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

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chesapeake cottages

A two-story house with a front porch, a garage, and a well-maintained lawn.

1. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
3.0 star property
Chesapeake
$552 nightly
The price is $637
Nov 23 - Nov 24
Total with taxes and fees
Entire Home in Chesapeake, Virginia
A beachside seating area with a wooden pergola, a blue and green slide, and a view of the beach and ocean.

2. 902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Kayaks, Beachfront Grilling

902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Kayaks, Beachfront Grilling
Willoughby Spit
$704 nightly
The price is $805
Nov 29 - Nov 30
Total with taxes and fees
902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Kayaks, Beachfront Grilling
A beachside seating area with a wooden pergola, a blue and green slide, and a view of the beach and ocean.

3. 900 A Seaside 2BR Duplex Steps to Bay w/ Veranda

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Willoughby Spit
$696 nightly
The price is $796
Nov 10 - Nov 11
Total with taxes and fees
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
A two-story house with a white porch and a mailbox.

4. Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (307 reviews)
"Great space, close to a great beach, loved that it’s pet friendly with space for our dog to run around, a good park within walking distance, and host was very communicative. Loved our time here!"
United States
Anonymous traveler
$346 nightly
The price is $401
Nov 10 - Nov 11
Total with taxes and fees
Norfolk Beach Cottage Rental
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
"A nice place to stay. The breakfast buffet was awesome. I will stay again when in Va. Beach."
Chapman 1-night trip
Posted 4 hours ago
Hyatt Place Virginia Beach / Oceanfront

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
307
Accommodation
144 Cottages
Lowest Price
$401
Highest Price
$805

Frequently asked questions

Why book your cottage in Chesapeake with Expedia?
We think that vacays should be a piece of cake, so if you're in search of cottages in Chesapeake at a competitive rate, Expedia has got you covered. Keep costs down and opt for a cheap option far from the hustle and bustle, or splurge on an upmarket cottage to spoil the ones you love most.
How can I find cheap cottages in Chesapeake?
With Expedia's handy filter tool, locating cheap cottages in Chesapeake couldn't be easier. To discover properties that'll make your hip pocket happy, refine your search by star rating, amenities and budget.
What is there to do in Chesapeake near my cottage?
Chesapeake has enough activities and sights to keep you amused for weeks (or months!), beginning with Chesapeake Golf Club. Oak Grove Lake Park, Cahoon Plantation Golf Course and Chesapeake Square Mall are other well-known attractions. If you have time to spare, Greenbrier Mall and Chesapeake Veterans' Memorial are nice finishing touches to your itinerary.

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