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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 76 Apartments in Chestertown with updated reviews, rates, and availability.

'At Fells Point' CitySide - 'Tons better than a hotel!'
CitySide Living Room & Sofa Bed

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (182)
"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 323
AED 747 total
includes taxes & fees
28 Jan - 29 Jan
'At Fells Point' CitySide - 'Tons better than a hotel!'
First Floor Studio Apartment in Historic Chestertown
Back Yard

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"Very clean, excellent communications,"
The price is AED 360
AED 579 total
includes taxes & fees
29 Jan - 30 Jan
First Floor Studio Apartment in Historic Chestertown
Bay View Studio Apartment
Property grounds

Bay View Studio Apartment

10.0 out of 10, Exceptional, (41)
"What a gem this place is! My fiance and I stayed here for a couple of nights after Christmas for a mini getaway, just the two of us. Fantastic views, super clean property, and this space had everything we needed. We grilled, relaxed in the hot tub, and enjoyed some time playing cards next to the fireplace. The location is also down the street from Starbucks, a liquor store, and a grocery store - our essentials ha! Cannot recommend this place enough, thank you! "
Bay View Studio Apartment
Spectacular Location: State Circle Apartment
Exterior

Spectacular Location: State Circle Apartment

10.0 out of 10, Exceptional, (11)
"Great location around the corner from our Thanksgiving celebration. "
Spectacular Location: State Circle Apartment
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Larger of the 2 bedrooms, with a queen bed and sitting area

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

9.6 out of 10, Exceptional, (22)
"Being able to walk down the sidewalk to the Visitor's Entrance at the USNA meant we got to maximize our time with our plebe. The best part about this location was we didn't have to stress over the traffic and parking situation at all (and the traffic was a lot!). We got to walk back with him each evening and on Sunday morning he was able to walk over to us when he was released. The second best part was while he was catching up with family and friends on his phone or just enjoying the peace...
The price is AED 735
AED 1,244 total
includes taxes & fees
29 Jan - 30 Jan
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
'At Fells Point' Courtyard - Your historically restored apartment
Living area

'At Fells Point' Courtyard - Your historically restored apartment

9.6 out of 10, Exceptional, (81)
"This apartment is 3 blocks from my daughter. Well located to everything you need!! Directions were great.!"
The price is AED 518
AED 997 total
includes taxes & fees
27 Jan - 28 Jan
'At Fells Point' Courtyard - Your historically restored apartment
Pristine Downtown 1-Bedroom Steps from State House
Steps from the Maryland state house

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
Cozy 2 bedroom apartment w/ free parking
Private kitchen

Cozy 2 bedroom apartment w/ free parking

8.6 out of 10, Excellent, (4)
"Very good communication, address was listed wrong on website but the host helped a lot, it wasn't his fault. It's in the basement, and it's really nice, but it's in the basement lol"
The price is AED 533
AED 1,408 total
includes taxes & fees
24 Jan - 25 Jan
Cozy 2 bedroom apartment w/ free parking
Newly restored apartment in the heart of Chestertown
Living area

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (19)
"We fell in love with Chestertown and are so glad we stayed in the heart of downtown at this charming vrbo. Everything was perfect. Will return and recommend "
Newly restored apartment in the heart of Chestertown
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Jacuzzi Jetted Hot Tub

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

9.6 out of 10, Exceptional, (27)
"Stayed for 3 nights in this clean, quiet loft at the end of a dead end 2-lane road. *Loved the dry sauna! Nice heat! *Loft is accessed through stairs inside the garage. *Kitchenette is small but works for breakfast and basics. *Love the large closet which is sunny and like another bedroom. *Easy communication with owner and easy access. * About 10m by car to Sandy Point State Park * About 15m by car into downtown Annapolis Great base for exploring the Annapolis area."
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Bel Air Vacation Rental | 1BR | 1BA | Steps Required | 680 Sq Ft

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

Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Charming Eastport
Living area

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
Relaxation Haven on the Shore near Choptank River
Bedroom Lotus

Relaxation Haven on the Shore near Choptank River

10.0 out of 10, Exceptional, (3)
"We were attending a wedding in Easton, MD. This was the perfect place to use as a base while attending wedding and get togethers "
Relaxation Haven on the Shore near Choptank River
Waterfront Oasis of Annapolis Star
Waterfront Oasis of Annapolis pool grandeur.

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (72)
"Beth and Andy were the most wonderful hosts who reached out ahead of my stay to make sure I was able to get to their property safely and provided all sorts of helpful amenities once I settled in! Beth was so kind to show me around the property and make sure I had everything I needed. Their Oasis getaway house was exactly that! Beautiful big ceilings, open floor plan, spacious bathroom and a fridge full of various beverages - I felt right at home! Beth and Andy’s house was spick and span and felt...
The price is AED 845
AED 1,620 total
includes taxes & fees
24 Jan - 25 Jan
Waterfront Oasis of Annapolis Star
Anchor's Away in the Heart of Eastport!
Living area

Anchor's Away in the Heart of Eastport!

9.8 out of 10, Exceptional, (37)
"We really enjoyed the location and Eastport. "
Anchor's Away in the Heart of Eastport!
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Room

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10.0 out of 10, Exceptional, (34)
"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 1st Floor King George one bedroom apartment right across from USNA
Exterior detail

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 !!
Interior

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 !!
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Entrance into kitchen

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

9.8 out of 10, Exceptional, (45)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
'At Fells Point' Topside - Exceeding your expectations!
Living Room w couch dining table and TV

'At Fells Point' Topside - Exceeding your expectations!

9.6 out of 10, Exceptional, (86)
"Nice place overall, but those were the most narrow and steep stairs I have ever experienced! This place is not suited for anyone that isn't in great physical shape. It is on second and third levels, so lots of stairs. We did enjoy the high ceilings and charm of this row house. The security gate was an added security measure and we liked having the little courtyard area away from the street. One of the reasons I selected this unit was it indicated there was off-street parking in the features and...
The price is AED 386
AED 887 total
includes taxes & fees
24 Jan - 25 Jan
'At Fells Point' Topside - Exceeding your expectations!
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

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Terrace/patio

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

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

10.0 out of 10, Exceptional, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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 7 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. ‘At Fells Point’ CitySide - ‘Tons better than a hotel!’: Located 28.3 mi/45.5 km away in Baltimore. Free WiFi and Smart TVs are included. Bay View Studio Apartment: Located in Annapolis, 28 mi/45 km away. Includes free WiFi, private patios, and fireplaces. A water park and a spa tub 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. ‘At Fells Point’ Courtyard - Your historically restored apartment: It’s located in Baltimore, 28.3 mi/45.5 km from Chestertown. Includes laundry facilities, free WiFi, and private patios.
How many apartments can I expect to find in Chestertown?
Expedia has 7 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 and Roundtop 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.