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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Chestertown apartments

Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is AED 364
AED 583 total
includes taxes & fees
15 Dec - 16 Dec
First Floor Studio Apartment in Historic Chestertown
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Apartment in Millington

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 AED 250
AED 459 total
includes taxes & fees
15 Dec - 16 Dec
Guest Suite for up to 2 in a Victorian on the Chester River
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 760
AED 1,520 total
includes taxes & fees
18 Dec - 19 Dec
Waterfront Oasis of Annapolis Star
Beach
Waterfront Retreat with Private Dock and Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is AED 643
AED 1,144 total
includes taxes & fees
14 Dec - 15 Dec
Waterfront Retreat with Private Dock and Beach
Marina
Cozy Fells Point Gem / In The Heart of Fells Point

Apartment in Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (200)
"Great place all around "
United States
Sophia F.
The price is AED 202
AED 725 total
includes taxes & fees
14 Dec - 15 Dec
Cozy Fells Point Gem / In The Heart of Fells Point
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Apartment in Greektown

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
9.6 out of 10, Exceptional, (8)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is AED 496
AED 827 total
includes taxes & fees
15 Dec - 16 Dec
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Apartment (4 Bedrooms) | Interior
Close to Hospital & White Marsh! Rosedale Townhome

Apartment in Nottingham

Close to Hospital & White Marsh! Rosedale Townhome
3.0 star property
The price is AED 698
AED 1,961 total
includes taxes & fees
17 Dec - 18 Dec
Close to Hospital & White Marsh! Rosedale Townhome
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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Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Really nice cozy room we had the terrace balcony would definitely stay again!"
Takema 1-night trip
Posted 2 days ago
Pendry Baltimore

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 6 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. Historic Downtown Garden Oasis with Private Patio: Free WiFi, outdoor space, and separate dining areas are included. Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access: Includes free WiFi, private balconies, and Smart TVs. Access to onsite 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 during my trip to 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
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 Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Crumpton Auction.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) 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, consider renting a car to take in more sights.