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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

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, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is AED 364
AED 583 total
includes taxes & fees
15 Jun - 16 Jun
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, (28 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is AED 918
AED 1,403 total
includes taxes & fees
7 Jun - 8 Jun
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
9.6 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 AED 250
AED 459 total
includes taxes & fees
24 Jun - 25 Jun
Guest Suite for up to 2 in a Victorian on the Chester River
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, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AED 455
AED 1,079 total
includes taxes & fees
8 Jun - 9 Jun
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (205 reviews)
"Place worked great for our overnight stay"
United States
Adrienne K.
The price is AED 228
AED 840 total
includes taxes & fees
15 Jun - 16 Jun
Cozy Fells Point Gem / In The Heart of Fells Point
Shower, hair dryer, towels, soap

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 AED 559
AED 775 total
includes taxes & fees
9 Jun - 10 Jun
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is AED 635
AED 785 total
includes taxes & fees
6 Jun - 7 Jun
Turtle Cove Room
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, (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 768
AED 1,842 total
includes taxes & fees
8 Jun - 9 Jun
Pool Loft Suite | Bay Access & Beach Passes
Interior

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 AED 496
AED 832 total
includes taxes & fees
15 Jun - 16 Jun
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Outdoor pool, a heated pool

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 AED 942
AED 1,757 total
includes taxes & fees
7 Jun - 8 Jun
Waterfront Oasis of Annapolis Star
Living area

The Sparrows Nest - in downtown Sparrows Point

The Sparrows Nest - in downtown Sparrows Point
Edgemere
The price is AED 264
AED 781 total
includes taxes & fees
7 Jun - 8 Jun
The Sparrows Nest - in downtown Sparrows Point
Beach

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 AED 826
AED 1,391 total
includes taxes & fees
15 Jun - 16 Jun
Waterfront Retreat with Private Dock and Beach
Shower, hair dryer, towels, soap

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 AED 423
AED 743 total
includes taxes & fees
15 Jun - 16 Jun
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
The price is AED 536
AED 662 total
includes taxes & fees
8 Jun - 9 Jun
Beachcomber Suite
Living area

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 AED 588
AED 815 total
includes taxes & fees
23 Jun - 24 Jun
Home away from home with WiFi and AC in delightful Parkville
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)
"Great experience"
United States
David P.
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

2/10 Terrible
"Pool was disgusting. Room Smelled like mildew. Too overpriced for the outdated room."
kenney 2-night trip
Posted 2 hours ago
Hilton Garden Inn Baltimore/White Marsh

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.