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Search Apartments in Chestertown

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Compare 77 Apartments in Chestertown with updated reviews, rates, and availability.

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, (38)
"The grounds, facilities and view are just great. Coffee at sunrise in an Adirondack chair right at the edge of the Chesapeake was amazing. Located at a marina/resort where the folks that work there staff are fantastic! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
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, (22)
"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
Bay View Studio Apartment
Property grounds
Bay View Studio Apartment
10.0 out of 10, Exceptional, (35)
"We are repeat visitors to this property because of the location, the owner, the comfort and the amazing view here. The owner is so nice and has excellent communication. The property has everything you need and more from the kitchen supplies to the water toys including a hot tub! We will be back again! "
Bay View Studio Apartment
Cozy 1st Floor King George one bedroom apartment right across from USNA
Property grounds
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (26)
"Always a great stay. Close to everything, from shops to restaurants and bars. Can’t wait to go back "
Cozy 1st Floor King George one bedroom apartment right across from USNA
First Floor Studio Apartment in Historic Chestertown
Back Yard
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (71)
"Just what we needed for the night! Thank you "
The price is SAR 368
SAR 569 total
includes taxes & fees
9 Oct - 10 Oct
First Floor Studio Apartment in Historic Chestertown
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
Main room lounge area. Sectional has a new pull out sofa bed (double).
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
10.0 out of 10, Exceptional, (7)
"The apartment had everything we needed and more for a nice weekend. I would definitely try to stay here again if we stay in Annapolis again. "
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
Waterfront Oasis of Annapolis Star
Waterfront Oasis of Annapolis pool grandeur.
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (69)
"Beautiful property and our quarters were perfectly comfortable for us."
The price is SAR 1,032
SAR 1,882 total
includes taxes & fees
24 Sep - 25 Sep
Waterfront Oasis of Annapolis Star
'At Fells Point' Courtyard - Your historically restored apartment
Living area
'At Fells Point' Courtyard - Your historically restored apartment
9.6 out of 10, Exceptional, (79)
"The place was just as expected, the neighborhood is cute and quiet, the pub next door is great, and the water is a short walk away. Will likely stay here again. "
The price is SAR 439
SAR 897 total
includes taxes & fees
26 Sep - 27 Sep
'At Fells Point' Courtyard - Your historically restored apartment
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Living area
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (27)
"The accomodations were VERY nice. The wifi was not sufficient for me to work in the room, but they allowed us to sit on the deck and work instead."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Historic Downtown Garden Oasis with Private Patio
Outdoor dining
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (22)
"We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!"
Historic Downtown Garden Oasis with Private Patio
Walk everywhere from this 1st floor apartment with parking, private backyard dog friendly
Welcome to Below Deck, the 1st floor of this charming Eastport 2-unit building.
Walk everywhere from this 1st floor apartment with parking, private backyard dog friendly
2.5 star property
Walk everywhere from this 1st floor apartment with parking, private backyard dog friendly
Stay in the heart of Historic Annapolis 2 blocks from Main Street
The King corner bedroom has views of the Annapolis cobblestone streets.
Stay in the heart of Historic Annapolis 2 blocks from Main Street
2.0 star property
10.0 out of 10, Exceptional, (2)
"nice location"
Stay in the heart of Historic Annapolis 2 blocks from Main Street
'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, (174)
"The location was perfect, within walking distance of everything we came to Baltimore to do. Overall it was clean but I provided 4 stars due to the shower caulking needing replaced due to mildew staining. The provided shampoo and conditioner products could use some sprucing up as well, I would bring my own next time. "
The price is SAR 330
SAR 771 total
includes taxes & fees
24 Sep - 25 Sep
'At Fells Point' CitySide - 'Tons better than a hotel!'
Coastal Kent Narrows Home on Bay
Living area
Coastal Kent Narrows Home on Bay
9.4 out of 10, Exceptional, (9)
"This place is a fantastic place to stay. Brandon was very responsive to any emails or questions sent to him. The place is very clean and tidy, very easy to get in and out of. We would definitely recommend this property to anybody. We will certainly be booking it again. "
The price is SAR 826
SAR 1,651 total
includes taxes & fees
26 Sep - 27 Sep
Coastal Kent Narrows Home on Bay
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River
10.0 out of 10, Exceptional, (7)
"Cozy, charming, lovely, many other descriptive words like that. Well kept laid back tiny community. The host was great super nice and helpful. Would totally recommend! "
The price is SAR 255
SAR 469 total
includes taxes & fees
1 Oct - 2 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
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
Charming Eastport
Interior
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
Relaxation Haven on the Shore near Choptank River
Bedroom Lotus
Relaxation Haven on the Shore near Choptank River
10.0 out of 10, Exceptional, (2)
"Helen was very helpful and very nice. She communicated quickly any time i needed to ask something. She checked in to see if everything was going well. Her place is clean and we had anything we needed. "
Relaxation Haven on the Shore near Choptank River
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Interior
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (46)
"This was an outstanding value. Just was a great communicator. Beautiful and spaciois suite that comfortable held five adults. "
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
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, (21)
"Loved the property."
Pristine Downtown 1-Bedroom Steps from State House
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See all available properties in Chestertown
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Other property types in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (60)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (75)
"Lovely house and location! Pat and Ken were rapid and personable with every interaction."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Cass-Away Luxury Houseboat
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
The price is SAR 525
SAR 1,313 total
includes taxes & fees
26 Sep - 27 Sep
Cass-Away Luxury Houseboat
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 5 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.
How many apartments can I expect to find in Chestertown?
Expedia has 5 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 is one spot to enjoy nature. Other places in town to visit include Rolphs Wharf Marina 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.