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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Chesapeake vacation homes

Terrace/patio

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, (48 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is ￥35,327
￥60,331 total
includes taxes & fees
Jul 29 - Jul 30
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Interior

Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk

Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk
Hampton
The price is ￥25,138
￥33,524 total
includes taxes & fees
Jul 13 - Jul 14
Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk
Exterior

Oceanfront Estate | 18BR | Private Pool & Hot Tub | Sleeps 40 | 4x4 OBX

Oceanfront Estate | 18BR | Private Pool & Hot Tub | Sleeps 40 | 4x4 OBX
Corolla
9.6 out of 10, Exceptional, (13 reviews)
"The property is amazing. We saw wild horses and wild pigs. The pool is fabulous and the beach beautiful. Driving on the sand was scary at first but we figured it out. Be sure to air down your tires."
United States
Adele W.
The price is ￥781,482
￥1,002,426 total
includes taxes & fees
Jul 10 - Jul 11
Oceanfront Estate | 18BR | Private Pool & Hot Tub | Sleeps 40 | 4x4 OBX
Beach nearby

Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach

Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach
Corolla
9.8 out of 10, Exceptional, (26 reviews)
"Property as described, we had a great time! Will definitely be back. "
United States
Linda B.
The price is ￥77,846
￥215,224 total
includes taxes & fees
Aug 8 - Aug 9
Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach
Terrace/patio

Carrick Bend -Balcony View of ICW- Dog Friendly!

Carrick Bend -Balcony View of ICW- Dog Friendly!
Coinjock
8.0 out of 10, Very Good, (3 reviews)
"There were already sheets in the machine, so I didnt strip beds. Also, locked door before we grabbed the trash, sorry."
United States
Kimberley M.
The price is ￥37,574
￥82,958 total
includes taxes & fees
Jul 22 - Jul 23
Carrick Bend -Balcony View of ICW- Dog Friendly!
Outdoor dining

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)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
United States
Pam P.
The price is ￥24,218
￥48,519 total
includes taxes & fees
Jul 22 - Jul 23
Knot Three- Balcony View of ICW- Dog Friendly!
TV

9BR Ocean Estate • Pool • Hot Tub, 350 FT to Beach

9BR Ocean Estate • Pool • Hot Tub, 350 FT to Beach
Sandbridge
9BR Ocean Estate • Pool • Hot Tub, 350 FT to Beach
Terrace/patio

New! / 5bd/3Bth, Boat, Surf, Swim, Kayak, Hot Tub

New! / 5bd/3Bth, Boat, Surf, Swim, Kayak, Hot Tub
Sandbridge
9.0 out of 10, Wonderful, (2 reviews)
"Family gathered for a wedding. Off-season so no pool or going to the beach (one street over). We loved the house and everything it offers!"
United States
Debrah M.
The price is ￥127,326
￥315,666 total
includes taxes & fees
Jul 22 - Jul 23
New! / 5bd/3Bth, Boat, Surf, Swim, Kayak, Hot Tub
Exterior

NEW! Boat Ramp, Pool, Hot Tub

NEW! Boat Ramp, Pool, Hot Tub
Sandbridge
10.0 out of 10, Exceptional, (2 reviews)
"Was great setup for our needs. Really good layout with the balcony upstairs and the enclosed patio beneath. Pool and being on the water was nice."
United States
Anonymous traveler
The price is ￥243,766
￥454,276 total
includes taxes & fees
Jul 22 - Jul 23
NEW! Boat Ramp, Pool, Hot Tub
Terrace/patio

New! Boat Dock /Pool /HotTub/ Waterfront/ Beach

New! Boat Dock /Pool /HotTub/ Waterfront/ Beach
Sandbridge
8.0 out of 10, Very Good, (1 review)
"Certain things could have been better, I think we got a lot of automated messages with wrong info which was infuriating but overall had a great trip"
United States
Ankit P.
The price is ￥225,519
￥415,040 total
includes taxes & fees
Jul 19 - Jul 20
New! Boat Dock /Pool /HotTub/ Waterfront/ Beach
Fridge, microwave, oven, stovetop

Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach

Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach
Dam Neck
9.4 out of 10, Exceptional, (101 reviews)
"Great location "
United States
chris m.
The price is ￥145,800
￥245,768 total
includes taxes & fees
Jul 30 - Jul 31
Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach
Outdoor dining

Spacious 5BR + 2 Bonus Sleeping Rooms Beach Retreat| Private Pool, Hot Tub & Game Room

