Holiday Rentals in Chesapeake

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Holiday Rentals in Chesapeake

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 €217
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

3.5 star property
8.2 out of 10, Very good, (1377)
"perfect location and comfortable stays "
The Atrium Resort, Virginia Beach by Vacatia

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1379)
"Staff was friendly, nice rooms"
The Ocean Key Virginia Beach Resort

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1090)
"very friendly, nice location"
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (26)
"Nice hotel, will stay again."
The price is €135
includes taxes & fees
10 Jul - 11 Jul
stayAPT Suites Suffolk-Chesapeake

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (212)
"Very Cozy and near the beach, Staff is very courteous and friendly. "
The price is €125
includes taxes & fees
13 Jul - 14 Jul
Angie's Guest Cottage

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (36)
"Very nice place"
Four Sails Resort

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

7.4 out of 10, Good, (3)
"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 €388
includes taxes & fees
5 Jul - 6 Jul
“Cozy VB Getaway” near Premium Outlets-Pet Friendly

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

6.0 out of 10, (2)
"Property is perfect for several college students on a shoe string budget."
The price is €227
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

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 €1,326
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.

9.8 out of 10, Exceptional, (103)
"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.

OBX 4X4 Ocean View- Pipers Place Wild Horse Haven!!!

9.6 out of 10, Exceptional, (4)
"Be prepared for a 10 mile drive on the beach! Would definitely stay in this area again."
OBX 4X4 Ocean View- Pipers Place Wild Horse Haven!!!

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 €309
includes taxes & fees
7 Jul - 8 Jul
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

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

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 €224
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!

6.4 out of 10, (5)
The price is €717
includes taxes & fees
7 Jul - 8 Jul
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

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

9.6 out of 10, Exceptional, (5)
"The suite was immaculate and comfortable, and perfect to accommodate a small party on a getaway to OBX! Our hosts were AMAZING. Our Jeep broke down and we were so thankful that our hosts also happen to own a towing and recovery business serving the Corolla area. They towed us, taxied us, and repaired our Jeep in less than 24 hours. We are so happy we found this place and that we got to meet our wonderful hosts. Awesome people! "
4x4 Corolla, Waterfront, Dock, Wild Horses, Kayak

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.
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.