Vacation Rentals in Chesapeake, VA
The Lucas Cheery House with Fenced Backyard!
No reviews
·
South Norfolk
·
4 br
·
Sleeps 8
·
Fireplace · Oven · In Unit Laundry ·
From
$174/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Fireplace
Oven
In Unit Laundry
Wifi
On Site Laundry
Free Parking
Furnished
Fitness Center
Other spaces
Kitchen
Bright Chesapeake Home Near Shopping and Dining
8.5
Very good
·
Western Branch North
·
2 br
·
Sleeps 4
·
Outdoor Space · Oven · In Unit Laundry ·
From
$143/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Oven
In Unit Laundry
Wifi
Free Parking
Furnished
Other spaces
Kitchen
Spacious Chesapeake Home with Pool Table!
No reviews
·
Western Branch North
·
4 br
·
Sleeps 8
·
Beach · Fireplace · Oven ·
From
$189/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Beach
Fireplace
Oven
Dishwasher
In Unit Laundry
Wifi
Free Parking
Furnished
Other spaces
Kitchen
Sleep Inn & Suites Chesapeake - Portsmouth
6.4
Good
·
Western Branch North
·
1 br
·
Sleeps 5
·
Assigned Parking · Hot Tub · Smoking Allowed ·
From
$71/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Hot Tub
Smoking Allowed
Pool
Wifi
On Site Laundry
Free Parking
Air Conditioning
Other spaces
Workspace
First Class Lvng - 1BR, 1.5BA, cool & cozy
No reviews
·
Western Branch North
·
1 br
·
Sleeps 3
·
Oven · Dishwasher · In Unit Laundry ·
From
$121/nightProperty
Apartment · 1 Bed · 2 baths
Amenities
Oven
Dishwasher
In Unit Laundry
Wifi
Free Parking
Air Conditioning
Furnished
Other spaces
Kitchen, Workspace
Five Star Stay - Downtown 1BR/1BA
No reviews
·
Western Branch North
·
1 br
·
Sleeps 3
·
Hot Tub · In Unit Laundry · Kitchen ·
From
$123/nightProperty
Apartment · 1 Bed · 2 baths
Amenities
Hot Tub
In Unit Laundry
Wifi
Air Conditioning
Furnished
Garage Parking
Other spaces
Kitchen
NEW! Bright Chesapeake Home Near Shopping & Dining
No reviews
·
Western Branch North
·
2 br
·
Sleeps 4
·
Ceiling Fan · Toiletries · Tv ·
From
$80/nightProperty
House · 2 Beds · 1 bath
Amenities
Ceiling Fan
Toiletries
Tv
Cable
Microwave
Oven
Assigned Parking
Wifi
Other spaces
Kitchen
Studio | Free Breakfast. Indoor Pool & Hot Tub
No reviews
·
Indian River
·
Studio
·
Sleeps 3
·
Fitness Center · Oven · Dishwasher ·
From
$139/nightProperty
Apartment · Studio · 1 bath
Amenities
Fitness Center
Oven
Dishwasher
Hot Tub
In Unit Laundry
Pool
On Site Laundry
Free Parking
Other spaces
Kitchen
The best of Zumper, delivered
Be the first to hear about new listings matching your search.
Convenient to all 7 cities
No reviews
·
Western Branch North
·
3 br
·
Sleeps 6
·
Oven · In Unit Laundry · Kitchen ·
From
$199/nightProperty
House · 3 Beds · 3 baths
Amenities
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Garage Parking
Other spaces
Kitchen
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
No reviews
·
Indian River
·
Studio
·
Sleeps 3
·
Fitness Center · Oven · Dishwasher ·
From
$109/nightProperty
Apartment · Studio · 1 bath
Amenities
Fitness Center
Oven
Dishwasher
Hot Tub
In Unit Laundry
Pool
On Site Laundry
Free Parking
Other spaces
Kitchen
Studio | Free Breakfast. Indoor Pool & Hot Tub.
