Photo by Patricia Knorr

Apartments in Chester

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Featured Apartments in Chester

Chesapeake Bayside Loft
Beach
Chesapeake Bayside Loft
8.6 out of 10, Excellent, (9)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
Chesapeake Bayside Loft
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Interior
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
9.6 out of 10, Exceptional, (23)
"Tucked away in the back of the neighborhood, its quiet and private. Nice spa amenities, and after a bunch of traveling it was nice to stay somewhere with a washer and dryer"
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Bay View Studio Apartment
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (36)
"We are repeat visitors to this property because of the location, the owner, the comfort and the amazing view here. The owner is so nice and has excellent communication. The property has everything you need and more from the kitchen supplies to the water toys including a hot tub! We will be back again! "
Bay View Studio Apartment
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (71)
"Just what we needed for the night! Thank you "
The price is AU$222
includes taxes & fees
23 Oct - 24 Oct
First Floor Studio Apartment in Historic Chestertown
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Fridge, microwave, oven, stovetop
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
9.8 out of 10, Exceptional, (39)
"The apartment was very clean, well stocked, tastefully decorated and comfortable. Sheets, towels, TP, kcups sugar, cream paper towels, hand soap dish soap, & ice pall conveniently provided. My mom and I really enjoyed being on the river front, such a lovely view and it’s a perfect location for visiting our Family in Pasadena. We lounged in the Adk chairs & also played horse shoes/bean bag toss. One thing I would suggest is a table lamp in the LR- I used one from the bedroom when I slept on the...
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (69)
"Beautiful property and our quarters were perfectly comfortable for us."
The price is AU$706
includes taxes & fees
3 Oct - 4 Oct
Waterfront Oasis of Annapolis Star
Cozy 1st Floor King George one bedroom apartment right across from USNA
Fridge, microwave, oven, stovetop
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (26)
"Always a great stay. Close to everything, from shops to restaurants and bars. Can’t wait to go back "
Cozy 1st Floor King George one bedroom apartment right across from USNA
Walk everywhere from this 1st floor dog-friendly apartment with parking, private backyard
Property grounds
Walk everywhere from this 1st floor dog-friendly apartment with parking, private backyard
2.5 star property
Walk everywhere from this 1st floor dog-friendly apartment with parking, private backyard
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (24)
"We booked the carriage house for a brief visit to USNA and could not have asked for a better experience! It was within walking distance of the stadium, a longer walking distance (but short driving distance) to the campus, and in a beautiful little neighborhood. We immediately felt at home and at ease with the property managers. We will definitely look to stay here again."
The price is AU$779
includes taxes & fees
25 Oct - 26 Oct
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Tranquility Awaits
Property grounds
Tranquility Awaits
10.0 out of 10, Exceptional, (11)
"Very convenient to Naval Academy and downtown Annapolis. "
Tranquility Awaits
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Pool
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (47)
"My partner and friends travelled to the area for a local festival and wanted a place to stay where we could all have our own rooms. This Vrbo was perfect for us! The place was super spacious, clean, and great for groups. It is very easy to find and check in is a breeze. There’s a darling breakfast spot just a couple minutes away and everything you could want is close by. We’re already talking about coming back again same time next year!"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Fridge, microwave, oven, stovetop
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
10.0 out of 10, Exceptional, (33)
"Outstanding property right by Gate 1 and DTA. We will book again. "
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Coastal Kent Narrows Home on Bay
Fridge, microwave, oven, stovetop
Coastal Kent Narrows Home on Bay
9.4 out of 10, Exceptional, (9)
"This place is a fantastic place to stay. Brandon was very responsive to any emails or questions sent to him. The place is very clean and tidy, very easy to get in and out of. We would definitely recommend this property to anybody. We will certainly be booking it again. "
Coastal Kent Narrows Home on Bay
Historic Downtown Garden Oasis with Private Patio
Property grounds
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (22)
"We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!"
Historic Downtown Garden Oasis with Private Patio
Guest Quarters at the Inn - 101
Iron/ironing board, free WiFi, bed sheets
Guest Quarters at the Inn - 101
9.8 out of 10, Exceptional, (12)
"This property is right in the Main Street running through Chesapeake Beach and North Beach. It's close to the beaches, restaurants, and close to all of the local attractions. The room itself was large, clean, and comfortable, and the building was both quiet, secure, and well kept. We'll definitely be back!"
Guest Quarters at the Inn - 101
Guest quarters at the inn - 204
1 bedroom, iron/ironing board, free WiFi, bed sheets
Guest quarters at the inn - 204
9.8 out of 10, Exceptional, (12)
"Overall great place. Couple of recommendations to make it even better. First, recommend a few more trash cans in the place. Only had one in the kitchen and bathroom. Also great to have them with trash liners. Same for tissue boxes. The one in the bathroom was empty. Would have appreciated more than one soap bar too.great Recommend checking that all the appliances work. The TV in the living room would not turn on.. Also te cabinet under the sink was loose. Again all minor things. F"
Guest quarters at the inn - 204
Charming Eastport
Beach
Charming Eastport
9.4 out of 10, Exceptional, (3)
"This was a charming apartment nestled in the quiet side of annapolis. Everything was within walking distance. The apartment had everything you needed if you wanted to cook. Just bring your food!"
Charming Eastport
Stay in the heart of Historic Annapolis 2 blocks from Main Street
Property grounds
Stay in the heart of Historic Annapolis 2 blocks from Main Street
2.0 star property
10.0 out of 10, Exceptional, (2)
"nice location"
Stay in the heart of Historic Annapolis 2 blocks from Main Street
Steps to marinas from 2nd floor apartment with parking, private balcony
Property grounds
Steps to marinas from 2nd floor apartment with parking, private balcony
2.0 star property
10.0 out of 10, Exceptional, (1)
Steps to marinas from 2nd floor apartment with parking, private balcony
Cozy place close to the city dock
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (62)
"Property host demonstrated amazing patience as arrival was delayed due to flight and ultimately canceled due to illness. I will definitely book again next time in town. "
Cozy place close to the city dock
Don't see what you're looking for?
See all available properties in Chester
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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Other property types in Chester

