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Vacations by Zumper

Vacation Rentals in Chester, MD

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Chester, MD

Book a vacation rental in Chester that has the highest visitor rating. Here are 3 of the best vacation rentals in Chester.
Waterfront home with private pier is A Shore Thing
10

Excellent

·
Chester
·
3 br
·
Sleeps 9
·
Swimming Pool · Waterfront · Balcony ·
From
$557/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
Swimming Pool
Waterfront
Fitness Center
On Site Laundry
Wifi
Oven
Dishwasher
Fireplace
Other spaces
Balcony, Kitchen
Bentons Pleasure- Cox Creek, Pier and Sunsets!
10

Excellent

·
Chester
·
4 br
·
Sleeps 10
·
Residents Lounge · Waterfront · Oven ·
From
$726/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Residents Lounge
Waterfront
Oven
Fitness Center
Dishwasher
On Site Laundry
Onsite Management
Furnished
Other spaces
Kitchen, Deck, Balcony
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
10

Excellent

·
Chester
·
4 br
·
Sleeps 8
·
Wifi · Waterfront · Furnished ·
From
$356/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Wifi
Waterfront
Furnished
Beach
Dishwasher
On Site Laundry
Air Conditioning
Other spaces
Workspace, Kitchen

Our Recommended Vacation Rentals in Chester, MD

We analyzed vacation rentals in Chester from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Chester to help you find a deal for your next trip.
Price drop
Cozy Waterfront Apartment Chester, MD

No rating

·
Chester
·
1 br
·
Sleeps 2
·
Wifi · Workspace · On Site Laundry ·
From
$141/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
On Site Laundry
Air Conditioning
Dishwasher
Oven
In Unit Laundry
Waterfront
Garage Parking
Other spaces
Workspace, Balcony, Kitchen
Price drop
Renovated Rancher on Kent Island near Chesapeake Bay Bridge

No rating

·
Chester
·
3 br
·
Sleeps 8
·
Dishwasher · Oven · Air Conditioning ·
From
$430/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Kitchen
Kent Island - Gorgeous Waterfront Home

No rating

·
Chester
·
3 br
·
Sleeps 8
·
In Unit Laundry · Outdoor Space · Oven ·
From
$1,150/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
In Unit Laundry
Oven
Furnished
Waterfront
On Site Laundry
Wifi
Dishwasher
Air Conditioning
Other spaces
Kitchen, Balcony
Expand your search criteria to see more vacation rentals near Chester.
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Updated: September 28, 2023