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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chesapeake cottages

Smart TV, DVD player

1. 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 €297
includes taxes & fees
6 Sept - 7 Sept
Comfortable & Private 2 Bedrm Cottage w/ King bed.
House (4 Bedrooms) | Interior

2. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is €537
includes taxes & fees
1 Sept - 2 Sept
Centrally Located Hampton Roads Home w/ Game Room!
Property grounds

3. 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 €771
includes taxes & fees
13 Aug - 14 Aug
902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Kayaks, Beachfront Grilling
Exterior

4. Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (297 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 €388
includes taxes & fees
31 Aug - 1 Sept
Norfolk Beach Cottage Rental
Exterior

5. 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)
"We had a great stay - very clean and inviting home, great location with an easy walk to a clean/friendly beach, and terrific hosts. Excellent!"
United States
Robert F.
The price is €630
includes taxes & fees
20 Aug - 21 Aug
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
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

Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

10/10 Excellent
"I was just there for a quick overnight stay. The staff was friendly. The room was clean. The parking lot is a bit run down, especially for the area, but the inside of the hotel is updated and very clean!"
Shannon 1-night trip
Posted less than an hour ago
Crowne Plaza Virginia Beach Town Center by IHG

Find out more about Chesapeake

Chesapeake Cottages information

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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.