Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1407)
"I love the rooms and the staff is very friendly. "
The Atrium Resort, Virginia Beach by Vacatia

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1396)
"The front desk staff who were working Tuesday, July 15th were nothing short of amazing and accommodating. I am truly thankful for the effort they made to make our stay as comfortable as possible!"
The price is AU$298
includes taxes & fees
29 July - 30 July
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, (1103)
"My family truly enjoyed our stay! Would definitely stay here again. "
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.4 out of 10, Exceptional, (29)
"Great place to stay!"
The price is AU$207
includes taxes & fees
4 Aug - 5 Aug
stayAPT Suites Suffolk-Chesapeake

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (217)
"Very Cozy and near the beach, Staff is very courteous and friendly. "
The price is AU$223
includes taxes & fees
27 July - 28 July
Angie's Guest Cottage

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

9.8 out of 10, Exceptional, (175)
"Amazing house, great location! This house was perfect for our family vacation. The wild horses strolled by a few times and the owner was great on giving helpful tips on where to find the horses. Highly suggest this house if you want to have a once in a lifetime experience in the Outer Banks! "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Four Sails Resort

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

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

8.6 out of 10, Excellent, (19)
"Our first family vacation to the Outer Banks and we couldn’t have picked a better location! The house is beautiful and the views are amazing. Saw the wild horses a few times on the beach and right at the house, so exciting! "
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

Loft Space Minutes from Beach

5.4 out of 10, (3)
"Location was good in terms of what we needed and property provided all necessary household things you would need to clean the place. However, owner was not and still is not responsive. Refrigerator did not work. A/C did not work. Lock on door was loose. Backyard had massive camping trailer through it. Save your money."
Loft Space Minutes from Beach

Nautical Dream, redecorated oceanfront home with incredible views and decks

10.0 out of 10, Exceptional, (12)
"Great set up and love the proximity to the beach!"
Nautical Dream, redecorated oceanfront home with incredible views and decks

Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

9.6 out of 10, Exceptional, (119)
"We stayed at Lightly Salted last week; my family of five [2 adults, 3 kids (11, 5, 1)]and out close friends family of three [2 adults, 1 kid (3)]. "
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

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

9.8 out of 10, Exceptional, (137)
"The house was beautiful, clean and plenty of room for all our guest! The view was amazing! "
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (83)
"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 AU$371
includes taxes & fees
6 Aug - 7 Aug
The Art Door only minutes from beach

Charming Tiny Cottage

10.0 out of 10, Exceptional, (35)
"This place is very nice, very clean, modern, private. "
Charming Tiny Cottage

Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home

9.4 out of 10, Exceptional, (22)
"As listed close to everything and made our stay very easy. Communication with owner was easy and all questions we had were answered."
The price is AU$936
includes taxes & fees
4 Aug - 5 Aug
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home

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

9.8 out of 10, Exceptional, (103)
"We stayed as a family for our spring break. House was clean, beds were comfortable, and location was great! The kids loved seeing wild horses right off the deck and we found more by driving around. We spent one day on the beach and that was a lot of fun. Weather was a bit chilly, but nothing we could control!"
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission

8.0 out of 10, Very good, (15)
"Loved the location and the avtivitoes/events in the neighborhood."
The price is AU$1,167
includes taxes & fees
3 Aug - 4 Aug
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission

Luxurious RV

7.8 out of 10, Good, (8)
"Great location, the rv itself was ok, spacious, does the job for a beach weekend. a little overpriced for what you get. The pull out couches were not comfortable at all and there was not much provided. One roll of toilet paper, one trash bag. It would have been nice to have a sponge to wash dishes and some basic spices. Maybe a couple K cups for coffee. I would rent again."
The price is AU$615
includes taxes & fees
27 July - 28 July
Luxurious RV

Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

4.0 star property
7.4 out of 10, Good, (41)
"First want to start off by saying the house is as described actually better then the photos online led us to believe. It's an older house but was clean and decorated beautifully. For the money, description, and space you get staying in this home I would definatley recomend you staying here. It's not a 5 star luxury resort, but I gave 5 stars for the house being it was better then what we expected. Our family enjoyed our stay."
The price is AU$697
includes taxes & fees
27 July - 28 July
Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

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 AU$393
includes taxes & fees
27 July - 28 July
Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV
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

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?

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi: This holiday home rental outside of Chesapeake is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Chesapeake?

Expedia has 37 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.