A golf course, a large building complex, and a marina by a river.

Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chesapeake vacation rentals

A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window.

1. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
3.0 star property
Chesapeake
The price is ₩246,786
₩849,478 total
includes taxes & fees
Nov 10 - Nov 11
Entire Home in Chesapeake, Virginia
A modern courtyard with white furniture, a central seating area, and a small lawn.

2. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (114 reviews)
"Theophilus was great at check in. Amazing customer service, quick check-in. The place was clean, the rooms were very clean. The overall atmosphere was great. I will definitely stay here again."
United States
Tarina
The price is ₩158,744
₩182,302 total
includes taxes & fees
Nov 9 - Nov 10
stayAPT Suites Suffolk-Chesapeake
Private kitchen

3. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.0 out of 10, Wonderful, (36 reviews)
"Great stay! Will be staying again!"
United States
Wakeelah
The price is ₩158,744
₩185,223 total
includes taxes & fees
Nov 1 - Nov 2
stayAPT Suites Hampton
A two-story house with a white porch, a red door, and a small Christmas tree.

4. Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.4 out of 10, Very good, (250 reviews)
"Not a top of the line hotel, but it was clean, good location, and it served our needs. We would definitely stay here again."
United States
Cheryl
The price is ₩105,651
₩137,213 total
includes taxes & fees
Nov 1 - Nov 2
Angie's Guest Cottage
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

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

10/10 Excellent
"Hotel was extremely nice an would stay again when get the chance"
Ebony 2-night trip
Posted 1 hour ago
Hyatt Place Virginia Beach / Oceanfront

Find out more about Chesapeake

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

  • View our selection of featured Vacation rentals in Chesapeake
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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 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.