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 villas in Chesapeake, VA

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
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 540 Rentals in the Chesapeake Area
loading...
From
€192
Per Night
Chesapeake
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
29 photos Details
Reviews (21) Make Enquiry

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

From
€75
Per Night
Virginia Beach
2 Bedrooms, 3 Bathrooms, Sleeps 4
Bookings
14 photos Details
Reviews (1) Make Enquiry
From
€112
Per Night
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
Reviews (1) Make Enquiry
Also consider
Quaint Beach Cottage, Walking Distance To Beach
2 Bedrooms, sleeps 6
€94 - €131 / night
BELLISSIMO
9 Bedrooms, sleeps 28
€412 - €1,472 / night
BELLA VITA DI MARE
11 Bedrooms, sleeps 32
€599 - €2,141 / night
LYNNHAVEN RESORT
10 Bedrooms, sleeps 30
€479 - €1,873 / night
From
€131
Per Night
Virginia Beach
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
18 photos Details
Reviews (1) Make Enquiry
From
€94
Per Night
Norfolk
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
4 photos Details
Reviews (1) Make Enquiry
From
€94
Per Night
Virginia Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
19 photos Details
Reviews (1) Make Enquiry
From
€139
Per Night
Virginia Beach
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
12 photos Details
Reviews (1) Make Enquiry
From
€94
Per Night
Virginia Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
13 photos Details
Reviews (2) Make Enquiry
Get the List
From
€131
Per Night
Virginia Beach
3 Bedrooms, 4 Bathrooms, Sleeps 6
Bookings
27 photos Details
Reviews (2) Make Enquiry
From
€160
Per Night
Virginia Beach
4 Bedrooms, 4 Bathrooms, Sleeps 10
43 photos Details
Reviews (6) Make Enquiry
From
€112
Per Night
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
11 photos Details
Reviews (1) Make Enquiry
From
€112
Per Night
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
Reviews (1) Make Enquiry
From
€194
Per Night
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
6 photos Details
Reviews (1) Make Enquiry
From
€119
Per Night
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
27 photos Details
Reviews (7) Make Enquiry
From
€101
Per Night
Virginia Beach
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
9 photos Details
Reviews (8) Make Enquiry
From
€1,443
Per Week
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
Reviews (1) Make Enquiry
From
€202
Per Night
Virginia Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
14 photos Details
Make Enquiry
From
€225
Per Night
Norfolk
3 Bedrooms, 3 Bathrooms, Sleeps 8
21 photos Details
Make Enquiry
From
€148
Per Night
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
Make Enquiry
From
€375
Per Night
Virginia Beach
8 Bedrooms, 6 Bathrooms, Sleeps 22
Booking
20 photos Details
Make Enquiry
From
€169
Per Night
Norfolk
1 Bedroom, 1 Bathroom, Sleeps 2
5 photos Details
Make Enquiry
From
€187
Per Night
Virginia Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
23 photos Details
Make Enquiry
From
€693
Per Week
Virginia Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
8 photos Details
Make Enquiry
From
€169
Per Night
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
Make Enquiry
From
€187
Per Night
Norfolk
4 Bedrooms, 4 Bathrooms, Sleeps 12
34 photos Details
Make Enquiry
From
€1,199
Per Week
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 6
Booking
5 photos Details
Make Enquiry
From
€3,935
Per Week
Virginia Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 photos Details
Make Enquiry
From
€268
Per Night
Virginia Beach
5 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
15 photos Details
Make Enquiry
From
€187
Per Night
Virginia Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
21 photos Details
Make Enquiry
From
€225
Per Night
Virginia Beach
4 Bedrooms, 3 Bathrooms, Sleeps 12
22 photos Details
Make Enquiry
From
€824
Per Week
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
Make Enquiry
From
€416
Per Night
Virginia Beach
3 Bedrooms, 3 Bathrooms, Sleeps 10
5 photos Details
Make Enquiry
From
€225
Per Night
Virginia Beach
3 Bedrooms, 4 Bathrooms, Sleeps 8
14 photos Details
Make Enquiry
From
€110
Per Night
Virginia Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
5 photos Details
Make Enquiry
From
€214
Per Night
Virginia Beach
5 Bedrooms, 4 Bathrooms, Sleeps 12
24 photos Details
Make Enquiry
From
€75
Per Night
Virginia Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
6 photos Details
Make Enquiry
From
€170
Per Night
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Make Enquiry
From
€146
Per Night
Virginia Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
7 photos Details
Make Enquiry
From
€225
Per Night
Virginia Beach
4 Bedrooms, 3 Bathrooms, Sleeps 12
23 photos Details
Make Enquiry
From
€225
Per Night
Virginia Beach
2 Bedrooms, 2 Bathrooms, Sleeps 8
10 photos Details
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