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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chesapeake cottages

Living area

1. Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.2 out of 10, Wonderful, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is £253
includes taxes & fees
14 Sept - 15 Sept
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Exterior

2. Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (302 reviews)
"This house served our large family well. Within walking distance (across the road) to a public beach on the bay. The beach was never busy and great for walking and swimming. As others have said, downside is only one restroom but we were able to make it work."
United States
Penny H.
The price is £317
includes taxes & fees
14 Sept - 15 Sept
Norfolk Beach Cottage Rental
Property grounds

3. 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 £637
includes taxes & fees
20 Sept - 21 Sept
902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & Kayaks
Property grounds

4. 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 £638
includes taxes & fees
6 Oct - 7 Oct
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Property grounds

5. 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 £641
includes taxes & fees
7 Oct - 8 Oct
902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Kayaks, Beachfront Grilling
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

Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach

10/10 Excellent
"Everything was excellent"
Jamie 3-night trip
Posted 1 hour ago
Hilton Vacation Club Ocean Beach Club Virginia Beach

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
329
Accommodation
146 Cottages
Lowest Price
£253
Highest Price
£641

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.