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Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (103)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
$144 nightly
The price is $159
Oct 20 - Oct 21
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Guest Suite for up to 2 in a Victorian on the Chester River
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.
$118 nightly
The price is $125
Oct 21 - Oct 22
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$296 nightly
The price is $314
Nov 16 - Nov 17
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (31)
"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
$243 nightly
The price is $257
Oct 21 - Oct 22
Total with taxes and fees
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
$411 nightly
The price is $474
Oct 20 - Oct 21
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
2.0 star property
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.
$179 nightly
The price is $207
Oct 21 - Oct 22
Total with taxes and fees
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Amazing Modern house with a full kitchen and parking
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.
$343 nightly
The price is $351
Oct 20 - Oct 21
Total with taxes and fees
Amazing Modern house with a full kitchen and parking
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
10.0 out of 10, Exceptional, (5)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
United States
Nathan M.
$330 nightly
The price is $376
Oct 22 - Oct 23
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (16)
"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.
$265 nightly
The price is $293
Oct 21 - Oct 22
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (88)
"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.
$177 nightly
The price is $204
Oct 22 - Oct 23
Total with taxes and fees
Hidden Fells Point Gem / Private Courtyard Patio
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
8.0 out of 10, Very Good, (1)
"The property itself was very clean and cozy, and having our own private entry was also very nice. Towels and shower supplies were provided, and the bed was nice and comfortable. The host was also very kind and answered any questions we had. However, every morning we were woken up at around 7:30 am by someone (I assume children) stomping around right over our heads. There were also times we didn't really feel comfortable hanging out to watch TV in the living room area, because we could hear the...
United States
Zach N.
$110 nightly
The price is $125
Oct 20 - Oct 21
Total with taxes and fees
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
$333 nightly
The price is $353
Oct 23 - Oct 24
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$282 nightly
The price is $311
Oct 23 - Oct 24
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Modern New Suite Close to US Capital and BWI Airport
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.
$127 nightly
The price is $144
Oct 20 - Oct 21
Total with taxes and fees
Modern New Suite Close to US Capital and BWI Airport
Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (3)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$333 nightly
The price is $358
Oct 20 - Oct 21
Total with taxes and fees
Luxury Pool Loft sleeps 4
HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (7)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
$420 nightly
The price is $445
Oct 27 - Oct 28
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
$284 nightly
The price is $328
Oct 20 - Oct 21
Total with taxes and fees
1-bedroom apartment just 8 minutes drive to Oriole Park at Camden Yards
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
$410 nightly
The price is $468
Oct 21 - Oct 22
Total with taxes and fees
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (198)
"Great place all around "
United States
Sophia F.
$177 nightly
The price is $204
Oct 20 - Oct 21
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
9.8 out of 10, Exceptional, (10)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
United States
Maggie P.
$489 nightly
The price is $574
Nov 3 - Nov 4
Total with taxes and fees
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
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

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 $125 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.

Frequently asked questions

Are there vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Crumpton Auction, 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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This vacation home rental outside of Chestertown offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chestertown?

Expedia has 23 vacation rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Chesapeake Bay and Chestertown Dog Park, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Rolphs Wharf Marina and Chestertown Historic District 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.