Chesapeake Vacation Rentals With Waterfront

Unobstructed view of the Chesapeake Bay, w/ a beach!
10

Excellent

·
·
3 br
·
Sleeps 6
·
Ceiling Fan · Ev Charging · Deck ·
From
$232/night
Check availability
Property
Condo · 3 Beds · 2 baths
Amenities
Ceiling Fan
Ev Charging
Pool
Beach
Dishwasher
Wifi
Air Conditioning
Waterfront
Other spaces
Deck, Workspace, Balcony, Kitchen
Waterfront Home w/ Pool and Hot Tub ~ 8000 sq ft
9.3

Excellent

·
·
4 br
·
Sleeps 16
·
On Site Laundry · Walk In Closets · Private Pool ·
From
$665/night
Check availability
Property
House · 4 Beds · 7 baths
Amenities
On Site Laundry
Walk In Closets
Private Pool
Pool
Hot Tub
Fireplace
Dishwasher
Wifi
Other spaces
Kitchen
Bonfire by the Creek!!!
9.6

Excellent

·
·
3 br
·
Sleeps 5
·
Fitness Center · Dishwasher · Outdoor Space ·
From
$245/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Fitness Center
Dishwasher
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Oven
Residents Lounge
Other spaces
Kitchen
Riverfront Retreat with panoramic water views and breathtaking sunsets.
9.4

Excellent

·
·
7 br
·
Sleeps 14
·
Private Pool · Pool · Hot Tub ·
From
$1,350/night
Check availability
Property
House · 7 Beds · 5 baths
Amenities
Private Pool
Pool
Hot Tub
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Other spaces
Kitchen
Private Waterfront Estate with Pool, Private Beach and Dock
10

Excellent

·
·
7 br
·
Sleeps 18
·
Private Pool · Pool · Beach ·
From
$1,237/night
Check availability
Property
House · 7 Beds · 5 baths
Amenities
Private Pool
Pool
Beach
Hot Tub
Dishwasher
Wifi
Air Conditioning
Waterfront
Other spaces
Kitchen
-Sunset River Shack-Amazing water views of the upper Chesapeake bay
9.6

Excellent

·
·
3 br
·
Sleeps 6
·
Hot Tub · Dishwasher · Outdoor Space ·
From
$282/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Hot Tub
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Oven
Other spaces
Kitchen
Professionally Cleaned Waterfront Property! - Dock, Beach,Bungalows & Boat Lift
9.9

Excellent

·
·
7 br
·
Sleeps 15
·
Beach · Fireplace · Dishwasher ·
From
$730/night
Check availability
Property
House · 7 Beds · 7 baths
Amenities
Beach
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Kitchen
Worlds End Chesapeake Cottage
10

Excellent

·
·
2 br
·
Sleeps 4
·
Fireplace · Dishwasher · Outdoor Space ·
From
$238/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Oven
Other spaces
Kitchen

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Vintage Waterfront Cottage with Stunning Sunsets

No reviews

·
·
2 br
·
Sleeps 4
·
Beach · Fireplace · Dishwasher ·
From
$415/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Beach
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Kitchen
Waterfront with Chesapeake Sunsets
9.9

Excellent

·
·
3 br
·
Sleeps 8
·
Beach · Fireplace · Dishwasher ·
From
$213/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Beach
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Kitchen
Breathtaking waterfront property with pool, private dock and open floor plan.
9.6

Excellent

·
·
4 br
·
Sleeps 8
·
Lake · Deck · Workspace ·
From
$469/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Lake
Private Pool
Pool
Fitness Center
Hot Tub
Fireplace
Dishwasher
Wifi
Other spaces
Deck, Workspace, Kitchen
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
9.9

Excellent

·
·
3 br
·
Sleeps 6
·
Hot Tub · Fireplace · Dishwasher ·
From
$402/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Hot Tub
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Kitchen
Endless Water Views in a 5-Star Sanctuary
10

Excellent

·
·
3 br
·
Sleeps 6
·
Walk In Closets · Fitness Center · Balcony ·
From
$392/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Walk In Closets
Fitness Center
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
Cozy private waterfront retreat
9.7

Excellent

·
·
1 br
·
Sleeps 4
·
Fitness Center · Beach · Outdoor Space ·
From
$192/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Beach
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Oven
Other spaces
Kitchen
Riverfront Country House on The Sassafras River
10

Excellent

·
·
10 br
·
Sleeps 13
·
Dishwasher · Outdoor Space · Wifi ·
From
$435/night
Check availability
Property
House · 10 Beds · 6 baths
Amenities
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Oven
Garage Parking
Other spaces
Kitchen
Amazing Waterfront Views at Sailor's River Cottage on the Upper Chesapeake Bay
9.7

Excellent

·
·
2 br
·
Sleeps 6
·
Fitness Center · Hot Tub · Outdoor Space ·
From
$255/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Fitness Center
Hot Tub
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Oven
Other spaces
Kitchen
Pets Welcome!! No Fees or Security Deposit
10

Excellent

·
·
1 br
·
Sleeps 3
·
Fireplace · Outdoor Space · Wifi ·
From
$261/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fireplace
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Oven
Residents Lounge
Other spaces
Kitchen
Short Term Water Oriented Furnished Apartment
10

Excellent

·
·
1 br
·
Sleeps 2
·
Beach · Wifi · Air Conditioning ·
From
$132/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Beach
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Oven
Other spaces
Kitchen
New! Chesapeake Bay house with amazing views
9.7

Excellent

·
·
4 br
·
Sleeps 13
·
Hardwood Floor · Balcony · Fireplace ·
From
$553/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Hardwood Floor
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
Waterfront Retreat for Weekends and More!
9.9

Excellent

·
·
3 br
·
Sleeps 8
·
Walk In Closets · Balcony · Beach ·
From
$322/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Walk In Closets
Beach
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
BEAUTIFUL BAY FRONT VIEW
10

Excellent

·
·
3 br
·
Sleeps 6
·
Pool · Balcony · Dishwasher ·
From
$270/night
Check availability
Property
Condo · 3 Beds · 2 baths
Amenities
Pool
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Oven
Other spaces
Balcony, Kitchen
Bella Vista Holiday Family Gatherings in Coastal Maryland!
9.7

Excellent

·
·
5 br
·
Sleeps 8
·
Workspace · Private Pool · Pool ·
From
$775/night
Check availability
Property
House · 5 Beds · 5 baths
Amenities
Private Pool
Pool
Hot Tub
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Other spaces
Workspace, Balcony, Kitchen
Top of the Chesapeake - Minutes from Historic Charlestown
9.8

Excellent

·
·
5 br
·
Sleeps 13
·
Smoking Allowed · Fitness Center · Balcony ·
From
$359/night
Check availability
Property
House · 5 Beds · 2 baths
Amenities
Smoking Allowed
Fitness Center
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
Captivating Chesapeake experience
9.9

Excellent

·
·
2 br
·
Sleeps 6
·
Fitness Center · Fireplace · Dishwasher ·
From
$285/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Fitness Center
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Kitchen
Nancy’s Touch, A Waterfront Paradise!
10

Excellent

·
·
3 br
·
On Site Laundry · Fireplace · Dishwasher ·
From
$402/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
On Site Laundry
Fireplace
Dishwasher
Wifi
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Other spaces
Kitchen
Showing 1 - 25 of 25 results
Home > Destinations Vacation Rentals > Chesapeake Vacation Rentals > Chesapeake waterfront Vacation Rentals
Updated: March 28, 2023

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