An aerial view of a town with a river, buildings, and surrounding greenery.

Apartments in Chestertown for Rent

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

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, (116 reviews)
"Hosts were extremely friendly and helpful!Parking was within feet of entrance. Studio and bathroom were spotless. Nice touches like coffee and accoutrements in the shower. Beautiful surroundings, everything was in bloom and spring beauty was everywhere!Washer and dryer in studio with soap and softener. Charming location!"
United States
Rob C.
The price is ￥15,973
￥25,628 total
includes taxes & fees
Jul 7 - Jul 8
First Floor Studio Apartment in Historic Chestertown
Smart TV, books

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥40,335
￥62,147 total
includes taxes & fees
Jul 9 - Jul 10
Newly restored apartment in the heart of Chestertown
Exterior

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
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is ￥10,971
￥20,180 total
includes taxes & fees
Jul 7 - Jul 8
Guest Suite for up to 2 in a Victorian on the Chester River
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, (206 reviews)
"Place worked great for our overnight stay"
United States
Adrienne K.
The price is ￥9,196
￥36,151 total
includes taxes & fees
Jul 19 - Jul 20
Cozy Fells Point Gem / In The Heart of Fells Point
Interior

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

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.8 out of 10, Exceptional, (13 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is ￥21,781
￥36,899 total
includes taxes & fees
Jul 12 - Jul 13
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Beach nearby

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 ￥36,302
￥61,081 total
includes taxes & fees
Jul 12 - Jul 13
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, (14 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
The price is ￥38,560
￥69,340 total
includes taxes & fees
Jul 28 - Jul 29
18th Cent. Charm in Historic Downtown Annapolis
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, (24 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ￥19,006
￥46,269 total
includes taxes & fees
Jul 7 - Jul 8
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
1 bedroom, in-room safe, desk, iron/ironing board

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

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
The price is ￥11,616
￥24,597 total
includes taxes & fees
Jul 14 - Jul 15
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Smart TV

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, (12 reviews)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
The price is ￥30,203
￥41,250 total
includes taxes & fees
Jul 7 - Jul 8
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Fridge, microwave, oven, stovetop

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (5 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 ￥30,332
￥76,698 total
includes taxes & fees
Jul 7 - Jul 8
Pool Loft Suite | Bay Access & Beach Passes
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is ￥24,395
￥30,182 total
includes taxes & fees
Jul 13 - Jul 14
Beachcomber Suite
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥22,652
￥28,110 total
includes taxes & fees
Jul 27 - Jul 28
Turtle Cove Room
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (84 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ￥43,683
￥80,147 total
includes taxes & fees
Jul 14 - Jul 15
Waterfront Oasis of Annapolis Star
Terrace/patio

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (1 review)
"Booked this property as a last minute, overnight getaway for myself and it was fantastic! The apartment, grounds and hot tub was squeaky clean. Kitchen was clean and stocked with utensils and even had a coffee bar, different tea packets and a snack basket. Bathroom was fully stocked with towels, basic toiletries and everything I needed. Bed was comfortable and closets had extra blankets if needed. Inside and outside patio furniture was comfy. I loved watching the sunset from the hot tub! Also...
United States
Kayla K.
The price is ￥27,428
￥32,494 total
includes taxes & fees
Aug 3 - Aug 4
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"The room was clean, beds were super comfortable, and free breakfast was a bonus. We stayed one night and used the transportation to the cruise ship that they offered. Would definitely recommend!"
Amber 1-night trip
Posted 2 hours ago
Best Western Plus Hotel & Conference Center

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
554
Accommodation
80 Apartments
Lowest Price
￥20,180
Highest Price
￥80,147

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
There are plenty of places to stay in Chestertown with 44 hotels and other accommodations. Though there aren't many apartments, we can help you find similar accommodations. When you search on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. Even filter by similar property types like vacation homes, condos, or cabins.
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, free WiFi, and private patios. 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 5 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.