Apartments in Chestertown

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

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, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is NZ$267
includes taxes & fees
26 Jan - 27 Jan
First Floor Studio Apartment in Historic Chestertown
Pool

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Chestertown
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
United States
Jason
The price is NZ$757
includes taxes & fees
21 Feb - 22 Feb
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
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
9.6 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 NZ$210
includes taxes & fees
4 Feb - 5 Feb
Guest Suite for up to 2 in a Victorian on the Chester River
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is NZ$677
includes taxes & fees
25 Jan - 26 Jan
Waterfront Oasis of Annapolis Star
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is NZ$515
includes taxes & fees
26 Jan - 27 Jan
Waterfront Retreat with Private Dock and Beach
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, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is NZ$477
includes taxes & fees
25 Jan - 26 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (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 NZ$338
includes taxes & fees
10 Feb - 11 Feb
Cozy Fells Point Gem / In The Heart of Fells Point
Interior

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

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.6 out of 10, Exceptional, (8 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is NZ$386
includes taxes & fees
26 Jan - 27 Jan
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Fridge, microwave, oven, stovetop

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
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 NZ$640
includes taxes & fees
25 Jan - 26 Jan
Luxury Pool Loft sleeps 4
Property grounds

Charming Downtown 3rd Floor 1 Bedroom Apt

Charming Downtown 3rd Floor 1 Bedroom Apt
Historic District
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.
The price is NZ$508
includes taxes & fees
25 Jan - 26 Jan
Charming Downtown 3rd Floor 1 Bedroom Apt
Exterior detail

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
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 NZ$531
includes taxes & fees
25 Jan - 26 Jan
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"The room was perfect and breakfast was delicious. Jeff was our server and he was awesome."
Dawn 1-night trip
Posted 16 hours ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
438
Accommodation
80 Apartments
Lowest Price
NZ$210
Highest Price
NZ$757

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 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.