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
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Chestertown vacation rentals

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (115 reviews)
"Hosts were extremely friendly and helpful!Parking was within feet of entrance. Studio and bathroom were spotless. Nice touches like coffee and accoutrements in the shower. Beautiful surroundings, everything was in bloom and spring beauty was everywhere!Washer and dryer in studio with soap and softener. Charming location!"
United States
Rob C.
$144 nightly
The price is $159
Jul 6 - Jul 7
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Smart TV, books

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (29 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$349 nightly
The price is $385
Jul 9 - Jul 10
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Property grounds

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)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
$441 nightly
The price is $459
Jul 5 - Jul 6
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
Property grounds

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
$400 nightly
The price is $456
Jul 13 - Jul 14
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
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
9.8 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.
$118 nightly
The price is $125
Jul 6 - Jul 7
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Marina

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, (206 reviews)
"Place worked great for our overnight stay"
United States
Adrienne K.
$194 nightly
The price is $224
Jul 5 - Jul 6
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.8 out of 10, Good, (17 reviews)
"Nice place"
United States
christine
$88 nightly
The price is $93
Jul 6 - Jul 7
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
Interior

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (96 reviews)
"Awesome place, great location"
United States
Mark M.
$196 nightly
The price is $226
Jul 12 - Jul 13
Total with taxes and fees
Hidden Fells Point Gem / Private Courtyard Patio
House (3 Bedrooms) | Front of property

Family Fun Awaits! Waterfront Home on Marley Creek

Family Fun Awaits! Waterfront Home on Marley Creek
3.0 star property
Marley
$361 nightly
The price is $411
Jul 5 - Jul 6
Total with taxes and fees
Family Fun Awaits! Waterfront Home on Marley Creek
1 bedroom, in-room safe, desk, iron/ironing board

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
$132 nightly
The price is $152
Jul 14 - Jul 15
Total with taxes and fees
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Exterior

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, (47 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
$273 nightly
The price is $294
Jul 6 - Jul 7
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Property grounds

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
$168 nightly
The price is $178
Jul 6 - Jul 7
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
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, (24 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$266 nightly
The price is $294
Jul 7 - Jul 8
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
$498 nightly
The price is $568
Jul 6 - Jul 7
Total with taxes and fees
Historic Row Home in Downtown Annapolis
Miscellaneous

Family Fun Awaits! Waterfront Home on Marley Creek

Family Fun Awaits! Waterfront Home on Marley Creek
Marley
$355 nightly
The price is $405
Jul 5 - Jul 6
Total with taxes and fees
Family Fun Awaits! Waterfront Home on Marley Creek
Outdoor dining

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
$476 nightly
The price is $538
Jul 6 - Jul 7
Total with taxes and fees
Chapel Gate 3BR Steps to City Dock & Naval Academy
Fridge, microwave, oven, stovetop

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.4 out of 10, Exceptional, (13 reviews)
"Just as advertised no issues. Great stay"
United States
Dan O.
$221 nightly
The price is $252
Jul 9 - Jul 10
Total with taxes and fees
Cute, Cozy 2-bedroom house near Annapolis with water access
Fridge, microwave, oven, stovetop

Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Dundalk
6.0 out of 10, (3 reviews)
"For an older property, the kitchen upgrade was nice, I like the basement level and the double queen bunk beds. The type of furniture, it can easily sleep the number of people I requested. I only had 3 adults and 1 child, which was more than enough space for the price."
United States
Linda T.
$184 nightly
The price is $212
Jul 7 - Jul 8
Total with taxes and fees
Gorgeous 3-bedroom townhome with AC in friendly Dundalk
House (4 Bedrooms) | Interior

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
3.0 star property
Glen Burnie
$1,192 nightly
The price is $1,359
Jul 9 - Jul 10
Total with taxes and fees
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
$160 nightly
The price is $174
Jul 27 - Jul 28
Total with taxes and fees
Turtle Cove Room
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

8/10 Good
"The staff was very nice and welcoming The room was little hot good thing i are able to adjust the temperature Pool was really nice my kids enjoy Didn’t do breakfast but it look really good we was already heading out tho"
Shermekqua 1-night trip
Posted 16 hours ago
Hilton Garden Inn Baltimore/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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chestertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

Circa 1700 Chesapeake Colonial home on the National Register.: This vacation home rental outside of Chestertown is located next to a golf course and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Chestertown?

Expedia has 28 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.