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10 Oct - 12 Oct
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31 Oct - 2 Nov
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Apartments in Chester

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, (66)
"Perfect for the wedding I attended and great place to host a short getaway with my brother and his kids."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Exterior

Modern Flat in the Heart of St. Michaels – Walk Everywhere

10.0 out of 10, Exceptional, (49)
"We had a wonderful weekend get away. Location is perfect to take advantage of the main restaurants and shopping in St. Michael’s."
Modern Flat in the Heart of St. Michaels – Walk Everywhere
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, (15)
"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 AED 436
AED 1,061 total
includes taxes & fees
3 Oct - 4 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (3)
"Loved our stay in this cute little home that is convenient to everything!"
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, (42)
"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 AED 1,405
AED 1,819 total
includes taxes & fees
5 Oct - 6 Oct
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (101)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is AED 364
AED 583 total
includes taxes & fees
6 Oct - 7 Oct
First Floor Studio Apartment in Historic 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, (31)
"Perfect place to go and relax and get away from the world. "
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, (53)
"This was our 2nd time staying here and we absolutely love it! Already booked us for another trip here! The view, property, and experience was amazing! "
Bay View Studio Apartment
Harbor View Suite Talbot County License Number STRN-25-58
Fridge, microwave, coffee/tea maker, toaster

Harbor View Suite Talbot County License Number STRN-25-58

10.0 out of 10, Exceptional, (31)
"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "
Harbor View Suite Talbot County License Number STRN-25-58
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.0 out of 10, Wonderful, (12)
"Property description is accurate, host is quickly responsive."
The price is AED 698
AED 1,357 total
includes taxes & fees
31 Oct - 1 Nov
18th Cent. Charm in Historic Downtown Annapolis
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, (81)
"Owner ensures all is clean and prepared and offers access to amenities needed"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
New Loft w/South River view from treehouse deck!
Terrace/patio

New Loft w/South River view from treehouse deck!

10.0 out of 10, Exceptional, (22)
"This is a great place to stay for a get-away time! The it's small but well laid out and the high ceilings give it a much larger feel. The place seems newly done-over and it's spotless."
New Loft w/South River view from treehouse deck!
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (79)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is AED 992
AED 1,817 total
includes taxes & fees
13 Oct - 14 Oct
Waterfront Oasis of Annapolis Star
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, (25)
"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
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (39)
"Loved the location and ease of access to downtown. Property was super clean, organized and beautifully appointed with original art too. "
Historic Downtown Garden Oasis with Private Patio
Chesapeake Bayside Loft
Property grounds

Chesapeake Bayside Loft

8.0 out of 10, Very Good, (12)
"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."
Chesapeake Bayside Loft
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

9.4 out of 10, Exceptional, (6)
"This property is near many of the downtown places you want to visit, and all are within walking distance. "
Knot's Landing, spacious Apt. downtown Rock Hall
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, (41)
"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 - 101
Iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 101

9.6 out of 10, Exceptional, (16)
"Very nice place. Will stay there again. "
Guest Quarters at the Inn - 101
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great"
BRIAN 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown

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 top apartments in the area: Riverfront Retreat 7mil from MD Renaissance Fest!: Situated in Riva, 16 mi/25.7 km from the heart of Chester. 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. 18th Cent. Charm in Historic Downtown Annapolis: Located 10.7 mi/17.3 km away in Annapolis. Free WiFi, private patios, and fireplaces are included. Onsite laundry facilities and a game room 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.