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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (129 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
The price is CA $141
CA $225 total
includes taxes & fees
Oct 6 - Oct 7
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, (33 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is CA $319
CA $501 total
includes taxes & fees
Oct 5 - Oct 6
Newly restored apartment in the heart of Chestertown
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

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 CA $261
CA $390 total
includes taxes & fees
Oct 11 - Oct 12
Secluded Cottage in Middle of Chestertown
A deck with outdoor furniture, a potted plant, and a house in the background.

4. 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 CA $312
CA $442 total
includes taxes & fees
Oct 7 - Oct 8
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A hallway with wooden flooring, a door on the right, and a window at the end.

5. 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 CA $438
CA $691 total
includes taxes & fees
Oct 6 - Oct 7
Wren Retweet- Country Estate in Center of C’Town
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $176
CA $420 total
includes taxes & fees
Oct 7 - Oct 8
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $284
CA $446 total
includes taxes & fees
Oct 4 - Oct 5
BAYSIDE BUNGALOW
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

8. 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, (28 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 CA $97
CA $178 total
includes taxes & fees
Oct 6 - Oct 7
Guest Suite for up to 2 in a Victorian on the Chester River
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

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

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
9.8 out of 10, Exceptional, (10 reviews)
"The host was incredibly friendly and communicative. The place was a lot bigger than I expected, and it was beautiful to sit out by the fire pit and look at the river nearby. And, she left us snacks and smores for the stay! A nice quiet spot to spend a night."
United States
Matthew
The price is CA $178
CA $219 total
includes taxes & fees
Nov 1 - Nov 2
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A modern kitchen with dark cabinets, a white countertop, and a large window.

10. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
The price is CA $128
CA $383 total
includes taxes & fees
Oct 8 - Oct 9
Cass-N-Reel Luxury Houseboat
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is CA $126
CA $409 total
includes taxes & fees
Oct 4 - Oct 5
Charming Coastal/Country Home w/3 Acres & Sauna!
A narrow hallway with a kitchen area on one side, featuring a microwave, oven, and cabinets. There are three black bar stools along the hallway, and a potted plant on the counter.

12. Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is CA $166
CA $543 total
includes taxes & fees
Oct 5 - Oct 6
Abingdon Haven Hideaway
A bunk bed room with white bedding and blue throw blankets.

13. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is CA $439
CA $465 total
includes taxes & fees
Oct 18 - Oct 19
Bohemia Manor Farm
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.

14. 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 CA $105
CA $142 total
includes taxes & fees
Oct 5 - Oct 6
Charming 2-bedroom house in Aberdeen with WiFi and AC
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

15. Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!

Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!
Essex
The price is CA $446
CA $797 total
includes taxes & fees
Oct 16 - Oct 17
Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

16. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (2 reviews)
"FLOHOM 14 did not disappoint!!! This was my first stay on a houseboat. Now I know why babies fall asleep when rocked. The boat is beautifully appointed & well equipped. Bring a good book. I’m already missing it!!!"
United States
Maria D.
The price is CA $257
CA $645 total
includes taxes & fees
Oct 8 - Oct 9
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

17. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (41 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is CA $199
CA $476 total
includes taxes & fees
Oct 5 - Oct 6
Large 2 bedroom house with private parking in a nice neighborhood
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

18. 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 CA $195
CA $530 total
includes taxes & fees
Oct 4 - Oct 5
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

19. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is CA $126
CA $408 total
includes taxes & fees
Oct 5 - Oct 6
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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, (15 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is CA $282
CA $495 total
includes taxes & fees
Oct 18 - Oct 19
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"The hotel was clean and neat. The staff was very friendly."
Dorothy 2-night trip
Posted 14 hours ago
Fairfield Inn & Suites by Marriott White Marsh

Find out more about Chestertown

Everything you need to know about Chestertown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chestertown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown vacation rentals we have selected for you start as low as CA $219 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.