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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chestertown vacation rentals

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is ￥15,690
￥23,830 total
includes taxes & fees
Nov 9 - Nov 10
First Floor Studio Apartment in Historic Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is ￥35,658
￥53,287 total
includes taxes & fees
Nov 9 - Nov 10
Newly restored apartment in the heart of Chestertown
A garden path leading to a wooden building with a rustic appearance.

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 ￥29,097
￥43,420 total
includes taxes & fees
Nov 9 - Nov 10
Secluded Cottage in Middle of Chestertown
A covered porch with a wooden bench, potted plants, and a decorative railing.

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 ￥48,267
￥72,408 total
includes taxes & fees
Nov 9 - Nov 10
Wren Retweet- Country Estate in Center of C’Town
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

5. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is ￥31,379
￥43,845 total
includes taxes & fees
Nov 14 - Nov 15
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

6. 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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is ￥10,777
￥18,479 total
includes taxes & fees
Nov 9 - Nov 10
Guest Suite for up to 2 in a Victorian on the Chester River
A building with a gabled roof and a circular vent on the roof.

7. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥31,696
￥47,674 total
includes taxes & fees
Nov 9 - Nov 10
BAYSIDE BUNGALOW
A house with a blue front door, two windows, and a small porch.

8. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥21,224
￥44,422 total
includes taxes & fees
Nov 12 - Nov 13
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

9. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is ￥25,674
￥30,336 total
includes taxes & fees
Nov 9 - Nov 10
Turtle Cove Room
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

10. 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 ￥27,576
￥31,570 total
includes taxes & fees
Nov 9 - Nov 10
Beachcomber Suite
A kitchen with wooden cabinets, a dining table, and a refrigerator.

11. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 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 ￥36,435
￥43,635 total
includes taxes & fees
Nov 9 - Nov 10
Family Retreat at Lansdowne Manor
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

12. 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, (13 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 ￥19,810
￥23,014 total
includes taxes & fees
Nov 11 - Nov 12
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A deck with a view of a marina, including boats and docks.

13. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is ￥14,263
￥40,845 total
includes taxes & fees
Nov 12 - Nov 13
Cass-N-Reel Luxury Houseboat
A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is ￥13,312
￥43,838 total
includes taxes & fees
Nov 9 - Nov 10
Charming Coastal/Country Home w/3 Acres & Sauna!
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

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

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is ￥12,409
￥15,170 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2-bedroom house in Aberdeen with WiFi and AC
A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

16. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (103 reviews)
"Awesome place, great location"
United States
Mark M.
The price is ￥9,350
￥34,596 total
includes taxes & fees
Nov 9 - Nov 10
Hidden Fells Point Gem / Private Courtyard Patio
A single-story white house with a front porch, a mailbox, and a number '715' on the door.

17. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage
Bel Air
10.0 out of 10, Exceptional, (7 reviews)
"Pet friendly."
United States
Claudia L.
The price is ￥20,206
￥47,674 total
includes taxes & fees
Nov 9 - Nov 10
Watch Deer from a Farm Cottage
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

18. Bay Sunsets for Two • Rooftop Fire Pit

Bay Sunsets for Two • Rooftop Fire Pit
Pasadena
10.0 out of 10, Exceptional, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
The price is ￥34,967
￥75,996 total
includes taxes & fees
Nov 15 - Nov 16
Bay Sunsets for Two • Rooftop Fire Pit
A kitchen with wooden cabinets, a microwave, a coffee maker, and a dishwasher.

19. 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, (217 reviews)
"It’s a cozy, clean, and cute apartment. We enjoyed our stay very much and the location is wonderful…within walking distance of all the restaurants and attractions you could want."
United States
Carol
The price is ￥9,350
￥34,596 total
includes taxes & fees
Nov 11 - Nov 12
Cozy Fells Point Gem / In The Heart of Fells Point
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

20. B’more Restful. Comfortable Townhome -Easy access to everywhere

B’more Restful. Comfortable Townhome -Easy access to everywhere
Dundalk
10.0 out of 10, Exceptional, (18 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is ￥29,319
￥49,606 total
includes taxes & fees
Nov 9 - Nov 10
B’more Restful. Comfortable Townhome -Easy access to everywhere
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

WoodSpring Suites Baltimore White Marsh - Nottingham

WoodSpring Suites Baltimore White Marsh - Nottingham

8/10 Good
"It was alright"
Jerry 1-night trip
Posted 4 hours ago
WoodSpring Suites Baltimore White Marsh - Nottingham

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

  • View our selection of featured holiday rentals in Chestertown
  • Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

Frequently asked questions

Are there vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Larrabee Arts Center, 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 29 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.