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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 90 Apartments in Chestertown with updated reviews, rates, and availability.

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Fridge, microwave, oven, stovetop

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (51)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
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

10.0 out of 10, Exceptional, (38)
"Great location, wonderful place and fantastic owner. Recommendations on restaurants and things to do were perfect. We had a great time and Betty Ann was very kind and responsive in communications. Will definitely visit again!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
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)
"Quaint clean comfortable affordable best stay yet in Baltimore after 3other attempts 🤪⁉"
The price is AED 239
AED 721 total
includes taxes & fees
10 Jun - 11 Jun
Cozy Fells Point Gem / In The Heart of Fells Point
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (85)
"Quiet neighborhood and the best place to stay."
The price is AED 364
AED 583 total
includes taxes & fees
11 Jun - 12 Jun
First Floor Studio Apartment in Historic Chestertown
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.6 out of 10, Exceptional, (7)
"Property description is accurate, host is quickly responsive."
18th Cent. Charm in Historic Downtown Annapolis
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, (25)
"Perfect location to downtown Annapolis; lovely, clean, and comfortable space. Owners make the stay enjoyable and easyy to navigate. "
Pristine Downtown 1-Bedroom Steps from State House
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Interior

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (30)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
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

9.6 out of 10, Exceptional, (5)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Studio apartment in water view Historic home with WiFi, separate AC/heat
Miscellaneous

Studio apartment in water view Historic home with WiFi, separate AC/heat

10.0 out of 10, Exceptional, (2)
"SMALL BUT EFFICIENT"
Studio apartment in water view Historic home with WiFi, separate AC/heat
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (33)
"Very quiet area and well kept properly. The unit very clean and well kept, the Internet is pretty good with good reception, what I like the most was that it was so close to everything with restaurants and museums close by the park that hosted most of the events was close enough for a short walk and all sort of streets that held events were close by, this is a great location of the memorial day events and I have to say the honest were great and very helpful."
Historic Downtown Garden Oasis with Private Patio
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Aerial view

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

10.0 out of 10, Exceptional, (2)
"We stayed for a night ahead of a local festival. While my husband and I had travel issues and got in super late, my in-laws really enjoyed the property. Very clean and convenient to everything. We will stay again. Thank you!"
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Walk everywhere from 1st floor dog-friendly apartment with parking and backyard
Fridge, microwave, oven, stovetop

Walk everywhere from 1st floor dog-friendly apartment with parking and backyard

2.5 star property
10.0 out of 10, Exceptional, (2)
"This tastefully decorated apartment is in a perfect location to enjoy all that is Annapolis. "
Walk everywhere from 1st floor dog-friendly apartment with parking and backyard
Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Property grounds

Bel Air Apartment w/ Pool ~ 2 Mi to Main St

Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Charming Eastport
Aerial view

Charming Eastport

9.4 out of 10, Exceptional, (3)
"We thoroughly enjoyed this section of Eastport. The views of the marina were beautiful and we found a couple new restaurants nearby! Excellent communication with the owners."
Charming Eastport
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is AED 893
AED 1,692 total
includes taxes & fees
6 Jun - 7 Jun
Waterfront Oasis of Annapolis Star
Waterfront Retreat with Private Dock and Beach
Miscellaneous

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (20)
"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 1,367 total
includes taxes & fees
8 Jun - 9 Jun
Waterfront Retreat with Private Dock and Beach
Charming apt in the heart of Eastport & Annapolis
Aerial view

Charming apt in the heart of Eastport & Annapolis

Charming apt in the heart of Eastport & Annapolis
Royalty Homes - 2 bedroom apartment
Exterior

Royalty Homes - 2 bedroom apartment

8.0 out of 10, Very Good, (2)
"Property location and size were good. Unit smelled like smoke the entire stay. "
Royalty Homes - 2 bedroom apartment
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, (29)
"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
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, (49)
"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 !!
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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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?
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 in Pasadena, 21.4 mi/34.4 km away. Includes free WiFi and Smart TVs. Access to an outdoor pool is available on site. WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: 16.1 mi/25.9 km away in Earleville. Free WiFi and Smart TVs are included. Waterfront Oasis of Annapolis Star: Located in Annapolis, 25.8 mi/41.5 km from Chestertown. Includes a private pool, free WiFi, and fireplaces. An outdoor pool and a water park are 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 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.