No reviews
·
Indian River
·
Studio
·
Sleeps 3
·
Fitness Center · Oven · Dishwasher ·
From
$109/nightProperty
Apartment · Studio · 1 bath
Amenities
Fitness Center
Oven
Dishwasher
Hot Tub
In Unit Laundry
Pool
On Site Laundry
Free Parking
Other spaces
Kitchen
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
8
Very good
·
Indian River
·
1 br
·
Sleeps 2
·
Fitness Center · Dishwasher · Hot Tub ·
From
$119/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Fitness Center
Dishwasher
Hot Tub
In Unit Laundry
Pool
On Site Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
No reviews
·
Indian River
·
1 br
·
Sleeps 4
·
Fitness Center · Dishwasher · Hot Tub ·
From
$119/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Fitness Center
Dishwasher
Hot Tub
In Unit Laundry
Pool
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
6
Good
·
Indian River
·
1 br
·
Sleeps 6
·
Fitness Center · Dishwasher · Hot Tub ·
From
$129/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Fitness Center
Dishwasher
Hot Tub
In Unit Laundry
Pool
On Site Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
9
Excellent
·
Indian River
·
2 br
·
Sleeps 6
·
Fitness Center · Dishwasher · Hot Tub ·
From
$299/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Fitness Center
Dishwasher
Hot Tub
In Unit Laundry
Pool
On Site Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Great Studio | Pool & Hot Tub. Your Next Vacation
No reviews
·
Indian River
·
Studio
·
Sleeps 2
·
Fitness Center · Oven · Dishwasher ·
From
$109/nightProperty
Apartment · Studio · 1 bath
Amenities
Fitness Center
Oven
Dishwasher
Hot Tub
In Unit Laundry
Pool
On Site Laundry
Free Parking
Other spaces
Kitchen
Luxurious home in Chesapeake
10
Excellent
·
Western Branch South
·
4 br
·
Sleeps 9
·
Fireplace · In Unit Laundry · Kitchen ·
From
$252/nightProperty
House · 4 Beds · 3 baths
Amenities
Fireplace
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Hidden gem in the heart of Chesapeake, Va. Minutes away from Chesapeake Regional
8
Very good
·
Greenbrier West
·
3 br
·
Sleeps 5
·
Outdoor Space · Oven · Dishwasher ·
From
$101/nightProperty
House · 3 Beds · 3 baths
Amenities
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
WoodSpring Suites Chesapeake-Norfolk Greenbrier
5.6
Good
·
Indian River
·
1 br
·
Sleeps 4
·
Smoking Allowed · Wifi · On Site Laundry ·
From
$48/nightProperty
Hotel · 1 Bed
Amenities
Smoking Allowed
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Wheelchair Accessible
Elevator
WoodSpring Suites Chesapeake-Norfolk South
5.4
Good
·
Greenbrier West
·
1 br
·
Sleeps 4
·
Smoking Allowed · Wifi · On Site Laundry ·
From
$59/nightProperty
Hotel · 1 Bed
Amenities
Smoking Allowed
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Wheelchair Accessible
Elevator
American Inn Chesapeake - Portsmouth
5.6
Good
·
Western Branch South
·
1 br
·
Sleeps 4
·
Assigned Parking · Smoking Allowed · Carpet ·
From
$56/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Smoking Allowed
Carpet
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Other spaces
Workspace
InTown Suites Extended Stay Chesapeake VA - Battlefield Blvd
3.8
Poor
·
Greenbrier West
·
1 br
·
Sleeps 4
·
Assigned Parking · Kitchen · Workspace ·
From
$36/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Other spaces
Kitchen, Workspace
Bowers Hill Inn Chesapeake
6.2
Good
·
Western Branch South
·
1 br
·
Sleeps 4
·
Assigned Parking · Carpet · Workspace ·
From
$50/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Carpet
