilyComfort

Top Guest favourite

A circular living area is surrounded by large windows that offer views of the serene woods. Comfortable seating includes a green sofa and two white chairs, complemented by a unique pendant light and a cozy rug on the carpeted floor.

Cabin in Hedgesville

4.98 out of 5 average rating, 95 reviews

Round 70s cabin-pickleball, golf, gym, pools

Experience this unique, authentic 1977 round cabin with amazing views from the curved wall of windows. Work from home with fast internet or unplug and simply relax in peaceful awe of the view. Located in The Woods resort, with 2 beautiful outdoor pools (open Memorial Day through Labor Day), large Sports Center (indoor pool), pickleball, tennis & golf! 25 minutes from Berkeley Springs with its famous hot springs, art center, and shops. Hiking, biking, river floats, horseback riding all nearby.

LocationFamilyWalkability

Superhost

Cabin in Hedgesville

4.84 out of 5 average rating, 202 reviews

Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access

Cozy up by the wood burning fireplace or head outside and enjoy the large semi-private yard and screened gazebo. Roast marshmallows by the fire pit after a day exploring nearby Sleepy Creek WMA, where you’ll enjoy fishing, public river access and white water rafting. Whether you’re looking for adventure, relaxation, or a little bit of both, it’s the perfect spot for your getaway! The highlights: - WiFi for streaming movies & remote work - The Woods Resort Access - Dog-Friendly - Modern Decor

LocationFamilyCleanliness

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

4.93 out of 5 average rating, 196 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.

FamilyValueKitchen

Top Guest favourite

Cabin in Hedgesville

5 out of 5 average rating, 36 reviews

Gem of the Woods- Cozy Cabin w/ Hot Tub, Game Room

Welcome to Gem of the Woods, a cozy cabin nestled in the forest, yet part of The Woods Resort. Unwind in the screened-in hot tub, gather by the fire pit, or enjoy a game of pool in the game room. The three-bedroom cabin has been thoughtfully curated with pet-friendly touches such as a dog run, an EV charger, perfect for all travelers. The resort features a spa, two 18- hole golf courses, seasonal outdoor pool, indoor pool, restaurant, & nearby hiking trails- perfect for a relaxing getaway

LocationValueHot tub

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

5 out of 5 average rating, 108 reviews

Cherry Run Chalet

Kick back and relax in this peaceful, stylish chalet at The Woods community in wild and wonderful West Virginia. The 2-acre property backs up to the 23,000-acre Sleepy Creek State Wildlife Area, a hikers dream. The Woods offers 2 golf courses, indoor and outdoor pools, indoor hot tub, tennis, exercise gym and more. The Sports and Spa center is within walking distance from the chalet for self-care pampering. The Clubhouse Grille and Pub is a great option for dine in and carry out. Enjoy!

FamilyValueOutdoor spaces

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, 136 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.

LocationFamilyLaundry

Guest favourite

The exterior view highlights a circular cabin surrounded by a forest. A spacious deck is visible, furnished with two red chairs, a small table, and a fire pit. Stacked firewood is neatly arranged, while a charcoal grill is positioned at the corner.

Home in Berkeley County

4.94 out of 5 average rating, 66 reviews

Mushroom Treehouse Woods Retreat (2br/1.5ba)

Meet The Mushroom Treehouse — a cozy, round yurt style cabin in The Woods Resort community. This 2 bedroom, 1.5 bath peaceful wooded oasis is the perfect rest & recharge spot before and after you explore all of its neighboring outdoor beauty! Access to indoor & outdoor pools & recreational courts, spa, golf and hiking trails — there are endless ways to create memorable stays each time you visit ALL YEAR ROUND!✨ “And into the forest I go, to lose my mind and find my soul”. 🌲🪵🍄

LocationFamilyIndoor spaces

Top Guest favourite

The entrance to the guest house is showcased, featuring a combination of brick and stone siding. A welcoming red door is flanked by large windows, and a decorative wreath adds a touch of charm. The pathway is lined with neatly trimmed shrubs and grass.

Home in Big Pool

4.94 out of 5 average rating, 68 reviews

Whitetail Meadows Guest House

Come enjoy the country lifestyle at Whitetail Meadows Guest House. No matter the season, Whitetail Meadows Guest House offers a location embedded in the casual country lifestyle of fishing, hiking, biking, boating, and a variety of winter sports. We aim to make your stay with us as pleasant as possible, so please feel free to reach out if there is anything we can do to improve your current or future stay. *See Property Information for Package Details on Larger Day Gatherings*

LocationFamilyPool

Top Guest favourite

A hot tub is situated on a wooden deck, surrounded by trees. Evening light casts a warm glow, enhancing the inviting turquoise water. The sky transitions from daylight to dusk, creating a serene atmosphere, perfect for relaxation.

Cabin in Hedgesville

4.96 out of 5 average rating, 83 reviews

Toasted Marshmallow Chalet | Hot Tub & Fire Pit

Some escapes you plan. Others you feel. At The Toasted Marshmallow Chalet, you’ll sink into a steaming hot tub under open skies, gather around a glowing fire pit, and finally let yourself exhale. Whether you’re escaping as a couple, with your closest, or the whole family — four-legged members included — this is yours. Nestled within the refined Woods Resort community, you’re moments from scenic trails, resort amenities, and local gems — just 90 minutes from DC.

FamilyLocationAccuracy

Guest favourite

An open living area features a comfortable gray sofa and a round wooden coffee table on a textured area rug. The kitchen showcases modern appliances and barstool seating at the island, with natural light filtering through windows that highlight the neutral tones and rustic ceiling beams.

Home in Hedgesville

4.91 out of 5 average rating, 67 reviews

The Stairway to Heaven

Private Boho Farmhouse Retreat | HOT TUB, Pools, Golf, Hiking Escape to a luxury boho farmhouse retreat just 90 minutes from Washington, DC, and Baltimore. Unwind in your private hot tub beneath the stars, sip your morning coffee on the screened porch, and enjoy resort-style amenities including pools and championship golf. Explore Harpers Ferry, relax in Berkeley Springs, or hike scenic trails—then return to your peaceful retreat to recharge.

FamilyLocationHospitality