Chesapeake Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 10 - Aug 11
Tomorrow
Aug 11 - Aug 12
Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24

Vacation Rentals in Chesapeake

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, (1424)
"My family has a really great time and stay"
The Atrium Resort, 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, (1410)
"Nice quiet hotel, very suitable for families with children. "
The Ocean Key Virginia Beach Resort
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, (1118)
"My family truly enjoyed our stay! Would definitely stay here again. "
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Four Sails Resort
Indoor pool

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
Property entrance

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (221)
"Very Cozy and near the beach, Staff is very courteous and friendly. "
The price is NT$2,367
NT$3,073 total
includes taxes & fees
Sep 1 - Sep 2
Angie's Guest Cottage
stayAPT Suites Suffolk-Chesapeake
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (32)
"Great place to stay!"
The price is NT$3,551
NT$4,078 total
includes taxes & fees
Sep 1 - Sep 2
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake Hotel Reviews

STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

10/10 Excellent
"Good"
Eric 4-night trip
Posted 7 hours ago
STUDIOS & SUITES 4 LESS 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 35 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 Crestwood 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.