Photo by Assya A

Apartments in Chestertown

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Apartments in Chestertown

Property grounds
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (105)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
The price is AU$247
includes taxes & fees
27 Oct - 28 Oct
First Floor Studio Apartment in Historic Chestertown
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River
Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AU$195
includes taxes & fees
23 Oct - 24 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (16)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is AU$441
includes taxes & fees
23 Oct - 24 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach
Waterfront Retreat with Private Dock and Beach
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AU$483
includes taxes & fees
23 Oct - 24 Oct
Waterfront Retreat with Private Dock and Beach
Marina
Cozy Fells Point Gem / In The Heart of Fells Point
Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (198)
"Great place all around "
United States
Sophia F.
The price is AU$317
includes taxes & fees
9 Nov - 10 Nov
Cozy Fells Point Gem / In The Heart of Fells Point
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (80)
"Clean, safe, joy and owners hospitality perfect"
United States
Ahmet S.
The price is AU$768
includes taxes & fees
27 Oct - 28 Oct
Waterfront Oasis of Annapolis Star
Smart TV
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
The price is AU$505
includes taxes & fees
27 Oct - 28 Oct
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
10.0 out of 10, Exceptional, (7)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is AU$356
includes taxes & fees
23 Oct - 24 Oct
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Pool
Luxury Pool Loft sleeps 4
Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (3)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is AU$555
includes taxes & fees
23 Oct - 24 Oct
Luxury Pool Loft sleeps 4
Apartment (4 Bedrooms) | Interior
Close to Hospital & White Marsh! Rosedale Townhome
Close to Hospital & White Marsh! Rosedale Townhome
3.0 star property
The price is AU$924
includes taxes & fees
23 Oct - 24 Oct
Close to Hospital & White Marsh! Rosedale Townhome
Fridge, microwave, oven, stovetop
18th Cent. Charm in Historic Downtown Annapolis
18th Cent. Charm in Historic Downtown Annapolis
9.0 out of 10, Wonderful, (12)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is AU$575
includes taxes & fees
27 Oct - 28 Oct
18th Cent. Charm in Historic Downtown Annapolis
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Loved everything. Perfect location right on the main drag "
Timothy 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
385
Accommodation
90 Apartments
Lowest Price
AU$195
Highest Price
AU$924

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can search through 6 apartments in Chestertown for your stay.
Why would you choose an apartment over a traditional hotel room?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for couples who want a more local feel, and also for families wanting the conveniences of home.
What's the best apartment I should consider for a stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: A private pool, a washer/dryer and free WiFi are included . A fitness centre and on-site laundry facilities are on site . Historic Downtown Garden Oasis with Private Patio: Includes free WiFi, a balcony and a dining area . Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access: Free WiFi, a balcony and a Smart TV are included . Access to on-site laundry facilities is available on site .
How many apartments can I expect to find in Chestertown?
Expedia has 6 apartments to book in Chestertown.
What can I expect from the weather in Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What should I see and do in Chestertown?
Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Chesapeake Bay and Chestertown Dog Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Rolphs Wharf Marina and Chestertown Historic District.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) away from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.