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Apartments in Chestertown for Rent

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Compare 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, (21)
"Especially nice for summer visits."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Bay View Studio Apartment
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio 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, (17)
"Our home is over 100 years old so staying here was like being home. Great location to the main st shopping and food."
The price is $251
$404 total
includes taxes & fees
Jun 29 - Jun 30
Cozy 1st Floor King George one bedroom apartment right across from USNA
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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, (17)
"The pictures don't do it Justice. Fine details, spacious, comfortable, most accommodating VRBO EVER for us. Great location. Owners are so nice, informative and take pride in their property. Very serene, comfortable and cozy. Hope to stay there every time we are visiting Annapolis. Close to everything. Able to walk to everything Annapolis had to offer."
Pristine Downtown 1-Bedroom Steps from State House
Coastal Kent Narrows Home on Bay
Fridge, microwave, oven, stovetop
Coastal Kent Narrows Home on Bay
10.0 out of 10, Exceptional, (4)
"Very nice place to stay, right on the bay"
The price is $225
$446 total
includes taxes & fees
Jun 2 - Jun 3
Coastal Kent Narrows Home on Bay
Charming Downtown 3rd Floor 1 Bedroom Apt
Property grounds
Charming Downtown 3rd Floor 1 Bedroom Apt
10.0 out of 10, Exceptional, (12)
"Nice place, nice owners, great location."
The price is $175
$303 total
includes taxes & fees
Jun 25 - Jun 26
Charming Downtown 3rd Floor 1 Bedroom Apt
Historic Downtown Garden Oasis with Private Patio
Property grounds
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (14)
"Stephen and Marianna were great hosts. The property was very clean and functional with beautiful artwork throughout the property. Great outdoor patio for relaxing plus excellent location for access to downtown Chestertown. We will be staying here again on our next visit."
Historic Downtown Garden Oasis with Private Patio
'At Fells Point' Topside - Exceeding your expectations!
'At Fells Point' Topside - Exceeding your expectations!
9.6 out of 10, Exceptional, (80)
"Great location. Very clean. Super comfortable bed. Wonderful location to get to everything downtown. Really enjoyed my stay"
The price is $133
$283 total
includes taxes & fees
Jun 9 - Jun 10
'At Fells Point' Topside - Exceeding your expectations!
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, (76)
"Bob and Beth's apartment was absolutely perfect for us. It was the cleanest VRBO that we have ever stayed in. All of the amenities were above and beyond what we expected. The apartment is in a great location and walkable into town and the WC campus. We will definitely stay again when we come back to town."
Carriage House Hideaway in Middle of Chestertown
'At Fells Point' CitySide - 'Tons better than a hotel!'
'At Fells Point' CitySide - 'Tons better than a hotel!'
9.8 out of 10, Exceptional, (161)
"This had everything we needed and Fells Point is a nice area!"
The price is $95
$215 total
includes taxes & fees
Jun 3 - Jun 4
'At Fells Point' CitySide - 'Tons better than a hotel!'
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Pool
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (34)
"The host was so friendly and easy to communicate with. The accommodations were very clean and organized. The location was perfect; cute shops only miles away, beach access, beautiful views, and short drive to downtown Annapolis!"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is $110
$164 total
includes taxes & fees
Jun 12 - Jun 13
First Floor Studio Apartment in Historic Chestertown
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, (15)
"This was a great apartment in an excellent location. We visited Washington college and attended a sailing regatta. The Evergrain Bakery across the street was amazing. Shops and restaurants all within walking distance! Apartment was well stocked, nicely decorated and clean! Also very close to the Hodson boathouse. It was a 3 minute drive!"
Newly restored apartment in the heart of Chestertown
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Sauna
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
9.6 out of 10, Exceptional, (15)
"Tim and his family are wonderful hosts and extremely responsive if there is a problem. My stay of three weeks is not the norm and enjoyable.The king size bed and wonderful linens and blankets provided an awesome night's sleep.The HUGE TV is beyond belief. An abundant supply of high quality towels and bath/shower products were greatly appreciated.The sauna...where do I begin??? Walking around the neighborhood is safe with plenty of docks and water views. Grocery stores and other retail and...
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Royalty Homes - 2 bedroom apartment
Exterior
Royalty Homes - 2 bedroom apartment
Royalty Homes - 2 bedroom apartment
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
Beach
Charming Eastport
9.4 out of 10, Exceptional, (3)
"This was a charming apartment nestled in the quiet side of annapolis. Everything was within walking distance. The apartment had everything you needed if you wanted to cook. Just bring your food!"
Charming Eastport
Milton Manor: W/D, WiFi, Free Street Parking
Private kitchen
Milton Manor: W/D, WiFi, Free Street Parking
2.0 out of 10, (2)
"Good day! I want to first start off by saying thank you for allowing us to stay in your place. However, I do have so things I want to bring to you attention before I leave a review. 1) There is only one Tv in thee entire place when there are two rooms. 2) The Tv that is there doesn’t even work. 3) The sink doesn’t drain and had old water sitting in it. So, we had to brush our teeth in the shower. 4) Very noisy area. Cars come by all day and night. The neighbors above are very loud not to mention...
The price is $65
$216 total
includes taxes & fees
Jun 3 - Jun 4
Milton Manor: W/D, WiFi, Free Street Parking
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (60)
"Most excellent space for a quiet retreat away from the city! The property and hosts were welcoming and super attentive. We will definitely be coming back!"
The price is $275
$499 total
includes taxes & fees
Jun 2 - Jun 3
Waterfront Oasis of Annapolis Star
Anchor's Away in the Heart of Eastport!
Fridge, microwave, oven, stovetop
Anchor's Away in the Heart of Eastport!
9.8 out of 10, Exceptional, (31)
"Great communication with the owner. Location was great and close to the Naval Academy. Parking spot was a plus, especially in the area where parking was tight. The place was clean and comfortable. Everything needed was on site. Would definitely recommend."
Anchor's Away in the Heart of Eastport!
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See all available properties in Chestertown
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.

Other property types in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (4)
"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"
The price is $629
$1,438 total
includes taxes & fees
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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.

Chestertown Apartments information

Number of reviews
Accommodation
 Apartments
Lowest Price
Highest Price

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 an outdoor pool are on site. Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!: Located 23 mi/36.9 km away in Annapolis. Free WiFi, private patios, and Smart TVs are included. A fitness center and a game room are on site. Milton Manor: W/D, WiFi, Free Street Parking: It’s located in Baltimore, 28 mi/45 km away. Bay View Studio Apartment: Located in Annapolis, 28 mi/45 km from Chestertown. Includes free WiFi, private patios, and fireplaces. A water park and a spa tub are 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 Wilmer Park is one spot to enjoy nature. 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.

Recent reviews of Chestertown hotels
Expedia verified reviews

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

5/5 Excellent
Convenient location for weekend
"Very impressed by breakfast service, availability of bar on site and waterfront seating. "
A verified traveler stayed at Hyatt Place Kent Narrows & Marina
Posted 17 hours ago
Hyatt Place Kent Narrows & Marina