Photo by Patricia Knorr

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Compare 63 Apartments in Chester with updated reviews, rates, and availability.

Spectacular Location: State Circle Apartment
Exterior

Spectacular Location: State Circle Apartment

10.0 out of 10, Exceptional, (11)
"Great location around the corner from our Thanksgiving celebration. "
Spectacular Location: State Circle Apartment
Guest quarters at the inn - 205
Exterior

Guest quarters at the inn - 205

9.4 out of 10, Exceptional, (12)
"The property was not only as described, but better than described, honestly words don’t do it justice. It was exactly what my best friend and I needed to get ready for a friends wedding, and have a comfortable place to stay for the weekend. We loved the classy decor, full length, mirror, soaking tub, and the big thank you for the welcome tray of snacks! The location is perfect, a block from the water, close to bars and restaurants, while being in a quiet neighborhood, and it’s proximity to...
Guest quarters at the inn - 205
Cozy 1st Floor King George one bedroom apartment right across from USNA
Exterior detail

Cozy 1st Floor King George one bedroom apartment right across from USNA

10.0 out of 10, Exceptional, (29)
"We enjoyed our stay at this prime location. First level floor was nicely equipped and had a lovely layout. Loved the historic finishes and charm of the place. Parking lot was a few blocks away near the private college."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Pristine Downtown 1-Bedroom Steps from State House
Steps from the Maryland state house

Pristine Downtown 1-Bedroom Steps from State House

10.0 out of 10, Exceptional, (24)
"We had never visited Annapolis before, but my husband found this on VRBO, and it was everything it advertised. Super central location; steps from the state house; a very short walk to the waterfront; and not a terribly long walk to the Eastport neighborhood. The apartment is small but comfortable, and we enjoyed the nice touches like toiletries, water bottles, snacks and two splits of chilled prosecco in the fridge! Annapolis was a fun town to explore and if we go back, I’d stay here again."
Pristine Downtown 1-Bedroom Steps from State House
First Floor Studio Apartment in Historic Chestertown
Back Yard

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"Very clean, excellent communications,"
The price is AED 360
AED 579 total
includes taxes & fees
15 Jan - 16 Jan
First Floor Studio Apartment in Historic Chestertown
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Jacuzzi Jetted Hot Tub

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

9.6 out of 10, Exceptional, (27)
"Stayed for 3 nights in this clean, quiet loft at the end of a dead end 2-lane road. *Loved the dry sauna! Nice heat! *Loft is accessed through stairs inside the garage. *Kitchenette is small but works for breakfast and basics. *Love the large closet which is sunny and like another bedroom. *Easy communication with owner and easy access. * About 10m by car to Sandy Point State Park * About 15m by car into downtown Annapolis Great base for exploring the Annapolis area."
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Chic Condo w/ Balcony in the Heart of Annapolis!
Living area

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!
Charming Eastport
Living area

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
Waterfront Oasis of Annapolis Star
Waterfront Oasis of Annapolis pool grandeur.

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (72)
"We had an amazing time! Beth and Andy are wonderful hosts! We are looking forward to another stay!"
The price is AED 845
AED 1,620 total
includes taxes & fees
12 Jan - 13 Jan
Waterfront Oasis of Annapolis Star
Anchor's Away in the Heart of Eastport!
Living area

Anchor's Away in the Heart of Eastport!

9.8 out of 10, Exceptional, (37)
"We really enjoyed the location and Eastport. "
Anchor's Away in the Heart of Eastport!
Cozy place close to the city dock
Room

Cozy place close to the city dock

9.8 out of 10, Exceptional, (68)
"Meet my son in Annapolis to attend the Military Bowl. Location was great, near the stadium and also close to downtown. Great place to stay when in Annapolis."
Cozy place close to the city dock
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
Terrace/patio

Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!

10.0 out of 10, Exceptional, (27)
"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!
Bay View Studio Apartment
Property grounds

Bay View Studio Apartment

10.0 out of 10, Exceptional, (40)
"The apartment is much larger than it looks in the photos and the view simply can't be beat. The host is very responsive and helpful. And who doesn't love a hot tub right on the water?! Would absolutely stay here again."
Bay View Studio Apartment
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Exterior

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

10.0 out of 10, Exceptional, (33)
"The Antonelli’s are wonderful hosts. Excellent communication, treated us like guests in their home. We had a three month old infant with us and the hosts had an adorable set up before we got there.But gave us plenty of room to do our own thing. The house is located near a walking path into town. We’ll definitely stay again. "
The price is AED 1,341
AED 1,746 total
includes taxes & fees
31 Jan - 1 Feb
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Tranquility Awaits
Interior

Tranquility Awaits

10.0 out of 10, Exceptional, (14)
"It was an awesome short weekend stay for Army Navy game. Will consider staying here again for sure."
Tranquility Awaits
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Interior

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

10.0 out of 10, Exceptional, (49)
"Wonderful hosts. Beautiful property. And a spacious yet cozy place to stay. We will book again next time we visit. "
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
New Loft w/South River view from treehouse deck!

New Loft w/South River view from treehouse deck!

10.0 out of 10, Exceptional, (20)
"The loft was very clean and modern inside. We enjoyed having our meals on the deck, with a nice calming view of South River. The owner was very flexible (e.g. check-in time) and easy to communicate with. Beware that the kitchenette is small (not much room to cook if that matters to you). I personally would prefer having a firmer mattress, but others may disagree."
New Loft w/South River view from treehouse deck!
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Entrance into kitchen

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

9.8 out of 10, Exceptional, (45)
"Wanted to fish Friday evening and again early Saturday morning. Eliminated the hour and a half drive back and forth. Great location and very nice accommodations"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Private kitchen

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

9.8 out of 10, Exceptional, (37)
"My husband and I stayed here with our two kids for his reunion weekend and it did not disappoint. The apartment is conveniently located right outside of Gate 1 and so close to the all of the downtown offerings. The apartment was super clean and had everything we needed for our stay. We would definitely stay here again!"
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Harbor View Suite
View of harbor 1/2 block from suite.

Harbor View Suite

10.0 out of 10, Exceptional, (19)
"Excellent!"
Harbor View Suite
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!
Ready to Relax and Enjoy the Water and Sunset Views?

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!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Exterior

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Terrace/patio

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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 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 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 Love Point State Park 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 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.