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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.

  • The Bittersweet
    SUPERHOSTEntire flat · 4 guests · 2 beds · 1 bathroom
    The Bittersweet

    A spacious private apartment right in the heart of beautiful downtown Chestertown! With food, drinks, and shopping literally steps from your front door, it doesn't get better than this. The Bittersweet Apartment is a subsidy of The White Swan Tavern.

    What guests are saying:

    “Cute spacious 1 bedroom apartment right in the heart of downtown Chestertown. Communication with Sarah was great. We loved the place. You can pretty much walk to everything from this location. There is a large living room, full kitchen and nice sized bedroom with a king bed and 1 bathroom. It was perfect for us and we would definitely stay here again!”

  • Rivershore Retreat
    SUPERHOSTEntire cabin · 6 guests · 3 beds · 1.5 bathrooms
    Rivershore Retreat

    Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

    What guests are saying:

    “Perfection. From Paris to Thailand to New York we have stayed in memorable Airbnb’s places. Pj’s place has a charm you won’t find anywhere else. My wife and I plus our 2 rescue pups Bella & Stella had the time of our lives. Fresh flowers, all the kitchen ware you can imagine, a ready to be sparked fire-pit, super clean quarters, romantic sunsets, breathtaking sunrises, coupled with amazing communication. What else can you ask for? If you see this place available, don’t think it twice 😎🙌🏽🔥”

  • RIVER WATCH
    SUPERHOSTEntire flat · 4 guests · 4 beds · 1 bathroom
    RIVER WATCH

    In town, overlooking the marina. A beautiful spot!

    What guests are saying:

    “Perfect little place with a beautiful view of the Marina. Everything you could ask for in the apartment with really neat little touches. Decorated beautifully, and while quaint, there are plenty of places to find a corner to yourself when you want it. The Grill across the street on the Marina is great, and it’s a super short walk to town square where there are some wonderful shops and restaurants. I highly recommend this town and accommodation. Only negative thing I have to say is we didn’t get to stay long enough.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
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Popular amenities for Chestertown holiday rentals

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

Other great holiday rentals in Chestertown

Cottage with Modern Updates - Walk to Waterfront!
SUPERHOSTEntire cottage
Cottage with Modern Updates - Walk to Waterfront!
Price:€133 / night
Beautiful Waterfront Chestertown Getaway
SUPERHOSTEntire guest suite
Beautiful Waterfront Chestertown Getaway
Price:€88 / night
Merry Manor 
Pet Friendly Home
SUPERHOSTEntire house
Merry Manor Pet Friendly Home
Price:€111 / night
Radcliffe Roost: Walk to College & Downtown
SUPERHOSTEntire flat
Radcliffe Roost: Walk to College & Downtown
Price:€88 / night
A Simple Stay...next door to Washington College
SUPERHOSTPrivate room
A Simple Stay...next door to Washington College
Price:€61 / night
Duchess of Kent: Walk to downtown & College
SUPERHOSTEntire house
Duchess of Kent: Walk to downtown & College
Price:€178 / night
Cottage by the Bay in Rock Hall, MD
SUPERHOSTEntire cottage
Cottage by the Bay in Rock Hall, MD
Price:€209 / night
Cozy Carriage House
SUPERHOSTEntire guest house
Cozy Carriage House
Price:€76 / night
Town House in the Heart of Chestertown
SUPERHOSTEntire house
Town House in the Heart of Chestertown
Price:€178 / night
Entire River Front Home - 4 Bedrooms 4.5 Baths
SUPERHOSTEntire house
Entire River Front Home - 4 Bedrooms 4.5 Baths
Price:€445 / night
Sunview Cottage on Chesapeake Bay
Entire cottage
Sunview Cottage on Chesapeake Bay
Price:€87 / night
Oyster Cottage
SUPERHOSTEntire cottage
Oyster Cottage
Price:€222 / night
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