Photo by Patricia Knorr

Search Apartments in Chester

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Compare 62 Apartments in Chester with updated reviews, rates, and availability.

Cozy place close to the city dock
10.0 out of 10, Exceptional, (54)
"It is a very nice home for our short stay. We came for a graduation ceremony and the convenience and location were perfect. We will stay here in the future."
Cozy place close to the city dock
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
9.8 out of 10, Exceptional, (21)
"Especially nice for summer visits."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Charming Downtown 3rd Floor 1 Bedroom Apt
10.0 out of 10, Exceptional, (12)
"Nice place, nice owners, great location."
The price is SAR 656
SAR 1,137 total
includes taxes & fees
25 Jum. II - 26 Jum. II
Charming Downtown 3rd Floor 1 Bedroom Apt
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Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (19)
"Ingrid was a fabulous host. We already plan to return. Beautiful property inside and out. Thank you beyond words, Ingrid!"
The price is SAR 1,482
SAR 2,176 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Pristine Downtown 1-Bedroom Steps from State House
10.0 out of 10, Exceptional, (17)
"The pictures don't do it Justice. Fine details, spacious, comfortable, most accommodating VRBO EVER for us. Great location. Owners are so nice, informative and take pride in their property. Very serene, comfortable and cozy. Hope to stay there every time we are visiting Annapolis. Close to everything. Able to walk to everything Annapolis had to offer."
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, (15)
"Tim and his family are wonderful hosts and extremely responsive if there is a problem. My stay of three weeks is not the norm and enjoyable.The king size bed and wonderful linens and blankets provided an awesome night's sleep.The HUGE TV is beyond belief. An abundant supply of high quality towels and bath/shower products were greatly appreciated.The sauna...where do I begin??? Walking around the neighborhood is safe with plenty of docks and water views. Grocery stores and other retail and...
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Guest Quarters at the Inn - 103
9.8 out of 10, Exceptional, (21)
"Quaint, quiet, clean, and close to restaurants and our wedding venue we attended. Would return and recommend! Thank you!"
Guest Quarters at the Inn - 103
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (60)
"Most excellent space for a quiet retreat away from the city! The property and hosts were welcoming and super attentive. We will definitely be coming back!"
The price is SAR 1,031
SAR 1,881 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Waterfront Oasis of Annapolis Star
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, (9)
"Great place, super neighborhood!"
Indulge or be still near Naval Academy/ Annapolis
Quaint cottage with serene water view!
10.0 out of 10, Exceptional, (24)
"Studio with plenty of space for one. Nicely decorated, ample supplies. Petite front porch to watch the river from. Pam was friendly and welcoming, and I will certainly happily stay here again!"
Quaint cottage with serene water view!
Tranquility Awaits
10.0 out of 10, Exceptional, (8)
"Everything was great! We will be back!"
Tranquility Awaits
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (17)
"Our home is over 100 years old so staying here was like being home. Great location to the main st shopping and food."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (34)
"The host was so friendly and easy to communicate with. The accommodations were very clean and organized. The location was perfect; cute shops only miles away, beach access, beautiful views, and short drive to downtown Annapolis!"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is SAR 413
SAR 616 total
includes taxes & fees
11 Jum. II - 12 Jum. II
First Floor Studio Apartment in Historic Chestertown
Coastal Kent Narrows Home on Bay
9.2 out of 10, Wonderful, (5)
"Very nice place to stay, right on the bay"
The price is SAR 825
SAR 1,658 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Coastal Kent Narrows Home on Bay
Serenity on the Water
10.0 out of 10, Exceptional, (2)
"My partner and I rented the beautiful "serenity on the water" to celebrate our anniversary over the Memorial Day holiday. We found the rental in immaculate condition. It is very large, and well appointed, even including a ping pong table. The place is beautifully decorated and located very close to all the amenities you could ask for. It was an awesome stay, and we were so happy with the recommendations for activities. You can even WALK to the near by vineyard."
Serenity on the Water
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (14)
"Stephen and Marianna were great hosts. The property was very clean and functional with beautiful artwork throughout the property. Great outdoor patio for relaxing plus excellent location for access to downtown Chestertown. We will be staying here again on our next visit."
Historic Downtown Garden Oasis with Private Patio
Newly restored apartment in the heart of Chestertown
9.8 out of 10, Exceptional, (15)
"This was a great apartment in an excellent location. We visited Washington college and attended a sailing regatta. The Evergrain Bakery across the street was amazing. Shops and restaurants all within walking distance! Apartment was well stocked, nicely decorated and clean! Also very close to the Hodson boathouse. It was a 3 minute drive!"
Newly restored apartment in the heart of Chestertown
Guest Quarters at the Inn - 101
9.6 out of 10, Exceptional, (10)
"The location of this room is perfect for your stay in North Beach! Walking distance to the beach/boardwalk, several stores, restaurants, coffee shop, and beer garden. The included beach pass was so helpful! The check-in, check-out process was so easy. Our only complaint was the noise from the guests in the room above us and you could hear the live music from the nearby beer garden until 10:30 pm - however, the positives FAR outweighed the noise."
Guest Quarters at the Inn - 101
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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.

Other property types in Chester

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (6)
"My sisters and I (5 total) visited in early November. Kent Island Time was a perfect fit. We were impressed by the cleanliness, spacious rooms, and well-equipped common areas. The best feature was the waterfront location. Even in November, we were able to sit outside on the patio and enjoy a glass of wine as we watched the amazing sunset. We all agreed we would absolutely stay again in the future."
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (4)
"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"
The price is SAR 2,359
SAR 5,392 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
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.

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 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 Matapeake State Park. In the larger area, you’ll find Chesapeake Bay Environmental Center and Sandy Point Beach.
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.

Recent reviews of Chester hotels
Expedia verified reviews