
Holiday Homes in Chesapeake
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chesapeake holiday homes

1. Entire Home in Chesapeake, Virginia
Entire Home in Chesapeake, VirginiaChesapeake
The price is €540
includes taxes & fees
23 Nov - 24 Nov

2. 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 €254
includes taxes & fees
16 Nov - 17 Nov

3. Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8
Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8Portsmouth
9.4 out of 10, Exceptional, (8 reviews)
The price is €280
includes taxes & fees
15 Nov - 16 Nov

4. 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 €227
includes taxes & fees
20 Nov - 21 Nov

5. 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 €249
includes taxes & fees
1 Dec - 2 Dec

6. 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 €209
includes taxes & fees
15 Nov - 16 Nov

7. Wooded Wonderland
Wooded WonderlandPortsmouth
9.6 out of 10, Exceptional, (15 reviews)
The price is €524
includes taxes & fees
16 Nov - 17 Nov

8. 3D Theater plus Dock on Small Lake
3D Theater plus Dock on Small LakePortsmouth
8.6 out of 10, Excellent, (4 reviews)
The price is €341
includes taxes & fees
15 Nov - 16 Nov

9. Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath HouseNorfolk
8.6 out of 10, Excellent, (93 reviews)

10. Beachfront Bungalow w/ BEST Location in Ocean View!
Beachfront Bungalow w/ BEST Location in Ocean View!Norfolk
8.4 out of 10, Very good, (28 reviews)

11. Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet FriendlyBayview
8.6 out of 10, Excellent, (10 reviews)
The price is €321
includes taxes & fees
18 Nov - 19 Nov

12. Bright 3-bedroom beach house with AC in charming Norfolk
Bright 3-bedroom beach house with AC in charming NorfolkWilloughby Spit
9.6 out of 10, Exceptional, (15 reviews)
The price is €316
includes taxes & fees
16 Nov - 17 Nov

13. Downtown Newport News | Great Area!
Downtown Newport News | Great Area!Hudson Terrace
6.8 out of 10, (11 reviews)
The price is €350
includes taxes & fees
12 Nov - 13 Nov

14. Charming 3bd - Near beaches - Foosball & Backyard
Charming 3bd - Near beaches - Foosball & BackyardBayview
9.8 out of 10, Exceptional, (16 reviews)
The price is €344
includes taxes & fees
22 Nov - 23 Nov

15. Cozy 1-bedroom barn in marvelous Hampton with AC
Cozy 1-bedroom barn in marvelous Hampton with ACHampton
10.0 out of 10, Exceptional, (2 reviews)
The price is €326
includes taxes & fees
12 Nov - 13 Nov

16. bedroom house in charming E City perfect for relaxing
bedroom house in charming E City perfect for relaxingElizabeth City
2.0 out of 10, (2 reviews)
The price is €137
includes taxes & fees
12 Nov - 13 Nov

17. Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable
Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cableElizabeth City
The price is €133
includes taxes & fees
8 Dec - 9 Dec

18. Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!Willoughby Spit
8.6 out of 10, Excellent, (10 reviews)
The price is €386
includes taxes & fees
12 Nov - 13 Nov
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.
Find holiday rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Chesapeake Hotel Reviews

YourSpace Hotels Chesapeake
10/10 Excellent
Find out more about Chesapeake
Chesapeake Holiday Homes information
Number of reviews | 205 |
|---|---|
Accommodation | 1258 Holiday Homes |
Lowest Price | €133 |
Highest Price | €540 |























































