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28 Nov - 30 Nov
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Apartments in Chester

Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
The price is AED 364
AED 583 total
includes taxes & fees
19 Nov - 20 Nov
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!

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 AED 433
AED 1,046 total
includes taxes & fees
19 Nov - 20 Nov
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

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
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star
Interior
Dean Street's Lower Deck House!

Dean Street's Lower Deck House!

Historic District
10.0 out of 10, Exceptional, (2)
"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 AED 775
AED 1,679 total
includes taxes & fees
24 Nov - 25 Nov
Dean Street's Lower Deck House!
Terrace/patio
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, (45)
"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 AED 1,306
AED 1,673 total
includes taxes & fees
1 Dec - 2 Dec
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Fridge, microwave, oven, stovetop
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 756
AED 1,574 total
includes taxes & fees
19 Nov - 20 Nov
Annapolis Gem: Stylish and Cozy
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

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

10/10 Excellent
"Very helpful and friendly front desk staff, clean and well-appointed rooms. The free laundry room was a real bonus for us. Having a spacious kitchen in our room made our four-day stay during a long road trip so appreciated. "
Janet 4-night trip
Posted 12 hours ago
Candlewood Suites Annapolis by IHG

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: 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. Modern Flat in the Heart of St. Michaels – Walk Everywhere: Located in St. Michaels, 13.6 mi/21.9 km away. Includes private balconies and fireplaces. Access to onsite laundry facilities is available on site. 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 located in St. Michaels, 13.5 mi/21.8 km from Chester. Includes private balconies.
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.