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

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 540 Rentals in the Chesapeake Area
loading...
From
$275
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
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
$1,054
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
Hot Tub
22 photos Details
Reviews (2) Make Enquiry
From
$1,097
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 7
19 photos Details
Reviews (6) Make Enquiry
Also consider
Cutty Sark Historic Beach Cottage White House -West Wing
2 Bedrooms, sleeps 8
$59 - $280 / night
Quaint Beach Cottage, Walking Distance To Beach
2 Bedrooms, sleeps 6
$134 - $188 / night
BELLISSIMO
9 Bedrooms, sleeps 28
$592 - $2,113 / night
BELLA VITA DI MARE
11 Bedrooms, sleeps 32
$859 - $3,072 / night
From
$188
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Other outdoor space, Pet friendly, Private Pool & more
19 photos Details
Reviews (1) Make Enquiry
From
$1,807
Per Week
5 Bedrooms, 3 Bathrooms, Sleeps 13
Hot Tub, Internet, Fireplace
15 photos Details
Reviews (3) Make Enquiry
From
$200
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Suitable for children, Elder access, Internet & more
12 photos Details
Reviews (1) Make Enquiry
From
$3,313
Per Week
10 Bedrooms, 10 Bathrooms, Sleeps 22
Internet, Hot Tub, Outdoor Pool
14 photos Details
Reviews (4) Make Enquiry
From
$108
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 4
Bookings
Pool, Public pool, Other outdoor space & more
14 photos Details
Reviews (1) Make Enquiry
Get the List
From
$161
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Elder access, Suitable for children & more
7 photos Details
Reviews (1) Make Enquiry
From
$188
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Public pool, Internet, Parking & more
18 photos Details
Reviews (1) Make Enquiry
From
$134
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Suitable for children, Pet friendly
4 photos Details
Reviews (1) Make Enquiry
From
$134
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Internet, Sauna, Elder access & more
19 photos Details
Reviews (1) Make Enquiry
From
$2,038
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
Grill, Elder access, Hot Tub & more
15 photos Details
Reviews (4) Make Enquiry
From
$134
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Fitness Room, Suitable for children, Elder access & more
13 photos Details
Reviews (2) Make Enquiry
From
$1,931
Per Week
5 Bedrooms, 3 Bathrooms, Sleeps 15
Grill, Internet, Suitable for children & more
19 photos Details
Reviews (1) Make Enquiry
From
$188
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
Bookings
Washer/Dryer, Garden, Other outdoor space & more
27 photos Details
Reviews (2) Make Enquiry
From
$645
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (1) Make Enquiry
From
$1,065
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details
Reviews (1) Make Enquiry
From
$1,291
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
30 photos Details
Reviews (5) Make Enquiry
From
$963
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details
Reviews (1) Make Enquiry
From
$796
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 10
20 photos Details
Reviews (1) Make Enquiry
From
$1,280
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 9
22 photos Details
Reviews (1) Make Enquiry
From
$1,614
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
22 photos Details
Reviews (3) Make Enquiry
From
$850
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Reviews (3) Make Enquiry
From
$785
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (1) Make Enquiry
From
$678
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (2) Make Enquiry
From
$1,108
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Reviews (1) Make Enquiry
From
$699
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (3) Make Enquiry
From
$1,635
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (3) Make Enquiry
From
$748
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Reviews (1) Make Enquiry
From
$1,070
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
22 photos Details
Reviews (1) Make Enquiry
From
$748
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (3) Make Enquiry
From
$1,178
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 5
18 photos Details
Reviews (1) Make Enquiry
From
$640
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (2) Make Enquiry
From
$775
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (3) Make Enquiry
From
$785
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (1) Make Enquiry
From
$1,323
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
21 photos Details
Reviews (1) Make Enquiry
From
$748
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (2) Make Enquiry
From
$678
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
Reviews (2) Make Enquiry
From
$1,097
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
21 photos Details
Reviews (2) Make Enquiry
Go to map view
Book Online(52)
Use filters to find the best results!

Suitability

  • Wheelchair access (30)
  • Elder access (119)
  • Suitable for children (138)
  • Pet friendly (64)
  • Smoking allowed (0)

Amenities

  • Internet (382)
  • All pools (265)
  • Hot Tub (186)
  • Grill (120)
  • Other outdoor space (115)
  • 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