A coastal town with a marina, a bridge, and a highway.

Apartments in Chester for Rent

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chester apartments

A house with a blue front door, two windows, and a small porch.

1. 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, (32 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$253 nightly
The price is $280
Nov 3 - Nov 4
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Stylish kitchen with open layout and island seating

2. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$407 nightly
The price is $464
Nov 4 - Nov 5
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$136 nightly
The price is $150
Nov 3 - Nov 4
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A kitchen with wooden cabinets, granite countertops, and a dining table set with blue and white dishes.

4. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
$462 nightly
The price is $527
Nov 3 - Nov 4
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A kitchen with a wooden countertop, a stove, and a refrigerator.

5. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (15 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
$356 nightly
The price is $406
Nov 3 - Nov 4
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
A living room with a brown sofa, a glass coffee table, and a beige armchair.

6. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"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.
$417 nightly
The price is $475
Nov 3 - Nov 4
Total with taxes and fees
Dean Street's Lower Deck House!
A house with a yellow door and a window with a lamp outside.

7. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
$276 nightly
The price is $314
Nov 15 - Nov 16
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A two-story house with a covered patio, a garage, and a well-maintained lawn.

8. 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, (56 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
$416 nightly
The price is $474
Nov 3 - Nov 4
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Living area

9. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
$378 nightly
The price is $401
Nov 9 - Nov 10
Total with taxes and fees
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A spacious living area with a dining table, sofa, and a kitchen in the background.

10. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
$304 nightly
The price is $336
Nov 3 - Nov 4
Total with taxes and fees
Newly restored apartment in the heart of 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.
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Top Chester Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"great location and access to Annapolis"
Alzbeta 1-night trip
Posted 6 hours ago
Crowne Plaza Annapolis by IHG

Find out more about Chester

Chester Apartments information

Number of reviews
266
Accommodation
58 Apartments
Lowest Price
$150
Highest Price
$527

Frequently asked questions

What's it like to stay at an apartment in Chester?
You'll find 9 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: New Loft w/South River view from treehouse deck!: Situated in Riva, 15.8 mi/25.4 km from the heart of Chester. Includes free WiFi, private patios, and premium mattresses. Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!: Located 13.1 mi/21 km away in Annapolis. Free WiFi, private balconies, and Smart TVs are included. Downtown St. Michaels Studio – Walk to Waterfront, Dining & Shops: It's situated in St. Michaels, 13.7 mi/22.1 km away. Includes private balconies. Harbor View Suite Talbot County License Number STRN-25-58: Located 13.9 mi/22.3 km away in St. Michaels. Amenities include free WiFi. Access to onsite laundry facilities is available on site.
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 Eastern Neck National Wildlife Refuge.
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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