Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

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, (111 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
May 11 - May 12
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
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 wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
$361 nightly
The price is $383
Jun 1 - Jun 2
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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, (20 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$264 nightly
The price is $292
May 10 - May 11
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (21 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
May 11 - May 12
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (28 reviews)
"Really cute little place - very clean and owners are great about checking in on you to make sure things are great."
United States
Cheryl
$298 nightly
The price is $316
May 10 - May 11
Total with taxes and fees
Adorable two-bedroom retreat close to Easton, Denton, Centreville
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, (205 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
$204 nightly
The price is $236
May 10 - May 11
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
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, (40 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
$287 nightly
The price is $327
May 10 - May 11
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Interior

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (95 reviews)
"Awesome place, great location"
United States
Mark M.
$211 nightly
The price is $244
May 19 - May 20
Total with taxes and fees
Hidden Fells Point Gem / Private Courtyard Patio
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)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
$395 nightly
The price is $419
May 8 - May 9
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (6 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
$186 nightly
The price is $197
May 11 - May 12
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Smart TV, printers

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
9.8 out of 10, Exceptional, (6 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
$244 nightly
The price is $282
May 10 - May 11
Total with taxes and fees
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"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.
$374 nightly
The price is $396
Jun 7 - Jun 8
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor
Interior

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.8 out of 10, Exceptional, (6 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
$639 nightly
The price is $728
May 11 - May 12
Total with taxes and fees
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Interior

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.6 out of 10, Exceptional, (10 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
$195 nightly
The price is $225
May 11 - May 12
Total with taxes and fees
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, 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)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$343 nightly
The price is $379
May 26 - May 27
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
$378 nightly
The price is $401
May 26 - May 27
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Terrace/patio

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
$380 nightly
The price is $433
May 11 - May 12
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Outdoor pool

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.6 out of 10, Excellent, (11 reviews)
"Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. "
United States
Ellie F.
$181 nightly
The price is $206
May 20 - May 21
Total with taxes and fees
Secluded Tiny Pool House -Private Pool -Self Check in
Outdoor dining

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, (13 reviews)
"Beautiful home. Great location. Super clean. Would definitely stay there again."
United States
Sean S.
$504 nightly
The price is $587
May 11 - May 12
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Breakfast"
Hector 13-night trip
Posted 4 hours ago
Best Western Plus Hotel & Conference Center

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?

NEW! Charming Farm House in Historic Kent Island : This vacation home rental outside of Chestertown is located on a river and has a balcony, a garden, 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.

How many vacation rentals are there in Chestertown?

Expedia has 26 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.