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Vacation rentals in Chestertown

Vacation rentals in Chestertown

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chestertown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Town House in the Heart of Chestertown
SUPERHOST
Entire house · 4 guests · 3 beds · 2.5 bathrooms

Town House in the Heart of ChestertownLocated in historic district of Chestertown. One block from the Chester River, walking distance to bakery, restaurants, coffee shops, book store, retail shops and Saturday's Farmer's Market.

Historic Chestertown
SUPERHOST
Entire house · 5 guests · 3 beds · 2.5 bathrooms

Historic ChestertownLovely home with great indoor-outdoor entertaining space. Fully renovated 3 bed, 2.5 bath. Top of the line open floor plan kitchen/family room. Located in Historic district on the main street only few blocks from restaurants, shops and river front.

Sunview Cottage on Chesapeake Bay
Entire cottage · 4 guests · 3 beds · 1 bathroom

Sunview Cottage on Chesapeake BaySunview is ideal for our times. Beautiful, in a natural setting, and clean. Modern, Cozy 2-Bedroom Cathedral-Ceiling Cottage with Central Air Conditioning and Heat, Fireplace, & Loft. Views of the Chesapeake Bay and sunsets from the house & wraparound deck. Perfect destination for a getaway with friends and family. Located in the scenic, serene environs of the Eastern Shore of Maryland in Tolchester.

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chestertown holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chestertown

Rivershore Retreat
SUPERHOSTEntire cabin
Rivershore Retreat
Price:£223 / night
Beautiful Waterfront Chestertown Getaway
SUPERHOSTEntire guest suite
Beautiful Waterfront Chestertown Getaway
Price:£77 / night
Merry Manor 
Pet Friendly Home
SUPERHOSTEntire house
Merry Manor Pet Friendly Home
Price:£98 / night
Cozy Carriage House
SUPERHOSTEntire guest house
Cozy Carriage House
Price:£70 / night
Private Bedroom and bath in Chestertown, MD
Private room
Private Bedroom and bath in Chestertown, MD
Price:£43 / night
83 steps to the beach...
SUPERHOSTEntire house
83 steps to the beach...
Price:£211 / night
Cottage with Modern Updates - Walk to Waterfront!
SUPERHOSTEntire cottage
Cottage with Modern Updates - Walk to Waterfront!
Price:£117 / night
Two bedroom one bath near Washington College
Entire house
Two bedroom one bath near Washington College
Price:£196 / night
Duchess of Kent: Walk to downtown & College
SUPERHOSTEntire house
Duchess of Kent: Walk to downtown & College
Price:£226 / night
Cottage by the Bay in Rock Hall, MD
SUPERHOSTEntire cottage
Cottage by the Bay in Rock Hall, MD
Price:£184 / night
Waterfront w/Pier &Walking Distance to Chestertown
SUPERHOSTEntire house
Waterfront w/Pier &Walking Distance to Chestertown
Price:£416 / night
Classic Victorian in Chestertown
SUPERHOSTEntire house
Classic Victorian in Chestertown
Price:£136 / night
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