Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Chestertown apartments

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (113 reviews)
"Every thing was great"
United States
lesia k.
The price is €141
includes taxes & fees
23 Jun - 24 Jun
First Floor Studio Apartment in Historic Chestertown
Smart TV, books

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (29 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is €332
includes taxes & fees
18 Jun - 19 Jun
Newly restored apartment in the heart of Chestertown
Exterior

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, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is €112
includes taxes & fees
25 Jun - 26 Jun
Guest Suite for up to 2 in a Victorian on the Chester River
Beach

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, (22 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is €256
includes taxes & fees
21 Jun - 22 Jun
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Shower, hair dryer, towels, soap

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (10 reviews)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
The price is €239
includes taxes & fees
22 Jun - 23 Jun
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is €154
includes taxes & fees
6 Jul - 7 Jul
Turtle Cove Room
Beach nearby

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is €327
includes taxes & fees
21 Jun - 22 Jun
Waterfront Retreat with Private Dock and Beach
Marina

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, (205 reviews)
"Place worked great for our overnight stay"
United States
Adrienne K.
The price is €194
includes taxes & fees
22 Jun - 23 Jun
Cozy Fells Point Gem / In The Heart of Fells Point
Terrace/patio

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

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
The price is €150
includes taxes & fees
22 Jun - 23 Jun
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Interior

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, (12 reviews)
"Our host and his instructions were wonderful. The home is impeccable and cozy. Highly recommend. "
United States
Ginnie H.
The price is €200
includes taxes & fees
23 Jun - 24 Jun
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
1 bedroom, in-room safe, desk, iron/ironing board

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

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
The price is €136
includes taxes & fees
22 Jun - 23 Jun
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Fridge, microwave, oven, stovetop

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 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 €435
includes taxes & fees
12 Jul - 13 Jul
Pool Loft Suite | Bay Access & Beach Passes
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (84 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is €427
includes taxes & fees
21 Jun - 22 Jun
Waterfront Oasis of Annapolis Star
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
The price is €159
includes taxes & fees
22 Jun - 23 Jun
Beachcomber Suite
Living area

Home away from home with WiFi and AC in delightful Parkville

Home away from home with WiFi and AC in delightful Parkville
Carney
The price is €194
includes taxes & fees
23 Jun - 24 Jun
Home away from home with WiFi and AC in delightful Parkville
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Clean"
Olagoke 1-night trip
Posted less than an hour ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
12,396
Accommodation
80 Apartments
Lowest Price
€51
Highest Price
€210

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You'll find a lot of options for your stay in Chestertown with 42 hotels and other accommodation options. Though there aren't many apartments, we can help you find accommodation that is similar. When you search on Expedia, you can use the filters to search for a kitchen— one of the conveniences often found in an apartment. Even filter by similar property types like holiday homes, condos or guest houses.
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, a washer/dryer and free WiFi . A fitness centre and on-site laundry facilities are on site . Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located 21.4 mi/34.4 km away in Pasadena . Free WiFi and a Smart TV are included . Access to an outdoor pool is available on site . Waterfront Oasis of Annapolis Star: Located in Annapolis , 25.8 mi/41.5 km away. Includes a private pool, free WiFi and a fireplace . Access to an outdoor pool is available on site . WORLD'S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: 16.1 mi/25.9 km away in Earleville . Free WiFi and a Smart TV are included .
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.