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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 90 Apartments in Chestertown with updated reviews, rates, and availability.

Bay View Studio Apartment
Outdoor spa tub

Bay View Studio Apartment

10.0 out of 10, Exceptional, (43)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment
Newly restored apartment in the heart of Chestertown
Fridge, microwave, oven, stovetop

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (23)
"Wonderful spot in the center of historical Chestertown,"
Newly restored apartment in the heart of Chestertown
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (31)
"Very nice place. Great location, close to dining, etc. No TVs. Would have liked to know that going in. Otherwise, prefect spot."
Historic Downtown Garden Oasis with Private Patio
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Aerial view

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

The price is AED 610
AED 822 total
includes taxes & fees
20 May - 21 May
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.6 out of 10, Exceptional, (7)
"Property description is accurate, host is quickly responsive."
The price is AED 698
AED 1,353 total
includes taxes & fees
15 May - 16 May
18th Cent. Charm in Historic Downtown Annapolis
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Fridge, microwave, oven, stovetop

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

9.8 out of 10, Exceptional, (38)
"Perfect location for walking around the Annapolis waterfront area! Clean, comfortable and well appointed. Would definitely stay here again!"
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Interior

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (30)
"Tucked away in the back of the neighborhood, its quiet and private. Nice spa amenities, and after a bunch of traveling it was nice to stay somewhere with a washer and dryer"
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Cityside Fells Point Apartment
Marina

Cityside Fells Point Apartment

9.8 out of 10, Exceptional, (187)
"Apartment was well appointed, we found everything we needed for a great stay. The place was super clean, check-in and check-out were simple and the location was perfect!"
The price is AED 301
AED 751 total
includes taxes & fees
26 May - 27 May
Cityside Fells Point Apartment
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (85)
"Quiet neighborhood and the best place to stay."
The price is AED 360
AED 579 total
includes taxes & fees
14 May - 15 May
First Floor Studio Apartment in Historic Chestertown
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Fridge, microwave, oven, stovetop

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (49)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Cozy 1st Floor King George one bedroom apartment right across from USNA
Fridge, microwave, oven, stovetop

Cozy 1st Floor King George one bedroom apartment right across from USNA

10.0 out of 10, Exceptional, (29)
"We were thrilled to be able to return to this great apartment.It is very close to Gate 1 and the sofa bed has a great mattress on it!We hope to continue to return to this rental."
Cozy 1st Floor King George one bedroom apartment right across from USNA
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Fridge, microwave, oven, stovetop

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

9.6 out of 10, Exceptional, (23)
"Loved this place - well appointed, convenient and great hosts ! Definitely will rent again!"
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Courtyard Fells Point Townhome
Fridge, microwave, oven, stovetop

Courtyard Fells Point Townhome

9.6 out of 10, Exceptional, (85)
"This apartment is 3 blocks from my daughter. Well located to everything you need!! Directions were great.!"
The price is AED 312
AED 772 total
includes taxes & fees
8 Jun - 9 Jun
Courtyard Fells Point Townhome
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Marina

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

10.0 out of 10, Exceptional, (49)
"Everything about our stay was outstanding. Beautiful, just like the pictures show. We highly recommend this property."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Apartment in Perry Hall area
Fridge, microwave, oven, stovetop

Apartment in Perry Hall area

2.0 star property
10.0 out of 10, Exceptional, (1)
"We are so excited to have such a lovely place to stay that’s close to family!"
Apartment in Perry Hall area
Home in Perry Hall area
Fridge, microwave, oven, stovetop

Home in Perry Hall area

2.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent Spot "
Home in Perry Hall area
Pristine Downtown 1-Bedroom Steps from State House
Fridge, microwave, oven, stovetop

Pristine Downtown 1-Bedroom Steps from State House

10.0 out of 10, Exceptional, (25)
"Perfect location to downtown Annapolis; lovely, clean, and comfortable space. Owners make the stay enjoyable and easyy to navigate. "
Pristine Downtown 1-Bedroom Steps from State House
Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Property grounds

Bel Air Apartment w/ Pool ~ 2 Mi to Main St

Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Relaxation Haven on the Shore near Choptank River
Fridge, microwave, oven, stovetop

Relaxation Haven on the Shore near Choptank River

10.0 out of 10, Exceptional, (4)
"The property is very quiet and peaceful! No issues at all! Helen was wonderful and very kind!"
Relaxation Haven on the Shore near Choptank River
Charming Eastport
Aerial view

Charming Eastport

9.4 out of 10, Exceptional, (3)
"We thoroughly enjoyed this section of Eastport. The views of the marina were beautiful and we found a couple new restaurants nearby! Excellent communication with the owners."
Charming Eastport
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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Other property types in Chestertown

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (216)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (35)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AED 735
AED 1,098 total
includes taxes & fees
14 May - 15 May
BAYSIDE BUNGALOW
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.6 out of 10, Exceptional, (24)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 8 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?
Here are some of the more popular apartments in the area to choose from: 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. Osprey’s Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located 21.4 mi/34.4 km away in Pasadena. Free WiFi and Smart TVs are included. Access to an outdoor pool is available on site. Cityside Fells Point Apartment: It’s situated in Baltimore, 28.3 mi/45.5 km away. Includes free WiFi and Smart TVs. COZY DOWNTOWN APARTMENT-Naval Academy Vicinity: Located 27.8 mi/44.8 km away in Annapolis. Free WiFi, sofa beds, and Smart TVs are included. Access to onsite laundry facilities is available on site. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located in Annapolis, 24.5 mi/39.4 km from Chestertown. Includes free WiFi, sofa beds, and jetted bathtubs. Onsite laundry facilities and a hot tub are on site.
How many apartments can I expect to find in Chestertown?
Expedia has 8 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 Chestertown Dog Park and Urieville Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Rolphs Wharf Marina and Sumner Hall.
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.