Photo by Assya A

Search Apartments in Chestertown

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Apartments in Chestertown

Our top choices for Chestertown apartments

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (64)
"Awesome place!"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (100)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is SAR 525
SAR 767 total
includes taxes & fees
11 Oct - 12 Oct
First Floor Studio Apartment in Historic Chestertown

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (79)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is SAR 1,126
SAR 1,968 total
includes taxes & fees
2 Oct - 3 Oct
Waterfront Oasis of Annapolis Star

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (13)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is SAR 442
SAR 1,068 total
includes taxes & fees
11 Sep - 12 Sep
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard

2.5 star property
10.0 out of 10, Exceptional, (3)
"Loved our stay in this cute little home that is convenient to everything!"
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (46)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

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

10.0 out of 10, Exceptional, (5)
The price is SAR 638
SAR 1,010 total
includes taxes & fees
10 Oct - 11 Oct
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (31)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (9)
"From the time we checked in til we checked out was a pleasure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (17)
"The staff was great"
The price is SAR 255
SAR 469 total
includes taxes & fees
11 Sep - 12 Sep
Guest Suite for up to 2 in a Victorian on the Chester River

Chic & Central 1BR Ideal for Work & Leisure Stay

Chic & Central 1BR Ideal for Work & Leisure Stay

18th Cent. Charm in Historic Downtown Annapolis

9.4 out of 10, Exceptional, (9)
"Property description is accurate, host is quickly responsive."
18th Cent. Charm in Historic Downtown Annapolis

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (39)
"Loved the location and ease of access to downtown. Property was super clean, organized and beautifully appointed with original art too. "
Historic Downtown Garden Oasis with Private Patio

Cozy Fells Point Gem / In The Heart of Fells Point

9.8 out of 10, Exceptional, (194)
"Great place close to eveything"
The price is SAR 233
SAR 767 total
includes taxes & fees
15 Sep - 16 Sep
Cozy Fells Point Gem / In The Heart of Fells Point

Bay View Studio Apartment

10.0 out of 10, Exceptional, (51)
"Wonderful place to stay for a peaceful weekend. The hot tub was definitely a highlight. Everything was clean and as described. I would stay there again!"
Bay View Studio Apartment

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

9.8 out of 10, Exceptional, (40)
"Perfect location for walking around the Annapolis waterfront area! Clean, comfortable and well appointed. Would definitely stay here again!"
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

Cozy 1st Floor King George one bedroom apartment right across from USNA

9.8 out of 10, Exceptional, (32)
"Great location. Good securityProperty & living space needs some TLC."
Cozy 1st Floor King George one bedroom apartment right across from USNA

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

10.0 out of 10, Exceptional, (2)
"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."
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (26)
"Nice downtown location."
Newly restored apartment in the heart of Chestertown

Spectacular Location: State Circle Apartment

10.0 out of 10, Exceptional, (12)
"Great location around the corner from our Thanksgiving celebration. "
Spectacular Location: State Circle Apartment
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 9 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 Downtown Garden Oasis with Private Patio: Free WiFi, outdoor space, and separate dining areas are included.
How many apartments can I expect to find in Chestertown?
Expedia has 9 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 Chestertown Dog Park and Urieville Park 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 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.