We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes and Apartments Chesapeake, VA and nearby

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 531 Rentals in the Chesapeake Area
loading...
From
$272
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 12
Other outdoor space, Air Conditioning, Private Beach & more
29 photos Details
Reviews (21) Make Enquiry

The following rentals are within 25 kilometres of Chesapeake, Virginia.

From
$1,053
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details
Reviews (1) Make Enquiry
From
$1,096
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
22 photos Details
Reviews (1) Make Enquiry
Also consider
LYNNHAVEN RESORT
10 Bedrooms, sleeps 30
$680 - $2,659 / night
Huge 5BR Rental on Resort Strip Va Beach, Va Just 2300.00 Wkly
5 Bedrooms, sleeps 12
$585 / night
Pinch Me
8 Bedrooms, sleeps 22
$532 - $638 / night
Sandbridge Beach Ocean Front Condo
3 Bedrooms, sleeps 8
$266 / night
From
$1,851
Per Week
6 Bedrooms, 4 Bathrooms, Sleeps 16
Outdoor Pool, Hot Tub, Internet & more
9 photos Details
Reviews (1) Make Enquiry
From
$1,484
Per Week
6 Bedrooms, 3 Bathrooms, Sleeps 16
Outdoor Pool, Internet, Pet friendly
17 photos Details
Reviews (2) Make Enquiry
From
$207
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Internet, Sauna, Elder access & more
19 photos Details
Reviews (1) Make Enquiry
From
$207
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Fitness Room, Suitable for children, Elder access & more
14 photos Details
Reviews (1) Make Enquiry
From
$169
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Internet, Elder access, Parking & more
27 photos Details
Reviews (7) Make Enquiry
Get the List
From
$186
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
Washer/Dryer, Garden, Other outdoor space & more
27 photos Details
Reviews (2) Make Enquiry
From
$2,016
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
Grill, Elder access, Hot Tub & more
15 photos Details
Reviews (3) Make Enquiry
From
$1,910
Per Week
5 Bedrooms, 3 Bathrooms, Sleeps 15
Grill, Internet, Suitable for children & more
19 photos Details
Reviews (1) Make Enquiry
From
$160
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Elder access, Suitable for children & more
7 photos Details
Reviews (1) Make Enquiry
From
$840
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Reviews (3) Make Enquiry
From
$1,165
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
21 photos Details
Reviews (3) Make Enquiry
From
$1,277
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
30 photos Details
Reviews (5) Make Enquiry
From
$1,043
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
Hot Tub
22 photos Details
Reviews (2) Make Enquiry
From
$1,165
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 5
18 photos Details
Reviews (1) Make Enquiry
From
$739
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Reviews (1) Make Enquiry
From
$1,309
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
21 photos Details
Reviews (1) Make Enquiry
From
$739
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
17 photos Details
Reviews (1) Make Enquiry
From
$1,085
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 7
19 photos Details
Reviews (6) Make Enquiry
From
$739
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (3) Make Enquiry
From
$1,085
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 9
21 photos Details
Reviews (4) Make Enquiry
From
$1,117
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Reviews (2) Make Enquiry
From
$830
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (3) Make Enquiry
From
$670
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
Reviews (2) Make Enquiry
From
$692
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (3) Make Enquiry
From
$1,085
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
21 photos Details
Reviews (2) Make Enquiry
From
$1,617
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (3) Make Enquiry
From
$633
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (2) Make Enquiry
From
$1,053
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 9
20 photos Details
Reviews (1) Make Enquiry
From
$777
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (2) Make Enquiry
From
$851
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (6) Make Enquiry
From
$692
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (1) Make Enquiry
From
$952
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details
Reviews (1) Make Enquiry
From
$947
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
Reviews (2) Make Enquiry
From
$766
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (3) Make Enquiry
From
$1,165
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
22 photos Details
Reviews (2) Make Enquiry
From
$638
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (1) Make Enquiry
From
$1,309
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
Boat Available
22 photos Details
Reviews (5) Make Enquiry
Go to map view
Book Online(50)
Use filters to find the best results!

Suitability

  • Wheelchair access (27)
  • Elder access (117)
  • Suitable for children (136)
  • Pet friendly (63)
  • Smoking allowed (0)

Amenities

  • Internet (376)
  • All pools (260)
  • Hot Tub (183)
  • Grill (113)
  • Other outdoor space (108)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities