Apartments in Chestertown

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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 AU$221
includes taxes & fees
18 Nov - 19 Nov
First Floor Studio Apartment in Historic Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (35 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 AU$481
includes taxes & fees
15 Nov - 16 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.

3. 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, (33 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is AU$171
includes taxes & fees
24 Nov - 25 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.

4. 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, (34 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AU$410
includes taxes & fees
13 Nov - 14 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.

5. 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 AU$282
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.

6. 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 AU$303
includes taxes & fees
23 Nov - 24 Nov
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.

7. 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 AU$202
includes taxes & fees
16 Nov - 17 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Stylish kitchen with open layout and island seating

8. 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 AU$664
includes taxes & fees
13 Nov - 14 Nov
Pool Loft Suite | Bay Access & Beach Passes
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, (218 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 AU$318
includes taxes & fees
17 Nov - 18 Nov
Cozy Fells Point Gem / In The Heart of Fells Point
A bed with a dark headboard, a mirror, a potted plant, and a snack basket on the bedside table.

10. 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 AU$373
includes taxes & fees
16 Nov - 17 Nov
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
A modern living room with a sofa, a television mounted on the wall, and a fireplace.

11. 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 AU$394
includes taxes & fees
19 Nov - 20 Nov
Crown Suite Slps 7 2 Full BR Wd Floor Free ST Prk
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 AU$349
includes taxes & fees
17 Nov - 18 Nov
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
A kitchen with a wooden countertop, a stove, and a refrigerator.

13. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (16 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is AU$581
includes taxes & fees
13 Nov - 14 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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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

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.