Photo by Patricia Knorr

Search Apartments in Chester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Chester apartments

Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is AED 364
AED 583 total
includes taxes & fees
12 Jan - 13 Jan
First Floor Studio Apartment in Historic Chestertown
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is AED 433
AED 1,042 total
includes taxes & fees
10 Jan - 11 Jan
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

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 760
AED 1,520 total
includes taxes & fees
10 Jan - 11 Jan
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop
Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
Cape Saint Claire
10.0 out of 10, Exceptional, (4)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is AED 459
AED 1,428 total
includes taxes & fees
10 Jan - 11 Jan
Luxury Pool Loft sleeps 4
Property grounds
Charming Downtown 3rd Floor 1 Bedroom Apt

Charming Downtown 3rd Floor 1 Bedroom Apt

Charming Downtown 3rd Floor 1 Bedroom Apt
Historic District
9.8 out of 10, Exceptional, (20)
"We had a great time staying that this home. It was a perfect stay for my wife and I."
United States
Eric S.
The price is AED 617
AED 1,101 total
includes taxes & fees
14 Jan - 15 Jan
Charming Downtown 3rd Floor 1 Bedroom Apt
Fridge, microwave, oven, stovetop
Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy
Eastport
10.0 out of 10, Exceptional, (3)
"Great spot"
United States
Brian F.
The price is AED 909
AED 1,774 total
includes taxes & fees
10 Jan - 11 Jan
Annapolis Gem: Stylish and Cozy
Interior
Dean Street's Lower Deck House!

Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4)
"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.
Dean Street's Lower Deck House!
Exterior
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

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (48)
"Convenient location, very clean, beautiful yard for a pet friendly visit. We had a great time! Would go back again. "
United States
Jackie C.
The price is AED 1,306
AED 1,669 total
includes taxes & fees
17 Jan - 18 Jan
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Exterior detail
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

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

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
9.6 out of 10, Exceptional, (27)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
The price is AED 624
AED 1,160 total
includes taxes & fees
11 Jan - 12 Jan
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

10/10 Excellent
"Everything was great about my stay. From checking in to checking out! The front desk staff as well as housekeeping were extremely helpful and kind! I look forward to my next visit!"
Tina 3-night trip
Posted 4 days ago
Hampton Inn & Suites Annapolis

Frequently asked questions

What's it like to stay at an apartment in Chester?
You'll find 11 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: First Floor Studio Apartment in Historic Chestertown: Located in Chestertown, 18.5 mi/29.8 km from the heart of Chester. Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. Modern Flat in the Heart of St. Michaels – Walk Everywhere: Located 13.6 mi/21.9 km away in St. Michaels. Private balconies and fireplaces are included. Access to onsite laundry facilities is available on site. Luxury Pool Loft sleeps 4: Located in Annapolis, 10.2 mi/16.4 km away. Includes fireplaces. Access to onsite laundry facilities is available on site. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located 8.3 mi/13.4 km away in Annapolis. Free WiFi, sofa beds, and jetted bathtubs are included. Onsite laundry facilities and a hot tub are 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 Chesapeake Bay Environmental Center.
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.

Explore a world of travel with Expedia