Book Vacation Apartments in Chestertown
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Apartments in Chestertown
Cozy 1st Floor King George one bedroom apartment right across from USNA
The price is NZ$483 per night
NZ$483
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this apartment in Annapolis. Enjoy free WiFi, patios, and in-room washers/dryers. Popular attractions John Smith House and William Paca House are located nearby.
Kitchen
Washer
'At Fells Point' CitySide - 'Tons better than a hotel!'
The price is NZ$360 per night
NZ$360
includes taxes & fees
2 Jan - 3 Jan 2025
Stay at this apartment in Baltimore. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Baltimore Inner Harbor Marina and Baltimore Cruise Terminal are located nearby.
Kitchen
Free WiFi
Spectacular Location: State Circle Apartment
Stay at this apartment in Annapolis. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Matthew Henson Plaque and Maryland State House are located nearby.
Kitchen
Washer
18th Cent. Charm in Historic Downtown Annapolis
The price is NZ$658 per night
NZ$658
includes taxes & fees
26 Dec - 27 Dec
Stay at this apartment in Annapolis. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions 97, 99 and 101 East Street and The Colonial Players are located nearby.
Kitchen
Washer
'At Fells Point' Courtyard - Your historically restored apartment
The price is NZ$366 per night
NZ$366
includes taxes & fees
20 Jan - 21 Jan 2025
Stay at this apartment in Baltimore. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Baltimore Inner Harbor Marina and National Aquarium in Baltimore are located nearby.
Kitchen
Washer
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Stay at this apartment in Annapolis. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions John Smith House and Annapolis City Dock are located nearby.
Kitchen
Washer
Charming Downtown 3rd Floor 1 Bedroom Apt
The price is NZ$424 per night
NZ$424
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this apartment in Annapolis. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions John Smith House and William Paca House are located nearby.
Kitchen
Washer
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Stay at this apartment in Annapolis. Enjoy free WiFi, a sauna, and a garden. Popular attractions U.S. Naval Academy Golf Club and Chesapeake Bay Bridge are located nearby.
Hot tub
Kitchen
Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Book a stay at this family-friendly apartment in Bel Air. Enjoy private pools, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Harford Artists Gallery and Harford Mall are located nearby.
Pool
Kitchen
Charming Eastport
Stay at this apartment in Annapolis. Popular attractions Annapolis Maritime Museum and Annapolis Landing Marina are located nearby.
Parking available
Relaxation Haven on the Shore near Choptank River
Stay at this apartment in Greensboro. Enjoy a garden, an in-room coffeemaker, and in-room fireplaces.
Kitchen
Washer
Waterfront Oasis of Annapolis Star
The price is NZ$785 per night
NZ$785
includes taxes & fees
26 Dec - 27 Dec
Stay at this apartment in Annapolis. Enjoy free WiFi, private pools, and a water park. Popular attractions U.S. Naval Academy Golf Club and Maryland World War II Memorial are located nearby.
Pool
Kitchen
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 | 74 Apartments |
|---|---|
Lowest Price | NZ$100 |
Highest Price | NZ$785 |
Popular accommodation | Cozy 1st Floor King George one bedroom apartment right across from USNA, 'At Fells Point' CitySide - 'Tons better than a hotel!', Spectacular Location: State Circle Apartment, 18th Cent. Charm in Historic Downtown Annapolis, 'At Fells Point' Courtyard - Your historically restored apartment, COZY DOWNTOWN APARTMENT-Naval Academy Vicinity, Charming Downtown 3rd Floor 1 Bedroom Apt, Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis, Bel Air Apartment w/ Pool ~ 2 Mi to Main St, Charming Eastport, Relaxation Haven on the Shore near Choptank River , Waterfront Oasis of Annapolis Star |
More accommodations in Chestertown
Top trending hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
The price is NZ$208 per night from 1 Jan to 2 Jan
NZ$208
includes taxes & fees
1 Jan - 2 Jan 2025
8.4/10 Very Good! (734 reviews)
^Eligibility requirements and conditions apply