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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Chesapeake cottages

Property grounds

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
10.0 out of 10, Exceptional, (16 reviews)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is €254
includes taxes & fees
8 Feb - 9 Feb
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Exterior

Cozy Bay Cottage private backyard blocks from beach!

Cozy Bay Cottage private backyard blocks from beach!
Bayview
9.0 out of 10, Wonderful, (43 reviews)
"Beautiful home! Spacious and very clean! Short walk to the beach! And very close to Virginia Beach board walk! Highly recommend for all!"
United States
Elizabeth B.
The price is €313
includes taxes & fees
7 Feb - 8 Feb
Cozy Bay Cottage private backyard blocks from beach!
Cottage, 3 Bedrooms | Balcony

Manor And Mutts #2 3 Bedroom Cottage by RedAwning

Manor And Mutts #2 3 Bedroom Cottage by RedAwning
3.5 star property
Willoughby Spit
The price is €503
includes taxes & fees
14 Feb - 15 Feb
Manor And Mutts #2 3 Bedroom Cottage by RedAwning
House (4 Bedrooms) | Interior

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is €524
includes taxes & fees
28 Feb - 1 Mar
Centrally Located Hampton Roads Home w/ Game Room!
Property grounds

Wild Horses - 4x4 Beach - Quiet & Cozy

Wild Horses - 4x4 Beach - Quiet & Cozy
Corolla
The price is €446
includes taxes & fees
19 Feb - 20 Feb
Wild Horses - 4x4 Beach - Quiet & Cozy
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

Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

10/10 Excellent
"Nice"
Jermaine 2-night trip
Posted 2 days ago
Embassy Suites by Hilton Hampton Convention Center

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
59
Accommodation
152 Cottages
Lowest Price
€254
Highest Price
€503

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.