Vacation Rentals in Chesapeake, VA

92 rentals

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.
The Sparks Home! Relaxing Space + Lux Kitchen
10

Excellent

·
chesapeake
·
2 br
·
Sleeps 4
·
Pool · Dishwasher · Outdoor Space ·
From
$325/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Pool
Dishwasher
On Site Laundry
Waterfront
Wifi
Air Conditioning
In Unit Laundry
Lake
Other spaces
Outdoor Space, Kitchen
Spacious Chesapeake Home w/ Pool Table!
10

Excellent

·
Western Branch North
·
4 br
·
Sleeps 8
·
Outdoor Space · Oven · Walk In Closets ·
From
$192/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Oven
Fireplace
Air Conditioning
Garage Parking
Furnished
Swimming Pool
In Unit Laundry
Ceiling Fan
Other spaces
Outdoor Space, Walk In Closets, Kitchen
Comfortable Home | Long Stay Discount Available
10

Excellent

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Indian River
·
3 br
·
Sleeps 6
·
Ocean · Workspace · Free Parking ·
From
$207/night
Check availability
Property
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, Outdoor Space
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
10

Excellent

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Indian River
·
1 br
·
Sleeps 4
·
Fitness Center · Elevator · Furnished ·
From
$185/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Fitness Center
Elevator
Furnished
On Site Laundry
Hot Tub
Dry Cleaning Service
Pool
Beach
Other spaces
Kitchen, Outdoor Space
Spacious tranquil 4 bedroom family home near everything
10

Excellent

·
Western Branch South
·
4 br
·
Sleeps 8
·
Dishwasher · Furnished · Kitchen ·
From
$251/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Dishwasher
Furnished
Oven
In Unit Laundry
Air Conditioning
Wifi
Other spaces
Kitchen
Country Escape Home in the Woods- Chesapeake VA
10

Excellent

·
Pleasant Grove West
·
3 br
·
Sleeps 6
·
Air Conditioning · Kitchen · Furnished ·
From
$108/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Air Conditioning
Furnished
On Site Laundry
Garage Parking
In Unit Laundry
Smoking Allowed
Oven
Wifi
Other spaces
Kitchen, Outdoor Space, 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 $36. Use the price filter at the top of the page to search for more specific prices.
InTown Suites Extended Stay Chesapeake VA - Battlefield Blvd
4.5

Good

·
Greenbrier West
·
1 br
·
Sleeps 4
·
Furnished · Wifi · Wheelchair Accessible ·
From
$36/night
Check availability
Property
Hotel · 1 Bed
Amenities
Furnished
Wifi
Wheelchair Accessible
Assigned Parking
Free Parking
Air Conditioning
On Site Laundry
Other spaces
Kitchen
Home Away from Home - One bedroom + personal living room and bathroom

No rating

·
Chesapeake
·
1 br
·
Sleeps 1
·
Garage Parking · Swimming Pool · Carpet ·
From
$38/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Garage Parking
Swimming Pool
Carpet
Oven
In Unit Laundry
Air Conditioning
Wifi
Fitness Center
Other spaces
Workspace, Kitchen, Outdoor Space
InTown Suites Extended Stay Chesapeake VA - I-64 Crossways Blvd
4.7

Good

·
Greenbrier East
·
1 br
·
Sleeps 4
·
Furnished · Kitchen · Free Parking ·
From
$42/night
Check availability
Property
Hotel · 1 Bed
Amenities
Furnished
Free Parking
On Site Laundry
Carpet
Hardwood Floor
Assigned Parking
Air Conditioning
Wifi
Other spaces
Kitchen, Workspace
Extended Stay America Suites - Chesapeake - Crossways Blvd
5.6

Good

·
Greenbrier East
·
1 br
·
Sleeps 10
·
Kitchen · Free Parking · Assigned Parking ·
From
$49/night
Check availability
Property
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
4.6

Good

·
Western Branch North
·
1 br
·
Sleeps 10
·
Carpet · Wifi · Wheelchair Accessible ·
From
$49/night
Check availability
Property
Hotel · 1 Bed · 1 bath
Amenities
Carpet
Wifi
Wheelchair Accessible
On Site Laundry
Air Conditioning
Furnished
Elevator
Other spaces
Workspace
Bowers Hill Inn Chesapeake
6.2

Good

·
Western Branch South
·
1 br
·
Sleeps 4
·
Workspace · Assigned Parking · Air Conditioning ·
From
$50/night
Check availability
Property
Hotel · 1 Bed
Amenities
Assigned Parking
Air Conditioning
Wifi
Furnished
Free Parking
Carpet
Other spaces
Workspace
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Updated: February 29, 2024