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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

Bay View Studio Apartment
Outdoor spa tub

Bay View Studio Apartment

10.0 out of 10, Exceptional, (42)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment
Newly restored apartment in the heart of Chestertown
Fridge, microwave, oven, stovetop

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (22)
"We loved this apartment. The communication with the owner was very timely and clear!"
Newly restored apartment in the heart of Chestertown
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (28)
"Your guest house was perfect. It had everything we needed. Short walk to town and the Chester River. Will definitely book again when we come to town for our son’s lacrosse games! "
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

The price is AED 610
AED 825 total
includes taxes & fees
20 May - 21 May
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.8 out of 10, Exceptional, (6)
"Had a great stay, super close to everything. Jennifer was very communicative!"
The price is AED 698
AED 1,353 total
includes taxes & fees
1 May - 2 May
18th Cent. Charm in Historic Downtown Annapolis
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Fridge, microwave, oven, stovetop

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

9.8 out of 10, Exceptional, (38)
"My husband and I stayed here with our two kids for his reunion weekend and it did not disappoint. The apartment is conveniently located right outside of Gate 1 and so close to the all of the downtown offerings. The apartment was super clean and had everything we needed for our stay. We would definitely stay here again!"
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
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)
"We had full and free access to the specificed areas with no impedement whatsoever. Checking in and out was seamless for us and the property was convenient 15 minutes from the historic downtown area. Would definitely reccomend for other couples and we will absolutely consider returning again in the future!"
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Cityside Fells Point Apartment
Marina

Cityside Fells Point Apartment

9.8 out of 10, Exceptional, (187)
"Quaint clean comfortable affordable best stay yet in Baltimore after 3other attempts 🤪⁉"
The price is AED 323
AED 781 total
includes taxes & fees
27 May - 28 May
Cityside Fells Point Apartment
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (82)
"Clean, well appointed, plenty of space, all small amenities were thought of. We would definitely come back. Very responsive owner too!"
The price is AED 360
AED 579 total
includes taxes & fees
6 May - 7 May
First Floor Studio Apartment in Historic Chestertown
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, (47)
"Stay was awesome. Definitely would stay here again if I had a reason to be in the area. Stayed because my wedding was being held at celebrations at the bay. I would recommend that a full length mirror either be brought in or have property owners install one. It was so hard to check yourself as you had to go to the bathroom everytime. Did contact host early on but never heard back. Ended up contacting the marina and emailed them for my questions. They did respond. Beautiful views too!! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
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
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Fridge, microwave, oven, stovetop

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

9.6 out of 10, Exceptional, (23)
"Cleaning of the apartment needs to improve "
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Courtyard Fells Point Townhome
Fridge, microwave, oven, stovetop

Courtyard Fells Point Townhome

9.6 out of 10, Exceptional, (85)
"Property is clean and efficiently designed, tastefully decorated and located in a safe, walkable area.I would recommend this location to anyone wanting to visitBaltimore."
The price is AED 349
AED 823 total
includes taxes & fees
15 May - 16 May
Courtyard Fells Point Townhome
Carriage House Hideaway in Middle of Chestertown
Iron/ironing board, travel crib, free WiFi, bed sheets

Carriage House Hideaway in Middle of Chestertown

10.0 out of 10, Exceptional, (87)
"If I could give these hosts 10 stars, I would! They went above and beyond for me! Their kindness and helpfulness was way beyond what I would have expected from a host. The carriage house is adorable! It is comfy, clean and quiet. It is stocked with a coffee maker, a toaster, an air fryer, a microwave, etc. If you need it, it probably there!I just cannot say enough about these hosts and their adorable carriage house rental. "
Carriage House Hideaway in Middle of Chestertown
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)
"Wonderful hosts. Beautiful property. And a spacious yet cozy place to stay. We will book again next time we visit. "
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Apartment in Perry Hall area
Fridge, microwave, oven, stovetop

Apartment in Perry Hall area

2.0 star property
10.0 out of 10, Exceptional, (1)
"We are so excited to have such a lovely place to stay that’s close to family!"
Apartment in Perry Hall area
Home in Perry Hall area
Fridge, microwave, oven, stovetop

Home in Perry Hall area

2.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent Spot "
Home in Perry Hall area
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, (24)
"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
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
Relaxation Haven on the Shore near Choptank River
Fridge, microwave, oven, stovetop

Relaxation Haven on the Shore near Choptank River

10.0 out of 10, Exceptional, (4)
"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
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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Other property types in Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (214)
"Great location near the Naval Academy, Main Street, Paca House, St. John's...loved walking the streets every evening with our dog. Helpful restaurant trips from John, convenient parking spot, everything was just right! Thank you!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.6 out of 10, Exceptional, (24)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 8 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. COZY DOWNTOWN APARTMENT-Naval Academy Vicinity: Located 27.8 mi/44.8 km away in Annapolis. Free WiFi, sofa beds, and Smart TVs are included. Access to onsite laundry facilities is available on site. Bay View Studio Apartment: Located in Annapolis, 28 mi/45 km away. Includes free WiFi, private patios, and fireplaces. Onsite laundry facilities and a water park are on site. ‘At Fells Point’ CitySide - ‘Tons better than a hotel!’: It’s located in Baltimore, 28.3 mi/45.5 km from Chestertown. Includes free WiFi and Smart TVs.
How many apartments can I expect to find in Chestertown?
Expedia has 8 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 Crumpton Auction.
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.