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.

Pet Friendly Vacation Rentals in Chesapeake

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
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
loading...

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

From
$187
Per Night
Virginia Beach
2 Bedrooms, 1 Bathroom, Sleeps 4
16 photos Details
Make Enquiry
From
$134
Per Night
Norfolk
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 photos Details
Make Enquiry
From
$214
Per Night
Virginia Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
12 photos Details
Make Enquiry
From
$213
Per Night
Virginia Beach
1 Bedroom, 1 Bathroom, Sleeps 4
1 photo Details
Make Enquiry
From
$208
Per Night
Virginia Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
19 photos Details
Make Enquiry
From
$1,816
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 12
11 photos Details
Reviews (2) Make Enquiry
From
$1,170
Per Week
Virginia Beach
5 Bedrooms, 4 Bathrooms, Sleeps 11
14 photos Details
Reviews (1) Make Enquiry
From
$1,773
Per Week
Virginia Beach
4 Bedrooms, 3 Bathrooms, Sleeps 12
12 photos Details
Reviews (1) Make Enquiry
Get the List
From
$1,656
Per Week
Virginia Beach
5 Bedrooms, 4 Bathrooms, Sleeps 16
16 photos Details
Reviews (1) Make Enquiry
From
$3,044
Per Week
Virginia Beach
7 Bedrooms, 4 Bathrooms, Sleeps 18
19 photos Details
Reviews (3) Make Enquiry
From
$2,297
Per Week
Virginia Beach
9 Bedrooms, 7 Bathrooms, Sleeps 20
16 photos Details
Reviews (1) Make Enquiry
From
$1,431
Per Week
Virginia Beach
4 Bedrooms, 3 Bathrooms, Sleeps 12
14 photos Details
Reviews (2) Make Enquiry
From
$1,325
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 14
18 photos Details
Reviews (2) Make Enquiry
From
$2,008
Per Week
Virginia Beach
6 Bedrooms, 5 Bathrooms, Sleeps 16
16 photos Details
Reviews (1) Make Enquiry
From
$1,597
Per Week
Virginia Beach
6 Bedrooms, 5 Bathrooms, Sleeps 20
16 photos Details
Reviews (1) Make Enquiry
From
$1,490
Per Week
Virginia Beach
6 Bedrooms, 3 Bathrooms, Sleeps 16
17 photos Details
Reviews (2) Make Enquiry
From
$2,131
Per Week
Virginia Beach
9 Bedrooms, 7 Bathrooms, Sleeps 20
18 photos Details
Reviews (2) Make Enquiry
From
$427
Per Night
Virginia Beach
7 Bedrooms, 5 Bathrooms, Sleeps 25
30 photos Details
Reviews (8) Make Enquiry
From
$1,730
Per Week
Virginia Beach
6 Bedrooms, 3 Bathrooms, Sleeps 15
24 photos Details
Reviews (3) Make Enquiry
From
$1,260
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 14
19 photos Details
Reviews (1) Make Enquiry
From
$636
Per Week
Virginia Beach
4 Bedrooms, 3 Bathrooms, Sleeps 12
11 photos Details
Reviews (1) Make Enquiry
From
$1,250
Per Week
Virginia Beach
4 Bedrooms, 3 Bathrooms, Sleeps 10
12 photos Details
Reviews (1) Make Enquiry
From
$1,442
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 12
13 photos Details
Reviews (3) Make Enquiry
From
$1,122
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 19
15 photos Details
Reviews (1) Make Enquiry
From
$1,704
Per Week
Virginia Beach
6 Bedrooms, 4 Bathrooms, Sleeps 17
19 photos Details
Reviews (2) Make Enquiry
From
$4,267
Per Week
Virginia Beach
11 Bedrooms, 10 Bathrooms, Sleeps 26
25 photos Details
Reviews (2) Make Enquiry
From
$1,538
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 13
15 photos Details
Reviews (2) Make Enquiry
From
$1,421
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 15
1 photo Details
Reviews (2) Make Enquiry
From
$2,254
Per Week
Virginia Beach
4 Bedrooms, 2 Bathrooms, Sleeps 8
16 photos Details
Reviews (1) Make Enquiry
From
$1,047
Per Week
Virginia Beach
6 Bedrooms, 3 Bathrooms, Sleeps 14
12 photos Details
Reviews (1) Make Enquiry
From
$1,250
Per Week
Virginia Beach
3 Bedrooms, 2 Bathrooms, Sleeps 10
11 photos Details
Reviews (2) Make Enquiry
From
$1,154
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 14
11 photos Details
Reviews (3) Make Enquiry
From
$1,228
Per Week
Virginia Beach
3 Bedrooms, 2 Bathrooms, Sleeps 11
13 photos Details
Reviews (2) Make Enquiry
From
$1,303
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 14
14 photos Details
Reviews (2) Make Enquiry
From
$620
Per Week
Virginia Beach
4 Bedrooms, 2 Bathrooms, Sleeps 10
11 photos Details
Reviews (2) Make Enquiry
From
$1,015
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 12
12 photos Details
Make Enquiry
From
$1,581
Per Week
Virginia Beach
6 Bedrooms, 3 Bathrooms, Sleeps 16
1 photo Details
Make Enquiry
From
$1,383
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 12
20 photos Details
Make Enquiry
From
$1,346
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 12
8 photos Details
Make Enquiry
From
$1,912
Per Week
Virginia Beach
6 Bedrooms, 4 Bathrooms, Sleeps 15
1 photo Details
Make Enquiry
From
$774
Per Week
Virginia Beach
5 Bedrooms, 3 Bathrooms, Sleeps 12
16 photos Details
Make Enquiry
Go to map view
Book Online(6)
Use filters to find the best results!

Suitability

  • Wheelchair access (1)
  • Elder access (15)
  • Suitable for children (17)
  • Pet friendly (59)
  • Smoking allowed (0)

Amenities

  • Internet (50)
  • All pools (32)
  • Hot Tub (25)
  • Grill (14)
  • Air Conditioning (11)
  • 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