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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

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 HK$774
HK$1,241 total
includes taxes & fees
26 Feb - 27 Feb
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 HK$1,963
HK$3,299 total
includes taxes & fees
21 Feb - 22 Feb
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
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$1,055
HK$1,491 total
includes taxes & fees
18 Feb - 19 Feb
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, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$921
HK$2,242 total
includes taxes & fees
18 Feb - 19 Feb
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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$1,368
HK$2,450 total
includes taxes & fees
19 Feb - 20 Feb
Waterfront Retreat with Private Dock and Beach
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, (13 reviews)
"Great experience"
United States
David P.
The price is HK$1,337
HK$2,700 total
includes taxes & fees
3 Mar - 4 Mar
18th Cent. Charm in Historic Downtown Annapolis
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 HK$453
HK$1,562 total
includes taxes & fees
22 Feb - 23 Feb
Cozy Fells Point Gem / In The Heart of Fells Point
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$1,618
HK$3,234 total
includes taxes & fees
19 Feb - 20 Feb
Waterfront Oasis of Annapolis Star
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 clean, spacious, and located right by everything we wanted to visit. 10/10 would definitely stay here again with my family."
United States
David M.
The price is HK$1,641
HK$2,905 total
includes taxes & fees
18 Feb - 19 Feb
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is HK$1,354
HK$1,585 total
includes taxes & fees
28 Feb - 1 Mar
High Tide Haven Suite
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, (9 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is HK$1,055
HK$1,760 total
includes taxes & fees
23 Feb - 24 Feb
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 HK$1,086
HK$3,199 total
includes taxes & fees
1 Mar - 2 Mar
Luxury Pool Loft sleeps 4
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 Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"I had a wonderful stay at Hampton Inn Baltimore Bayview this weekend. The room was spotless and very well kept, which made it easy to relax as soon as we walked in. The staff was beyond nice welcoming, professional, and genuinely friendly the entire time. Everything about the stay felt smooth and comfortable. I would absolutely return without hesitation and would recommend this hotel to anyone visiting the area. A great experience from start to finish. ⭐⭐⭐⭐⭐"
Brenda 1-night trip
Posted 1 day ago
Hampton Inn Baltimore Bayview Campus

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
404
Accommodation
80 Apartments
Lowest Price
HK$1,241
Highest Price
HK$3,299

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 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.

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