Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Chestertown holiday 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 HK$775
HK$1,244 total
includes taxes & fees
27 Apr - 28 Apr
First Floor Studio Apartment in Historic Chestertown
Interior

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is HK$2,740
HK$3,320 total
includes taxes & fees
16 Apr - 17 Apr
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
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 HK$533
HK$980 total
includes taxes & fees
22 Apr - 23 Apr
Guest Suite for up to 2 in a Victorian on the Chester River
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.
The price is HK$462
HK$1,574 total
includes taxes & fees
16 Apr - 17 Apr
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.
The price is HK$1,958
HK$3,304 total
includes taxes & fees
16 Apr - 17 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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)
"Quiet, quaint....perfect"
United States
Catherine M.
The price is HK$1,363
HK$2,665 total
includes taxes & fees
10 May - 11 May
Adorable two-bedroom retreat close to Easton, Denton, Centreville
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 HK$1,057
HK$2,553 total
includes taxes & fees
16 Apr - 17 Apr
Large 2 bedroom house with private parking in a nice neighborhood
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 HK$529
HK$726 total
includes taxes & fees
16 Apr - 17 Apr
Charming 2-bedroom house in Aberdeen with WiFi and AC
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 HK$1,159
HK$2,705 total
includes taxes & fees
5 May - 6 May
Cozy 2br home w/ parking in downtown Annapolis
Dining

Charming Historic Row House in The Heart of Eastport's Horn Point

Charming Historic Row House in The Heart of Eastport's Horn Point
Eastport
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful home. Close to everything including great restaurants and our favorite coffee place Oscar’s."
United States
Marja H.
The price is HK$6,265
HK$9,026 total
includes taxes & fees
14 May - 15 May
Charming Historic Row House in The Heart of Eastport's Horn Point
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 HK$1,370
HK$2,847 total
includes taxes & fees
16 Apr - 17 Apr
Bayside Cottage steps from Rock Hall Harbor
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 HK$1,163
HK$1,607 total
includes taxes & fees
20 Apr - 21 Apr
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,938
HK$3,647 total
includes taxes & fees
18 Apr - 19 Apr
Waterfront Oasis of Annapolis Star
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.
The price is HK$1,762
HK$2,965 total
includes taxes & fees
6 May - 7 May
Waterfront Retreat with Private Dock and Beach
Marina

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (19 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is HK$2,820
HK$4,885 total
includes taxes & fees
16 Apr - 17 Apr
Secluded Cozy Cottage in Historic Downtown
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.

Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (8 reviews)
"Great experience. "
United States
Shana F.
The price is HK$1,958
HK$2,500 total
includes taxes & fees
16 Apr - 17 Apr
Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
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
The price is HK$909
HK$2,208 total
includes taxes & fees
16 Apr - 17 Apr
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
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 HK$1,098
HK$2,393 total
includes taxes & fees
16 Apr - 17 Apr
Amazing Modern house with a full kitchen and parking
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 HK$923
HK$2,221 total
includes taxes & fees
16 Apr - 17 Apr
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,566
HK$2,366 total
includes taxes & fees
30 Apr - 1 May
BAYSIDE BUNGALOW
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

Historic Inns of Annapolis

Historic Inns of Annapolis

6/10 Okay
"The room was very small. The elevator was not working. I am too old to be hauling bags up the stairs. Parking was $50 and Historical fee was another $53 dollars so it was more expensive that necessary. I would not stay there again."
john 1-night trip
Posted 7 hours ago
Historic Inns of Annapolis

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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  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

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

Frequently asked questions

Are there holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Garfield Center for the Arts at the Prince Theater, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chestertown has to offer?

Captivating Chesapeake experience: This holiday home rental outside of Chestertown is located on the waterfront, and has a fireplace, a patio and a BBQ 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 holiday with amenities such as a selection of books.

How many holiday rentals are there in Chestertown?

Expedia has 26 holiday 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 Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. Rolphs Wharf Marina and Chestertown Historic District are other places to visit while you're in town.

What are holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.