Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

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)
"Every thing was great"
United States
lesia k.
The price is ￥15,793
￥25,339 total
includes taxes & fees
Apr 6 - Apr 7
First Floor Studio Apartment in Historic Chestertown
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, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is ￥10,848
￥19,954 total
includes taxes & fees
Apr 8 - Apr 9
Guest Suite for up to 2 in a Victorian on the Chester River
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Great experience"
United States
David P.
The price is ￥38,128
￥68,381 total
includes taxes & fees
Apr 19 - Apr 20
18th Cent. Charm in Historic Downtown Annapolis
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.
The price is ￥39,883
￥67,303 total
includes taxes & fees
Apr 6 - Apr 7
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is ￥28,715
￥61,470 total
includes taxes & fees
Apr 19 - Apr 20
Cozy 2br home w/ parking in downtown Annapolis
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, (10 reviews)
"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 ￥21,537
￥46,915 total
includes taxes & fees
Apr 11 - Apr 12
Amazing Modern house with a full kitchen and parking
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, (38 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is ￥21,537
￥52,377 total
includes taxes & fees
Apr 5 - Apr 6
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, (94 reviews)
"Awesome place, great location"
United States
Mark M.
The price is ￥9,891
￥32,614 total
includes taxes & fees
Apr 5 - Apr 6
Hidden Fells Point Gem / Private Courtyard Patio
Smart TV, printers

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
9.6 out of 10, Exceptional, (5 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
The price is ￥16,463
￥42,230 total
includes taxes & fees
Apr 4 - Apr 5
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
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.
The price is ￥13,302
￥42,340 total
includes taxes & fees
Apr 8 - Apr 9
Charming Coastal/Country Home w/3 Acres & Sauna!
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (13 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is ￥10,768
￥14,796 total
includes taxes & fees
Apr 5 - Apr 6
Charming 2-bedroom house in Aberdeen with WiFi and AC
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is ￥27,639
￥31,851 total
includes taxes & fees
Apr 4 - Apr 5
High Tide Haven Suite
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.
The price is ￥27,918
￥58,002 total
includes taxes & fees
Apr 16 - Apr 17
Bayside Cottage steps from Rock Hall Harbor
Property grounds

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is ￥25,126
￥67,199 total
includes taxes & fees
Apr 6 - Apr 7
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Interior

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

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 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.
The price is ￥31,587
￥114,938 total
includes taxes & fees
Apr 6 - Apr 7
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Oven, stovetop

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is ￥47,859
￥68,655 total
includes taxes & fees
Apr 5 - Apr 6
40' Bristol sailboat with spectacular views
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.
The price is ￥13,929
￥42,836 total
includes taxes & fees
Apr 5 - Apr 6
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Living area

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, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is ￥24,089
￥33,144 total
includes taxes & fees
Apr 28 - Apr 29
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Dining

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

Grandma’s Cottage will wrap around you like a warm hug
Betterton
The price is ￥35,894
￥67,640 total
includes taxes & fees
Apr 4 - Apr 5
Grandma’s Cottage will wrap around you like a warm hug
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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ￥19,782
￥46,510 total
includes taxes & fees
Apr 9 - Apr 10
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"The breakfast was fresh, all the staff were friendly and very helpful. My only critique is the shower needs an update, our shower had a huge crack that’s had glue. Everything else was great so we just didn’t feel it was worth requesting a room change or complaint."
Elisabeth 6-night trip
Posted 2 hours ago
Fairfield Inn & Suites by Marriott White Marsh

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
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Look no further and take a look at our great range of rental properties in Chestertown!

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?

Captivating Chesapeake experience: This vacation home rental outside of Chestertown is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of books.

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. 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.