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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chester apartments

Beach

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (27 reviews)
"This is an excellent cute little bungalow close to the beautiful town of Rock Hall. My wife and I enjoyed this very clean and neat place to stay while we enjoyed visiting our family. The host keeps everything very well kept on this property for his visitors! Highly recommend!!"
United States
DEAN
The price is CA $174
CA $413 total
includes taxes & fees
Aug 2 - Aug 3
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is CA $139
CA $222 total
includes taxes & fees
Aug 3 - Aug 4
First Floor Studio Apartment in Historic Chestertown
Coffee/tea maker, fridge, microwave, oven

3. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (5 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is CA $270
CA $664 total
includes taxes & fees
Aug 2 - Aug 3
Pool Loft Suite | Bay Access & Beach Passes
Outdoor pool, a heated pool

4. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (86 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is CA $366
CA $674 total
includes taxes & fees
Aug 2 - Aug 3
Waterfront Oasis of Annapolis Star
Exterior detail

5. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is CA $178
CA $452 total
includes taxes & fees
Aug 11 - Aug 12
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Coffee/tea maker, fridge, microwave, oven

6. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
The price is CA $301
CA $567 total
includes taxes & fees
Aug 11 - Aug 12
18th Cent. Charm in Historic Downtown Annapolis
Exterior

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

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (52 reviews)
"Great stay in Annapolis. The property is gorgeous. Everything you need for a great weekend in Annapolis. "
United States
Jennifer G.
The price is CA $536
CA $699 total
includes taxes & fees
Aug 4 - Aug 5
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Great place but a little too secluded from service if needed."
Janette 2-night trip
Posted 5 hours ago
Historic Inns of Annapolis

Find out more about Chester

Chester Apartments information

Number of reviews
302
Accommodation
70 Apartments
Lowest Price
CA $222
Highest Price
CA $699

Frequently asked questions

What's it like to stay at an apartment in Chester?
You'll find 9 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. First Floor Studio Apartment in Historic Chestertown: Located 18.5 mi/29.8 km away in Chestertown. A private pool, free WiFi, and private patios are included. A fitness center and onsite laundry facilities are on site. Annapolis Spa Retreat, Sauna, Jacuzzi, King Bed Couples Quiet Loft Apt. Getaway: Located in Annapolis, 8.3 mi/13.4 km away. Includes free WiFi, sofa beds, and jetted bathtubs. Onsite laundry facilities 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 Paul Reed Smith Guitars, or get out into nature at a spot like Northern Chesapeake Bay. In the larger area, you'll find Matapeake State Park and Chesapeake Bay Environmental Center.
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.

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