Photo by Patricia Knorr

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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 64 Apartments in Chester with updated reviews, rates, and availability.

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
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
22 Feb - 23 Feb
First Floor Studio Apartment in Historic Chestertown
Bay View Studio Apartment
Property grounds

Bay View Studio Apartment

10.0 out of 10, Exceptional, (42)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Larger of the 2 bedrooms, with a queen bed and sitting area

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

9.6 out of 10, Exceptional, (23)
"Cleaning of the apartment needs to improve "
The price is AED 474
AED 971 total
includes taxes & fees
24 Feb - 25 Feb
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
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
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
Newly restored apartment in the heart of Chestertown
Living area

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (19)
"We fell in love with Chestertown and are so glad we stayed in the heart of downtown at this charming vrbo. Everything was perfect. Will return and recommend "
Newly restored apartment in the heart of Chestertown
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)
"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
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)
"Beth and Andy were the most wonderful hosts who reached out ahead of my stay to make sure I was able to get to their property safely and provided all sorts of helpful amenities once I settled in! Beth was so kind to show me around the property and make sure I had everything I needed. Their Oasis getaway house was exactly that! Beautiful big ceilings, open floor plan, spacious bathroom and a fridge full of various beverages - I felt right at home! Beth and Andy’s house was spick and span and felt...
The price is AED 845
AED 1,620 total
includes taxes & fees
20 Feb - 21 Feb
Waterfront Oasis of Annapolis Star
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)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
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
St Michaels is waiting for you. Join us at CoCo's

St Michaels is waiting for you. Join us at CoCo's

St Michaels is waiting for you. Join us at CoCo's
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 1,451
AED 1,876 total
includes taxes & fees
20 Feb - 21 Feb
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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 were thrilled to be able to return to this great apartment.It is very close to Gate 1 and the sofa bed has a great mattress on it!We hope to continue to return to this rental."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Five Star Charmer! Great Location Downtown & Stadium! Parking too!
Front entrance and porch welcome you.

Five Star Charmer! Great Location Downtown & Stadium! Parking too!

10.0 out of 10, Exceptional, (3)
"Jennifer met us at check in, ensured we had what we needed. Well appointed, assigned parking, coffee, water and snacks for the late night munchies. Had a great time, will return - thanks ! "
Five Star Charmer! Great Location Downtown & Stadium! Parking too!
Chesapeake Bayside Loft
Room

Chesapeake Bayside Loft

8.0 out of 10, Very Good, (12)
"Great property, needs some TLC in areas to really make this be an amazing property...overall it's very clean, soft beds and has a fantastic 2 min walk to the bay for coffee or a beer/ wine...quiet neighborhood, easy access...I think the owner is really miss out on the opportunity to make this home a must rent ..back yard needs some love, lights, fire pit, corn hole etc...overall, great stay, compared to DTA this is excellent "
Chesapeake Bayside Loft
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

Cass-N-Reel Luxury Houseboat
Exterior

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
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)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Front of Carpenter St. Cottage

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (173)
"Great location! Antique furniture in a well maintained beautiful old house. Exactly what we needed."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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's the top apartment for a stay in Chester?
Listed below are some of the favorite apartments in the area: Tranquility Awaits: Located 15 mi/24.1 km away in Annapolis. Free WiFi, private patios, and sofa beds are included. First Floor Studio Apartment in Historic Chestertown: Located in Chestertown, 18.5 mi/29.8 km away. Includes a private pool, laundry facilities, and free WiFi. A fitness center and an outdoor pool are on site. Bay View Studio Apartment: Located 9.9 mi/16 km away in Annapolis. Free WiFi, private patios, and fireplaces are included. A water park 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 Chesapeake Bay Environmental Center. 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.