
Vacation rentals with a kayak in Dorchester County
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Dorchester County
Guests agree: these kayak rentals 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 kayak rentals
House rentals with a kayak

Rumbley Retreat

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Waterfront with sweeping bay view & private beach

Serene getaway with great waterfront views!

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

Riverview Retreat

Stunning Chesapeake waterfront home

Cove Point Cottage with Chesapeake Bay views
Cottage rentals with a kayak

Sailor's Cottage - Private Waterfront

Trinity Oaks Farm (Formerly D and D Farm)

Waterfront! Hot Tub! w/Guest House, Pier, Kayaks

Cozy Cottage on the Bay

Stunning Secluded Luxury waterfront cottage!

Rodo Beach Cottage - Dog Friendly Private Beach wi

Cottage on Cabin Creek

Hot Tub Hideaway by Shark Tooth Shores
Cabin rentals with a kayak

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Covenant Cove (Cove Point Beach)

Pizza Friday

Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!

Your own private beach? Horizon views of the bay?
Destinations to explore
- Rentals with a fireplace Dorchester County
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- Kid-friendly rentals Dorchester County
- Apartment rentals Dorchester County
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- Rentals with a hot tub Dorchester County
- Rentals with outdoor seating Dorchester County
- House rentals Dorchester County
- Pet-friendly rentals Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Beachfront rentals Dorchester County
- Rentals with pools Dorchester County
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- Sandy Point State Park
- Six Flags America
- Heritage Shores
- Maryland Renaissance Festival
- Gerry Boyle Park
- Idlewilde Restoration Project
- Quiet Waters Park
- Guard Shore
- Ragged Point Beach
- Quiet Waters Dog Beach
- Sparrows Beach
- Matapeake Clubhouse and Beach
- Plantation Lakes Golf and Country Club
- Saint Jerome Beach
- Langford Sand
- Severn Beach
- Flounder Pavilion Beach Front - Sandy Point State Park
- Lake Presidential Golf Club
- Piney Point Beach
- Lane Beach
- Brownies Beach
- Chesapeake Beach Water Park
- Rose Haven Memorial Park
- Triton Beach