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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Apartments in Chester

Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is SAR 372
SAR 596 total
includes taxes & fees
8 Dec - 9 Dec
First Floor Studio Apartment in Historic Chestertown
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in 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.
The price is SAR 465
SAR 1,094 total
includes taxes & fees
9 Dec - 10 Dec
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

10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is SAR 777
SAR 1,553 total
includes taxes & fees
5 Dec - 6 Dec
Waterfront Oasis of Annapolis Star
Interior
Dean Street's Lower Deck House!

Apartment in Historic District

10.0 out of 10, Exceptional, (3)
"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.
The price is SAR 714
SAR 1,614 total
includes taxes & fees
28 Dec - 29 Dec
Dean Street's Lower Deck House!
Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Apartment in Admiral Heights

10.0 out of 10, Exceptional, (48)
"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.
The price is SAR 1,334
SAR 1,727 total
includes taxes & fees
5 Dec - 6 Dec
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great Hotel, Amazing location, very clean, everyone is friendly and helpful. Always recommend staying here if you are in Annapolis"
Tatiana 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

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: 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 situated in St. Michaels, 13.5 mi/21.8 km away. Includes private balconies. 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. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located in Annapolis, 8.3 mi/13.4 km from Chester. Includes free WiFi, sofa beds, and jetted bathtubs. 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 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.