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Our top choices for Chestertown apartments

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is CA $137
CA $220 total
includes taxes & fees
Jun 8 - Jun 9
First Floor Studio Apartment in Historic Chestertown

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (28 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is CA $346
CA $533 total
includes taxes & fees
Jun 4 - Jun 5
Newly restored apartment in the heart of Chestertown

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
9.6 out of 10, Exceptional, (24 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 CA $94
CA $173 total
includes taxes & fees
Jun 8 - Jun 9
Guest Suite for up to 2 in a Victorian on the Chester River

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, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $163
CA $398 total
includes taxes & fees
Jun 4 - Jun 5
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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, (205 reviews)
"Place worked great for our overnight stay"
United States
Adrienne K.
The price is CA $86
CA $321 total
includes taxes & fees
Jun 4 - Jun 5
Cozy Fells Point Gem / In The Heart of Fells Point

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, (10 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 CA $213
CA $301 total
includes taxes & fees
Jun 9 - Jun 10
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $239
CA $294 total
includes taxes & fees
Jun 4 - Jun 5
Turtle Cove Room

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
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 CA $289
CA $693 total
includes taxes & fees
Jun 8 - Jun 9
Pool Loft Suite | Bay Access & Beach Passes

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, (10 reviews)
"Our host and his instructions were wonderful. The home is impeccable and cozy. Highly recommend. "
United States
Ginnie H.
The price is CA $182
CA $311 total
includes taxes & fees
Jun 4 - Jun 5
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

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 CA $355
CA $662 total
includes taxes & fees
Jun 7 - Jun 8
Waterfront Oasis of Annapolis Star

The Sparrows Nest - in downtown Sparrows Point

The Sparrows Nest - in downtown Sparrows Point
Edgemere
The price is CA $106
CA $301 total
includes taxes & fees
Jun 7 - Jun 8
The Sparrows Nest - in downtown Sparrows Point

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 CA $311
CA $524 total
includes taxes & fees
Jun 15 - Jun 16
Waterfront Retreat with Private Dock and Beach

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 CA $159
CA $280 total
includes taxes & fees
Jun 15 - Jun 16
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Beachcomber Suite

Beachcomber Suite
Kent County
The price is CA $202
CA $249 total
includes taxes & fees
Jun 8 - Jun 9
Beachcomber Suite

Home away from home with WiFi and AC in delightful Parkville

Home away from home with WiFi and AC in delightful Parkville
Carney
The price is CA $221
CA $309 total
includes taxes & fees
Jun 23 - Jun 24
Home away from home with WiFi and AC in delightful Parkville

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Great experience"
United States
David P.
The price is CA $323
CA $592 total
includes taxes & fees
Jun 4 - Jun 5
18th Cent. Charm in Historic Downtown Annapolis
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

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
529
Accommodation
81 Apartments
Lowest Price
CA $173
Highest Price
CA $693

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 5 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?
Here are some of the more popular apartments in the area to choose from: 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. Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located 21.4 mi/34.4 km away in Pasadena. Free WiFi and Smart TVs are included. Access to an outdoor pool is available on site. Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace: Located in Havre De Grace, 22.3 mi/35.9 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Annapolis Spa Retreat, Sauna, Jacuzzi, King Bed Couples Quiet Loft Apt. Getaway: Located 24.5 mi/39.4 km away in Annapolis. Free WiFi, sofa beds, and jetted bathtubs are included. Onsite laundry facilities and a hot tub are on site. Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC: Located in Baltimore, 26.5 mi/42.7 km from Chestertown. Includes free WiFi, private patios, and Smart TVs. Access to onsite laundry facilities is available on site.
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.

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