Chesapeake Holiday Rentals

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Check prices for these dates

Tonight
30 Jun - 1 Jul
Tomorrow
1 Jul - 2 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Holiday Rentals in Chesapeake

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Indoor pool

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

2.5 star property
9.0 out of 10, Wonderful, (2)
"Good location and spacious rooms. Good stay!"
The price is HK$1,529
HK$1,965 total
includes taxes & fees
14 Jul - 15 Jul
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
The Atrium Resort, Virginia Beach by Vacatia
Beach nearby

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1372)
"perfect location and comfortable stays "
The Atrium Resort, Virginia Beach by Vacatia
The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1378)
"Staff was friendly, nice rooms"
The Ocean Key Virginia Beach Resort
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Terrace/patio

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1087)
"very friendly, nice location"
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
stayAPT Suites Suffolk-Chesapeake
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (25)
"Nice hotel, will stay again."
The price is HK$934
HK$1,073 total
includes taxes & fees
1 Jul - 2 Jul
stayAPT Suites Suffolk-Chesapeake
Angie's Guest Cottage
Property entrance

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (208)
"Room was very clean staff was very pleasant"
The price is HK$933
HK$1,166 total
includes taxes & fees
2 Jul - 3 Jul
Angie's Guest Cottage
Four Sails Resort
Indoor pool

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (35)
"Very nice place"
Four Sails Resort
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Smart TV, fireplace, video games, DVD player

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

9.8 out of 10, Exceptional, (173)
"This property is well maintained and is just as promised in the description. Owner is very helpful and responsive."
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
“Cozy VB Getaway” near Premium Outlets-Pet Friendly
Private kitchen

“Cozy VB Getaway” near Premium Outlets-Pet Friendly

10.0 out of 10, Exceptional, (2)
"My girlfriend and I really enjoyed our stay, its really bigger than it looks in the pics. The assistant keep in constant contact with us to make sure we were enjoying our stay. Definitely would recommend this property!"
The price is HK$1,295
HK$3,527 total
includes taxes & fees
1 Jul - 2 Jul
“Cozy VB Getaway” near Premium Outlets-Pet Friendly
C9083 Cavallo Dunes. Oceanfront, 3 Bedrooms, Hot Tub, Pets OK, 4x4 Area
TV

C9083 Cavallo Dunes. Oceanfront, 3 Bedrooms, Hot Tub, Pets OK, 4x4 Area

8.8 out of 10, Excellent, (6)
"The place was as advertised. There was one lamp in the living room that's cord ran under a chair to a socket. The socket didn't work, so i rerouted to a hallway socket at night. Everything else worked perfectly fine. The beach was spacious and the house was nice. "
C9083 Cavallo Dunes. Oceanfront, 3 Bedrooms, Hot Tub, Pets OK, 4x4 Area
Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV
Microwave, oven, stovetop, cookware/dishes/utensils

Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV

6.0 out of 10, (2)
"Property is perfect for several college students on a shoe string budget."
The price is HK$1,170
HK$2,055 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV
Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach
Property grounds

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 HK$6,947
HK$11,643 total
includes taxes & fees
24 Jul - 25 Jul
Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
Exterior

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

9.8 out of 10, Exceptional, (102)
"Property was perfect for a small family trip to the beach. Just a short walk to a beautiful beach. House was clean and well appointed"
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
On the beach, sun-loungers

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

9.0 out of 10, Wonderful, (63)
"We had a great time"
The price is HK$1,562
HK$2,795 total
includes taxes & fees
1 Jul - 2 Jul
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Charming Tiny Cottage
1 bedroom, WiFi, bed sheets

Charming Tiny Cottage

10.0 out of 10, Exceptional, (32)
"Quiet area, great proximity to beach. Can hear waves and watch sunrise on front deck while sipping coffee. Wild horses walk through yard. "
Charming Tiny Cottage
The Art Door only minutes from beach
Property grounds

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (80)
"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 HK$942
HK$2,020 total
includes taxes & fees
23 Jul - 24 Jul
The Art Door only minutes from beach
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Terrace/patio

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

6.4 out of 10, (5)
The price is HK$3,132
HK$5,467 total
includes taxes & fees
1 Jul - 2 Jul
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
4x4 Corolla, Waterfront, Dock, Wild Horses, Kayak
Property grounds

4x4 Corolla, Waterfront, Dock, Wild Horses, Kayak

9.6 out of 10, Exceptional, (4)
"Everything was as described. Very clean"
4x4 Corolla, Waterfront, Dock, Wild Horses, Kayak
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
Smart TV, video games, DVD player, video library

Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

9.0 out of 10, Wonderful, (16)
"Great location and views. Property needs some updates and fixes. Good connectivity, TV's etc. We enjoyed our stay. "
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub
On the beach, sun-loungers

Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub

9.8 out of 10, Exceptional, (136)
"The house is absolutely incredible and a very nice place to stay. The homeowner is a joy to work with. The horses come right around the house and the ocean never disappoints! Hope to stay again! "
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub
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 38 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 Oak Grove Lake Park and Chesapeake City 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.