Holiday rentals with a pool in Berkeley County

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.

Cozy Cabin For All The Family!

Nestled in the Shenandoah Valley, surrounded by golf course views and peaceful wildlife, lies this 3-bedroom, 2.5-bathroom vacation rental! Indulge in the finer things when you book this charming cabin that’s spacious enough to make memories with your family, friends, and beloved pups. Spend your days swimming in the pool, relaxing in the hot tub, competing in foosball matches, and cozying up with a movie. Enjoy a home-grilled meal on the screened-in patio, followed by s’mores by the fire pit!

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!

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.

Secluded Mtn Chalet-HotTub -Clean-Spacious-Fenced

Toboggan Hill Hideaway is a chalet style house nestled in The Woods Resort. This spacious retreat sleeps 10, has 2 separate living areas, & a private hot tub to enjoy. Perfect for family gatherings. Located high on the mountain, with scenic views. Perfect for outdoor enthusiasts, those who want to enjoy all the amenities of The Woods Resort, or just hang-out in the house with your family or friends. Come immerse yourself in rustic charm with modern amenities at Toboggan Hill Hideaway!

4BR Cabin | HotTub | GameRm | FirePit | PoolAccess

Come and enjoy Acorn & Antler, a pet-friendly, four-bedroom cabin in The Woods resort! The spacious home has all of the amenities you need for a quick weekend trip or an extended stay. Cozy nights by the fireplace, a peaceful soak in the private hot tub, cookouts with the griddle and nights at the fire pit will keep you feeling relaxed before and after your trip. Resort access for $5/person/day (see below for details). Close to Berkeley Springs and only two hours from DC or Baltimore.

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!

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.

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”. 🌲🪵🍄

Fire Pit, Arcade Games, Deck, Grill & Pool Access

A four season destination with arcade games and nearby public river access. Enjoy magnificent views from just about every room in this 3 story retreat. Cozy up by the fireplace or enjoy a good book in the reading nook. Located in the Woods Resort where you’ll enjoy a community lake, beach and resort amenities. Perfect for family, friends or small groups! The highlights: - Wood burning fireplace - Roast s’mores by the fire pit - WiFi for streaming movies & remote work

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.

The Cabin on the Run

We have a generator! Never be without power during your vacation. Come spend the winter by the woodstove! Take a trip to The Woods in Wild, Wonderful West Virginia. Cabin on the Run is named after the beautiful run running behind the property with a babbling soundscape that can be heard from the expansive deck. Cabin on the Run provides all modern amenities so that you only need to bring clothes and food for a trip away.