Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

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, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
$144 nightly
The price is $159
Jan 27 - Jan 28
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Pool

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Chestertown
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
United States
Jason
$426 nightly
The price is $452
Feb 21 - Feb 22
Total with taxes and fees
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Terrace/patio

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, (7 reviews)
"Enjoyed the stay"
United States
Kedra B.
$320 nightly
The price is $365
Jan 27 - Jan 28
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Fridge, microwave, oven, stovetop

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Baltimore
10.0 out of 10, Exceptional, (12 reviews)
"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.
$460 nightly
The price is $537
Jan 27 - Jan 28
Total with taxes and fees
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Property grounds

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
$374 nightly
The price is $426
Jan 28 - Jan 29
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
9.6 out of 10, Exceptional, (19 reviews)
"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
Feb 4 - Feb 5
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
House (3 Bedrooms) | Interior

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
Rosedale
9.0 out of 10, Wonderful, (2 reviews)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
$431 nightly
The price is $498
Feb 10 - Feb 11
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Terrace/patio

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (9 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
$349 nightly
The price is $357
Jan 27 - Jan 28
Total with taxes and fees
Amazing Modern house with a full kitchen and parking
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
$243 nightly
The price is $258
Jan 29 - Jan 30
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
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, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$232 nightly
The price is $246
Jan 28 - Jan 29
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.0 out of 10, Very Good, (11 reviews)
"Pleasant stay"
United States
Yommali G.
$88 nightly
The price is $93
Feb 4 - Feb 5
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
$283 nightly
The price is $312
Jan 27 - Jan 28
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
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 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$257 nightly
The price is $284
Jan 27 - Jan 28
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Interior

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, (36 reviews)
"Just as advertised. Clean and quiet."
United States
Robert B.
$267 nightly
The price is $304
Jan 27 - Jan 28
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Interior

Hobbit House one of a kind home

Hobbit House one of a kind home
Bel Air
10.0 out of 10, Exceptional, (8 reviews)
"We had a great stay! "
United States
Courtney H.
$293 nightly
The price is $295
Feb 2 - Feb 3
Total with taxes and fees
Hobbit House one of a kind home
Dining

Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug
Betterton
$396 nightly
The price is $420
Jan 27 - Jan 28
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Smart TV, printers

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
10.0 out of 10, Exceptional, (1 review)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
$232 nightly
The price is $268
Jan 27 - Jan 28
Total with taxes and fees
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
$193 nightly
The price is $200
Jan 27 - Jan 28
Total with taxes and fees
High Tide Haven Suite
Fridge, microwave, oven, stovetop

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$342 nightly
The price is $390
Jan 27 - Jan 28
Total with taxes and fees
Luxury Pool Loft sleeps 4
Dining

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$396 nightly
The price is $420
Jan 27 - Jan 28
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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
"Polite and kind hotel manager"
Richard 1-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown

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 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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This vacation home rental outside of Chestertown is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 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.