Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Chesapeake

Terrace/patio
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
Northeast Virginia Beach
8.2 out of 10, Very Good, (1167)
"Clean room, staff friendly, beach view 1st floor "
United States
Montoya
The price is P5,932
P10,335 total
includes taxes & fees
Nov 23 - Nov 24
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Indoor pool
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3.0 star property
Northeast Virginia Beach
7.8 out of 10, Good, (1448)
"Excellent location! Best restaurant in VAB is right across the street and so is the boardwalk. The quieter end of the beach but so close to many great restaurants and the marina."
United States
Barbara
The Ocean Key Virginia Beach Resort
Indoor pool
Four Sails Resort

Four Sails Resort

4.0 star property
Northeast Virginia Beach
7.6 out of 10, Good, (47)
"It was peaceful"
United States
Sheimka
The price is P6,092
P7,743 total
includes taxes & fees
Nov 26 - Nov 27
Four Sails Resort
Terrace/patio
stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake

2.5 star property
Suffolk
9.6 out of 10, Exceptional, (51)
"Great place to stay!"
United States
Devecia
The price is P7,024
P8,067 total
includes taxes & fees
Nov 16 - Nov 17
stayAPT Suites Suffolk-Chesapeake
Property entrance
Angie's Guest Cottage

Angie's Guest Cottage

2.0 star property
Northeast Virginia Beach
8.6 out of 10, Excellent, (225)
"Central location to boardwalk music venues. Friendly staff, clean, quiet. "
United States
Robert
The price is P4,675
P6,072 total
includes taxes & fees
Nov 11 - Nov 12
Angie's Guest Cottage
Beach nearby
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
Northeast Virginia Beach
8.2 out of 10, Very Good, (1478)
"Very helpful staff. Location is perfect."
United States
Diane
The Atrium Resort, Virginia Beach by Vacatia
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

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

10/10 Excellent
"Actually, we (2 other couples besides us) got a call a few days before and were told that they were CLOSING during our stay! However, they upgraded our accommodations to the Hampton Inn South. Which is a nicer hotel right next door. The downside was we didn’t get a king bed, instead we were given 2 queen beds, not a big deal unless you are a larger person (my wife and I are both small). Our group likes Calypso’s Grill which is connected to the Surfbreak…hence our original choice. But I think the Hampton Inn will have new customers."
alfred 4-night trip
Posted 16 hours ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

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
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  • 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 38 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 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 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.