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

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (69)
"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 Condo Near City Dock - Your Perfect Annapolis Getaway!

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

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (23)
"Wonderful spot in the center of historical Chestertown,"
Newly restored apartment in the heart of Chestertown

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (29)
"The cottage was comfortable and welcoming. It was close to restaurants, the Farmers' Market and delightful shops and galleries."
Historic Downtown Garden Oasis with Private Patio

18th Cent. Charm in Historic Downtown Annapolis

9.8 out of 10, Exceptional, (6)
"Property description is accurate, host is quickly responsive."
The price is AED 698
AED 1,352 total
includes taxes & fees
4 May - 5 May
18th Cent. Charm in Historic Downtown Annapolis

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

9.8 out of 10, Exceptional, (38)
"Perfect location for walking around the Annapolis waterfront area! Clean, comfortable and well appointed. Would definitely stay here again!"
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

Guest quarters at the inn - 205

9.4 out of 10, Exceptional, (12)
"Great stay"
Guest quarters at the inn - 205

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

9.6 out of 10, Exceptional, (30)
"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

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (83)
"Quiet neighborhood and the best place to stay."
The price is AED 360
AED 579 total
includes taxes & fees
6 May - 7 May
First Floor Studio Apartment in Historic Chestertown

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

9.8 out of 10, Exceptional, (49)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

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

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

10.0 out of 10, Exceptional, (34)
"We stayed for the Annapolis 10-miler and it was a great location for runners and spectators! "
The price is AED 1,653
AED 2,127 total
includes taxes & fees
26 May - 27 May
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Apartment in Downtown – Walk to Everything!

9.0 out of 10, Wonderful, (2)
"We loved the property and the location (can’t be beat!). We walked to shops, restaurants, and bars all over town. It also had convenient parking. The apartment was clean and had everything we needed for a short stay. "
Apartment in Downtown – Walk to Everything!

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

9.6 out of 10, Exceptional, (23)
"Loved this place - well appointed, convenient and great hosts ! Definitely will rent again!"
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

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

10.0 out of 10, Exceptional, (49)
"Everything about our stay was outstanding. Beautiful, just like the pictures show. We highly recommend this property."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

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

9.8 out of 10, Exceptional, (12)
"We had a great stay at the Guest Quarters. The place is very clean and has recently been updated. We lucked out and hit Fist Friday in North Beach and enjoyed live music and great food just a block away."
Guest Quarters at the Inn - 101

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

9.4 out of 10, Exceptional, (3)
"We thoroughly enjoyed this section of Eastport. The views of the marina were beautiful and we found a couple new restaurants nearby! Excellent communication with the owners."
Charming Eastport

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"We had an amazing time! Beth and Andy are wonderful hosts! We are looking forward to another stay!"
The price is AED 845
AED 1,616 total
includes taxes & fees
26 May - 27 May
Waterfront Oasis of Annapolis Star
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

10.0 out of 10, Exceptional, (14)
"Loved the location, the property, and amenities. Would definitely stay again!"
Waterfront Sunset Bayview: sleeps 6

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

10.0 out of 10, Exceptional, (214)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
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 12 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 Condo Near City Dock - Your Perfect Annapolis Getaway!: Situated in Annapolis, 13.1 mi/21 km from the heart of Chester. Includes free WiFi and private balconies. Osprey’s Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located 14.8 mi/23.9 km away in Pasadena. Free WiFi and Smart TVs are included. Access to an outdoor pool is available on site. COZY DOWNTOWN APARTMENT-Naval Academy Vicinity: Located in Annapolis, 10.6 mi/17 km away. Includes free WiFi, sofa beds, and Smart TVs. Access to onsite laundry facilities is available on site. Bay View Studio Apartment: Located in Annapolis, 9.9 mi/16 km from Chester. Includes free WiFi, private patios, and fireplaces. Onsite laundry facilities 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 Matapeake State Park and Love Point State Park.
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.