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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

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
The price is S$829
includes taxes & fees
3 Dec - 4 Dec
Entire Home in Chesapeake, Virginia
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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Learn more about Chesapeake

Explore the Great Dismal Swamp's boardwalk trails where kayakers glide past cypress trees and wildlife thrives. The Chesapeake Arboretum's 48 acres of forests and gardens offer peaceful hiking, while nearby waterfront restaurants serve the bay's famous blue crabs.

See all hotels in Chesapeake
A beach at sunset with a pier extending into the water.

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.