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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chesapeake holiday homes

A covered porch with a hanging chair, a small table, and a view of a snowy yard.

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, (55 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.
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

2. 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)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

3. 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 €264
includes taxes & fees
28 Sept - 29 Sept
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

4. 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 €227
includes taxes & fees
18 Oct - 19 Oct
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A modern kitchen with white cabinets, stainless steel appliances, a double sink, and a window with a view.

5. Spacious Portsmouth Getaway w/Game Room

Spacious Portsmouth Getaway w/Game Room
Portsmouth
7.0 out of 10, Good, (2 reviews)
"This property is in a great location near beach and also casino"
United States
JOSIE G.
The price is €373
includes taxes & fees
27 Sept - 28 Sept
Spacious Portsmouth Getaway w/Game Room
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

6. 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 €308
includes taxes & fees
27 Oct - 28 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A beach with a wooden boardwalk leading to the water, sandy dunes, and a clear sky.

7. 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)
5 Min Walk to the Beach • Spacious 3BR/2.5BA Home
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

8. 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, (13 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 €332
includes taxes & fees
30 Sept - 1 Oct
Bright 3-bedroom beach house with AC in charming Norfolk
A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

9. Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.6 out of 10, Exceptional, (23 reviews)
"The property was conveniently located at the beach yet close to Regent University. A great parents’ weekend and graduation getaway spot."
United States
Thomas M.
Beach Bungalow King Bed 1 Floor Living
A garage with a green sofa, a white table, and a patterned chair.

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

Cozy 1-bedroom barn in marvelous Hampton with AC
Hampton
10.0 out of 10, Exceptional, (1 review)
The price is €180
includes taxes & fees
4 Oct - 5 Oct
Cozy 1-bedroom barn in marvelous Hampton with AC
A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

11. 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.
Charming 3bd - Near beaches - Foosball & Backyard
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

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 €597
includes taxes & fees
27 Sept - 28 Sept
Wooded Wonderland
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
9.0 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
A kitchen with a wooden island, bar stools, a ceiling fan, and a refrigerator.

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 €340
includes taxes & fees
13 Oct - 14 Oct
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
A waterfront view from a wooden deck with a white railing, a dock extending into the water, and a clear blue sky.

15. 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, (6 reviews)
The price is €389
includes taxes & fees
30 Sept - 1 Oct
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
A compact room with a teal sofa, a white table, and a black chair.

16. 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, (4 reviews)
"Great place and great value!"
United States
Jim K.
The price is €142
includes taxes & fees
18 Oct - 19 Oct
Cozy 1-bedroom barn in amazing Hampton with cool AC
A loft-style living room with a wooden ceiling, a ping pong table, a sofa, and a ladder leading to a lofted area.

17. 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.
3BR East Ocean View Home/Game Room on 3rd Floor + Fire Pit Yard/Walk to Beach
A modern interior with a staircase leading to a second floor, a living area with a grey sofa, and a kitchen with wooden cabinets.

18. 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 €529
includes taxes & fees
18 Oct - 19 Oct
Unique Luxurious Waterfront in Hampton
A two-story house with a porch, a covered front entry, and a small front yard with landscaping.

19. Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (44 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is €473
includes taxes & fees
29 Sept - 30 Sept
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
A view through a window with a grid pattern, overlooking a calm sea and a sandy beach with a small structure and a lifebuoy.

20. Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.8 out of 10, Exceptional, (32 reviews)
"Great location. Excellent view. The F22 Raptors were cool to see. Not so loud. Host was great. The place does not have a full size oven, so plan accordingly. Beds were comfy."
United States
Jim G.
The price is €471
includes taxes & fees
18 Oct - 19 Oct
Sojourn Aviators Dream on Back River
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

Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

8/10 Good
"This was one of the best hotels I've ever stayed in. The guest services/concierge desk personnel were friendly and helpful. Unfortunately the information they have for the hours that the kitchen is in operation is wrong. The website for both Kascades lounge, and Crown Plaza list the hours for dinner service as being from 4-10pm. I arrived at Kascades Lounge at 9:15pm and I was told that the kitchen had already been closed for 15 minutes. The housekeeping staff need to.leave the thermostat for the rooms alone while a guest is checked in. When I initially got to the room, the thermostat was set for 62° but it couldn't register the temperature well because it was definitely colder than that in the room. I personally set the temperature at 72° so that the room would be more comfortable for me, after the 1st night, I did what I needed to do throughout the day and when I returned to the room, the thermostat had been set back to 62° and the towels had not been refilled, I had to call and ask if someone could be sent up with fresh towels. I left some soft and energy drinks in the mini fridge so they would be cold when I wanted then, when I got into the room before the 2nd night, the mini fridge was empty and the drinks were nowhere to be found."
Joseph 2-night trip
Posted 3 hours ago
Crowne Plaza Virginia Beach Town Center by IHG

Find out more about Chesapeake

Chesapeake Holiday Homes information

Number of reviews
325
Accommodation
1298 Holiday Homes
Lowest Price
€142
Highest Price
€597