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Chestertown Holiday Rentals

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Check prices for these dates

Tonight
18 Nov - 19 Nov
Tomorrow
19 Nov - 20 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Holiday Rentals in Chestertown

Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
The price is HK$770
HK$1,235 total
includes taxes & fees
20 Nov - 21 Nov
First Floor Studio Apartment in Historic Chestertown
Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
Rosedale
10.0 out of 10, Exceptional, (1)
The price is HK$1,368
HK$3,578 total
includes taxes & fees
19 Nov - 20 Nov
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Exterior
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
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is HK$529
HK$972 total
includes taxes & fees
19 Nov - 20 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
Fridge, microwave, oven, stovetop
Small House on Gentleman’s Farm

Small House on Gentleman’s Farm

Bel Air
10.0 out of 10, Exceptional, (12)
"Wonderful property located in a peaceful setting. This is our next stay at the Gentlemen’s Farm. Pastoral location that is convenient to Bel Air. House is so clean and well maintained. We had everything available that we needed. Tracey is so responsive in providing information that makes the stay even better. We will stay here again when in the area visiting family."
United States
Jim S.
The price is HK$797
HK$2,259 total
includes taxes & fees
9 Dec - 10 Dec
Small House on Gentleman’s Farm
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview!

Relax on Kent Island in 3 Bedroom Home w/Waterview!

Stevensville
9.8 out of 10, Exceptional, (42)
"Wonderful home and host. Very easy to check-in and communication was excellent. "
United States
Ann T.
The price is HK$531
HK$1,930 total
includes taxes & fees
19 Nov - 20 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview!
Printers
Hudson house

Hudson house

3.5 star property
Canton
The price is HK$1,169
HK$2,540 total
includes taxes & fees
19 Nov - 20 Nov
Hudson house
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

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

Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is HK$294
HK$1,646 total
includes taxes & fees
19 Nov - 20 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
Dining
Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

Smyrna
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is HK$1,399
HK$2,776 total
includes taxes & fees
19 Nov - 20 Nov
Amazing Modern house with a full kitchen and parking
Fridge, microwave, oven, stovetop
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

2.0 star property
Berea
9.6 out of 10, Exceptional, (4)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
United States
michael t.
The price is HK$791
HK$1,632 total
includes taxes & fees
24 Nov - 25 Nov
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie
8.4 out of 10, Very good, (7)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
The price is HK$847
HK$2,702 total
includes taxes & fees
21 Nov - 22 Nov
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,609
HK$3,217 total
includes taxes & fees
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star
Property grounds
Hobbit House one of a kind home

Hobbit House one of a kind home

Bel Air
10.0 out of 10, Exceptional, (7)
"We had a great stay! "
United States
Courtney H.
The price is HK$865
HK$2,327 total
includes taxes & fees
19 Nov - 20 Nov
Hobbit House one of a kind home
Marina
Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio

Fells Point
9.6 out of 10, Exceptional, (90)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
The price is HK$459
HK$1,562 total
includes taxes & fees
23 Nov - 24 Nov
Hidden Fells Point Gem / Private Courtyard Patio
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is HK$1,532
HK$3,461 total
includes taxes & fees
19 Nov - 20 Nov
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Fridge, microwave, oven, stovetop
Modern New Suite Close to US Capital and BWI Airport

Modern New Suite Close to US Capital and BWI Airport

Pasadena
7.0 out of 10, Good, (2)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
United States
Brittnie A.
The price is HK$544
HK$1,143 total
includes taxes & fees
6 Dec - 7 Dec
Modern New Suite Close to US Capital and BWI Airport
Interior
Exclusive Sunken Living Room Soaring Exposed Brick

Exclusive Sunken Living Room Soaring Exposed Brick

Patterson Place
10.0 out of 10, Exceptional, (6)
"Place was amazing. So many amenities. So close to all the tourist attractions as well. Tons of street parking even at late night. Neighborhood is nice and secure. Would certainly stay again! Communication was excellent. "
United States
Mike J.
The price is HK$972
HK$2,487 total
includes taxes & fees
19 Nov - 20 Nov
Exclusive Sunken Living Room Soaring Exposed Brick
Beach
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, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is HK$916
HK$2,213 total
includes taxes & fees
19 Nov - 20 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV, books
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, (33)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is HK$1,015
HK$2,521 total
includes taxes & fees
20 Nov - 21 Nov
Large 2 bedroom house with private parking in a nice neighborhood
Outdoor pool
Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in

Glen Burnie
8.8 out of 10, Excellent, (9)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
United States
Robert F.
The price is HK$770
HK$1,055 total
includes taxes & fees
19 Nov - 20 Nov
Secluded Tiny Pool House -Private Pool -Self Check in
Beach
Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach

Worton
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is HK$1,360
HK$2,421 total
includes taxes & fees
20 Nov - 21 Nov
Waterfront Retreat with Private Dock and Beach
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Good location. Very pricey but not much competition "
jason 2-night trip
Posted 19 hours ago
Comfort Inn & Suites Chestertown

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 holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Crumpton Auction, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chestertown has to offer?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This holiday home rental outside of Chestertown is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a pool table.

How many holiday rentals are there in Chestertown?

Expedia has 24 holiday 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 holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.