Chesapeake Vacation Rentals

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Check prices for these dates

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Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
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Nov 21 - Nov 23
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Dec 19 - Dec 21

Vacation Rentals in Chesapeake

Our top choices for Chesapeake vacation rentals

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, (1151)
"We love staying here everyone is very helpful and it’s right in the middle of the boardwalk "
The price is P7,530
P12,054 total
includes taxes & fees
Oct 12 - Oct 13
Ocean Sands Resort, Oceanfront, 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, (1434)
"The hotel and staff were excellent. Even housekeeping were friendly and professional. I love this hotel. I come every year with my family. "
The price is P5,290
P9,478 total
includes taxes & fees
Oct 13 - Oct 14
The Ocean Key Virginia Beach Resort
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, (1469)
"Room was clean and well appointed. Staff was friendly. Located within easy walking distance of the beach and some nice restaurants. I would stay there again."
The price is P4,564
P8,643 total
includes taxes & fees
Oct 7 - Oct 8
The Atrium Resort, Virginia Beach by Vacatia
Four Sails Resort
Indoor pool

Four Sails Resort

4.0 star property
7.6 out of 10, Good, (43)
"It was peaceful"
The price is P7,710
P9,664 total
includes taxes & fees
Oct 5 - Oct 6
Four Sails Resort
Angie's Guest Cottage
Property entrance

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (224)
"Central location to boardwalk music venues. Friendly staff, clean, quiet. "
The price is P4,270
P5,581 total
includes taxes & fees
Sep 25 - Sep 26
Angie's Guest Cottage
stayAPT Suites Suffolk-Chesapeake
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.4 out of 10, Exceptional, (45)
"Nice cozy place to go with your family "
The price is P6,817
P7,829 total
includes taxes & fees
Sep 28 - Sep 29
stayAPT Suites Suffolk-Chesapeake
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

Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

10/10 Excellent
"Indoor Pools and breakfast spread were amazing. The room and view were also topnotch. Just hoping that the kids playroom was open when we got there."
Eunice Alexis 1-night trip
Posted 11 hours ago
Holiday Inn & Suites Virginia Beach North Beach by IHG

Find out more about Chesapeake

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake
  • Use the map to find apartments and other holiday homes in the Chesapeake neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake while they last

Look no further and take a look at our great range of rental properties in Chesapeake!

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Broadmoor Play Area, or you can go with a more remote 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.

How many vacation rentals are there in Chesapeake?

Expedia has 36 vacation 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 like Naval Station Norfolk and Sandbridge Beach.

What’s a vacation rental in Chesapeake like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chesapeake. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips.