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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chesapeake holiday homes

A two-story house with a front porch, a garage, and a well-maintained lawn.

1. Hike, Beach & Explore! Family Home in Chesapeake

Hike, Beach & Explore! Family Home in Chesapeake
Chesapeake
Hike, Beach & Explore! Family Home in Chesapeake
A living room with a flat-screen TV mounted on the wall, a dark leather couch, and a coffee table with game cases.

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 HK$1,208
HK$2,316 total
includes taxes & fees
20 Oct - 21 Oct
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A bedroom with a bed, a ceiling fan, and a view of a balcony.

3. Spacious 4-bedroom townhome in gorgeous Chesapeake with AC and fitness room

Spacious 4-bedroom townhome in gorgeous Chesapeake with AC and fitness room
Deep Creek South
The price is HK$2,747
HK$6,126 total
includes taxes & fees
17 Nov - 18 Nov
Spacious 4-bedroom townhome in gorgeous Chesapeake with AC and fitness room
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

4. 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 HK$629
HK$2,064 total
includes taxes & fees
20 Oct - 21 Oct
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A living room with a beige sofa, a green armchair, and a white armchair. There is a large plant, a wooden floor, and a ceiling vent.

5. 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 8
Portsmouth
9.4 out of 10, Exceptional, (8 reviews)
"There for a softball Tournament. Close to the highway easy to find"
United States
Ryan H.
Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

6. 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, (31 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 HK$785
HK$2,262 total
includes taxes & fees
2 Nov - 3 Nov
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.

7. 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 HK$1,118
HK$1,887 total
includes taxes & fees
19 Oct - 20 Oct
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

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

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.0 out of 10, Very good, (48 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is HK$1,012
HK$2,740 total
includes taxes & fees
21 Oct - 22 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A kitchen with wooden cabinets, a stainless steel stove, a refrigerator, and a washing machine.

9. ODU Cozy Cottage with river views near bars, grills, brewery! 2 br/1 bath house!

ODU Cozy Cottage with river views near bars, grills, brewery! 2 br/1 bath house!
Norfolk
10.0 out of 10, Exceptional, (1 review)
"Great stay"
United States
Anonymous traveller
The price is HK$1,264
HK$2,443 total
includes taxes & fees
22 Oct - 23 Oct
ODU Cozy Cottage with river views near bars, grills, brewery! 2 br/1 bath house!
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

10. 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 HK$2,437
HK$5,218 total
includes taxes & fees
19 Oct - 20 Oct
Wooded Wonderland
A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

11. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very nice! And the host was in full contact with us throughout our stay to make sure we had everything we needed. Also, our family LOVED the video games. "
United States
Elaine P.
The price is HK$1,852
HK$4,906 total
includes taxes & fees
5 Nov - 6 Nov
Centrally Located Hampton Roads Home w/ Game Room!
A room with a pool table, a refrigerator, a staircase, and walls decorated with vinyl records.

12. 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, (5 reviews)
The price is HK$615
HK$2,103 total
includes taxes & fees
19 Oct - 20 Oct
Cozy 1-bedroom barn in amazing Hampton with cool AC
A kitchen with a wooden island, bar stools, a ceiling fan, and a refrigerator.

13. 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 HK$1,059
HK$2,939 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

14. 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
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.

15. 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.
The price is HK$1,256
HK$3,649 total
includes taxes & fees
20 Oct - 21 Oct
Beach Bungalow King Bed 1 Floor Living
A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

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

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.6 out of 10, Exceptional, (15 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 HK$1,144
HK$3,361 total
includes taxes & fees
20 Oct - 21 Oct
Charming 3bd - Near beaches - Foosball & Backyard
A staircase with white railings and a blue wall. There is a white door with glass panels and a fire extinguisher on a shelf.

17. Coastal home w/ pool, hot tub & fire pit

Coastal home w/ pool, hot tub & fire pit
Willoughby Spit
8.0 out of 10, Very good, (4 reviews)
"The property was very accommodating for all us who stayed there. The pool area was great and enjoyed by all. Enjoyed home-cooked meals vs. going out. Great location, close to Walmart and other fast food restaurants."
United States
Kyle H.
The price is HK$1,044
HK$3,834 total
includes taxes & fees
28 Oct - 29 Oct
Coastal home w/ pool, hot tub & fire pit
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 HK$1,151
HK$4,084 total
includes taxes & fees
26 Oct - 27 Oct
Unique Luxurious Waterfront in Hampton
A sunlit room with a ceiling fan, two wicker chairs with cushions, a striped rug, and a small table with a plant.

19. 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 HK$1,288
HK$3,707 total
includes taxes & fees
20 Oct - 21 Oct
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
A balcony with a table and two chairs, overlooking a body of water with boats and buildings in the background.

20. 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 HK$827
HK$1,897 total
includes taxes & fees
19 Oct - 20 Oct
Knot Three- Balcony View of ICW- Dog Friendly!
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

Schooner Inn

Schooner Inn

10/10 Excellent
"Wonderful stay while there the view was amazing and the price was perfect"
Tyler 2-night trip
Posted 5 hours ago
Schooner Inn

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
190
Accommodation
1274 Vacation Homes
Lowest Price
HK$1,887
Highest Price
HK$5,218

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