Photo by Patricia Knorr

Apartments in Chester for Rent

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Apartments in Chester

Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Nov 19 - Nov 20
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Exterior detail
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
$258 nightly
The price is $285
Nov 19 - Nov 20
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Dec 1 - Dec 2
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Interior
Dean Street's Lower Deck House!

Dean Street's Lower Deck House!

Historic District
10.0 out of 10, Exceptional, (2)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
$401 nightly
The price is $457
Nov 24 - Nov 25
Total with taxes and fees
Dean Street's Lower Deck House!
Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Admiral Heights
10.0 out of 10, Exceptional, (45)
"Perfect hideaway for a weekend trip to Annapolis. Great location and had everything we needed for the kids. Host was very accommodating and communicative, would come back!"
United States
Jay B.
$400 nightly
The price is $455
Dec 1 - Dec 2
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Fridge, microwave, oven, stovetop
Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy

Eastport
10.0 out of 10, Exceptional, (3)
"Great spot"
United States
Brian F.
$376 nightly
The price is $429
Nov 19 - Nov 20
Total with taxes and fees
Annapolis Gem: Stylish and Cozy
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 Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Friendly staff. Enjoyed the room. "
John 2-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Chester

Chester Apartments information

Number of reviews
250
Accommodation
80 Apartments
Lowest Price
$159
Highest Price
$457

Frequently asked questions

What's it like to stay at an apartment in Chester?
You'll find 12 hotels and other accommodations in Chester. Though there aren't many apartments, we can help you search for accommodations that are similar. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can also filter by similar properties such as condos, vacation homes, or cottages.
How do you know if an apartment is the best choice for you?
Often offering more space than a traditional hotel room, an apartment includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for solo travelers who want to stay in at night and plan out their next day.
What's the top apartment for a stay in Chester?
Listed below are some of the favorite apartments in the area: Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!: Located 11.5 mi/18.5 km away in Rock Hall. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Modern Flat in the Heart of St. Michaels – Walk Everywhere: Located in St. Michaels, 13.6 mi/21.9 km away. Includes private balconies and fireplaces. Access to onsite laundry facilities is available on site. First Floor Studio Apartment in Historic Chestertown: Located 18.5 mi/29.8 km away in Chestertown. A private pool, laundry facilities, and free WiFi are included. A fitness center and onsite laundry facilities are on site. Downtown St. Michaels | Porch + Pet-Friendly: It's located in St. Michaels, 13.5 mi/21.8 km from Chester. Includes private balconies.
What will the weather be like during my trip to Chester?
Though weather is just one factor, it can really affect your travel plans, especially if you're planning an extended stay in Chester. 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 Chester is 56 inches.
What should I see in Chester?
Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Northern Chesapeake Bay. In the larger area, you'll find Matapeake State Park and Love Point State Park.
What's the best way to get to and around Chester?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Easton, MD (ESN-Easton - Newnam), which is located 16.6 mi (26.7 km) away from the heart of the city. You can also search for flights into Baltimore Washington Intl. Airport (BWI), which is 24.8 mi (39.9 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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