Chesapeake Vacation Rentals With Waterfront
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.
Price drop
Chesapeake Bay House with Dock & Private Beach
10
Excellent
·
·
5 br
·
Sleeps 12
·
Furnished · Dishwasher · Residents Lounge ·
From
$452/nightProperty
House · 5 Beds · 4 baths
Amenities
Furnished
Dishwasher
Residents Lounge
In Unit Laundry
Beach
Oven
Wifi
Fireplace
Other spaces
Kitchen
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
10
Excellent
·
·
3 br
·
Sleeps 8
·
Kitchen · Garage Parking · Waterfront ·
From
$390/nightProperty
House · 3 Beds · 3 baths
Amenities
Garage Parking
Waterfront
Hot Tub
Air Conditioning
Dishwasher
Oven
Wifi
Lake
Other spaces
Kitchen
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Waterfront house with amazing views Top of the Chesapeake, MD's best kept secret
10
Excellent
·
·
3 br
·
Sleeps 10
·
Wheelchair Accessible · Kitchen · Wifi ·
From
$378/nightProperty
House · 3 Beds · 2 baths
Amenities
Wheelchair Accessible
Wifi
Beach
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen, Balcony
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The Cove On The Waterfront
10
Excellent
·
·
3 br
·
Sleeps 8
·
In Unit Laundry · Air Conditioning · Kitchen ·
From
$189/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
In Unit Laundry
Air Conditioning
Oven
Waterfront
Dishwasher
Furnished
Fireplace
Wifi
Other spaces
Kitchen, Deck
Price drop
Amazing 432-Acre Waterfront Estate ~ Dock ~ Kayaks ~ Beaches ~ Fire Pit
10
Excellent
·
·
11 br
·
Sleeps 24
·
In Unit Laundry · Waterfront · Fireplace ·
From
$1,247/nightProperty
House · 11 Beds · 10 baths
Amenities
In Unit Laundry
Waterfront
Fireplace
Lake
Wifi
Furnished
Wheelchair Accessible
Dishwasher
Other spaces
Kitchen
Waterfront Home w/ a Hot Tub, Beach + Private Dock that Sleeps 20 People
10
Excellent
·
·
7 br
·
Sleeps 20
·
Outdoor Space · Fitness Center · Residents Lounge ·
From
$992/nightProperty
House · 7 Beds · 5 baths
Amenities
Fitness Center
Residents Lounge
On Site Laundry
Ev Charging
Beach
Air Conditioning
Fireplace
Garage Parking
Other spaces
Kitchen, Balcony
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 $60. Use the price filter at the top of the page to search for more specific prices.
CHESAPEAKE CITY DIRECT VIEW OF C&D CANAL WITH WATER TOY PARKING
10
Excellent
·
·
1 br
·
Sleeps 4
·
Wifi · Fireplace · Outdoor Space ·
From
$60/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Fireplace
Air Conditioning
Waterfront
Furnished
Oven
Other spaces
Kitchen, Workspace
Remodeled Luxury furnished 2 bedroom apartment.
No rating
·
·
2 br
·
Sleeps 2
·
Furnished · Ceiling Fan · In Unit Laundry ·
From
$105/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Furnished
Ceiling Fan
In Unit Laundry
Oven
Air Conditioning
Wifi
Hardwood Floor
Waterfront
Other spaces
Balcony, Kitchen
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10
Excellent
·
·
1 br
·
Sleeps 3
·
Oven · Ocean · Garage Parking ·
From
$118/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Oven
Ocean
Garage Parking
Wifi
Beach
Air Conditioning
Residents Lounge
Waterfront
Other spaces
Kitchen
Short Term Water Oriented Furnished Apartment
10
Excellent
·
·
1 br
·
Sleeps 2
·
Waterfront · Beach · In Unit Laundry ·
From
$132/nightProperty
House · 1 Bed · 1 bath
Amenities
Waterfront
Beach
In Unit Laundry
Oven
Wifi
Furnished
Air Conditioning
Other spaces
Kitchen
Cozy private waterfront retreat
10
Excellent
·
·
1 br
·
Sleeps 4
·
Wifi · Kitchen · In Unit Laundry ·
From
$199/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Wifi
In Unit Laundry
Residents Lounge
Furnished
Oven
Beach
Waterfront
Air Conditioning
Other spaces
Kitchen
Furnished Vacation Rentals in Chesapeake, MD
We've collected furnished vacation rentals in Chesapeake so you can spend more time relaxing and enjoying your trip.
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Wilmington Apartment Day Trip to Dtwn Philly
No rating
·
·
4 br
·
Sleeps 8
·
Furnished · Wifi · Free Parking ·
From
$252/nightProperty
Apartment · 4 Beds · 1 bath
Amenities
Furnished
Wifi
Free Parking
Other spaces
Kitchen
Price drop
Staybridge Suites Wilmington Downtown, an IHG Hotel
9
Excellent
·
·
1 br
·
Sleeps 5
·
Furnished · Business Center · On Site Laundry ·
From
$181/nightProperty
Hotel · 1 Bed
Amenities
Furnished
Business Center
On Site Laundry
Fitness Center
Storage
Assigned Parking
Air Conditioning
Other spaces
Workspace
Price drop
Wilmington Vacation Rental Near River and Downtown!
No rating
·
·
2 br
·
Sleeps 4
·
Oven · Kitchen · Air Conditioning ·
From
$169/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Oven
Air Conditioning
Wifi
Furnished
In Unit Laundry
Other spaces
Kitchen
Vacation Rentals With A Pool in Chesapeake, MD
Want to relax by the pool? Book one of these Chesapeake vacation rentals with a pool.
Fairfield by Marriott Inn & Suites Middletown
9.2
Excellent
·
·
1 br
·
Sleeps 4
·
Fitness Center · Swimming Pool · Pool ·
From
$185/nightProperty
Hotel · 1 Bed
Amenities
Fitness Center
Swimming Pool
Pool
Furnished
Air Conditioning
Other spaces
Workspace
Price drop
Hyatt Place Newark-Main Street
9
Excellent
·
·
1 br
·
Sleeps 6
·
On Site Laundry · Fitness Center · Free Parking ·
From
$198/nightProperty
Hotel · 1 Bed
Amenities
On Site Laundry
Fitness Center
Free Parking
Air Conditioning
Residents Lounge
Fireplace
Wheelchair Accessible
Smoking Allowed
Other spaces
Workspace
Budget-Friendly Getaway! 2 Modern Units, Pet-Friendly, with Free Breakfast
No rating
·
·
4 br
·
Sleeps 12
·
Business Center · Dishwasher · Storage ·
From
$465/nightProperty
House · 4 Beds · 2 baths
Amenities
Business Center
Dishwasher
Storage
Pool
Air Conditioning
Concierge Service
Oven
On Site Laundry
Other spaces
Workspace, Kitchen
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
·
·
4 br
·
Sleeps 8
·
Dishwasher · Wifi · Air Conditioning ·
From
$216/nightProperty
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
·
·
2 br
·
Sleeps 6
·
Oven · Microwave · Walk In Closets ·
From
$175/nightProperty
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
·
·
5 br
·
Sleeps 10
·
Outdoor Space · Free Parking · Air Conditioning ·
From
$600/nightProperty
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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Home > Destinations Vacation Rentals > Chesapeake Vacation Rentals > Chesapeake waterfront Vacation Rentals
Updated: September 6, 2023
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