
Kid-friendly holiday rentals in Western Maryland
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Western Maryland
Guests agree: these family-friendly 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 Western Maryland family-friendly rentals
Kid-friendly house rentals

Jacob's Cottage

Eclectic & Romantic - Walk to Historic Downtown!

Grouseland's Pondside Vacation Cottage

Cameron Charmer pristine w/double master suites

Round Mountn Top House! Prof. Cleaned w EV-chrger

Mountaintop Cabin w/ Outdoor Tub

Steps to Winery & Battlefield-Pvt Acre w/ Hot Tub!

The Inwood House- easy on/off I-81
Family-friendly apartment rentals

New! The Nest near Deep Creek

Private efficiency apartment

The Tatunka Trail House

Modern Twist in Old Town! Rock n' Roll FUN!

Steeple View Flat in Historic District

Newly repurposed Historic Home in Winchester VA!

Oldtown Schoolhouse. C&O Canal Lock 70.

The Lodge at Turkey Creek
Family-friendly apartment rentals

Lake Access/2BR/2Bath/kitchen/pool/5m to Wisp

2 Queen & 1 Twin Bed / Mountain & Museum Fun

Historic Two Bedroom in Old Town Warrenton

Quiet Stay + Huge Apt + Hot Tub + Dogs, Walkable

Stunning Remodeled 1 BR Condo Steps to Everything.

Lovely, Country Apartment, Just Minutes From Town.

Your Hideaway awaits/1-bedroom downtown pad.

Historic & Cozy ~ Near Antietam Battle & WhiteTail
Destinations to explore
- Pittsburgh Holiday rentals
- Western North Carolina Holiday rentals
- Ocean City Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- Mississauga Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Fitness-friendly rentals Western Maryland
- Cottage rentals Western Maryland
- Rentals with outdoor seating Western Maryland
- Flat rentals Western Maryland
- Bed and breakfasts Western Maryland
- Rentals with a sauna Western Maryland
- Farm stay rentals Western Maryland
- Pet-friendly rentals Western Maryland
- House rentals Western Maryland
- Private suite rentals Western Maryland
- Rentals with a washing machine and dryer Western Maryland
- Cabin rentals Western Maryland
- Family-friendly rentals Western Maryland
- Rentals with breakfast Western Maryland
- Smoking-friendly rentals Western Maryland
- Hotel rentals Western Maryland
- Tiny house rentals Western Maryland
- Waterfront rentals Western Maryland
- Rentals with an EV charger Western Maryland
- Rentals with a kayak Western Maryland
- Rentals with lake access Western Maryland
- Rentals with a patio Western Maryland
- Guest house rentals Western Maryland
- Ski-in/ski-out rentals Western Maryland
- Rentals with a fireplace Western Maryland
- Chalet rentals Western Maryland
- Rentals with pools Western Maryland
- Apartment rentals Western Maryland
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- Townhouse rentals Western Maryland
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- Family-friendly rentals Maryland
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- Fallingwater
- Seven Springs Mountain Resort
- Ohiopyle State Park
- Idlewild & SoakZone
- Blackwater Falls State Park
- Timberline Mountain
- Wisp Resort
- Flight 93 National Memorial
- Hidden Valley Resort
- Shawnee State Park
- Pikewood National Golf Club
- Bella Terra Vineyards
- Canaan Valley Resort & Conference Center
- Lakeview Golf Resort
- Canaan Valley Ski Resort
- Lodestone Golf Course
- White Grass
- Laurel Mountain Ski Resort
- Warden Lake