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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Chestertown apartments

Property grounds

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is €141
includes taxes & fees
19 Jan - 20 Jan
First Floor Studio Apartment in Historic Chestertown
Exterior

Apartment in Millington

Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is €112
includes taxes & fees
22 Jan - 23 Jan
Guest Suite for up to 2 in a Victorian on the Chester River
Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is €270
includes taxes & fees
19 Jan - 20 Jan
Waterfront Retreat with Private Dock and Beach
Beach

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (17 reviews)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is €250
includes taxes & fees
19 Jan - 20 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Outdoor pool, a heated pool

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is €351
includes taxes & fees
19 Jan - 20 Jan
Waterfront Oasis of Annapolis Star
Interior

Apartment in Greektown

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
9.6 out of 10, Exceptional, (8 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is €199
includes taxes & fees
19 Jan - 20 Jan
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Apartment (4 Bedrooms) | Interior

Apartment in Nottingham

Close to Hospital & White Marsh! Rosedale Townhome
3.0 star property
The price is €441
includes taxes & fees
19 Jan - 20 Jan
Close to Hospital & White Marsh! Rosedale Townhome
Marina

Apartment in Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (201 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
The price is €180
includes taxes & fees
10 Feb - 11 Feb
Cozy Fells Point Gem / In The Heart of Fells Point
Fridge, microwave, oven, stovetop

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
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 €332
includes taxes & fees
21 Jan - 22 Jan
Luxury Pool Loft sleeps 4
Exterior detail

Apartment in Historic District

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
9.6 out of 10, Exceptional, (27 reviews)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
The price is €286
includes taxes & fees
19 Jan - 20 Jan
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Property grounds

Apartment in Historic District

Charming Downtown 3rd Floor 1 Bedroom Apt
9.8 out of 10, Exceptional, (20 reviews)
"We had a great time staying that this home. It was a perfect stay for my wife and I."
United States
Eric S.
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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Top Chestertown Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Clean room. Very courteous staff. Overall, very pleasant experience!"
Ajith 1-night trip
Posted 3 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
435
Accommodation
80 Apartments
Lowest Price
€112
Highest Price
€441

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can search through 6 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?
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 . Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access: Free WiFi, a balcony and a Smart TV are included . Access to on-site laundry facilities is available on site .
How many apartments can I expect to find in Chestertown?
Expedia has 6 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 Sumner Hall.
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.