Wifi
Free Parking
Air Conditioning
Furnished
Other spaces
Workspace
Extended Stay America Suites - Chesapeake - Churchland Blvd
5.5
Good
·
Western Branch North
·
1 br
·
Sleeps 10
·
Assigned Parking · Carpet · Kitchen ·
From
$57/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Carpet
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Other spaces
Kitchen, Workspace
Extended Stay America Suites - Chesapeake - Greenbrier Circle
6.6
Good
·
Indian River
·
1 br
·
Sleeps 10
·
Assigned Parking · Carpet · Kitchen ·
From
$58/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Carpet
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Other spaces
Kitchen, Workspace
Wingate by Wyndham Chesapeake
7.7
Very good
·
Indian River
·
1 br
·
Sleeps 4
·
Hot Tub · Carpet · In Unit Laundry ·
From
$69/nightProperty
Hotel · 1 Bed
Amenities
Hot Tub
Carpet
In Unit Laundry
Pool
Wifi
On Site Laundry
Free Parking
Air Conditioning
Other spaces
Workspace
Hyatt Place Chesapeake
8
Very good
·
Greenbrier East
·
1 br
·
Sleeps 6
·
Pool · Workspace · Wifi ·
From
$84/nightProperty
Hotel · 1 Bed
Amenities
Pool
Wifi
Free Parking
Air Conditioning
Furnished
Business Center
Swimming Pool
Fitness Center
Other spaces
Workspace
Extended Stay America Suites - Chesapeake - Crossways Blvd
6
Good
·
Greenbrier East
·
1 br
·
Sleeps 10
·
Assigned Parking · Carpet · Kitchen ·
From
$49/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Carpet
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Other spaces
Kitchen, Workspace
Days Inn by Wyndham Chesapeake
5.1
Good
·
Deep Creek North
·
1 br
·
Sleeps 10
·
Assigned Parking · Workspace · Wifi ·
From
$54/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Wifi
Free Parking
Air Conditioning
Furnished
Other spaces
Workspace
Quality Inn Chesapeake
4.5
Good
·
Greenbrier West
·
1 br
·
Sleeps 4
·
Assigned Parking · Workspace · Wifi ·
From
$52/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Other spaces
Workspace
Economy 7 Inn Chesapeake - Portsmouth
5
Good
·
Western Branch North
·
1 br
·
Sleeps 10
·
Carpet · Workspace · Wifi ·
From
$49/nightProperty
Hotel · 1 Bed · 1 bath
Amenities
Carpet
Wifi
On Site Laundry
Air Conditioning
Furnished
Wheelchair Accessible
Elevator
Other spaces
Workspace
Aloft Chesapeake
7.8
Very good
·
Greenbrier East
·
1 br
·
Sleeps 5
·
Fireplace · Outdoor Space · Smoking Allowed ·
From
$76/nightProperty
Hotel · 1 Bed
Amenities
Fireplace
Smoking Allowed
Pool
Wifi
On Site Laundry
Air Conditioning
Furnished
Fitness Center
Other spaces
Workspace
Comfort Suites Chesapeake - Norfolk
7.6
Very good
·
Greenbrier East
·
1 br
·
Sleeps 4
·
Assigned Parking · Smoking Allowed · Workspace ·
From
$67/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Smoking Allowed
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Other spaces
Workspace
Econo Lodge Chesapeake Route 13 and I-464
5.7
Good
·
South Norfolk
·
1 br
·
Sleeps 4
·
Carpet · Workspace · Wifi ·
From
$61/nightProperty
Hotel · 1 Bed
Amenities
Carpet
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Other spaces
Workspace
Comfort Inn & Suites Chesapeake - Portsmouth
5.3
Good
·
Deep Creek North
·
1 br
·
Sleeps 10
·
Assigned Parking · Pool · Workspace ·
From
$54/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Pool
Wifi
Free Parking
Furnished
Swimming Pool
Other spaces
Workspace
InTown Suites Extended Stay Chesapeake VA - I-64 Crossways Blvd
5.5
Good
·
Greenbrier East
·
1 br
·
Sleeps 4
·
Hardwood Floor · Assigned Parking · Carpet ·
From