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Interior
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (8)
"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
View from property
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Property grounds
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (76)
"Lovely house and location! Pat and Ken were rapid and personable with every interaction."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
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 lodging options in Chester. Though there aren’t many apartments, we can help you find accommodation that is similar. When you search for a place to stay on Expedia, you can filter by amenities such as a kitchen— one of the conveniences often found in an apartment. You can also search for similar properties such as holiday homes, condos or cabins.
How do you know if an apartment is a good option for you?
Often offering more space than a traditional hotel room, an apartment comes with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for solo travellers who want to stay in a quieter area.
What's a favourite apartment for my stay in Chester?
Here are some of the more popular apartments in the area: Bay View Studio Apartment: Located in Annapolis , 9.9 mi/16 km from the heart of Chester. Includes free WiFi, a patio and a fireplace . Access to a water park is available on site . Waterfront Oasis of Annapolis Star: Located 10 mi/16 km away in Annapolis . A private pool, free WiFi and a fireplace are included . An outdoor pool and a water park are on site . Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown: Located 10.8 mi/17.3 km away in Annapolis . Free WiFi, a patio and a Smart TV are included . Access to a water park is available on site . Anchor’s Away in the Heart of Eastport!: It’s located in Annapolis , 10.1 mi/16.3 km from Chester. Includes free WiFi and a Smart TV .
What will the weather be like when I travel to Chester?
Although 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.
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 wider area, you’ll find Chesapeake Bay Environmental Center and Eastern Neck National Wildlife Refuge.
What's the best way to get to and around Chester?
Knowing a bit about the transportation options can save you time 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. Otherwise, you can search for flights to Baltimore Washington International Airport (BWI), which is 24.8 mi (39.9 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.