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Our top choices for Chesapeake holiday rentals

1. Great Studio | Pool & Hot Tub. Your Next Vacation
Great Studio | Pool & Hot Tub. Your Next VacationChesapeake
10.0 out of 10, Exceptional, (3 reviews)
The price is NZ$271
includes taxes & fees
29 Nov - 30 Nov

2. Entire Home in Chesapeake, Virginia
Entire Home in Chesapeake, VirginiaChesapeake
The price is NZ$1,173
includes taxes & fees
29 Nov - 30 Nov

3. King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!Chesapeake
9.0 out of 10, Wonderful, (2 reviews)
The price is NZ$296
includes taxes & fees
29 Nov - 30 Nov

4. Entire Home in Chesapeake, Virginia
Entire Home in Chesapeake, VirginiaChesapeake
The price is NZ$1,090
includes taxes & fees
29 Nov - 30 Nov

5. 3-bedroom home away from home in fabulous Chesapeake, Virginia.
3-bedroom home away from home in fabulous Chesapeake, Virginia.Chesapeake
10.0 out of 10, Exceptional, (56 reviews)
The price is NZ$495
includes taxes & fees
16 Nov - 17 Nov

6. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
1 Bedroom | Free Breakfast. Indoor Pool & Hot TubChesapeake
The price is NZ$442
includes taxes & fees
27 Nov - 28 Nov

7. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!Chesapeake
The price is NZ$320
includes taxes & fees
29 Nov - 30 Nov

8. King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!Chesapeake
The price is NZ$296
includes taxes & fees
29 Nov - 30 Nov

9. Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!Chesapeake
7.8 out of 10, Good, (7 reviews)
The price is NZ$320
includes taxes & fees
29 Nov - 30 Nov

10. Studio | Free Breakfast. Indoor Pool & Hot Tub.
Studio | Free Breakfast. Indoor Pool & Hot Tub.Chesapeake
The price is NZ$271
includes taxes & fees
29 Nov - 30 Nov

11. Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!Chesapeake
9.4 out of 10, Exceptional, (8 reviews)
The price is NZ$626
includes taxes & fees
29 Nov - 30 Nov

12. stayAPT Suites Suffolk-Chesapeake
stayAPT Suites Suffolk-ChesapeakeSuffolk
9.6 out of 10, Exceptional, (119 reviews)
The price is NZ$247
includes taxes & fees
23 Nov - 24 Nov

13. Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in PortsmouthPortsmouth
9.4 out of 10, Exceptional, (10 reviews)
The price is NZ$455
includes taxes & fees
20 Nov - 21 Nov

14. Private 1 Bed Apt - Historic Olde Towne Portsmouth
Private 1 Bed Apt - Historic Olde Towne PortsmouthPortsmouth
9.8 out of 10, Exceptional, (21 reviews)
The price is NZ$311
includes taxes & fees
16 Nov - 17 Nov

15. Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!Portsmouth
9.2 out of 10, Wonderful, (29 reviews)
The price is NZ$617
includes taxes & fees
16 Nov - 17 Nov

16. Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!Portsmouth
9.2 out of 10, Wonderful, (33 reviews)
The price is NZ$492
includes taxes & fees
30 Nov - 1 Dec

17. stayAPT Suites Hampton
stayAPT Suites HamptonColiseum Central
9.2 out of 10, Wonderful, (42 reviews)
The price is NZ$239
includes taxes & fees
16 Nov - 17 Nov

18. Guesthouse in ideal location with private entrance
Guesthouse in ideal location with private entranceSuffolk
10.0 out of 10, Exceptional, (7 reviews)
The price is NZ$521
includes taxes & fees
16 Nov - 17 Nov

19. The SEA-renity 11 cozy apartment across from the beach
The SEA-renity 11 cozy apartment across from the beachCottage Line
The price is NZ$180
includes taxes & fees
7 Dec - 8 Dec

20. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Charming 1-bedroom in-law suite with functional kitchen in pleasant PortsmouthPortsmouth
8.8 out of 10, Excellent, (13 reviews)
The price is NZ$426
includes taxes & fees
1 Dec - 2 Dec
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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