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Our top choices for Chestertown apartments

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is €139
includes taxes & fees
7 May - 8 May
First Floor Studio Apartment in Historic Chestertown

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.
Newly restored apartment in the heart of Chestertown

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 €111
includes taxes & fees
6 May - 7 May
Guest Suite for up to 2 in a Victorian on the Chester River

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, (6 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is €195
includes taxes & fees
7 May - 8 May
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

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, (19 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is €253
includes taxes & fees
10 May - 11 May
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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 €345
includes taxes & fees
3 May - 4 May
18th Cent. Charm in Historic Downtown Annapolis

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 €199
includes taxes & fees
4 May - 5 May
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

High Tide Haven Suite

High Tide Haven Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"The suite was really nice and extremely clean. Comfy, memory foam bed. Excellent shower with great water pressure. The ambiance in the room is serene and beachy making for a wonderful escape. Absolutely loved their screened in porch and view from the back deck. The hosts were very nice, had great communication and served the most delicious bagels. We left our phone charger there and they promptly called us in time to turn around and get it. Highly recommend this location and will stay there...
United States
Joell V.
The price is €158
includes taxes & fees
4 May - 5 May
High Tide Haven Suite

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 €317
includes taxes & fees
1 Jun - 2 Jun
Waterfront Retreat with Private Dock and Beach

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 €419
includes taxes & fees
1 Jun - 2 Jun
Waterfront Oasis of Annapolis Star

Beachcomber Suite

Beachcomber Suite
Kent County
The price is €157
includes taxes & fees
1 Jun - 2 Jun
Beachcomber Suite

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 €385
includes taxes & fees
2 May - 3 May
Pool Loft Suite | Bay Access & Beach Passes

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

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
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.
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Top Chestertown Hotel Reviews

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
315
Accommodation
80 Apartments
Lowest Price
€111
Highest Price
€419

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 Downtown Garden Oasis with Private Patio: Free WiFi, a balcony and a dining area are included .
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.