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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 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 AED 364
AED 583 total
includes taxes & fees
28 Jan - 29 Jan
First Floor Studio Apartment in Historic Chestertown
Pool

Apartment in Chestertown

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
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 AED 1,025
AED 1,659 total
includes taxes & fees
21 Feb - 22 Feb
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
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 AED 250
AED 459 total
includes taxes & fees
4 Feb - 5 Feb
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)
"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 AED 643
AED 1,148 total
includes taxes & fees
28 Jan - 29 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)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AED 433
AED 1,046 total
includes taxes & fees
28 Jan - 29 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 AED 760
AED 1,520 total
includes taxes & fees
28 Jan - 29 Jan
Waterfront Oasis of Annapolis Star
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 AED 459
AED 1,432 total
includes taxes & fees
29 Jan - 30 Jan
Luxury Pool Loft sleeps 4
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 AED 217
AED 738 total
includes taxes & fees
10 Feb - 11 Feb
Cozy Fells Point Gem / In The Heart of Fells Point
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 AED 496
AED 827 total
includes taxes & fees
28 Jan - 29 Jan
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
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 AED 643
AED 1,193 total
includes taxes & fees
28 Jan - 29 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.
The price is AED 624
AED 1,110 total
includes taxes & fees
28 Jan - 29 Jan
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"The room was spacious and clean. The staff were friendly. Special thanks to Aung for his help and thoughtfulness! Thanks to Paul also!"
Ling 4-night trip
Posted 23 hours ago
Hyatt Place Kent Narrows & Marina

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 6 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access: Free WiFi, private balconies, and Smart TVs are included. Access to onsite 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 during my trip to 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
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 make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) 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, consider renting a car to take in more sights.