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Apartments in Chester

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (51)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (70)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

The heart of St Michaels awaits.

10.0 out of 10, Exceptional, (37)
"This flat/apartment is perfect, exactly as described. Located in the heart of town, convenient to all restaurants and shops. The flat beautifully updated and appointed, and spotlessly clean. We were extremely comfortable and will definitely return."
The heart of St Michaels awaits.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (85)
"Quiet neighborhood and the best place to stay."
The price is AED 364
AED 583 total
includes taxes & fees
12 Jun - 13 Jun
First Floor Studio Apartment in Historic Chestertown

18th Cent. Charm in Historic Downtown Annapolis

9.6 out of 10, Exceptional, (7)
"Property description is accurate, host is quickly responsive."
18th Cent. Charm in Historic Downtown Annapolis

Guest Quarters at the Inn - 102

9.8 out of 10, Exceptional, (18)
"Close to many restaurants and activities "
Guest Quarters at the Inn - 102

Harbor View Suite

10.0 out of 10, Exceptional, (22)
"Excellent!"
Harbor View Suite

Pristine Downtown 1-Bedroom Steps from State House

10.0 out of 10, Exceptional, (25)
"Perfect location to downtown Annapolis; lovely, clean, and comfortable space. Owners make the stay enjoyable and easyy to navigate. "
Pristine Downtown 1-Bedroom Steps from State House

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (30)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Apartment in Downtown – Walk to Everything!

9.0 out of 10, Wonderful, (2)
"We loved the property and the location (can’t be beat!). We walked to shops, restaurants, and bars all over town. It also had convenient parking. The apartment was clean and had everything we needed for a short stay. "
Apartment in Downtown – Walk to Everything!

Tranquility Awaits

10.0 out of 10, Exceptional, (18)
"It was an awesome short weekend stay for Army Navy game. Will consider staying here again for sure."
Tranquility Awaits

Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!

10.0 out of 10, Exceptional, (31)
"Well decorated and comfortable stay. Very quiet and great place to sit and enjoy the sunrise/sunset."
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (33)
"Very quiet area and well kept properly. The unit very clean and well kept, the Internet is pretty good with good reception, what I like the most was that it was so close to everything with restaurants and museums close by the park that hosted most of the events was close enough for a short walk and all sort of streets that held events were close by, this is a great location of the memorial day events and I have to say the honest were great and very helpful."
Historic Downtown Garden Oasis with Private Patio

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

10.0 out of 10, Exceptional, (35)
"We stayed for the Annapolis 10-miler and it was a great location for runners and spectators! "
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Walk everywhere from 1st floor dog-friendly apartment with parking and backyard

2.5 star property
10.0 out of 10, Exceptional, (2)
"This tastefully decorated apartment is in a perfect location to enjoy all that is Annapolis. "
Walk everywhere from 1st floor dog-friendly apartment with parking and backyard

Chic Condo w/ Balcony in the Heart of Annapolis!

3.0 star property
8.0 out of 10, Very Good, (1)
Chic Condo w/ Balcony in the Heart of Annapolis!

Guest quarters at the inn - 205

9.4 out of 10, Exceptional, (12)
"Great stay"
Guest quarters at the inn - 205

Charming Eastport

9.4 out of 10, Exceptional, (3)
"We thoroughly enjoyed this section of Eastport. The views of the marina were beautiful and we found a couple new restaurants nearby! Excellent communication with the owners."
Charming Eastport

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is AED 893
AED 1,692 total
includes taxes & fees
12 Jun - 13 Jun
Waterfront Oasis of Annapolis Star

Charming apt in the heart of Eastport & Annapolis

Charming apt in the heart of Eastport & Annapolis
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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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: 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. An outdoor pool and a water park are 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 and private balconies. The heart of St Michaels awaits.: 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. Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!: Located in Annapolis, 9.6 mi/15.4 km from Chester. Includes free WiFi, private patios, and Smart TVs. A fitness center and onsite laundry facilities 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 Chesapeake Bay Environmental Center. 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.