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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
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21 Nov - 23 Nov
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19 Dec - 21 Dec

Apartments in Chestertown

Property grounds
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (105)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
The price is AED 364
AED 583 total
includes taxes & fees
27 Oct - 28 Oct
First Floor Studio Apartment in Historic 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
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AED 250
AED 459 total
includes taxes & fees
29 Oct - 30 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
Beach
Waterfront Retreat with Private Dock and Beach
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AED 643
AED 1,144 total
includes taxes & fees
26 Oct - 27 Oct
Waterfront Retreat with Private Dock and Beach
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!
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is AED 433
AED 1,046 total
includes taxes & fees
26 Oct - 27 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
10.0 out of 10, Exceptional, (7)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is AED 496
AED 836 total
includes taxes & fees
28 Oct - 29 Oct
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Marina
Cozy Fells Point Gem / In The Heart of Fells Point
Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (198)
"Great place all around "
United States
Sophia F.
The price is AED 228
AED 751 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Fells Point Gem / In The Heart of Fells Point
Smart TV
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
The price is AED 364
AED 1,192 total
includes taxes & fees
27 Oct - 28 Oct
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
Pool
Luxury Pool Loft sleeps 4
Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (3)
"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 459
AED 1,313 total
includes taxes & fees
26 Oct - 27 Oct
Luxury Pool Loft sleeps 4
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (80)
"Clean, safe, joy and owners hospitality perfect"
United States
Ahmet S.
The price is AED 992
AED 1,817 total
includes taxes & fees
27 Oct - 28 Oct
Waterfront Oasis of Annapolis Star
Apartment (4 Bedrooms) | Interior
Close to Hospital & White Marsh! Rosedale Townhome
Close to Hospital & White Marsh! Rosedale Townhome
3.0 star property
The price is AED 970
AED 2,212 total
includes taxes & fees
26 Oct - 27 Oct
Close to Hospital & White Marsh! Rosedale Townhome
Fridge, microwave, oven, stovetop
18th Cent. Charm in Historic Downtown Annapolis
18th Cent. Charm in Historic Downtown Annapolis
9.0 out of 10, Wonderful, (12)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is AED 628
AED 1,269 total
includes taxes & fees
27 Oct - 28 Oct
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

10/10 Excellent
"On arrival we met Catalina on reception. An extremely pleasant and helpful girl. After that our stay was very comfortable."
Christopher 1-night trip
Posted 1 day 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 6 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: A private pool, laundry facilities, and free WiFi are included. A fitness center and onsite laundry facilities are on site. Historic Downtown Garden Oasis with Private Patio: Includes free WiFi, outdoor space, and separate dining areas. Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access: Free WiFi, private balconies, and Smart TVs are included. Access to onsite laundry facilities is available on site.
How many apartments can I expect to find in Chestertown?
Expedia has 6 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 Chesapeake Bay and Chestertown Dog 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.