Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

3-bedroom home away from home in fabulous Chesapeake, Virginia.

2.0 star property
10.0 out of 10, Exceptional, (27)
"The house is very cozy for my husband, furkidz, and I! The furkidz enjoyed being in a fenced in back yard with places to run!"
The price is NZ$540
includes taxes & fees
8 Aug - 9 Aug
3-bedroom home away from home in fabulous Chesapeake, Virginia.

4x4 Carova, WaterFront, Dock, Wild Horses, Hot Tub

10.0 out of 10, Exceptional, (6)
"We were looking for a quite place to get away and this was it."
4x4 Carova, WaterFront, Dock, Wild Horses, Hot Tub

Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

10.0 out of 10, Exceptional, (30)
"Quiet, great views, great property and dock, overall amazing experience for me and my family."
The price is NZ$846
includes taxes & fees
17 July - 18 July
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

Carrick Bend -Balcony View of ICW- Dog Friendly!

The price is NZ$854
includes taxes & fees
21 July - 22 July
Carrick Bend -Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!

9.6 out of 10, Exceptional, (4)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
The price is NZ$490
includes taxes & fees
13 July - 14 July
Knot Three- Balcony View of ICW- Dog Friendly!

New! Sandbridge Beach, 5bd/3Bth, Boat, Surf, Swim

10.0 out of 10, Exceptional, (1)
"Very clean- lots of spaces to relax - the game room was a HUGH hit with our teens! "
The price is NZ$2,951
includes taxes & fees
14 July - 15 July
New! Sandbridge Beach, 5bd/3Bth, Boat, Surf, Swim

New! VA Beach, 5bd/3Bth, Boat, Surf, Swim, Kayak

The price is NZ$2,845
includes taxes & fees
10 Aug - 11 Aug
New! VA Beach, 5bd/3Bth, Boat, Surf, Swim, Kayak

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

8.0 out of 10, Very good, (1)
"We loved the location of this property. We were only 2 blocks from the beach so we didn't have to deal with finding parking for our cars. (The driveway had plenty of room for us to park our 4 cars).The house was very spaceous. There were 13 of us and everyone had a bed. There were 3 bathrooms which was great too. The dining table was big enough to allow us all to gather around for meals. The pool was a big hit with the three kids and everyone enjoyed the multilevel deck. Ryan was our host and...
The price is NZ$3,405
includes taxes & fees
3 Aug - 4 Aug
New! Boat Dock /Pool /HotTub/ Waterfront/ Beach

Reunion Paradise! Upscale 5300 SQ FT PLUS Hot Tub, Sauna, Steam Shower, 50' Pool

8.4 out of 10, Very good, (61)
"Everything was great had a fantastic stay!"
The price is NZ$4,178
includes taxes & fees
15 July - 16 July
Reunion Paradise! Upscale 5300 SQ FT PLUS Hot Tub, Sauna, Steam Shower, 50' Pool

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

9.4 out of 10, Exceptional, (92)
"Great spot with lots of room. Beautiful neighborhood. Easy walk to the beach. Great amenities!"
The price is NZ$2,438
includes taxes & fees
10 Aug - 11 Aug
Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach

Peaceful Bliss Retreat Free Parking

Peaceful Bliss Retreat Free Parking

Coastal Serenity Retreat

9.0 out of 10, Wonderful, (2)
"Nice and quiet, no problem checking in. Would have appreciated a few more towels for the bathroom but other than that we enjoyed our visit."
The price is NZ$388
includes taxes & fees
11 Aug - 12 Aug
Coastal Serenity Retreat

Beachside Bliss Hideaway

The price is NZ$1,282
includes taxes & fees
21 July - 22 July
Beachside Bliss Hideaway

Sojourn The Ocean Breeze in Virginia Beach

10.0 out of 10, Exceptional, (5)
"This was the perfect rental for a weekend in VA Beach while attending an event at the Sports Center. The unit is very comfortable, clean, and super cute! The owner was extremely communicative and even left us some snacks and a bottle of wine. There are a ton of cute restaurants and coffee shops within walking distance."
The price is NZ$965
includes taxes & fees
10 Aug - 11 Aug
Sojourn The Ocean Breeze in Virginia Beach

2 min walk to the beach! Gorgeous and spacious home perfect for a group!

10.0 out of 10, Exceptional, (17)
"From the initial reservation through check out, everything went smoothly. Our host, Yun, was very gracious and accommodating. The house was well kept, clean and very comfortable for our party of six adults. Great location just off the beach and within walking distance to many restaurants and bars. "
The price is NZ$1,849
includes taxes & fees
10 Aug - 11 Aug
2 min walk to the beach! Gorgeous and spacious home perfect for a group!

2 Bedroom Townhome 2 blks to VB Boardwalk

The price is NZ$790
includes taxes & fees
13 July - 14 July
2 Bedroom Townhome 2 blks to VB Boardwalk

Townhome 3 Blks from Boardwalk

The price is NZ$802
includes taxes & fees
14 July - 15 July
Townhome 3 Blks from Boardwalk

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (81)
"Loved the stay! Property was very clean, quiet and easy to get to everything Virginia Beach has to offer. The property manager was very quick to respond and helpful. Will stay there again"
The price is NZ$429
includes taxes & fees
6 Aug - 7 Aug
The Art Door only minutes from beach

{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach

8.8 out of 10, Excellent, (35)
"Beach Baby Bingo place is nice, neat, and comfortable. It is near the places (15 to 17 minutes drive )where we would like to visit in VA Beach like the VA aquarium and VA Beach front plus it is also nearby an Asian store. "
The price is NZ$981
includes taxes & fees
13 July - 14 July
{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach

Charming 3-bedroom upstairs unit apartment with WiFi and AC in Virginia Beach!!!

2.0 star property
8.0 out of 10, Very good, (3)
"Would do it again "
Charming 3-bedroom upstairs unit apartment with WiFi and AC in Virginia Beach!!!
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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Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Broadmoor Play Area, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and popular beaches in Chesapeake. While you're in the area, you can also enjoy the top-notch restaurants and live music.

What are some of the best holiday rentals that Chesapeake has to offer?

C9083 Cavallo Dunes. Oceanfront, 3 Bedrooms, Hot Tub, Pets OK, 4x4 Area: This holiday home rental outside of Chesapeake is located by the ocean, and offers 1 hot tub, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chesapeake?

Expedia has 36 holiday rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Broadmoor Play Area and Parkview Play Area, whereas Chesapeake City Park and Oak Grove Lake Park are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Naval Station Norfolk and Sandbridge Beach.

What’s a holiday rental in Chesapeake like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for small groups.