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Vacations by Zumper

Chesapeake Vacation Rentals

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Chesapeake, MD

Book a vacation rental in Chesapeake that has the highest visitor rating. Here are 6 of the best vacation rentals in Chesapeake.
Wilmington Apartment: Day Trip to Dtwn Philly
10

Excellent

·
Apartment
·
4 br
·
Sleeps 8
·
Free Parking · Tv · Ceiling Fan ·
From
$105/night
Check availability
Property
Apartment · 4 Beds · 1 bath
Amenities
Free Parking
Tv
Ceiling Fan
Assigned Parking
Cable
Toiletries
Air Conditioning
Wifi
Other spaces
Kitchen
Chesapeake Bay House with Dock & Private Beach
10

Excellent

·
House
·
5 br
·
Sleeps 12
·
Furnished · Dishwasher · Residents Lounge ·
From
$469/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Furnished
Dishwasher
Residents Lounge
In Unit Laundry
Beach
Oven
Wifi
Fireplace
Other spaces
Kitchen
*NEW LISTING* Upper Chesapeake Getaway
10

Excellent

·
House
·
3 br
·
Sleeps 8
·
Waterfront · Wifi · Beach ·
From
$284/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Waterfront
Wifi
Beach
Dishwasher
Oven
Furnished
Air Conditioning
In Unit Laundry
Other spaces
Kitchen, Workspace
Quaint and private home within the UD Campus area.
10

Excellent

·
House
·
2 br
·
Sleeps 4
·
Kitchen · Oven · Furnished ·
From
$155/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Oven
Furnished
Wifi
Fitness Center
In Unit Laundry
Dishwasher
Air Conditioning
Other spaces
Kitchen, Workspace
Little River Cottage - Tiny Beach for Enjoying and Welcoming Backyard Retreat
10

Excellent

·
Apartment
·
2 br
·
Sleeps 4
·
In Unit Laundry · Kitchen · Dishwasher ·
From
$114/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
In Unit Laundry
Dishwasher
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Courtyard by Marriott New Castle
9.4

Excellent

·
Hotel
·
1 br
·
Sleeps 4
·
Furnished ·
From
$186/night
Check availability
Property
Hotel · 1 Bed
Amenities
Furnished

Our Recommended Vacation Rentals in Chesapeake, MD

We analyzed vacation rentals in Chesapeake 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 Chesapeake to help you find a deal for your next trip.
Fairfield by Marriott Inn & Suites Middletown
9.1

Excellent

·
Hotel
·
1 br
·
Sleeps 4
·
Fitness Center · Swimming Pool · Pool ·
From
$166/night
Check availability
Property
Hotel · 1 Bed
Amenities
Fitness Center
Swimming Pool
Pool
Furnished
Air Conditioning
Other spaces
Workspace
Welcome to The Richfield!
9

Excellent

·
Apartment
·
4 br
·
Sleeps 10
·
Dishwasher · Workspace · In Unit Laundry ·
From
$560/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Dishwasher
In Unit Laundry
Air Conditioning
Free Parking
Furnished
Oven
Assigned Parking
Wifi
Other spaces
Workspace, Kitchen
Hyatt Place Newark-Main Street
9

Excellent

·
Hotel
·
1 br
·
Sleeps 6
·
On Site Laundry · Fitness Center · Free Parking ·
From
$185/night
Check availability
Property
Hotel · 1 Bed
Amenities
On Site Laundry
Fitness Center
Free Parking
Air Conditioning
Residents Lounge
Fireplace
Wheelchair Accessible
Smoking Allowed
Other spaces
Workspace
Staybridge Suites Wilmington Downtown, an IHG Hotel
9

Excellent

·
Hotel
·
1 br
·
Sleeps 5
·
On Site Laundry · Workspace · Business Center ·
From
$196/night
Check availability
Property
Hotel · 1 Bed
Amenities
On Site Laundry
Business Center
Wifi
Air Conditioning
Free Parking
Storage
Furnished
Fitness Center
Other spaces
Workspace
Wilmington Apartment Day Trip to Dtwn Philly

