Western Maryland


Properties Available 110 properties available
Please note There is a 13 night limit on reservations per local regulations. Reservations over 13 nights are prohibited and cannot be honored. Originally a farmhouse built in 1936, this beautiful home has an enormous backyard and plenty of room for activities. The beautiful stone fireplace, wet bar, and game table make the living room a wonderful
Amazing Grace (286546)
McHenry, MD
House
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
No matter the season, Nimba Cabin boasts a peaceful wilderness retreat for you and your favorite people. Nestled near a plethora of outdoor recreation hotspots, your time spent at Nimba Cabin is guaranteed to be memorable! When the snow is falling, nearby Wisp Resort offers excellent skiing and snowboarding opportunities. The sunny season is best s
Nimba Cabin (593702)
Oakland, MD
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 4 baths
Guests 10 guests
Pack your bags and slip away to this incredible condo with stunning lake views. A sound machine, highchair, and Pack 'N Play make this the ideal place to bring your little ones and the family chef will love cooking up something delicious on the stainless steel grill on the deck or inside in the full kitchen. Take in the serene view from the balcony
Owl's Landing (256394)
Oakland, MD
House
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Take in the beauty of Deep Creek Lake during every season at this Gambrel-style cabin, beautifully secluded in the woods of Oakland. Hiker, skier, or water sports enthusiast, you'll love coming home to a brand-new hot tub June 2023, a wraparound deck, and a firepit where you can roast s'mores at the edge of the forest. This two-story cabin is par
Woodsy Way Cabin (580087)
Oakland, MD
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 9 guests
Please note There is a 13 night limit on reservations per local regulations. Reservations over 13 nights are prohibited and cannot be honored. Bring your family and friends along any time of year for a peaceful getaway in western Maryland. This Oakland home's peaceful location balances isolation with convenience, while providing all the perks you
Tees 'N Skis (243020)
Oakland, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Nestled on 1.5 acres of wooded land near Deep Creek Lake, you'll find this rustic Sky Valley chalet. Located in the forested Sky Valley Community, enjoy having access to the swimming docks at Deep Creek Lake and hiking at several close state parks. Constructed in a chalet style, this wooden A-frame's gingerbread detailing, modern finishes, and rus
Summit Hill (580225)
Swanton, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Bring the entire family and enjoy the pleasant Maryland weather when you call Tall Castles your Oakland hideaway! Boasting four bedrooms, an updated interior, and stellar amenities both inside and outside - everything you could possibly want in a vacation home is here. Surrounded by mountain views, lounge on the oversized sofa in the sun-filled l
Tall Castles (582493)
Oakland, MD
House
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Come and create everlasting memories with your family and friends at Slips amp Slopes, a recently-updated lake-view home that is centrally located to put the best of Deep Creek Lake at your fingertips! Within a three-mile drive, you will find numerous activities, restaurants, and shops. The kids will love the ziplines at Monkey Business Adventure
Slips and Slopes (579169)
McHenry, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Perched near skiing and endless adventure, this beautiful cabin is perfect for a family mountain getaway! The high ceilings and open floor plan are perfect for gatherings around the grand stone fireplace after a full day on the slopes. This two-story mountain gem has direct access to ski slopes and gorgeous views. The main floor boasts a fully equi
Top of the Slopes (259096)
McHenry, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Please note There is a 13 night limit on reservations per local regulations. Reservations over 13 nights are prohibited and cannot be honored. Escape to northwest Maryland with the whole family at this comfortable, three-level townhouse with a private, furnished deck, a foosball table, a wood-burning fireplace, and space for up to eight guests. P
VOW Winding Way 11 (284204)
McHenry, MD
House
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Please note There is a 13-night limit on reservations per local regulations. Reservations over 13 nights are prohibited and cannot be honored. Come up to the lake and relax in style at this unique chalet, completely renovated with modern amenities and appliances while still retaining its rustic charm! Golden A-Frame is located at the end of a priv
Golden A-Frame (251589)
Swanton, MD
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
True ski-inski-out access is just one perk that makes this Wisp Resort condo the ideal choice for your next getaway. Boasting more than 2000 sq ft of living space spread out across four floors, this amazing escape also features three private decks and a private hot tub! During the winter months, you'll be able to access Wisp's East Ridge and Chairl
Bright Passage Getaway (586884)
McHenry, MD
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests

Tell us what you're looking for and someone will contact you with available options.