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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 78 Apartments in Chestertown with updated reviews, rates, and availability.

'At Fells Point' CitySide - 'Tons better than a hotel!'
CitySide Living Room & Sofa Bed

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (185)
"The property is compact but cute. They have a door that slides across doorway between the bedroom and the living room that blocks noise from the outside. We did find the property chilly but when we contacted the owner, he had one of his staff come over, wait a few minutes for us outside, and provide us with space heaters that warmed the place up very effectively and quietly. We felt valued and cared for. I highly recommend this cozy little place and the people who manage it!"
The price is AED 323
AED 747 total
includes taxes & fees
25 Feb - 26 Feb
'At Fells Point' CitySide - 'Tons better than a hotel!'
First Floor Studio Apartment in Historic Chestertown
Back Yard

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"Very clean, excellent communications,"
The price is AED 360
AED 579 total
includes taxes & fees
26 Feb - 27 Feb
First Floor Studio Apartment in Historic Chestertown
Bay View Studio Apartment
Property grounds

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
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Larger of the 2 bedrooms, with a queen bed and sitting area

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 AED 474
AED 971 total
includes taxes & fees
24 Feb - 25 Feb
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Spectacular Location: State Circle Apartment
Exterior

Spectacular Location: State Circle Apartment

10.0 out of 10, Exceptional, (11)
"Great location around the corner from our Thanksgiving celebration. "
Spectacular Location: State Circle Apartment
'At Fells Point' Courtyard - Your historically restored apartment
Living area

'At Fells Point' Courtyard - Your historically restored apartment

9.6 out of 10, Exceptional, (82)
"This apartment is 3 blocks from my daughter. Well located to everything you need!! Directions were great.!"
The price is AED 349
AED 768 total
includes taxes & fees
25 Feb - 26 Feb
'At Fells Point' Courtyard - Your historically restored apartment
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Jacuzzi Jetted Hot Tub

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

9.6 out of 10, Exceptional, (28)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Cozy 2 bedroom apartment w/ free parking
Private kitchen

Cozy 2 bedroom apartment w/ free parking

8.8 out of 10, Excellent, (5)
"Very good communication, address was listed wrong on website but the host helped a lot, it wasn't his fault. It's in the basement, and it's really nice, but it's in the basement lol"
The price is AED 533
AED 1,400 total
includes taxes & fees
23 Feb - 24 Feb
Cozy 2 bedroom apartment w/ free parking
Newly restored apartment in the heart of Chestertown
Living area

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (19)
"We fell in love with Chestertown and are so glad we stayed in the heart of downtown at this charming vrbo. Everything was perfect. Will return and recommend "
Newly restored apartment in the heart of Chestertown
Pristine Downtown 1-Bedroom Steps from State House
Steps from the Maryland state house

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
Bel Air Vacation Rental | 1BR | 1BA | Steps Required | 680 Sq Ft

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
Bedroom Lotus

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
Living area

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
Waterfront Oasis of Annapolis pool grandeur.

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (72)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is AED 845
AED 1,620 total
includes taxes & fees
23 Feb - 24 Feb
Waterfront Oasis of Annapolis Star
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Entrance into kitchen

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

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

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
'At Fells Point' Topside - Exceeding your expectations!
Living Room w couch dining table and TV

'At Fells Point' Topside - Exceeding your expectations!

9.6 out of 10, Exceptional, (86)
"Nice place overall, but those were the most narrow and steep stairs I have ever experienced! This place is not suited for anyone that isn't in great physical shape. It is on second and third levels, so lots of stairs. We did enjoy the high ceilings and charm of this row house. The security gate was an added security measure and we liked having the little courtyard area away from the street. One of the reasons I selected this unit was it indicated there was off-street parking in the features and...
The price is AED 349
AED 840 total
includes taxes & fees
25 Feb - 26 Feb
'At Fells Point' Topside - Exceeding your expectations!
18th Cent. Charm in Historic Downtown Annapolis
Room

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!"
18th Cent. Charm in Historic Downtown Annapolis
Charming Downtown 3rd Floor 1 Bedroom Apt
The bedroom with a queen sized bed.

Charming Downtown 3rd Floor 1 Bedroom Apt

9.8 out of 10, Exceptional, (18)
"Great location for place to stay during weekend when you need convenient accommodation "
The price is AED 643
AED 1,131 total
includes taxes & fees
23 Feb - 24 Feb
Charming Downtown 3rd Floor 1 Bedroom Apt
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

'At Fells Point' CitySide - 'Tons better than a hotel!'
CitySide Living Room & Sofa Bed

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (185)
"The property is compact but cute. They have a door that slides across doorway between the bedroom and the living room that blocks noise from the outside. We did find the property chilly but when we contacted the owner, he had one of his staff come over, wait a few minutes for us outside, and provide us with space heaters that warmed the place up very effectively and quietly. We felt valued and cared for. I highly recommend this cozy little place and the people who manage it!"
The price is AED 323
AED 747 total
includes taxes & fees
25 Feb - 26 Feb
'At Fells Point' CitySide - 'Tons better than a hotel!'
Cass-N-Reel Luxury Houseboat
Exterior

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Chesapeake Houseboat Getaway on Kent Island, Maryland
Exterior

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.6 out of 10, Exceptional, (20)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
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?
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 an outdoor pool are on site. ‘At Fells Point’ CitySide - ‘Tons better than a hotel!’: Located 28.3 mi/45.5 km away in Baltimore. Free WiFi and Smart TVs are included. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located in Annapolis, 24.5 mi/39.4 km away. Includes free WiFi, sofa beds, and jetted bathtubs. A hot tub and a sauna are on site. Bay View Studio Apartment: Located 28 mi/45 km away in Annapolis. Free WiFi, private patios, and fireplaces are included. A water park and a hot tub 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 Wilmer Park and Kings Town Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Rolphs Wharf Marina and Rolling Road Park.
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.