Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

Interior
The Atrium Resort by VSA Resorts
3.5 star property
8.2 out of 10, Very good, (1073)
"Very convenient to everything you need on Vaction! Very pleasant staff! "
The price is S$254
per night
14 May - 15 May
The Atrium Resort by VSA Resorts
Exterior
The Ocean Sands Resort by VSA Resorts
3.0 star property
8.0 out of 10, Very good, (1266)
"The staff treated me with so much kindness and respect. ESPECIALLY the lady property manger thank you! The room was extraordinary and the view was amazing I will definitely come here for a stay again."
The price is S$270
per night
14 May - 15 May
The Ocean Sands Resort by VSA Resorts
Indoor pool
The Ocean Key Resort by VSA Resorts
3.0 star property
7.6 out of 10, Good, (1122)
"Great "
The price is S$284
per night
14 May - 15 May
The Ocean Key Resort by VSA Resorts
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Property entrance
Angie's Guest Cottage
2.0 star property
8.6 out of 10, Excellent, (177)
"Honestly the only negative was the tiny parking space but it's beachfront cottage. having parking included at all was nice. Friendly clean and close to everything"
The price is S$158
per night
14 May - 15 May
Angie's Guest Cottage
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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.

Other types of properties in Chesapeake you may be interested in

Lobby lounge
Wingate by Wyndham Chesapeake
2.5 star property
8.0 out of 10, Very good, (1007)
"The staff were very helpful and professional "
The price is S$199
per night
14 May - 15 May
Wingate by Wyndham Chesapeake
Desk, laptop workspace, blackout curtains, iron/ironing board
Fairfield Inn and Suites By Marriott Chesapeake
2.5 star property
8.8 out of 10, Excellent, (806)
"The rooms are beautifully modern and comfortable. "
The price is S$154
per night
28 May - 29 May
Fairfield Inn and Suites By Marriott Chesapeake
Seasonal outdoor pool
Delta Hotels by Marriott Virginia Beach Waterfront
4.0 star property
8.6 out of 10, Excellent, (962)
"This is probably one of the best hotels that we have ever stayed at. Staff was very kind and accommodating to our needs and let us know everything we needed to know about during our stay. The hotel itself was beautiful and very well kept. Sheets were clean along with the bathroom, balcony and suite entirely. Area around the hotel was very quiet for us and it’s nice to be away from the main point of VA Beach. We definitely will be back to visit again soon! "
The price is S$250
per night
16 May - 17 May
Delta Hotels by Marriott Virginia Beach Waterfront
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.

Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Jillian's Billiards, 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?

The Atrium Resort by VSA Resorts: This holiday home rental outside of Chesapeake is located by the ocean, and has an indoor pool, an arcade/games room and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

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?

Great Dismal Swamp National Wildlife Refuge and Oak Grove Lake Park are a couple of scenic spots to enjoy the outdoors, whereas Portlock Galleries at SoNo is one of the cultural attractions. 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.

Recent reviews of Chesapeake properties
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