Holiday rentals with a pool in Berkeley County

4.95 out of 5 average rating, 134 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!

5 out of 5 average rating, 101 reviews

Home in Hedgesville

Spacious & Charming! Large deck+Game shed+Firepit

Get away and play at this spacious cabin. Sip your morning coffee on the large deck as the sun rises through the trees. By day, swim, explore nearby hiking trails, play tennis or golf at The Woods facilities, or lounge while the kids play in the fenced yard. As the sun sets, dine outdoors on the picnic table, or indoors on the large dining room table. At night, retire to the detached game shed for a nightcap or gather around the fire while you cherish the serenity and search the sky for Orion.

4.92 out of 5 average rating, 273 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.

5 out of 5 average rating, 46 reviews

Round 70s cabin-pickleball, golf, gym, indoor pool

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.

4.93 out of 5 average rating, 42 reviews

Cozy Chalet w Hot Tub ~EV~Gym~Pool~Fire pit

Escape to our cozy chalet in the woods, a perfect mix of relaxation and adventure! Unwind in the hot tub, relax by the electric fireplace with wooded views, or make s’mores at the fire pit. Enjoy a fully stocked kitchen, plus complimentary coffee, tea, and hot cocoa. Access the gym, indoor pool, multipurpose court, and seasonal outdoor pool. One-day guest passes included, with extra passes available to purchase. Hiking trails and golf courses are minutes away. Your ideal getaway is waiting!

4.94 out of 5 average rating, 155 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.

4.94 out of 5 average rating, 194 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.

4.97 out of 5 average rating, 34 reviews

Home in Hedgesville

'Little Blue Bungalow' in The Woods-pool access

Escape from the hustle-and-bustle of everyday life at The Little Blue Bungalow! The perfect getaway spot located in The Woods community in Hedgesville, WV, just under two hours from the D.C./Baltimore area. It’s the ideal place for couples, families, or groups of friends. Come for a weekend retreat or week-long vacation! Our cozy home offers plenty of privacy and space to explore, with all of the modern comforts you need. **Pool/tennis access. Message us for details on day passes!**

Superhost

4.87 out of 5 average rating, 122 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.

Superhost

4.84 out of 5 average rating, 207 reviews

Stylish Retreat w Fireplace, Games & Pool Access

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! Access to two outdoor pools, an indoor pool with hot tub, tennis and pickleball courts, a gym, and 36 holes of golf. Enjoy the indoors and outdoors in any season! The highlights: - Wood burning fireplace - Screened Porch with seating for the group - WiFi for streaming movies & remote work - Resort Amenities

4.97 out of 5 average rating, 93 reviews

Home in Hedgesville

Peaceful Pines, luxury 4-bed cabin, EV, Pool, Golf

Peaceful Pines is a beautiful, luxurious mid-century cabin where the main objective is relaxation. Great for a girls weekend, multiple family or generation trips! Plenty of room to stretch out and have your own space. Go hiking, swim at the pools, go golfing, use the projector on the covered porch, curl up in front of the fire with a good book or play board games. Peaceful Pines cabin offers all of that and more. We are less than 2 hours outside of DC, but it feels like a world away.