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Vacations by Zumper

Vacation Rentals in Chestertown, MD

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Chestertown, MD

Book a vacation rental in Chestertown that has the highest visitor rating. Here are 6 of the best vacation rentals in Chestertown.
Price drop
Breathtaking waterfront home on the Chester River
10

Excellent

·
Chestertown
·
4 br
·
Sleeps 10
·
Outdoor Space · Fitness Center · Private Pool ·
From
$621/night
Check availability
Property
House · 4 Beds · 5 baths
Amenities
Fitness Center
Private Pool
Oven
Swimming Pool
On Site Laundry
Waterfront
Pool
Dishwasher
Other spaces
Kitchen, Workspace, Balcony
Price drop
Waterfront Home w/ Private Dock & Hot Tub - Harbor View Haven
10

Excellent

·
Chestertown
·
3 br
·
Sleeps 10
·
Waterfront · Dishwasher · Hot Tub ·
From
$567/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Waterfront
Dishwasher
Hot Tub
Air Conditioning
Oven
Storage
Fireplace
On Site Laundry
Other spaces
Kitchen, Workspace, Balcony
Private pier and pool at this waterfront Chestertown home
10

Excellent

·
Chestertown
·
5 br
·
Sleeps 14
·
Workspace · Swimming Pool · Pool ·
From
$501/night
Check availability
Property
House · 5 Beds · 5 baths
Amenities
Swimming Pool
Pool
Air Conditioning
Waterfront
Private Pool
Fitness Center
Dishwasher
Beach
Other spaces
Workspace, Kitchen
Price drop
The Lazy River House
10

Excellent

·
Chestertown
·
3 br
·
Sleeps 10
·
Waterfront · Fitness Center · Kitchen ·
From
$450/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
Waterfront
Fitness Center
Furnished
Other spaces
Kitchen
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
10

Excellent

·
Chestertown
·
3 br
·
Sleeps 10
·
Furnished · Outdoor Space · Residents Lounge ·
From
$405/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Furnished
Residents Lounge
Fireplace
Waterfront
Wheelchair Accessible
Wifi
Air Conditioning
Fitness Center
Other spaces
Kitchen
Price drop
Country Estate in Historic District
10

Excellent

·
Chestertown
·
5 br
·
Sleeps 10
·
Air Conditioning · Wifi · Outdoor Space ·
From
$238/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Air Conditioning
Wifi
Oven
Dishwasher
Furnished
On Site Laundry
Fireplace
Residents Lounge
Other spaces
Workspace, Kitchen, Balcony

Budget-Friendly Vacation Rentals in Chestertown, MD

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Chestertown starting at $110. Use the price filter at the top of the page to search for more specific prices.
First Floor Studio Apartment in Historic Chestertown
10

Excellent

·
Chestertown
·
1 br
·
Sleeps 3
·
Fitness Center · Furnished · Hot Tub ·
From
$110/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Furnished
Hot Tub
Private Pool
Wifi
Air Conditioning
In Unit Laundry
Swimming Pool
Carriage House Hideaway in Middle of Chestertown
10

Excellent

·
Chestertown
·
Studio
·
Sleeps 2
·
Air Conditioning · Furnished · Kitchen ·
From
$125/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
Air Conditioning
Furnished
Wifi
Fireplace
Assigned Parking
In Unit Laundry
Oven
Other spaces
Kitchen, Workspace
Historic Downtown Garden Oasis with Private Patio
10

Excellent

·
Chestertown
·
1 br
·
Sleeps 3
·
On Site Laundry · Fitness Center · Outdoor Space ·
From
$149/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Fitness Center
Air Conditioning
Furnished
Business Center
Wifi
Other spaces
Kitchen
Price drop
2 Beds, 2.5 Baths, Perfect Downtown Location
10

Excellent

·
Chestertown
·
2 br
·
Sleeps 4
·
Workspace · Air Conditioning · Oven ·
From
$179/night
Check availability
Property
House · 2 Beds · 3 baths
Amenities
Air Conditioning
Oven
Dishwasher
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
Price drop
Newly restored apartment in the heart of Chestertown
10

Excellent

·
Chestertown
·
2 br
·
Sleeps 4
·
Air Conditioning · Furnished · Workspace ·
From
$225/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Air Conditioning
Furnished
In Unit Laundry
Dishwasher
Oven
Wifi
Other spaces
Workspace, Kitchen
Chestertown's Pet-Friendly Little Red Cottage
10

Excellent

·
Chestertown
·
2 br
·
Sleeps 4
·
Kitchen · Dishwasher · Oven ·
From
$235/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Dishwasher
Oven
Furnished
Air Conditioning
Wifi
In Unit Laundry
Other spaces
Kitchen, Workspace
Expand your search criteria to see more vacation rentals near Chestertown.
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Updated: September 27, 2023