
Guest house holiday rentals in Western Maryland
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Top-rated guest house rentals in Western Maryland
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for guest house rentals in Western Maryland
Family-friendly guest house rentals

Mountain Retreat | Hot Tub • Pool • Trails • Views

Berlin Mini Suite

The Nest on Nixon Road

Peggy's Guest Hideaway

Coorie Inn

Private Luxury Retreat Close to everything!

Updated Mercersburg Carriage House on Main Street

The Cock and Feather Guesthouse
Guest house rentals with a patio

Wine Country Loft

Between the Rivers Guest House

The Villa

18th Century Middleburg Cottage

A lovely cottage in The Plains, Virginia

Cozy Shenandoah River Cabin (10min to Nat’l Park!)

The Woodstock (VA) Hippie House

Riverfront Oasis with Mountain Views, Near Town
Guest house rentals with a washing machine and dryer

Barn Apartment in VA Wine Country

Skyhorse Retreat Guest House

Riverkeeper Inn

Bluemont Escape:Walk to Bears Den; Bear Chase Brew

Private 2 BR, 1 Bath Carriage House Near Wineries!

CozyLeesburgCottage-Private Home Downtown Leesburg

Mountain Home with a View

"Cabbin" at Mountain Home B&B
Destinations to explore
- New York City Holiday rentals
- Western North Carolina Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- Ocean City Holiday rentals
- Virginia Beach Holiday rentals
- Rentals with a patio Western Maryland
- Chalet rentals Western Maryland
- Cabin rentals Western Maryland
- Private suite rentals Western Maryland
- Rentals with a fireplace Western Maryland
- House rentals Western Maryland
- Flat rentals Western Maryland
- Rentals with an EV charger Western Maryland
- Pet-friendly rentals Western Maryland
- Fitness-friendly rentals Western Maryland
- Apartment rentals Western Maryland
- Rentals with a hot tub Western Maryland
- Ski-in/ski-out rentals Western Maryland
- Hotel rentals Western Maryland
- Rentals with breakfast Western Maryland
- Rentals with a washing machine and dryer Western Maryland
- Rentals with a kayak Western Maryland
- Cottage rentals Western Maryland
- Rentals with outdoor seating Western Maryland
- Bed and breakfasts Western Maryland
- Farm stay rentals Western Maryland
- Rentals with lake access Western Maryland
- Family-friendly rentals Western Maryland
- Rentals with a sauna Western Maryland
- Rentals with pools Western Maryland
- Tiny house rentals Western Maryland
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- Rentals with a firepit Western Maryland
- Townhouse rentals Western Maryland
- Guest house rentals Maryland
- Guest house rentals United States
- Fallingwater
- Seven Springs Mountain Resort
- Timberline Mountain
- Idlewild & SoakZone
- Ohiopyle State Park
- Wisp Resort
- Blackwater Falls State Park
- Shawnee State Park
- Hidden Valley Resort
- Lakeview Golf Resort
- Bella Terra Vineyards
- Canaan Valley Resort & Conference Center
- White Grass
- Pikewood National Golf Club
- Canaan Valley Ski Resort
- Lodestone Golf Course
- Laurel Mountain Ski Resort
- Winter Experiences at The Peak
- Warden Lake
- Forks of Cheat Winery
- West Whitehill Winery