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

Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chestertown vacation rentals

Property grounds

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (120 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is AED 364
AED 583 total
includes taxes & fees
20 Aug - 21 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, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is AED 826
AED 1,297 total
includes taxes & fees
19 Aug - 20 Aug
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 AED 674
AED 1,037 total
includes taxes & fees
19 Aug - 20 Aug
Secluded Cottage in Middle of Chestertown
Property grounds

4. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is AED 1,178
AED 1,838 total
includes taxes & fees
1 Sep - 2 Sep
Wren Retweet- Country Estate in Center of C’Town
Exterior

5. 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, (26 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 AED 250
AED 459 total
includes taxes & fees
9 Sep - 10 Sep
Guest Suite for up to 2 in a Victorian on the Chester River
Beach

6. 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, (28 reviews)
"What a great apartment and location for a getaway. Had everything we needed and so convenient! I will absolutely stay here again."
United States
Charlotte M.
The price is AED 455
AED 1,086 total
includes taxes & fees
23 Aug - 24 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
1 bedroom, WiFi, bed sheets

7. Turtle Cove Room

Turtle Cove Room
Kent County
The price is AED 516
AED 640 total
includes taxes & fees
17 Aug - 18 Aug
Turtle Cove Room
Beach nearby

8. 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 AED 826
AED 1,390 total
includes taxes & fees
30 Aug - 31 Aug
Waterfront Retreat with Private Dock and Beach
Property grounds

9. 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 AED 586
AED 728 total
includes taxes & fees
24 Aug - 25 Aug
Beachcomber Suite
Exterior detail

10. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AED 661
AED 1,062 total
includes taxes & fees
14 Sep - 15 Sep
BAYSIDE BUNGALOW
Smart TV

11. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is AED 746
AED 1,460 total
includes taxes & fees
24 Aug - 25 Aug
Bayside Cottage steps from Rock Hall Harbor
TV

12. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is AED 288
AED 383 total
includes taxes & fees
27 Aug - 28 Aug
Charming 2-bedroom house in Aberdeen with WiFi and AC
Exterior

13. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is AED 407
AED 1,133 total
includes taxes & fees
18 Aug - 19 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

14. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (53 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is AED 514
AED 1,237 total
includes taxes & fees
25 Aug - 26 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Interior

15. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (98 reviews)
"Awesome place, great location"
United States
Mark M.
The price is AED 191
AED 810 total
includes taxes & fees
19 Aug - 20 Aug
Hidden Fells Point Gem / Private Courtyard Patio
Marina

16. 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, (210 reviews)
"We enjoyed our stay. It was a cute little place and perfect for 3 of us. The area is pretty quiet for the most part. We would definitely stay here again."
United States
Tammy
The price is AED 191
AED 810 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Fells Point Gem / In The Heart of Fells Point
Interior

17. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is AED 1,175
AED 1,421 total
includes taxes & fees
2 Sep - 3 Sep
Family Retreat at Lansdowne Manor
Dining

18. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is AED 918
AED 1,557 total
includes taxes & fees
17 Aug - 18 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Terrace/patio

19. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Chris A.
The price is AED 505
AED 1,317 total
includes taxes & fees
16 Aug - 17 Aug
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Coffee/tea maker, fridge, microwave, oven

20. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (19 reviews)
"Highly recommend this property! Great location. Place is clean and host was very accommodating."
United States
Abi O.
The price is AED 314
AED 865 total
includes taxes & fees
16 Aug - 17 Aug
Cute, Cozy 2-bedroom house near Annapolis with water access
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

8/10 Good
"Todo estuvo muy bien. Gracias"
Bibiana 2-night trip
Posted 4 hours ago
Best Western Plus Hotel & Conference Center

Frequently asked questions

Are there vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Garfield Center for the Arts at the Prince Theater, or you can go with a more secluded option if you're looking for extra privacy while you relax. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

What are some of the best vacation home rentals that Chestertown has to offer?

Cute, Cozy 2-bedroom house near Annapolis with water access: This vacation home rental outside of Chestertown offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Chestertown?

Expedia has 27 vacation rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Northern Chesapeake Bay and Chesapeake Bay, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Chestertown Historic District and Rolphs Wharf Marina are other places to visit while you're in town.

What are vacation rentals like in Chestertown?

Vacation rentals are private properties you can stay in for a couple days or more in Chestertown. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family getaway.