$42/nightProperty
Hotel · 1 Bed
Amenities
Hardwood Floor
Assigned Parking
Carpet
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Other spaces
Kitchen, Workspace
Fairfield by Marriott Chesapeake
8.3
Very good
·
Greenbrier East
·
1 br
·
Sleeps 4
·
Smoking Allowed · Pool · Workspace ·
From
$67/nightProperty
Hotel · 1 Bed
Amenities
Smoking Allowed
Pool
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Dry Cleaning Service
Other spaces
Workspace
Courtyard Chesapeake Greenbrier
6.7
Good
·
Greenbrier East
·
1 br
·
Sleeps 4
·
Fireplace · Outdoor Space · Smoking Allowed ·
From
$63/nightProperty
Hotel · 1 Bed
Amenities
Fireplace
Smoking Allowed
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Other spaces
Workspace
Residence Inn by Marriott Chesapeake Greenbrier
8.1
Very good
·
Greenbrier East
·
1 br
·
Sleeps 6
·
Fireplace · Outdoor Space · Dishwasher ·
From
$96/nightProperty
Hotel · 1 Bed
Amenities
Fireplace
Dishwasher
Smoking Allowed
Carpet
Pool
Wifi
On Site Laundry
Free Parking
Other spaces
Kitchen, Workspace
SpringHill Suites Chesapeake Greenbrier
7.8
Very good
·
Greenbrier East
·
1 br
·
Sleeps 5
·
Smoking Allowed · Pool · Workspace ·
From
$76/nightProperty
Hotel · 1 Bed
Amenities
Smoking Allowed
Pool
On Site Laundry
Air Conditioning
Furnished
Fitness Center
Residents Lounge
Dry Cleaning Service
Other spaces
Workspace
Delta Hotels by Marriott Chesapeake Norfolk
8
Very good
·
Indian River
·
1 br
·
Sleeps 4
·
Fireplace · Outdoor Space · Smoking Allowed ·
From
$73/nightProperty
Hotel · 1 Bed
Amenities
Fireplace
Smoking Allowed
Carpet
Pool
Wifi
On Site Laundry
Free Parking
Air Conditioning
Other spaces
Workspace
Hampton Inn & Suites Chesapeake-Square Mall
7.6
Very good
·
Western Branch South
·
1 br
·
Sleeps 5
·
Assigned Parking · Smoking Allowed · Carpet ·
From
$80/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Smoking Allowed
Carpet
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Other spaces
Workspace
Homewood Suites by Hilton Chesapeake - Greenbrier
7.9
Very good
·
Greenbrier East
·
1 br
·
Sleeps 6
·
Outdoor Space · Dishwasher · Smoking Allowed ·
From
$88/nightProperty
Hotel · 1 Bed
Amenities
Dishwasher
Smoking Allowed
Pool
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Other spaces
Kitchen, Workspace
Hilton Garden Inn Chesapeake Greenbrier
7.5
Very good
·
Greenbrier East
·
1 br
·
Sleeps 5
·
Outdoor Space · Carpet · Workspace ·
From
$74/nightProperty
Hotel · 1 Bed
Amenities
Carpet
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Dry Cleaning Service
Other spaces
Workspace
Holiday Inn Express Chesapeake - Norfolk, an IHG Hotel
8.2
Very good
·
Indian River
·
1 br
·
Sleeps 4
·
Outdoor Space · Carpet · Pool ·
From
$66/nightProperty
Hotel · 1 Bed
Amenities
Carpet
Pool
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Other spaces
Workspace
Fairfield Inn & Suites by Marriott Chesapeake Suffolk
8
Very good
·
Western Branch North
·
1 br
·
Sleeps 6
·
Hot Tub · Smoking Allowed · Workspace ·
From
$92/nightProperty
Hotel · 1 Bed
Amenities
Hot Tub
Smoking Allowed
Wifi
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Other spaces
Workspace
Holiday Inn Express & Suites Chesapeake, an IHG Hotel
7.8
Very good
·
Western Branch North
·
1 br
·
Sleeps 4
·
Hot Tub · Carpet · Pool ·
From
$75/nightProperty
Hotel · 1 Bed
Amenities
Hot Tub
Carpet
Pool
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Other spaces
Workspace
Candlewood Suites Chesapeake-Suffolk, an IHG Hotel
7.3
Very good
·
Western Branch North
