Search Apartments in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

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)
"Every thing was great"
United States
lesia k.
The price is HK$776
HK$1,245 total
includes taxes & fees
6 Apr - 7 Apr
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, (28 reviews)
"Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!""
United States
Maggie D.
The price is HK$2,586
HK$3,806 total
includes taxes & fees
4 Apr - 5 Apr
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
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is HK$533
HK$980 total
includes taxes & fees
8 Apr - 9 Apr
Guest Suite for up to 2 in a Victorian on the Chester River
Living area

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, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is HK$1,192
HK$1,679 total
includes taxes & fees
6 Apr - 7 Apr
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$972
HK$2,243 total
includes taxes & fees
14 Apr - 15 Apr
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (10 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is HK$1,058
HK$1,765 total
includes taxes & fees
5 Apr - 6 Apr
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
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, (203 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
The price is HK$509
HK$1,629 total
includes taxes & fees
14 Apr - 15 Apr
Cozy Fells Point Gem / In The Heart of Fells Point
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 HK$1,372
HK$2,457 total
includes taxes & fees
20 Apr - 21 Apr
Waterfront Retreat with Private Dock and Beach
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 HK$1,940
HK$3,650 total
includes taxes & fees
4 Apr - 5 Apr
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Great experience"
United States
David P.
The price is HK$1,686
HK$3,119 total
includes taxes & fees
4 May - 5 May
18th Cent. Charm in Historic Downtown Annapolis
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is HK$1,358
HK$1,565 total
includes taxes & fees
5 Apr - 6 Apr
High Tide Haven Suite
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 HK$980
HK$3,047 total
includes taxes & fees
5 Apr - 6 Apr
Pool Loft Suite | Bay Access & Beach Passes
Room

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 HK$903
HK$1,586 total
includes taxes & fees
14 Apr - 15 Apr
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Always love the Maryland Inn"
Donna 1-night trip
Posted 3 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
309
Accommodation
80 Apartments
Lowest Price
HK$980
Highest Price
HK$3,806

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?
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 . 18th Cent. Charm in Historic Downtown Annapolis: Located 28 mi/45.1 km away in Annapolis . Free WiFi, a patio and a fireplace are included . On-site laundry facilities and a games room are on site . Cozy Fells Point Gem / In The Heart of Fells Point: It's situated in Baltimore , 28.3 mi/45.5 km away. Includes free WiFi and a Smart TV . 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 from Chestertown. Includes a private pool, free WiFi and a fireplace . Access to an outdoor pool 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 Rolphs Wharf Marina and Chestertown Historic District.
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.

Explore a world of travel with Expedia