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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 85 Apartments in Chestertown with updated reviews, rates, and availability.

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, (20)
"Nice downtown location."
Newly restored apartment in the heart of Chestertown
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, (29)
"We really enjoyed our stay! Very peaceful and relaxing, the bed felt like lying on a cloud! It was like having a spa in your room we loved the sauna especially. We look forward to booking again. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Bay View Studio Apartment
Outdoor spa tub

Bay View Studio Apartment

10.0 out of 10, Exceptional, (42)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment
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
Carriage House Hideaway in Middle of Chestertown
Iron/ironing board, travel crib, free WiFi, bed sheets

Carriage House Hideaway in Middle of Chestertown

10.0 out of 10, Exceptional, (86)
"Very sweet studio with everything you need for your stay. Extremely quiet and walking distance to great restaurants and shops. Hosts were very gracious and available if needed. We definitely will book again. Thank you!"
Carriage House Hideaway in Middle of Chestertown
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (25)
"This is the second time I stayed here and will be back. I was able to work from here and enjoyed breakfast and lunch on the covered porch with a sweet companion (the owners' totally chill dog). Walking distance to everything. Check out the new wetland preserve at the end of the street. "
Historic Downtown Garden Oasis with Private Patio
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10.0 out of 10, Exceptional, (34)
"Great location, wonderful place and fantastic owner. Recommendations on restaurants and things to do were perfect. We had a great time and Betty Ann was very kind and responsive in communications. Will definitely visit again!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
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, (45)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is SAR 368
SAR 592 total
includes taxes & fees
26 Mar - 27 Mar
First Floor Studio Apartment in Historic Chestertown
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)
"Cleaning of the apartment needs to improve "
The price is SAR 656
SAR 1,210 total
includes taxes & fees
23 Mar - 24 Mar
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
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
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, (24)
"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, (3)
"We were attending a wedding in Easton, MD. This was the perfect place to use as a base while attending wedding and get togethers "
Relaxation Haven on the Shore near Choptank River
Charming Eastport
Aerial view

Charming Eastport

9.4 out of 10, Exceptional, (3)
"This was a charming apartment nestled in the quiet side of annapolis. Everything was within walking distance. The apartment had everything you needed if you wanted to cook. Just bring your food!"
Charming Eastport
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is SAR 863
SAR 1,651 total
includes taxes & fees
23 Mar - 24 Mar
Waterfront Oasis of Annapolis Star
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.8 out of 10, Exceptional, (6)
"Had a great stay, super close to everything. Jennifer was very communicative!"
The price is SAR 713
SAR 1,334 total
includes taxes & fees
13 Apr - 14 Apr
18th Cent. Charm in Historic Downtown Annapolis
Waterfront Retreat with Private Dock and Beach
Miscellaneous

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (17)
"This property was exactly what we needed! The apartment was very clean and well maintained making it such a pleasant experience. Even though the property is shared with the owners, they weren’t constantly around or hovering over us allowing us to enjoy our time together. We loved having the dock and availability of the kayaks so we didn’t have to bring us along for the long trip there. We found some small shops and cute little towns along with a wonderful winery all within a short drive from...
The price is SAR 656
SAR 1,144 total
includes taxes & fees
3 Apr - 4 Apr
Waterfront Retreat with Private Dock and Beach
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Fridge, microwave, oven, stovetop

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

9.8 out of 10, Exceptional, (38)
"My husband and I stayed here with our two kids for his reunion weekend and it did not disappoint. The apartment is conveniently located right outside of Gate 1 and so close to the all of the downtown offerings. The apartment was super clean and had everything we needed for our stay. We would definitely stay here again!"
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
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 SAR 604
SAR 819 total
includes taxes & fees
14 Apr - 15 Apr
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
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

First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is SAR 368
SAR 592 total
includes taxes & fees
26 Mar - 27 Mar
First Floor Studio Apartment in Historic 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, (209)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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 7 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?
Carriage House Hideaway in Middle of Chestertown: Includes free WiFi, fireplaces, and Smart TVs. First Floor Studio Apartment in Historic Chestertown: A private pool, laundry facilities, and free WiFi are included. A fitness center and an outdoor pool are on site.
How many apartments can I expect to find in Chestertown?
Expedia has 7 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 Urieville Lake Fish Management Area.
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.