An aerial view of a town with a river, buildings, and surrounding greenery.

Search Apartments in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chestertown apartments

Property grounds

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is £121
includes taxes & fees
10 Aug - 11 Aug
First Floor Studio Apartment in Historic Chestertown
Smart TV, books

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (31 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is £285
includes taxes & fees
31 Aug - 1 Sept
Newly restored apartment in the heart of Chestertown
TV, fireplace

3. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is £212
includes taxes & fees
19 Aug - 20 Aug
Secluded Cottage in Middle of Chestertown
Exterior

4. 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, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is £96
includes taxes & fees
10 Aug - 11 Aug
Guest Suite for up to 2 in a Victorian on the Chester River
Beach

5. 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)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is £215
includes taxes & fees
6 Aug - 7 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach nearby

6. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is £279
includes taxes & fees
30 Aug - 31 Aug
Waterfront Retreat with Private Dock and Beach
Property grounds

7. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is £148
includes taxes & fees
31 Aug - 1 Sept
Beachcomber Suite
1 bedroom, WiFi, bed sheets

8. Turtle Cove Room

Turtle Cove Room
Kent County
The price is £133
includes taxes & fees
10 Aug - 11 Aug
Turtle Cove Room
Terrace/patio

9. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is £185
includes taxes & fees
1 Sept - 2 Sept
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Smart TV

10. 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, (12 reviews)
"Very cool place, walking distance to everything."
United States
Brett S.
The price is £203
includes taxes & fees
18 Aug - 19 Aug
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Coffee/tea maker, fridge, microwave, oven

11. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 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 £377
includes taxes & fees
9 Aug - 10 Aug
Pool Loft Suite | Bay Access & Beach Passes
Marina

12. 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, (208 reviews)
"Appreciated the privacy."
United States
Marie
The price is £167
includes taxes & fees
12 Aug - 13 Aug
Cozy Fells Point Gem / In The Heart of Fells Point
Outdoor pool, a heated pool

13. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is £347
includes taxes & fees
1 Sept - 2 Sept
Waterfront Oasis of Annapolis Star
1 bedroom, in-room safe, desk, iron/ironing board

14. 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 £134
includes taxes & fees
19 Aug - 20 Aug
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Coffee/tea maker, fridge, microwave, oven

15. 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 £298
includes taxes & fees
17 Aug - 18 Aug
18th Cent. Charm in Historic Downtown Annapolis
Living area

16. Home away from home with WiFi and AC in delightful Parkville

Home away from home with WiFi and AC in delightful Parkville
Carney
The price is £170
includes taxes & fees
1 Sept - 2 Sept
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"clean, extremely helpful staff, exactly as described"
Sasha 3-night trip
Posted 4 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
522
Accommodation
79 Apartments
Lowest Price
£96
Highest Price
£347

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can search through 5 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?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, free WiFi and a patio . A fitness centre and on-site laundry facilities are on site . Historic Downtown Garden Oasis with Private Patio: Free WiFi, a balcony and a dining area are included .
How many apartments can I expect to find in Chestertown?
Expedia has 5 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.