An aerial view of a town with a river, buildings, and surrounding greenery.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chestertown apartments

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is £114
includes taxes & fees
9 Nov - 10 Nov
First Floor Studio Apartment in Historic Chestertown
A garden with a wooden bridge, lush greenery, and a variety of plants.

2. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is £207
includes taxes & fees
15 Nov - 16 Nov
Secluded Cottage in Middle of Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

3. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is £240
includes taxes & fees
8 Nov - 9 Nov
Newly restored apartment in the heart of Chestertown
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

4. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is £88
includes taxes & fees
10 Nov - 11 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

5. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is £215
includes taxes & fees
9 Nov - 10 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

6. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is £143
includes taxes & fees
23 Nov - 24 Nov
Turtle Cove Room
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

7. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is £148
includes taxes & fees
30 Nov - 1 Dec
Beachcomber Suite
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

8. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is £110
includes taxes & fees
11 Nov - 12 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A waterfront with docked boats, a water taxi, and historic buildings.

9. Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (217 reviews)
"It’s a cozy, clean, and cute apartment. We enjoyed our stay very much and the location is wonderful…within walking distance of all the restaurants and attractions you could want."
United States
Carol
The price is £164
includes taxes & fees
11 Nov - 12 Nov
Cozy Fells Point Gem / In The Heart of Fells Point
Stylish kitchen with open layout and island seating

10. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is £349
includes taxes & fees
9 Nov - 10 Nov
Pool Loft Suite | Bay Access & Beach Passes
A bed with a dark headboard, a mirror, a potted plant, and a snack basket on the bedside table.

11. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
10.0 out of 10, Exceptional, (1 review)
"At the end of a multi-city trip filled with mixed hotel experiences, this stay was a true breath of fresh air. Everything was spotlessly clean, beautifully organized, and exactly as pictured. What truly set it apart were the thoughtful touches throughout the space—it was clear our host anticipated our every need, which even saved us an extra trip to the store! Parking was effortless, and the location made getting into the city by car or public transit super easy. Communication with our host was...
United States
Jennifer R.
The price is £186
includes taxes & fees
11 Nov - 12 Nov
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
A spacious hallway with a staircase, a seating area with a sofa and armchairs, and a large window with a stained glass design.

12. Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.8 out of 10, Exceptional, (18 reviews)
"Perfect Maryland trip"
United States
Rosa E.
The price is £179
includes taxes & fees
8 Nov - 9 Nov
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
A modern living room with a sofa, a television mounted on the wall, and a fireplace.

13. Crown Suite Slps 7 2 Full BR Wd Floor Free ST Prk

Crown Suite Slps 7 2 Full BR Wd Floor Free ST Prk
Berea
The price is £173
includes taxes & fees
13 Nov - 14 Nov
Crown Suite Slps 7 2 Full BR Wd Floor Free ST Prk
A kitchen with a wooden countertop, a stove, and a refrigerator.

14. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (15 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is £327
includes taxes & fees
10 Nov - 11 Nov
18th Cent. Charm in Historic Downtown Annapolis
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

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Beautiful property. Brand new and very well done. Incredibly nice staff."
gary 3-night trip
Posted 3 hours ago
The Inn at Chesapeake Bay Beach Club

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
443
Accommodation
74 Apartments
Lowest Price
£110
Highest Price
£349

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can search through 5 apartments in Chestertown for your stay.
Why would you choose an apartment over a traditional hotel room?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for couples who want a more local feel, and also for families wanting the conveniences of home.
What's the best apartment I should consider for a stay in Chestertown?
Below are some of the favourite apartments in the area to choose from: First Floor Studio Apartment in Historic Chestertown: Includes a private pool, free WiFi and a patio . A fitness centre and on-site laundry facilities are on site . WORLD'S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Located 16.1 mi/25.9 km away in Earleville . Free WiFi and a Smart TV are included . WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL: Located in Aberdeen , 18.4 mi/29.5 km away. Includes free WiFi, a patio and a Smart TV . On-site laundry facilities and 1 hot tub are on site . Cozy Fells Point Gem / In The Heart of Fells Point: It's located in Baltimore , 28.3 mi/45.5 km from Chestertown. Includes free WiFi and a Smart TV .
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 in 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 Rolphs Wharf Marina.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) away 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, you may want to rent a car for your trip.