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Apartments in Chester for Rent

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chester apartments

Beach

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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$257 nightly
The price is $284
Sep 17 - Sep 18
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Private kitchen

2. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$423 nightly
The price is $482
Sep 17 - Sep 18
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
Property grounds

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Sep 29 - Sep 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Interior

4. 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.
$390 nightly
The price is $445
Sep 21 - Sep 22
Total with taxes and fees
Dean Street's Lower Deck House!
Private kitchen

5. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
$399 nightly
The price is $455
Sep 20 - Sep 21
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Exterior detail

6. 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.
$294 nightly
The price is $335
Oct 8 - Oct 9
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Exterior

7. 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, (55 reviews)
"Great stay in Annapolis. The property is gorgeous. Everything you need for a great weekend in Annapolis. "
United States
Jennifer G.
$432 nightly
The price is $492
Sep 17 - Sep 18
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Living area

8. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$320 nightly
The price is $353
Sep 17 - Sep 18
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Every thing was amazing. The staff was extremely helpful and the parking situation was perfect. Room was top notch."
Jennifer 4-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Chester

Chester Apartments information

Number of reviews
280
Accommodation
60 Apartments
Lowest Price
$159
Highest Price
$492

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. 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 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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