Spacious 5BR + 2 Bonus Sleeping Rooms Beach Retreat| Private Pool, Hot Tub & Game Room
Dam Neck
10.0 out of 10, Exceptional, (1 review)
"Perfect beach house for a big familyWe had a great stay! The house was in a perfect location just one block from the beach, spacious, and fit my family of 15 comfortably. There were plenty of beach chairs, wagons, and toys, which made it perfect for the whole family.The only small issue was limited towels (1 per person) and missing shampoo/body wash. The host was quick to respond and delivered body wash and shampoo early the next morning.Def recommend it to families looking for a spacious home...
United States
Ashley A.
The price is ￥224,204
￥477,737 total
includes taxes & fees
Aug 5 - Aug 6
Spacious 5BR + 2 Bonus Sleeping Rooms Beach Retreat| Private Pool, Hot Tub & Game Room
Beach nearby, sun loungers, beach towels

The Rooftop Coastal Escape @ 10 Ocean: Modern Luxury home with Oceanview!

The Rooftop Coastal Escape @ 10 Ocean: Modern Luxury home with Oceanview!
Northeast Virginia Beach
The Rooftop Coastal Escape @ 10 Ocean: Modern Luxury home with Oceanview!
Sun loungers, beach towels

Oceanfront Oasis — Steps to Sand & Surf

Oceanfront Oasis — Steps to Sand & Surf
Northeast Virginia Beach
10.0 out of 10, Exceptional, (5 reviews)
"There was a lot of things I loved about this place very ez to find key less entrance and garage even my car was safe "
United States
Yvette b.
Oceanfront Oasis — Steps to Sand & Surf
Pool

Cozy 2-bedroom townhome in gorgeous Virginia Beach 3 blocks to the beach!

Cozy 2-bedroom townhome in gorgeous Virginia Beach 3 blocks to the beach!
Northeast Virginia Beach
The price is ￥51,817
￥100,388 total
includes taxes & fees
Jul 15 - Jul 16
Cozy 2-bedroom townhome in gorgeous Virginia Beach 3 blocks to the beach!
2 bedrooms, iron/ironing board, WiFi, bed sheets

Townhome 3 Blks from Boardwalk uC

Townhome 3 Blks from Boardwalk uC
Northeast Virginia Beach
The price is ￥43,626
￥91,996 total
includes taxes & fees
Jul 13 - Jul 14
Townhome 3 Blks from Boardwalk uC
Exterior detail

Magnificent, original Va Beach home located a 3 minute walk from the ocean!

Magnificent, original Va Beach home located a 3 minute walk from the ocean!
Northeast Virginia Beach
9.8 out of 10, Exceptional, (87 reviews)
"Beautiful home, close to the beach and restaurants! Beds were comfortable and neighborhood was nice and quiet. "
United States
constance s.
The price is ￥64,658
￥110,834 total
includes taxes & fees
Jul 27 - Jul 28
Magnificent, original Va Beach home located a 3 minute walk from the ocean!
Smart TV, fireplace

Comfort near the water and University

Comfort near the water and University
Elizabeth city
8.0 out of 10, Very Good, (7 reviews)
"Everything was wonderful"
United States
Marc
The price is ￥14,596
￥48,198 total
includes taxes & fees
Aug 3 - Aug 4
Comfort near the water and University
Exterior

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 ￥14,888
￥25,988 total
includes taxes & fees
Jul 9 - Jul 10
bedroom house in charming E City perfect for relaxing
Smart TV

Comfort & Quiet in a Central location

Comfort & Quiet in a Central location
Elizabeth City
4.0 out of 10, (2 reviews)
"It is in a nice, quiet neighborhood with a good location. The place was clean-ish, but could be more clean. There were no exhaust fans in the bathrooms, which made for a damp smell and a humid area to get ready for the day. Barely any extra amenities like linens, pillows, towels, washcloths, or toilet paper. There is a washer and drier but no laundry soap to use. An ok place to stay in a pinch, but not my first choice."
United States
Amanda R.
The price is ￥16,218
￥58,278 total
includes taxes & fees
Aug 3 - Aug 4
Comfort & Quiet in a Central location
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

Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

8/10 Good
"Everything was great about the property but 2 things. One, when we took showers there was standing water that eventually drained, not a major issue, but still. Two, there were WAY too many kids up on the rooftop pool where the sky bar was located. It almost seemed like the pool was a babysitting tool for the parents drinking at the bar. Other than that, I would recommend this place still."
Jamie 3-night trip
Posted less than an hour ago
Hilton Virginia Beach Oceanfront

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
258
Accommodation
1353 Vacation Homes
Lowest Price
￥25,988
Highest Price
￥1,002,426