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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chesapeake cottages

A two-story house with a front porch, a garage, and a well-maintained lawn.

1. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
3.0 star property
Chesapeake
The price is NZ$1,169
includes taxes & fees
29 Nov - 30 Nov
Entire Home in Chesapeake, Virginia
A modern living room with a wooden coffee table, a large white orchid, and a flat-screen TV.

2. Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!

Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
Portsmouth
9.2 out of 10, Wonderful, (29 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is NZ$611
includes taxes & fees
8 Nov - 9 Nov
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
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 NZ$1,483
includes taxes & fees
29 Nov - 30 Nov
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, (307 reviews)
"Great space, close to a great beach, loved that it’s pet friendly with space for our dog to run around, a good park within walking distance, and host was very communicative. Loved our time here!"
United States
Anonymous traveller
The price is NZ$713
includes taxes & fees
8 Nov - 9 Nov
Norfolk Beach Cottage Rental
A beachside seating area with a wooden pergola, a blue and green slide, and a view of the beach and ocean.

5. 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 NZ$1,447
includes taxes & fees
18 Nov - 19 Nov
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
A beachside seating area with a wooden deck and a view of the ocean.

6. 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 NZ$1,483
includes taxes & fees
12 Nov - 13 Nov
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

Schooner Inn

Schooner Inn

10/10 Excellent
"Beautiful views, Relaxed environment."
Sabra 2-night trip
Posted 20 hours ago
Schooner Inn

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
307
Accommodation
142 Cottages
Lowest Price
NZ$611
Highest Price
NZ$1,483

Frequently asked questions

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.