Holiday rentals with a pool in Western Maryland

*Cottage @ Firefly Cellars* VA Wine Country escape

The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

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!

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.

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May 1- Sept 29 ** PRIVATE 3 hours pool time daily. Plus private patio, grill and fire pit! Horses outside every window! The Cottage is located on a 230 acre horse farm. Red Gate Farm is a full-service, upscale equestrian farm, containing the Cottage, original farm house and 50 horses & ponies. Convenient to Middleburg and Purcellville, you are surrounded by mountains, wineries, breweries, and hiking, with horses right at your doorstep. All in the beautiful town of Bluemont.

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

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.

Fall foliage soon! Coffee bar, swim, fish, firepit

PET FRIENDLY Come experience Reel and Relax!! Hike, explore the trails, fish, float, go rafting, read, enjoy a fire, grill, shop/eat in super cute country towns... Whether its the river, the rolling mountains, the whispering breeze or the cozy cottage, this property offers all of the feels you are searching for without ever leaving! Every season is magical and offers its own reason to visit!!! "This place is amazing; you have literally thought of EVERYTHING! -past guest.

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!

Tiny Cabin Retreat 1 @ Camp Shenandoah Meadows

The Cabin sits on 40 acres in the heart of Fort Valley with views of the blue ridge mountains Across the property. The Cabin is part of the larger Shenandoah Meadows Camp with great amenities as the summer camps only operates June-August. Within a short drive there are hiking, biking, rock climbing, and many local attractions like Luray Caverns, Skyline Drive, vineyards and breweries. Firewood is included! *Pet Fee of $20.00