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Featured Apartments in Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown MD

NZ$272

25 Dec - 26 Dec

includes taxes & fees

Stay at this golf apartment in Chestertown. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Wilmer Park and Sumner Hall are located nearby.

Pool

Hot tub

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall MD

Stay at this apartment in Rock Hall. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions The Mainstay and Rock Hall Harbor are located nearby.

Kitchen

Washing machine

Bay View Studio Apartment

Annapolis MD

Stay at this apartment in Annapolis. Enjoy free Wi-Fi, a water park and a garden. Popular attractions Annapolis Landing Marina and Annapolis Maritime Museum are located nearby.

Hot tub

Kitchen

Stunning 2-Bedroom loft apartment in waterfront community near BWI

Glen Burnie MD

Stay at this apartment in Glen Burnie. Enjoy air conditioning. Popular attractions Baltimore Cruise Terminal and Bingo World are located nearby.

Pet-friendly

Air conditioning

Pristine Downtown 1-Bedroom Steps from State House

Annapolis MD

Stay at this apartment in Annapolis. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions The Colonial Players and 97, 99 and 101 East Street are located nearby.

Kitchen

Washing machine

Charming Downtown 3rd Floor 1 Bedroom Apt

Annapolis MD

NZ$492

28 Dec - 29 Dec

includes taxes & fees

Stay at this apartment in Annapolis. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions John Smith House and William Paca House are located nearby.

Kitchen

Washing machine

Newly restored apartment in the heart of Chestertown

Chestertown MD

Stay at this apartment in Chestertown. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Chestertown Historic District and Garfield Center for the Arts at the Prince Theater are located nearby.

Kitchen

Washing machine

Trendy Baltimore Townhome: 2 Mi to Downtown!

Baltimore MD

Stay at this apartment in Baltimore. Enjoy free parking, a marina and balconies. Popular attractions Baltimore Inner Harbor Marina and National Aquarium in Baltimore are located nearby.

Kitchen

Washing machine

Waterfront Retreat with Private Dock and Beach

Worton MD

NZ$537

6 Jan - 7 Jan 2026

includes taxes & fees

Stay at this apartment in Worton. Enjoy free Wi-Fi, an in-room coffee maker and air conditioning. Popular attractions Kinnairds Point Drive and Still Pond Station Park are located nearby.

Kitchen

Free WiFi

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Baltimore MD

NZ$395

6 Jan - 7 Jan 2026

includes taxes & fees

Stay at this apartment in Baltimore. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Baltimore Inner Harbor Marina and Baltimore Cruise Terminal are located nearby.

Kitchen

Washing machine

Waterfront Oasis of Annapolis Star

Annapolis MD

NZ$714

29 Dec - 30 Dec

includes taxes & fees

Stay at this apartment in Annapolis. Enjoy free Wi-Fi, private pools and cable/satellite TV service. Popular attractions U.S. Naval Academy Golf Club and Maryland World War II Memorial are located nearby.

Pool

Kitchen

Luxury Pool Loft sleeps 4

Annapolis MD

Stay at this apartment in Annapolis. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions Bay Hills Golf Club and U.S. Naval Academy Golf Club are located nearby.

Pool

Kitchen

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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.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.

^Eligibility requirements and conditions apply.

Chestertown Apartments essential information

Accommodation	80 Apartments
Lowest Price	NZ$136
Highest Price	NZ$714
Popular accommodation	First Floor Studio Apartment in Historic Chestertown, Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!, Bay View Studio Apartment, Stunning 2-Bedroom loft apartment in waterfront community near BWI, Pristine Downtown 1-Bedroom Steps from State House , Charming Downtown 3rd Floor 1 Bedroom Apt, Newly restored apartment in the heart of Chestertown, Trendy Baltimore Townhome: 2 Mi to Downtown!, Waterfront Retreat with Private Dock and Beach, Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC, Waterfront Oasis of Annapolis Star, Luxury Pool Loft sleeps 4