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

Holiday Homes in Chesapeake

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chesapeake holiday homes

A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window.

1. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
Chesapeake
The price is AU$841
includes taxes & fees
9 Nov - 10 Nov
Entire Home in Chesapeake, Virginia
A covered porch with a hanging chair, a small table, and a view of a snowy yard.

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)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is AU$396
includes taxes & fees
4 Nov - 5 Nov
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

3. Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect experience for our vacation and we highly recommend this property and the host was so easy to get in contact with!"
United States
Coachmeech Gaming O.
The price is AU$376
includes taxes & fees
20 Nov - 21 Nov
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

4. 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, (32 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$390
includes taxes & fees
1 Dec - 2 Dec
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

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

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.0 out of 10, Very good, (49 reviews)
"The location suited our business travel needs. Never received checkin details so had to call. WiFi did not work and no response to multiple inquiries about the issue. Areas of damage throughout the house."
United States
Jebediah
The price is AU$464
includes taxes & fees
2 Nov - 3 Nov
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A poolside area with a covered seating area, a pool, and a white fence.

6. 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, (13 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$329
includes taxes & fees
4 Nov - 5 Nov
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

7. 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$823
includes taxes & fees
8 Nov - 9 Nov
Wooded Wonderland
A wooden deck with a railing overlooking a lake, surrounded by lush greenery.

8. 3D Theater plus Dock on Small Lake

3D Theater plus Dock on Small Lake
Portsmouth
8.6 out of 10, Excellent, (4 reviews)
"Very nice property. Quiet neighborhood with a beautiful lake view."
United States
Muun Queen M.
The price is AU$589
includes taxes & fees
2 Nov - 3 Nov
3D Theater plus Dock on Small Lake
A beach with a pier extending into the water, featuring a building labeled 'BART & GRILL'.

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 House
Willoughby Spit
8.8 out of 10, Excellent, (92 reviews)
"Nice small rustic cottage right on the beach. Enjoyed my time there."
United States
Mary W.
The price is AU$365
includes taxes & fees
2 Nov - 3 Nov
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

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

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.6 out of 10, Exceptional, (14 reviews)
"The property is spacious and conveniently located near the beach and restaurants. It is family-friendly and the host is exceptionally communicative. I plan to return in the future."
United States
Sheryll
The price is AU$449
includes taxes & fees
2 Nov - 3 Nov
Bright 3-bedroom beach house with AC in charming Norfolk
A kitchen with a wooden island, bar stools, a ceiling fan, and a refrigerator.

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

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
8.6 out of 10, Excellent, (10 reviews)
"Very Clean, beautiful property situated just blocks from the beach. Neighborhood was very friendly. The entire stay in this charming cottage was delightful!"
United States
Todd C.
The price is AU$501
includes taxes & fees
9 Nov - 10 Nov
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

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

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.8 out of 10, Exceptional, (16 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
22 Nov - 23 Nov
Charming 3bd - Near beaches - Foosball & Backyard
A sunlit room with a ceiling fan, two wicker chairs with cushions, a striped rug, and a small table with a plant.

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

Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
Cottage Park
9.2 out of 10, Wonderful, (7 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.
The price is AU$647
includes taxes & fees
2 Nov - 3 Nov
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
A waterfront view from a wooden deck with a white railing, a dock extending into the water, and a clear blue sky.

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

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
8.8 out of 10, Excellent, (9 reviews)
"Wake Up early for the views"
United States
Dylan
The price is AU$623
includes taxes & fees
2 Nov - 3 Nov
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
A staircase with a black metal railing leading to a bedroom with a bed and a gray blanket.

15. Townhome 3 Blks from Boardwalk uC

Townhome 3 Blks from Boardwalk uC
Northeast Virginia Beach
10.0 out of 10, Exceptional, (4 reviews)
"Owner was very responsive and great location"
United States
Sarah S.
The price is AU$419
includes taxes & fees
2 Nov - 3 Nov
Townhome 3 Blks from Boardwalk uC
A two-story building with a balcony, a satellite dish, and a small garden area.

16. bedroom house in charming E City perfect for relaxing

bedroom house in charming E City perfect for relaxing
Elizabeth City
2.0 out of 10, (2 reviews)
"They didn't tell me they had somebody living on site until I was on my way there, between midnight and 2:30 a.m., because I told them I would be late, getting there.There was somebody else there when I got there in the room that I was supposed to be in, plus the person that lives on site.The key was where it was supposed to be, but the outside door was locked, and I rang the doorbell several times, and contacted the host, by calling and sending messages, and I still had to wait about 20 minutes...
United States
Thomas M.
The price is AU$217
includes taxes & fees
2 Nov - 3 Nov
bedroom house in charming E City perfect for relaxing
A balcony with a table and two chairs, overlooking a body of water with boats and buildings in the background.

17. Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
8.4 out of 10, Very good, (6 reviews)
"Nice! "
United States
Sawyer P.
The price is AU$345
includes taxes & fees
2 Nov - 3 Nov
Knot Three- Balcony View of ICW- Dog Friendly!
A spacious living room with hardwood flooring, a ceiling fan, a large plant, and a sofa.

18. Downtown Newport News | Great Area!

Downtown Newport News | Great Area!
Hudson Terrace
6.8 out of 10, (11 reviews)
"Nice check in "
United States
Brian S.
The price is AU$585
includes taxes & fees
2 Nov - 3 Nov
Downtown Newport News | Great Area!
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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Top Chesapeake Hotel Reviews

Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

8/10 Good
"Nice place and clean and outside was clean didn't eat brebut smelt good."
Katrina 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Hampton near Coliseum

Find out more about Chesapeake

Chesapeake Holiday Homes information

Number of reviews
253
Accommodation
1296 Holiday Homes
Lowest Price
AU$217
Highest Price
AU$841