Photo by Patricia Knorr

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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 77 Apartments in Chester with updated reviews, rates, and availability.

Cozy place close to the city dock
Beach

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
Newly restored apartment in the heart of Chestertown
Fridge, microwave, oven, stovetop

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (20)
"Nice downtown location."
Newly restored apartment in the heart of Chestertown
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, (29)
"We really enjoyed our stay! Very peaceful and relaxing, the bed felt like lying on a cloud! It was like having a spa in your room we loved the sauna especially. We look forward to booking again. "
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, (42)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment
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, (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
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (25)
"This is the second time I stayed here and will be back. I was able to work from here and enjoyed breakfast and lunch on the covered porch with a sweet companion (the owners' totally chill dog). Walking distance to everything. Check out the new wetland preserve at the end of the street. "
Historic Downtown Garden Oasis with Private Patio
Guest quarters at the inn - 205
TV

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
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, (45)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is SAR 368
SAR 592 total
includes taxes & fees
26 Mar - 27 Mar
First Floor Studio Apartment in Historic Chestertown
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Property grounds

HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!

9.8 out of 10, Exceptional, (16)
"What a beautiful and welcoming property! Tons of wildlife activity to view and great water views. Amenities were great. Really appreciate everything! Lovely host!"
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
St Michaels is waiting for you. Join us at CoCo's
Living area

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

St Michaels is waiting for you. Join us at CoCo's
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Fridge, microwave, oven, stovetop

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 SAR 656
SAR 1,210 total
includes taxes & fees
23 Mar - 24 Mar
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Pristine Downtown 1-Bedroom Steps from State House
Fridge, microwave, oven, stovetop

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
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
Chic Condo w/ Balcony in the Heart of Annapolis!
Interior

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
Aerial view

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
Outdoor pool, a heated pool

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 SAR 863
SAR 1,663 total
includes taxes & fees
6 Apr - 7 Apr
Waterfront Oasis of Annapolis Star
Tranquility Awaits
Property grounds

Tranquility Awaits

10.0 out of 10, Exceptional, (15)
"We absolutely loved our stay here. Everything was perfect from the communication with the owners to the cleanliness of the apartment. We could not have found a better place to stay for our trip. Perfect for kids and teens. "
Tranquility Awaits
Chesapeake Bayside Loft
Beach

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
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.8 out of 10, Exceptional, (6)
"Had a great stay, super close to everything. Jennifer was very communicative!"
The price is SAR 713
SAR 1,334 total
includes taxes & fees
13 Apr - 14 Apr
18th Cent. Charm in Historic Downtown 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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Other property types in Chester

Waterfront Sunset Bayview: sleeps 6
Beach

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (12)
"Great house, great owner, family had a blast! Thank you!"
Waterfront Sunset Bayview: sleeps 6
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Beach

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

10.0 out of 10, Exceptional, (118)
"comfortable and very cozy. Wonderful crabbing and sunsets."
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (209)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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: Cozy place close to the city dock: Located 13.1 mi/21 km away in Annapolis. Free WiFi and private balconies are included. Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis: Located in Annapolis, 8.3 mi/13.4 km away. Includes free WiFi, sofa beds, and jetted bathtubs. A hot tub and a sauna are 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.
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 Eastern Neck National Wildlife Refuge 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.