Photo by Assya A

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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Sept - 14 Sept
In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

Featured Apartments in Chestertown

Our top choices for Chestertown apartments

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

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
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (99)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is AU$246
includes taxes & fees
8 Sept - 9 Sept
First Floor Studio Apartment in Historic Chestertown
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

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 AU$765
includes taxes & fees
9 Sept - 10 Sept
Waterfront Oasis of Annapolis Star
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

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 AU$452
includes taxes & fees
7 Sept - 8 Sept
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
Terrace/patio

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

2.5 star property
10.0 out of 10, Exceptional, (2)
"This tastefully decorated apartment is in a perfect location to enjoy all that is Annapolis. "
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard
Pristine Downtown 1-Bedroom Steps from State House
Fridge, microwave, oven, stovetop

Pristine Downtown 1-Bedroom Steps from State House

10.0 out of 10, Exceptional, (30)
"Our family loved having this as a short-term rental to visit our midshipman and give him the ability to relax off campus. The owners were communicative and amazing to work with for the entire 3 months! Would absolutely stay here again."
Pristine Downtown 1-Bedroom Steps from State House
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (5)
The price is AU$332
includes taxes & fees
7 Sept - 8 Sept
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Interior

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
1 bedroom, bed sheets

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

9.8 out of 10, Exceptional, (9)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
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
Exterior

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 AU$194
includes taxes & fees
8 Sept - 9 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
Chic & Central 1BR Ideal for Work & Leisure Stay
Smart TV

Chic & Central 1BR Ideal for Work & Leisure Stay

Chic & Central 1BR Ideal for Work & Leisure Stay
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.4 out of 10, Exceptional, (8)
"Property description is accurate, host is quickly responsive."
The price is AU$600
includes taxes & fees
22 Sept - 23 Sept
18th Cent. Charm in Historic Downtown Annapolis
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (38)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Cozy Fells Point Gem / In The Heart of Fells Point
Marina

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 AU$319
includes taxes & fees
8 Sept - 9 Sept
Cozy Fells Point Gem / In The Heart of Fells Point
Bay View Studio Apartment
Outdoor spa tub

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
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (32)
"The location is excellent. We rarely needed a car. The heating and AC worked great. We had several issues with the lights and the full size bed’s mattress sagged in the middle- so one of us slept on the sofa.We sent some suggestions to Julie for enhancing the property."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Property grounds

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
Fridge, microwave, oven, stovetop

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
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
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Find out more about Chestertown

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
Accommodation
87 Apartments
Lowest Price
AU$194
Highest Price
AU$765

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can search through 9 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 9 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 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 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.