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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Chesapeake cottages

Property grounds

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

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Willoughby Spit
The price is £907
includes taxes & fees
21 Jun - 22 Jun
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Smart TV, DVD player

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.6 out of 10, Exceptional, (21 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is £251
includes taxes & fees
4 Jun - 5 Jun
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Exterior

Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking

Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
Northeast Virginia Beach
9.8 out of 10, Exceptional, (264 reviews)
"Clean well taken care of property. Process to rent is easy and the owner was extremely accommodating. Thanks for a great stay"
United States
Kevin P.
The price is £612
includes taxes & fees
12 Jun - 13 Jun
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
Interior

508 A The Shore Break Cottage

508 A The Shore Break Cottage
3.0 star property
Northeast Virginia Beach
The price is £2,146
includes taxes & fees
7 Jun - 8 Jun
508 A The Shore Break 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

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

10/10 Excellent
"Everything great except pool pretty cold and jacuzzi was out of order all 3 days of stay."
sharon 2-night trip
Posted 1 hour ago
Wingate by Wyndham Chesapeake

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
285
Accommodation
167 Cottages
Lowest Price
£251
Highest Price
£2,146

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.