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A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Chestertown Vacation Rentals

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    Check prices for these dates, December 15–16, 2026

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    Our top choices for Chestertown vacation homes

    1. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

    A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

    2. BAYSIDE BUNGALOW

    A house with a front porch, a pathway leading to the entrance, and a bicycle parked outside.

    3. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

    A wooden staircase leading to a beach with a clear view of the sea.

    4. Peaceful Farmhouse Getaway on a Working Farm

    A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

    5. Family Retreat at Lansdowne Manor

    An outdoor patio with a brick wall, a grill, and metal chairs.

    6. Charming 2-bedroom house in Aberdeen with WiFi and AC

    A kitchen with white cabinets, a wooden island, and a washing machine.

    7. Family Friendly Cozy 3 Bedroom Duplex

    A kitchen with wooden cabinets, a stove, and a dining table with chairs.

    8. Charming Coastal/Country Home w/3 Acres & Sauna!

    A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

    9. Bohemia Manor Farm

    Beach bar

    10. Relax on Kent Island in 4 Bedroom Home w/Waterview

    A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

    11. Watch Deer from a Farm Cottage

    A wooden deck with a white railing, surrounded by a lawn and trees.

    12. Cute, Cozy 2-bedroom house near Annapolis with water access

    A sandy beach with a boat docked on the left and calm water.

    13. Large 2 bedroom house with private parking in a nice neighborhood

    A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

    14. 5-bedroom vacation home 5 minutes from historic Charlestown

    A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

    15. Waterfront house with amazing views. Top of the Chesapeake

    A wooden deck with lounge chairs and a dock extending into calm water.

    16. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

    A modern living room with a flat-screen TV, a brown sofa, a dining table with placemats, wicker chairs, and a kitchen area with a microwave and stove.

    17. The Hideaway Spot- Waterfront w/ Dock on Long Cove

    A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

    18. Hidden Fells Point Gem / Private Courtyard Patio

    A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

    19. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

    A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

    20. Idyllic Pasadena Retreat with Garden + Hot Tub!

    A hot tub area with a covered patio, outdoor seating, and a view of the surrounding landscape.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Chestertown

    Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

    See all hotels in Chestertown

    A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

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