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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chesapeake cottages

A living room with a sectional sofa, a round ottoman, a globe on a shelf, and artwork on the walls.

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

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.2 out of 10, Wonderful, (26 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is AU$471
includes taxes & fees
27 Aug - 28 Aug
Comfortable & Private 2 Bedrm Cottage w/ King bed.
A wooden deck with a white railing, a wicker sofa with cushions, and a glass-top table.

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 AU$864
includes taxes & fees
3 Sept - 4 Sept
Centrally Located Hampton Roads Home w/ Game Room!
A beachside seating area with a wooden pergola, a blue and green slide, and a view of the beach and ocean.

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 AU$1,258
includes taxes & fees
31 Aug - 1 Sept
902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Kayaks, Beachfront Grilling
A two-story house with a white porch and a mailbox.

4. Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (300 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 AU$575
includes taxes & fees
22 Sept - 23 Sept
Norfolk Beach Cottage Rental
A beachside seating area with a wooden deck and a view of the ocean.

5. 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 AU$1,253
includes taxes & fees
27 Aug - 28 Aug
902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & Kayaks
A single-story house with a front porch, a garage, and a well-maintained lawn.

6. 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, (266 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 AU$803
includes taxes & fees
3 Sept - 4 Sept
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

Marriott Virginia Beach Oceanfront Resort

Marriott Virginia Beach Oceanfront Resort

10/10 Excellent
"An overall great experience !"
TIMOTHY 2-night trip
Posted 11 hours ago
Marriott Virginia Beach Oceanfront Resort

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
592
Accommodation
151 Cottages
Lowest Price
AU$471
Highest Price
AU$1,258

Frequently asked questions

What is there to do in Chesapeake near my cottage?
There are lots of superb things to put on your itinerary in Chesapeake. Don't miss major attractions like Portlock Galleries at SoNo, Jillians Billiards and Chesapeake City Park. Oak Grove Lake Park, Cahoon Plantation Golf Course and Chesapeake Golf Club are also visitor favourites.