A golf course, a large building complex, and a marina by a river.

Holiday Homes in Chesapeake

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chesapeake holiday homes

Terrace/patio

1. 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, (54 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Private kitchen

2. 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, (30 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is AU$439
includes taxes & fees
22 Sept - 23 Sept
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Living area

3. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
8.8 out of 10, Excellent, (12 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
The price is AU$314
includes taxes & fees
21 Sept - 22 Sept
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Private kitchen

4. Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.0 out of 10, Very good, (47 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is AU$479
includes taxes & fees
1 Oct - 2 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Beach

5. 5 Min Walk to the Beach • Spacious 3BR/2.5BA Home

5 Min Walk to the Beach • Spacious 3BR/2.5BA Home
East Ocean View
10.0 out of 10, Exceptional, (1 review)
The price is AU$749
includes taxes & fees
21 Sept - 22 Sept
5 Min Walk to the Beach • Spacious 3BR/2.5BA Home
Dining

6. Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (36 reviews)
"Great little house beach was good for small kids first trip to beach"
United States
Layton H.
The price is AU$556
includes taxes & fees
24 Sept - 25 Sept
Sojourn | Coastal Cottage | 3 BR
Interior

7. Cozy 1-bedroom barn in amazing Hampton with cool AC

Cozy 1-bedroom barn in amazing Hampton with cool AC
Hampton
10.0 out of 10, Exceptional, (3 reviews)
"Great place and great value!"
United States
Jim K.
The price is AU$245
includes taxes & fees
18 Sept - 19 Sept
Cozy 1-bedroom barn in amazing Hampton with cool AC
Beach

8. Cozy Beach Home in Oceanview

Cozy Beach Home in Oceanview
Bayview
9.8 out of 10, Exceptional, (47 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
United States
Conor L.
Cozy Beach Home in Oceanview
Interior

9. Bright 3-bedroom beach house with AC in charming Norfolk

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.4 out of 10, Exceptional, (10 reviews)
The price is AU$541
includes taxes & fees
21 Sept - 22 Sept
Bright 3-bedroom beach house with AC in charming Norfolk
Private kitchen

10. Charming 3bd - Near beaches - Foosball & Backyard

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.6 out of 10, Exceptional, (13 reviews)
"The property was great, 5 min walk to the beach. House was bright and cheery with plenty of space for our stay."
United States
Debbie M.
The price is AU$617
includes taxes & fees
21 Sept - 22 Sept
Charming 3bd - Near beaches - Foosball & Backyard
Living area

11. Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard

Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
Bayview
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home that is very close to the ocean with lots of options of things to do. We had a wonderful stay!"
United States
Nate K.
The price is AU$803
includes taxes & fees
21 Sept - 22 Sept
Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
Dining

12. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Great property not too far from the beaches! Between the pool, hot tub, mini golf, and theater room, our family had plenty to do at the house when we weren't out exploring Virginia Beach. Owner was quick to respond to any questions or needs as well."
United States
Erin W.
The price is AU$947
includes taxes & fees
20 Sept - 21 Sept
Wooded Wonderland
Living area

13. Beautiful, spacious home in welcoming Norfolk.

Beautiful, spacious home in welcoming Norfolk.
Norfolk
7.4 out of 10, Good, (3 reviews)
"Host was great, very responsive. The house was great and very clean. Very quiet neighborhood. Short drive to everything Norfolk and Virginia Beach had to offer."
United States
shereece t.
The price is AU$862
includes taxes & fees
20 Sept - 21 Sept
Beautiful, spacious home in welcoming Norfolk.
Living area

14. Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
8.8 out of 10, Excellent, (8 reviews)
The price is AU$551
includes taxes & fees
28 Sept - 29 Sept
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Interior

15. Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
Cottage Park
9.0 out of 10, Wonderful, (6 reviews)
"Very nice place. We enjoyed the fire pit every night and the easy walk to the beach was a plus."
United States
Robin T.
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
Property grounds

16. Cozy 1-bedroom barn in marvelous Hampton with AC

Cozy 1-bedroom barn in marvelous Hampton with AC
Hampton
The price is AU$281
includes taxes & fees
13 Oct - 14 Oct
Cozy 1-bedroom barn in marvelous Hampton with AC
Property grounds

17. Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
8.0 out of 10, Very good, (4 reviews)
"Great house"
United States
sarah a.
The price is AU$637
includes taxes & fees
20 Sept - 21 Sept
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Interior

18. 2 Minutes Walk to the BEACH

2 Minutes Walk to the BEACH
East Ocean View
10.0 out of 10, Exceptional, (1 review)
"Convenient location. Nice big rooms and great bathrooms. A lot of room to gather with open concept 1st floor. I would recommend this property."
United States
Lisa A.
2 Minutes Walk to the BEACH
Exterior

19. 3BR East Ocean View Home/Game Room on 3rd Floor + Fire Pit Yard/Walk to Beach

3BR East Ocean View Home/Game Room on 3rd Floor + Fire Pit Yard/Walk to Beach
East Ocean View
10.0 out of 10, Exceptional, (3 reviews)
"The house was immaculate and well-appointed throughout. A great place for family vacations!"
United States
Larkin J.
The price is AU$803
includes taxes & fees
30 Sept - 1 Oct
3BR East Ocean View Home/Game Room on 3rd Floor + Fire Pit Yard/Walk to Beach
Living area

20. Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
10.0 out of 10, Exceptional, (3 reviews)
"Great value for the money, great hosts, very renter friendly"
United States
WILLIAM M.
The price is AU$761
includes taxes & fees
22 Sept - 23 Sept
Unique Luxurious Waterfront in Hampton
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake Hotel Reviews

Ocean Resort

Ocean Resort

10/10 Excellent
"The view was great, and the fact that it was close to everything, made it easy access to everything that we wanted to do."
Melissa 5-night trip
Posted 2 hours ago
Ocean Resort

Find out more about Chesapeake

Chesapeake Holiday Homes information

Number of reviews
313
Accommodation
1296 Holiday Homes
Lowest Price
AU$245
Highest Price
AU$947