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, (1425)
"My family has a really great time and stay"
The Atrium Resort, Virginia Beach by Vacatia

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1412)
"10/10 staying here again "
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, (1119)
"My family truly enjoyed our stay! Would definitely stay here again. "
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (37)
"Great balcony with a great view"
Four Sails Resort

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (221)
"Will definitely stay again. Very very clean and everyone was so amazing and welcoming. "
The price is NZ$173
includes taxes & fees
1 Sept - 2 Sept
Angie's Guest Cottage

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (32)
"Excellent hotel. I will definitely stay there again. "
The price is NZ$229
includes taxes & fees
1 Sept - 2 Sept
stayAPT Suites Suffolk-Chesapeake

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

9.8 out of 10, Exceptional, (177)
"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

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

8.4 out of 10, Very good, (21)
"I visited the Outer Banks with my daughters and honestly the stay was amazing, the views, house, location this place had it all. "
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

Loft Space Minutes from Beach

5.0 out of 10, (4)
"Overall the stay was good but they have a roach problem which in my opinion is very disgusting and would make me want to not stay here ever again. They also during our stay did not have functioning AC and just had a bunch of fans and a small mobile AC unit in the downstairs. Other than these two things it’s a very nice place and in a good convenient spot. "
Loft Space Minutes from Beach

10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

9.4 out of 10, Exceptional, (102)
"Our family enjoyed the property rental at VA Beach. The owners responded "
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse

9.8 out of 10, Exceptional, (48)
"Wonderful trip with an awesome house. Very quiet and the house is beautiful. Lots of room. Thank you so much."
OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse

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

9.6 out of 10, Exceptional, (121)
"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

Nautical Dream, redecorated oceanfront home with incredible views and decks

10.0 out of 10, Exceptional, (12)
"Wonderful location, generous floor plan."
Nautical Dream, redecorated oceanfront home with incredible views and decks

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 NZ$720
includes taxes & fees
1 Sept - 2 Sept
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home

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

9.8 out of 10, Exceptional, (139)
"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

Luxurious RV

8.0 out of 10, Very good, (9)
"Upon arriving it was dark & I was having a hard time finding the residence. I gave the host a call & he was very friendly and helpful, was able to find it right after speaking with him. The RV is super cute, very relaxing view in the back."
The price is NZ$674
includes taxes & fees
13 Aug - 14 Aug
Luxurious RV

Horse Inn Around: Pet Friendly-so bring the whole family! Just 3 mins to beach

9.6 out of 10, Exceptional, (118)
"Great location and accomadations"
Horse Inn Around: Pet Friendly-so bring the whole family! Just 3 mins to beach

Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

4.0 star property
7.4 out of 10, Good, (42)
"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 NZ$613
includes taxes & fees
2 Sept - 3 Sept
Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

Glamping your way-close to beach in Virginia Beach with AC

Glamping your way-close to beach in Virginia Beach with AC

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 NZ$1,280
includes taxes & fees
31 Aug - 1 Sept
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
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 35 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 Crestwood 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.