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
24 July - 26 July
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Chesapeake cottages

Beach nearby, fishing

Rustic Chesapeake Bay Beachfront Retreat with Private Porch Virginia

Rustic Chesapeake Bay Beachfront Retreat with Private Porch Virginia
Cottage Park
The price is AU$1,328
includes taxes & fees
16 July - 17 July
Rustic Chesapeake Bay Beachfront Retreat with Private Porch Virginia
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)
"The place was clean and well stocked."
United States
David R.
The price is AU$1,073
includes taxes & fees
21 July - 22 July
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
Exterior

Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (293 reviews)
"Loved the house. Was perfect for an extended stay. Host are great and kind. Thank you"
United States
Desiree M.
The price is AU$658
includes taxes & fees
11 Aug - 12 Aug
Norfolk Beach Cottage Rental
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
Outdoor dining

Pet-Friendly Waterfront Cottage on the Chesapeake Bay, Virginia

Pet-Friendly Waterfront Cottage on the Chesapeake Bay, Virginia
Willoughby Spit
Pet-Friendly Waterfront Cottage on the Chesapeake Bay, Virginia
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, (22 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is AU$485
includes taxes & fees
13 July - 14 July
Comfortable & Private 2 Bedrm Cottage w/ King bed.
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

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

10/10 Excellent
"Surf Break is a great property. The staff is helpful, check-in was seamless and the location is perfect. We enjoyed the view from our balcony each morning and evening. The AC was cool and refreshing, bed was comfy and the room was spacious. There are a few dated items/features and the parking situation isn’t perfect but neither should be considered a deal breaker."
Lauren 2-night trip
Posted 9 hours ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
579
Accommodation
164 Cottages
Lowest Price
AU$485
Highest Price
AU$1,073

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.