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19 Sep - 21 Sep
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3 Oct - 5 Oct
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28 Nov - 30 Nov

Apartments in Chester

Our top choices for Chester apartments

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
Iron/ironing board, WiFi, bed sheets

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

10.0 out of 10, Exceptional, (22)
"Stayed for the weekend- parked the car and could walk to everything- perfect. Host was super responsive and the place was super clean!"
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Marina

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

9.8 out of 10, Exceptional, (63)
"Awesome place!"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Harbor View Suite
Fridge, microwave, coffee/tea maker, toaster

Harbor View Suite

10.0 out of 10, Exceptional, (27)
"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "
Harbor View Suite
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (99)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is SAR 338
SAR 559 total
includes taxes & fees
3 Sep - 4 Sep
First Floor Studio Apartment in Historic Chestertown
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (78)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is SAR 1,013
SAR 1,857 total
includes taxes & fees
3 Sep - 4 Sep
Waterfront Oasis of Annapolis Star
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (38)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Guest Quarters at the Inn - 103
Iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 103

9.6 out of 10, Exceptional, (24)
"Very nice room with good accessibility for someone with limited mobility. The room description in Expedia was completely accurate, and we loved the accessibility features. The location is very close to good restaurants that also have good accessibility."
Guest Quarters at the Inn - 103
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (13)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is SAR 442
SAR 1,068 total
includes taxes & fees
3 Sep - 4 Sep
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Fridge, microwave, oven, stovetop

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (77)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard
Terrace/patio

Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard

2.5 star property
10.0 out of 10, Exceptional, (2)
"This tastefully decorated apartment is in a perfect location to enjoy all that is Annapolis. "
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and 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, (38)
"Everything was really lovely- clean, comfortable, beautifully decorated rooms. Loved the little things like all the fresh flowers in rooms - would definitely recommend!"
The price is SAR 1,435
SAR 1,859 total
includes taxes & fees
11 Sep - 12 Sep
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Marina

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

10.0 out of 10, Exceptional, (54)
"Wonderful place!"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Dean Street's Lower Deck House!
Interior

Dean Street's Lower Deck House!

The price is SAR 769
SAR 1,681 total
includes taxes & fees
10 Sep - 11 Sep
Dean Street's Lower Deck House!
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, (30)
"Our family loved having this as a short-term rental to visit our midshipman and give him the ability to relax off campus. The owners were communicative and amazing to work with for the entire 3 months! Would absolutely stay here again."
Pristine Downtown 1-Bedroom Steps from State House
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, (31)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Tranquility Awaits
Property grounds

Tranquility Awaits

10.0 out of 10, Exceptional, (20)
"It was an awesome short weekend stay for Army Navy game. Will consider staying here again for sure."
Tranquility Awaits
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Fridge, microwave, oven, stovetop

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

9.8 out of 10, Exceptional, (40)
"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
Downtown furnished apartment - walking distance to restaurants
Interior

Downtown furnished apartment - walking distance to restaurants

10.0 out of 10, Exceptional, (6)
"The home is beautiful and exceptionally maintained! The management of the property is fantastic and they are lovely to work with. They thoughtfully had fresh fruit and some light & healthy munchies in the kitchen when I checked in. The history of the home is also quite interesting! I look forward to a return stay."
Downtown furnished apartment - walking distance to restaurants
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, (31)
"The location is excellent. We rarely needed a car. The heating and AC worked great. We had several issues with the lights and the full size bed’s mattress sagged in the middle- so one of us slept on the sofa.We sent some suggestions to Julie for enhancing the property."
Cozy 1st Floor King George one bedroom apartment right across from USNA
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, (14)
"Loved the place! Plenty of room. Hubby and I snuggled in the comfy robes most of the time! Only thing I’d recommend is WiFi for tvs so visitors can log on to their personal streaming apps. "
Guest quarters at the inn - 204
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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Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"There were two great guys at the bar; they were fun, friendly, and good company. The staff at the front desk was very knowledgeable and friendly."
Michele 3-night trip
Posted 3 days ago
Graduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Adorable hotel in Annapolis. Walking distance to everything. I liked everything about it except for the pillows on the beds. They were so firm that I had trouble sleeping. But the staff was very friendly and the vibe of the place was quaint. I would definitely stay here again but would bring my own pillow!"
Karen Glou 2-night trip
Posted 4 days ago
Historic Inns of Annapolis

Frequently asked questions

What's it like to stay at an apartment in Chester?
You'll find 16 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: Waterfront Oasis of Annapolis Star: Located in Annapolis, 10 mi/16 km from the heart of Chester. Includes a private pool, free WiFi, and fireplaces. Access to an outdoor pool is available on site. Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops: Located 13.7 mi/22.1 km away in St. Michaels. Amenities include private balconies. Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located in Pasadena, 14.8 mi/23.9 km away. Includes free WiFi and Smart TVs. Access to an outdoor pool is available on site. Harbor View Suite: Located 13.9 mi/22.3 km away in St. Michaels. Amenities include free WiFi. Access to onsite laundry facilities is available on site. First Floor Studio Apartment in Historic Chestertown: Located in Chestertown, 18.5 mi/29.8 km from Chester. Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities 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.