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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Chesapeake cottages

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, (24 reviews)
"Quite little cottage. Great for a quick stay."
United States
Debbie M.
The price is £255
includes taxes & fees
2 Aug - 3 Aug
Comfortable & Private 2 Bedrm Cottage w/ King bed.
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 £465
includes taxes & fees
16 Aug - 17 Aug
Centrally Located Hampton Roads Home w/ Game Room!
Exterior

Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (295 reviews)
"3rd year in a row staying here. The house is beautiful and in a great location if you want to go to the beach. "
United States
Justin N.
The price is £336
includes taxes & fees
25 Aug - 26 Aug
Norfolk Beach Cottage Rental
Property grounds

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
The price is £631
includes taxes & fees
13 Aug - 14 Aug
902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Kayaks, Beachfront Grilling
Property grounds

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

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Willoughby Spit
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
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, (265 reviews)
"The place was clean and well stocked."
United States
David R.
The price is £568
includes taxes & fees
20 Aug - 21 Aug
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
Property grounds

902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & Kayaks

902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & Kayaks
Willoughby Spit
The price is £745
includes taxes & fees
4 Aug - 5 Aug
902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & Kayaks
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

Ocean Resort

Ocean Resort

8/10 Good
"the rooms were clean, the staff helpful and really good view. we had the double queeen beds with ocean view. only complaint, the coffee was never really full but had a great time."
MICHAEL 3-night trip
Posted 4 hours ago
Ocean Resort

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
584
Accommodation
158 Cottages
Lowest Price
£255
Highest Price
£745

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.