
Family-friendly vacation rentals in Dorchester County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Dorchester County
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Dorchester County family-friendly rentals
Family-friendly home rentals with a hot tub

Peace Point - Waterfront, Secluded, Home w/hot tub

Reel Relaxation-Waterfront

Starboard on McKeil Point, w/heated pool & hot tub

Waterfront Cottage & Guesthouse Near Cambridge

Riverside Haven w/ Hot Tub

Peaceful Historic House Near Water, with Hot Tub!

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
Family- and pet-friendly home rentals

Deal Island Bay Cottage - Maryland

High St. Art Gallery Suite

Cozy Cottage on the Bay

Historic St. Mary's City, MD

Waterfront Cottage in Mt. Vernon

Cozy & Spacious, The Calway Inn

Spacious Gorgeous Waterfront Home with Sunset View

Charming cottage, 1 blk water, historic area
Family-friendly home rentals with a pool

The Place in Cambridge-Sailing into Autumn

New, Intown Waterfront Townhome w/Pool + Location!

Gorgeous, waterfront home - Perfect for Families.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Spacious and private waterfront, sleeps 10

Turtle's Nest - Hist. Cambridge

Chesapeake Bay Retreat! Spectacular Views!

Rosses Chance Guest House
Destinations to explore
- Apartment rentals Dorchester County
- Beachfront rentals Dorchester County
- Rentals with a kayak Dorchester County
- Rentals with a firepit Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Rentals with breakfast Dorchester County
- Rentals with a fireplace Dorchester County
- Rentals with outdoor seating Dorchester County
- Rentals with a washer and dryer Dorchester County
- Rentals with a hot tub Dorchester County
- Rentals with pools Dorchester County
- Rentals with lake access Dorchester County
- House rentals Dorchester County
- Pet-friendly rentals Dorchester County
- Cottage rentals Dorchester County
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Sandy Point State Park
- Six Flags America
- Breezy Point Beach & Campground
- Piney Point Beach
- Plantation Lakes Golf and Country Club
- Ragged Point Beach
- Quiet Waters Park
- Chesapeake Beach Water Park
- Sandyland Beach
- Heritage Shores
- Rose Haven Memorial Park
- Gerry Boyle Park
- Flounder Pavilion Beach Front - Sandy Point State Park
- North Beach Boardwalk/Beach
- Bayfront Beach
- St George Island Beach
- Franklin Manor Community Private Park
- Guard Shore
- Idlewilde Restoration Project
- Matapeake Clubhouse and Beach
- Lake Presidential Golf Club
- Brownies Beach
- Oxford Beach
- Triton Beach