·
1 br
·
Sleeps 4
·
Dishwasher · Kitchen · Workspace ·
From
$83/nightProperty
Hotel · 1 Bed
Amenities
Dishwasher
On Site Laundry
Free Parking
Air Conditioning
Furnished
Fitness Center
Dry Cleaning Service
Business Center
Other spaces
Kitchen, Workspace
Staybridge Suites Chesapeake-Virginia Beach, an IHG Hotel
8.4
Very good
·
Indian River
·
1 br
·
Sleeps 6
·
Fireplace · Outdoor Space · Dishwasher ·
From
$99/nightProperty
Hotel · 1 Bed
Amenities
Fireplace
Dishwasher
Hot Tub
Smoking Allowed
Pool
Wifi
On Site Laundry
Free Parking
Other spaces
Kitchen, Workspace
Hampton Inn & Suites Chesapeake-Battlefield Boulevard
8
Very good
·
Greenbrier West
·
1 br
·
Sleeps 6
·
Hot Tub · Smoking Allowed · Carpet ·
From
$84/nightProperty
Hotel · 1 Bed
Amenities
Hot Tub
Smoking Allowed
Carpet
Pool
On Site Laundry
Free Parking
Air Conditioning
Furnished
Other spaces
Workspace
Showing 1 - 50 of 68 results
Updated: March 19, 2023
Learn about vacation rentals in
Chesapeake
Explore 69 vacation rentals near Chesapeake, Virginia. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Chesapeake, you can see photos of Chesapeake vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Chesapeake vacation rentals in specific areas. Whether you’re looking for a Chesapeake staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Chesapeake is $36 per night and the highest price is $299 per night.
16 of the vacation rentals near Chesapeake are
apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation
units is $120 per night. There are
currently 7 vacation units under this
price. 19 of the vacation rentals near Chesapeake are houses.
The average bathroom count for a vacation house near Chesapeake is
2. The average price for vacation houses near Chesapeake is $163 per night. There are 8 vacation homes under this price. The most common
amenities for vacation rentals near Chesapeake are: furnished, air conditioning, and free parking. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
43 available
2 bed rentals
6 available
3 bed rentals
9 available
4+ bed rentals
7 available
Getting around Chesapeake
Walking
1/10
You’ll need another mode of transportation for getting around. Scooter, anyone?
Car
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit
0/10
FYI, there are little to no public transit options within walking distance.
Points of interest in Chesapeake
Groceries
1/10
No grocery stores within walking distance
Shopping
1/10
Few or no shops within walking distance
Cafes
1/10
Few or no cafés within walking distance
Restaurants
1/10
Few or no restaurants within walking distance
Parks
1/10
Minimal park space nearby
Nightlife
0/10
Few or no bars within walking distance
Vacation Rentals in Chesapeake, VA FAQ
How many vacation rentals in Chesapeake are available?
There are currently 69 vacation rentals in Chesapeake available. Our vacation rentals in Chesapeake include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Chesapeake?
Yes, right now there are 24 pet friendly vacation rentals in Chesapeake. A pet friendly vacation rental in Chesapeake means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Chesapeake with a pool?
Yes there are vacation rentals with a pool available in Chesapeake, VA. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Chesapeake with internet access?
As of March 19, 2023, there are vacation rentals with internet access available in Chesapeake, Virginia. Check out more enjoyable destinations on Vacations by Zumper.