No rating

·
Apartment
·
4 br
·
Sleeps 8
·
Wifi · Kitchen · Furnished ·
From
$213/night
Check availability
Property
Apartment · 4 Beds · 1 bath
Amenities
Wifi
Furnished
Air Conditioning
Free Parking
Other spaces
Kitchen

Budget-Friendly Vacation Rentals in Chesapeake, MD

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Chesapeake starting at $40. Use the price filter at the top of the page to search for more specific prices.
1 Bedroom with Shared Bathroom

No rating

·
House
·
1 br
·
Hardwood Floor · Fitness Center · On Site Laundry ·
From
$40/night
Min stay: 30 nights
Property
House · 1 Bed · 1 bath
Amenities
Hardwood Floor
Fitness Center
On Site Laundry
Fireplace
Furnished
In Unit Laundry
Microwave
Dishwasher
Whispering Oak Mansion
9.2

Excellent

·
Apartment
·
1 br
·
Sleeps 2
·
On Site Laundry · Air Conditioning · Furnished ·
From
$44/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Air Conditioning
Furnished
Assigned Parking
Residents Lounge
Carpet
Free Parking
Wifi
Other spaces
Workspace
Rodeway Inn Newark
4.7

Good

·
Hotel
·
1 br
·
Sleeps 10
·
Furnished · Free Parking · Carpet ·
From
$51/night
Check availability
Property
Hotel · 1 Bed
Amenities
Furnished
Free Parking
Carpet
Air Conditioning
On Site Laundry
Business Center
Wifi
Other spaces
Workspace
Motel 6-Elkton, MD
4.9

Good

·
Hotel
·
1 br
·
Sleeps 4
·
Furnished · Wifi · Wheelchair Accessible ·
From
$52/night
Check availability
Property
Hotel · 1 Bed
Amenities
Furnished
Wifi
Wheelchair Accessible
Air Conditioning
Other spaces
Workspace
Quality Inn Newark
4.9

Good

·
Hotel
·
1 br
·
Sleeps 10
·
Swimming Pool · Dry Cleaning Service · Carpet ·
From
$53/night
Check availability
Property
Hotel · 1 Bed
Amenities
Swimming Pool
Dry Cleaning Service
Carpet
Residents Lounge
Business Center
Air Conditioning
Fitness Center
Free Parking
Other spaces
Workspace
Days Inn by Wyndham Newark Wilmington
5.6

Good

·
Hotel
·
1 br
·
Sleeps 10
·
Furnished · Workspace · On Site Laundry ·
From
$55/night
Check availability
Property
Hotel · 1 Bed · 1 bath
Amenities
Furnished
On Site Laundry
Wifi
Free Parking
Assigned Parking
Hardwood Floor
Air Conditioning
Elevator
Other spaces
Workspace

Vacation Rentals With AC and/or Heat in Chesapeake, MD

Whether you need air conditioning or central heating, these vacation rentals are for you.
Wilmington Apartment: Day Trip to Dtwn Philly
10

Excellent

·
Apartment
·
4 br
·
Sleeps 8
·
Dishwasher · Wifi · Air Conditioning ·
From
$150/night
Check availability
Property
Apartment · 4 Beds · 1 bath
Amenities
Dishwasher
Wifi
Air Conditioning
In Unit Laundry
Central Heat
Ceiling Fan
Furnished
Other spaces
Kitchen
Family-Friendly Cottage, Walk to the Beach!
10

Excellent

·
House
·
2 br
·
Sleeps 6
·
Oven · Microwave · Walk In Closets ·
From
$175/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Oven
Microwave
Walk In Closets
Wifi
Garage Parking
Central Heat
Dishwasher
Ceiling Fan
Other spaces
Kitchen
Five Bedroom Villa & Pool on North East Harbor
10

Excellent

·
Apartment
·
5 br
·
Sleeps 10
·
Outdoor Space · Free Parking · Air Conditioning ·
From
$600/night
Check availability
Property
Apartment · 5 Beds · 5 baths
Amenities
Free Parking
Air Conditioning
Private Pool
In Unit Laundry
Wifi
Furnished
Dishwasher
Pool
Other spaces
Kitchen, Balcony
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Updated: November 28, 2023