Best Apartments in Chester, MD for Your Vacation from $89

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Our top choices for Chester apartments

First Floor Studio Apartment in Historic Chestertown

Chestertown

lesia k.

$144 nightly

Jun 8 - Jun 9

Total with taxes and fees

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

Michael D.

$266 nightly

Jun 8 - Jun 9

Total with taxes and fees

The Sparrows Nest - in downtown Sparrows Point

Edgemere

$180 nightly

Jun 7 - Jun 8

Total with taxes and fees

Waterfront Oasis of Annapolis Star

Annapolis

Thomas

$436 nightly

Jun 7 - Jun 8

Total with taxes and fees

Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

$440 nightly

Jun 8 - Jun 9

Total with taxes and fees

Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveler

$346 nightly

Jun 7 - Jun 8

Total with taxes and fees

Annapolis Gem: Stylish and Cozy

Eastport

Brian F.

$477 nightly

Jun 6 - Jun 7

Total with taxes and fees

18th Cent. Charm in Historic Downtown Annapolis

Historic District

David P.

$374 nightly

Jun 8 - Jun 9

Total with taxes and fees

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Top Chester Hotel Reviews

The Wildset

10/10 Excellent

"My husband and I stayed here one night to celebrate his birthday. The hotel was beautiful and so convenient to everything. The room was immaculate with comfortable bedding, beautiful bathroom and wonderful amenities. Loved the breakfast and staff were efficient and informative about places to see in the area. The garden area and fire pit were a bonus. Park your car in the off street lot and explore beautiful St. Michael’s. Can’t wait to come back."

Hilton Garden Inn Annapolis Downtown

6/10 Okay

"While the staff were very pleasant and helpful—the physical property has seen better days. Our first room had a leaking shower and a non-working refrigerator. We were moved to a different room without question. This room was laid out a little better. But, both rooms had the a/c & heat vents right next to the bed. We had to turn the system off at night so the cold air wouldn’t blast onto the person on that side of the bed."

Hampton Inn & Suites Annapolis

6/10 Okay

"Several cleanliness issues: The microwave was filthy and the top of the refrigerator looked caked with dust. Under the sink with the trash can was severely water damaged and there were a number of stains on the floors and furniture. Hampton Inn and Suites used to be renowned for being upscale. Obviously, the standards have changed."

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"It would have been a nicer stay if they weren’t ripping up flooring and had the awful headache causing smell of epoxy everywhere. The hotel room we were in was in another wing- and you had to pass all around the convention rooms to get there. Thankfully we were able to use the shuttle to go into downtown Annapolis and enjoy the nice weather. We tried to spend as much time outside as possible."

Find out more about Chester

Chester Apartments information

Number of reviews	13,017
Accommodation	73 Apartments
Lowest Price	$89
Highest Price	$285

Frequently asked questions

What's it like to stay at an apartment in Chester?

You'll find 10 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: Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located in Pasadena, 14.8 mi/23.9 km from the heart of Chester. Includes free WiFi and Smart TVs. Access to an outdoor pool is available on site. Waterfront Oasis of Annapolis Star: Located 10 mi/16 km away in Annapolis. A private pool, free WiFi, and fireplaces are included. Access to an outdoor pool is available on site. Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!: It's situated in Annapolis, 13.1 mi/21 km away. Includes free WiFi, private balconies, and Smart TVs. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids: Located 12 mi/19.3 km away in Annapolis. Private patios and fireplaces are included. Access to onsite laundry facilities is available on site. Annapolis Spa Retreat, Sauna, Jacuzzi, King Bed Couples Quiet Loft Apt. Getaway: 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 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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Our top choices for Chester apartments

First Floor Studio Apartment in Historic Chestertown

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!