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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Apartments in Chestertown

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, (191)
"Apartment was well appointed, we found everything we needed for a great stay. The place was super clean, check-in and check-out were simple and the location was perfect!"
The price is AED 239
AED 764 total
includes taxes & fees
18 Aug - 19 Aug
Cozy Fells Point Gem / In The Heart of Fells Point
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, (57)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (75)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is AED 909
AED 1,710 total
includes taxes & fees
21 Jul - 22 Jul
Waterfront Oasis of Annapolis Star
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (90)
"Very pretty location. Few minutes drive to town center."
The price is AED 404
AED 628 total
includes taxes & fees
4 Aug - 5 Aug
First Floor Studio Apartment in Historic Chestertown
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

10.0 out of 10, Exceptional, (31)
"We were thrilled to be able to return to this great apartment.It is very close to Gate 1 and the sofa bed has a great mattress on it!We hope to continue to return to this rental."
Cozy 1st Floor King George one bedroom apartment right across from USNA
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, (28)
"Loved the property."
Pristine Downtown 1-Bedroom Steps from State House
Relaxation Haven on the Shore near Choptank River
Property grounds

Relaxation Haven on the Shore near Choptank River

9.2 out of 10, Wonderful, (7)
"The property is very quiet and peaceful! No issues at all! Helen was wonderful and very kind!"
Relaxation Haven on the Shore near Choptank River
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, (7)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Marina

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

10.0 out of 10, Exceptional, (50)
"Everything about our stay was outstanding. Beautiful, just like the pictures show. We highly recommend this property."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
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, (10)
"Perfection"
The price is AED 433
AED 1,057 total
includes taxes & fees
21 Jul - 22 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Charming apt in the heart of Eastport & Annapolis
Dining

Charming apt in the heart of Eastport & Annapolis

Charming apt in the heart of Eastport & Annapolis
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (35)
"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
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (21)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is AED 826
AED 1,391 total
includes taxes & fees
23 Jul - 24 Jul
Waterfront Retreat with Private Dock and Beach
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, (43)
"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
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, (15)
"Fantastic accommodations! Many amenities! Friendly hostess! "
The price is AED 225
AED 433 total
includes taxes & fees
22 Jul - 23 Jul
Guest Suite for up to 2 in a Victorian on the Chester River
Downtown furnished apartment - walking distance to restaurants
Interior

Downtown furnished apartment - walking distance to restaurants

10.0 out of 10, Exceptional, (5)
"The home is beautiful and exceptionally maintained! The management of the property is fantastic and they are lovely to work with. They thoughtfully had fresh fruit and some light & healthy munchies in the kitchen when I checked in. The history of the home is also quite interesting! I look forward to a return stay."
Downtown furnished apartment - walking distance to restaurants
Cute waterfront apartment -- 8 min from the beach!
Outdoor dining

Cute waterfront apartment -- 8 min from the beach!

10.0 out of 10, Exceptional, (6)
"Nice and quiet with a great location and amazing view!!!"
Cute waterfront apartment -- 8 min from the beach!
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

9.0 out of 10, Wonderful, (4)
"This property is near many of the downtown places you want to visit, and all are within walking distance. "
Knot's Landing, spacious Apt. downtown Rock Hall
Chic and cozy apartment with WiFi and AC in Parkville
Living area

Chic and cozy apartment with WiFi and AC in Parkville

Chic and cozy apartment with WiFi and AC in Parkville
Spectacular Location: State Circle Apartment
Dining

Spectacular Location: State Circle Apartment

10.0 out of 10, Exceptional, (12)
"Great location around the corner from our Thanksgiving celebration. "
Spectacular Location: State Circle Apartment
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The Inn was the perfect location for a visit to Annapolis-right in the heart of the downtown! Friendly staff and nice accommodations! I will definitely stay there again when I return to Annapolis. "
Mary 1-night trip
Posted 1 day ago
Historic Inns of Annapolis

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 9 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. Waterfront Oasis of Annapolis Star: Located 25.8 mi/41.5 km away in Annapolis. A private pool, free WiFi, and fireplaces are included. An outdoor pool and a water park are on site. Cozy Fells Point Gem / In The Heart of Fells Point: It's situated in Baltimore, 28.3 mi/45.5 km away. Includes free WiFi and Smart TVs. 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. Pristine Downtown 1-Bedroom Steps from State House: Located in Annapolis, 28 mi/45 km from Chestertown. Includes free WiFi, sofa beds, and Smart TVs. Access to onsite laundry facilities is available on site.
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 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 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 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.