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Our top choices for Chestertown apartments

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is HK$775
HK$1,244 total
includes taxes & fees
19 May - 20 May
First Floor Studio Apartment in Historic Chestertown

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (21 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is HK$533
HK$980 total
includes taxes & fees
7 May - 8 May
Guest Suite for up to 2 in a Victorian on the Chester River

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (6 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is HK$1,248
HK$1,713 total
includes taxes & fees
11 May - 12 May
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

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, (20 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$923
HK$2,221 total
includes taxes & fees
7 May - 8 May
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (205 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
The price is HK$525
HK$1,864 total
includes taxes & fees
25 May - 26 May
Cozy Fells Point Gem / In The Heart of Fells Point

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.6 out of 10, Exceptional, (10 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is HK$1,058
HK$1,765 total
includes taxes & fees
11 May - 12 May
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

High Tide Haven Suite

High Tide Haven Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"The suite was really nice and extremely clean. Comfy, memory foam bed. Excellent shower with great water pressure. The ambiance in the room is serene and beachy making for a wonderful escape. Absolutely loved their screened in porch and view from the back deck. The hosts were very nice, had great communication and served the most delicious bagels. We left our phone charger there and they promptly called us in time to turn around and get it. Highly recommend this location and will stay there...
United States
Joell V.
The price is HK$1,142
HK$1,411 total
includes taxes & fees
11 May - 12 May
High Tide Haven Suite

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is HK$1,762
HK$2,965 total
includes taxes & fees
26 May - 27 May
Waterfront Retreat with Private Dock and Beach

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Great experience"
United States
David P.
18th Cent. Charm in Historic Downtown Annapolis

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$2,115
HK$3,875 total
includes taxes & fees
1 Jun - 2 Jun
Waterfront Oasis of Annapolis Star

Beachcomber Suite

Beachcomber Suite
Kent County
The price is HK$1,142
HK$1,411 total
includes taxes & fees
11 May - 12 May
Beachcomber Suite

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
The price is HK$903
HK$1,586 total
includes taxes & fees
13 May - 14 May
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 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 HK$1,520
HK$3,742 total
includes taxes & fees
7 May - 8 May
Pool Loft Suite | Bay Access & Beach Passes

Home away from home with WiFi and AC in delightful Parkville

Home away from home with WiFi and AC in delightful Parkville
Carney
Home away from home with WiFi and AC in delightful Parkville
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 Chestertown Hotel Reviews

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
289
Accommodation
81 Apartments
Lowest Price
HK$980
Highest Price
HK$3,875

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can search through 6 apartments in Chestertown for your stay.
Why would you choose an apartment over a traditional hotel room?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for couples who want a more local feel, and also for families wanting the conveniences of home.
What's the best apartment I should consider for a stay in Chestertown?
Below are some of the favourite apartments in the area to choose from: First Floor Studio Apartment in Historic Chestertown: Includes a private pool, a washer/dryer and free WiFi . A fitness centre and on-site laundry facilities are on site . Annapolis Spa Retreat, Sauna, Jacuzzi, King Bed Couples Quiet Loft Apt. Getaway: Located 24.5 mi/39.4 km away in Annapolis . Free WiFi, a sofa bed and in-room jetted baths are included . On-site laundry facilities and 1 hot tub are on site . Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace: Located in Havre De Grace , 22.3 mi/35.9 km away. Includes free WiFi and a Smart TV . Access to on-site laundry facilities is available on site . Waterfront Oasis of Annapolis Star: Located in Annapolis , 25.8 mi/41.5 km from Chestertown. Includes a private pool, free WiFi and a fireplace . Access to an outdoor pool is available on site .
How many apartments can I expect to find in Chestertown?
Expedia has 6 apartments to book in Chestertown.
What can I expect from the weather in Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What should I see and do in Chestertown?
Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) away from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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