Vacation Rentals in Chesapeake, VA
PRICE PER NIGHT
ACCOMMODATION TYPES
Top-Rated Vacation Rentals in Chesapeake, VA
Book a vacation rental in Chesapeake that has the highest visitor rating. Here are 6 of the best vacation rentals in Chesapeake.
Cozy New Build on a private street near the downtown Norfolk and Greenbrier.
10
Excellent
·
South Norfolk
·
3 br
·
Sleeps 6
·
Workspace · Fireplace · In Unit Laundry ·
From
$180/nightProperty
House · 3 Beds · 3 baths
Amenities
Fireplace
In Unit Laundry
Furnished
Air Conditioning
Dishwasher
Oven
Wifi
Garage Parking
Other spaces
Workspace, Kitchen
Price drop
Beautifully appointed, spacious ranch style home located in Greenbrier!
10
Excellent
·
Indian River
·
3 br
·
Sleeps 2
·
Dishwasher · Furnished · In Unit Laundry ·
From
$185/nightProperty
House · 3 Beds · 3 baths
Amenities
Dishwasher
Furnished
In Unit Laundry
Air Conditioning
Oven
Wifi
Other spaces
Kitchen, Workspace
Price drop
A Quiet Chesapeake Escape! Close to Rivers Casino!
10
Excellent
·
Western Branch South
·
3 br
·
Sleeps 6
·
Oven · Wifi · Dishwasher ·
From
$145/nightProperty
House · 3 Beds · 1 bath
Amenities
Oven
Wifi
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Other spaces
Kitchen
Price drop
Spacious Chesapeake Home w/ Pool Table!
10
Excellent
·
Western Branch North
·
4 br
·
Sleeps 8
·
Outdoor Space · Oven · Walk In Closets ·
From
$124/nightProperty
House · 4 Beds · 3 baths
Amenities
Oven
Walk In Closets
Fireplace
Air Conditioning
Garage Parking
Furnished
Swimming Pool
In Unit Laundry
Other spaces
Kitchen
Comfortable Home | Long Stay Discount Available
10
Excellent
·
Indian River
·
3 br
·
Sleeps 6
·
Ocean · Workspace · Free Parking ·
From
$253/nightProperty
House · 3 Beds · 1 bath
Amenities
Ocean
Free Parking
Oven
Furnished
In Unit Laundry
Air Conditioning
Garage Parking
On Site Laundry
Other spaces
Workspace, Kitchen
Peace on the lake
10
Excellent
·
Western Branch South
·
4 br
·
Sleeps 13
·
Furnished · Fireplace · In Unit Laundry ·
From
$675/nightProperty
House · 4 Beds · 3 baths
Amenities
Furnished
Fireplace
In Unit Laundry
Swimming Pool
Wifi
Air Conditioning
Pool
Other spaces
Kitchen
Our Recommended Vacation Rentals in Chesapeake, VA
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.
Price drop
The Lucas Cheery House with Fenced Backyard!
No rating
·
South Norfolk
·
4 br
·
Sleeps 8
·
Fitness Center · Furnished · In Unit Laundry ·
From
$248/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Fitness Center
Furnished
In Unit Laundry
Air Conditioning
Wifi
Fireplace
Free Parking
On Site Laundry
Other spaces
Workspace, Kitchen
Price drop
I'm only renting a fairly large room in the home!
No rating
·
Chesapeake
·
1 br
·
Garage Parking · Microwave · Cable ·
From
$27/nightMin stay: 30 nights
Property
House · 1 Bed · 1 bath
Amenities
Garage Parking
Microwave
Cable
Furnished
Carpet
Fitness Center
Swimming Pool
In Unit Laundry
Price drop
Bright Chesapeake Home Near Shopping and Dining
8.7
Very good
·
Western Branch North
·
2 br
·
Sleeps 4
·
In Unit Laundry · Furnished · Oven ·
From
$199/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
In Unit Laundry
Furnished
Oven
Wifi
Free Parking
Other spaces
Kitchen
Price drop
Spacious Chesapeake Home with Pool Table!
9
Excellent
·
Western Branch North
·
4 br
·
Sleeps 8
·
Free Parking · Beach · Dishwasher ·
From
$293/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Free Parking
Beach
Dishwasher
Oven
In Unit Laundry
Furnished
Wifi
Fireplace
Other spaces
Workspace, Kitchen
Sleep Inn & Suites Chesapeake - Portsmouth
6.4
Good
·
Western Branch North
·
1 br
·
Sleeps 5
·
Hot Tub · Air Conditioning · Business Center ·
From
$142/nightProperty
Hotel · 1 Bed
Amenities
Hot Tub
Air Conditioning
Business Center
On Site Laundry
Free Parking
Pool
Swimming Pool
Fitness Center
Other spaces
Workspace
Price drop
Tru By Hilton Chesapeake- Greenbrier
No rating
·
Greenbrier East
·
1 br
·
Sleeps 4
·
Assigned Parking · Furnished · Air Conditioning ·
From
$135/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Furnished
Air Conditioning
Fitness Center
Smoking Allowed
Free Parking
On Site Laundry
Residents Lounge
Other spaces
Workspace
Budget-Friendly Vacation Rentals in Chesapeake, VA
Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Chesapeake starting at $27. Use the price filter at the top of the page to search for more specific prices.
InTown Suites Extended Stay Chesapeake VA - Battlefield Blvd
4.3
Good
·
Greenbrier West
·
1 br
·
Sleeps 4
·
Furnished · Wifi · Wheelchair Accessible ·
From
$36/nightProperty
Hotel · 1 Bed
Amenities
Furnished
Wifi
Wheelchair Accessible
Assigned Parking
Free Parking
Air Conditioning
On Site Laundry
Other spaces
Kitchen
InTown Suites Extended Stay Chesapeake VA - I-64 Crossways Blvd
4.8
Good
·
Greenbrier East
·
1 br
·
Sleeps 4
·
Furnished · Kitchen · Free Parking ·
From
$42/nightProperty
Hotel · 1 Bed
Amenities
Furnished
Free Parking
On Site Laundry
Carpet
Hardwood Floor
Assigned Parking
Air Conditioning
Wifi
Other spaces
Kitchen, Workspace
WoodSpring Suites Chesapeake-Norfolk Greenbrier
5.6
Good
·
Indian River
·
1 br
·
Sleeps 4
·
Elevator · On Site Laundry · Smoking Allowed ·
From
$48/nightProperty
Hotel · 1 Bed
Amenities
Elevator
On Site Laundry
Smoking Allowed
Free Parking
Wheelchair Accessible
Air Conditioning
Furnished
Wifi
Extended Stay America Suites - Chesapeake - Crossways Blvd
5.8
Good
·
Greenbrier East
·
1 br
·
Sleeps 10
·
Kitchen · Free Parking · Assigned Parking ·
From
$49/nightProperty
Hotel · 1 Bed
Amenities
Free Parking
Assigned Parking
Furnished
Carpet
Air Conditioning
On Site Laundry
Wifi
Other spaces
Kitchen, Workspace
Economy 7 Inn Chesapeake - Portsmouth
4.8
Good
·
Western Branch North
·
1 br
·
Sleeps 10
·
Carpet · Wifi · Wheelchair Accessible ·
From
$49/nightProperty
Hotel · 1 Bed · 1 bath
Amenities
Carpet
Wifi
Wheelchair Accessible
On Site Laundry
Air Conditioning
Furnished
Elevator
Other spaces
Workspace
Expand your search criteria to see more vacation rentals near Chesapeake.
Updated: September 19, 2023
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