Holiday rentals with a pool in Western Maryland

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

Beautifully renovated Swiss Mountain 2 bedroom condo comfortably sleeps 6 with two full baths. The open flow of the living room into the kitchen is the perfect place to unwind after a long day. Tucked away in the Mountains, this condo makes you feel like you are in a forest with resort amenities just up the road. 24/7 shuttle service to & from the Seven Springs Mountain Resort provides round-the-clock fun for the whole family! Pool access during the summer months make this a year round getaway!

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!

Romantic, hot tub, king bed, private, pet-friendly

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

Mountain & Lake Retreat: 2x Queen, saltH2O Hottub

The Tortoise and the Bear B&B: Where Relaxation Meets Adventure Features: - 6-person premium saltwater hot tub - 1 Gbps fiber internet for seamless remote work/streaming - Two bedrooms with Sleep Number dual-side queen beds - Fully stocked kitchen - Multiple outdoor dining/seating areas Location: - 10-minute walk to Lake Laura with a 3-mile path - 5-minute drive to Bryce mountain skiing, biking, and golf Our home features a spiral staircase which may not be suitable for very young children

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.

Seven Springs *Ski-in/out Condo 1 Bed.(king),1 Bth

Nestle into this cozy, one bedroom condo in The Villages at Seven Springs Mountain Resort. This retreat boasts easy ski-in/ski-out access to the slopes via the Villages Trail behind the condo building (weather permitting). What makes this condo special is the private entrance, large living space, a bedroom with king bed, a full kitchen, and a balcony. As a guest, you have access to the free shuttle service or visit the clubhouse with pool, hot-tub, basketball and tennis in the summer months.

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.

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.

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.

The Davis Ridge - Mt Views, Fireplace, Balcony

This beautiful property 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.

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!