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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Chester apartments

Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"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
14 Jan - 15 Jan
First Floor Studio Apartment in Historic Chestertown
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (17 reviews)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is AED 433
AED 1,046 total
includes taxes & fees
14 Jan - 15 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 760
AED 1,520 total
includes taxes & fees
14 Jan - 15 Jan
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop
Luxury Pool Loft sleeps 4

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (4 reviews)
"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 1,432 total
includes taxes & fees
14 Jan - 15 Jan
Luxury Pool Loft sleeps 4
Exterior detail
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

Apartment in Historic District

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
9.6 out of 10, Exceptional, (27 reviews)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Fridge, microwave, oven, stovetop
Annapolis Gem: Stylish and Cozy

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is AED 909
AED 1,778 total
includes taxes & fees
16 Jan - 17 Jan
Annapolis Gem: Stylish and Cozy
Smart TV
Five Star Charmer! Great Location Downtown & Stadium! Parking too!

Apartment in Annapolis

Five Star Charmer! Great Location Downtown & Stadium! Parking too!
9.6 out of 10, Exceptional, (5 reviews)
"Jennifer met us at check in, ensured we had what we needed. Well appointed, assigned parking, coffee, water and snacks for the late night munchies. Had a great time, will return - thanks ! "
United States
Darcy W.
The price is AED 808
AED 1,386 total
includes taxes & fees
7 Feb - 8 Feb
Five Star Charmer! Great Location Downtown & Stadium! Parking too!
Exterior
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Apartment in Admiral Heights

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (48 reviews)
"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 1,702 total
includes taxes & fees
21 Jan - 22 Jan
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Property grounds
Charming Downtown 3rd Floor 1 Bedroom Apt

Apartment in Historic District

Charming Downtown 3rd Floor 1 Bedroom Apt
9.8 out of 10, Exceptional, (20 reviews)
"We had a great time staying that this home. It was a perfect stay for my wife and I."
United States
Eric S.
Charming Downtown 3rd Floor 1 Bedroom Apt
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"The staff was great and helpful. The room was fresh, clean and everything worked very well. The only thing I wish the room had was the ability to cast to the TV versus traditional stations so we did not use the TV for lack of streaming services."
Scott 1-night trip
Posted 1 day ago
Hilton Garden Inn Annapolis Downtown

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.

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