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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chesapeake cottages

A patio with a wooden table and chairs, a red door, and a wooden fence with string lights.

1. 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, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is AU$499
includes taxes & fees
16 Oct - 17 Oct
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
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$886
includes taxes & fees
5 Nov - 6 Nov
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$1,205
includes taxes & fees
25 Oct - 26 Oct
902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Kayaks, Beachfront Grilling
A beachside seating area with a wooden pergola, a blue and green slide, and a view of the beach and ocean.

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 AU$1,193
includes taxes & fees
25 Oct - 26 Oct
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
A two-story house with a white porch and a mailbox.

5. Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (305 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 AU$583
includes taxes & fees
13 Oct - 14 Oct
Norfolk Beach Cottage Rental
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 AU$1,207
includes taxes & fees
18 Oct - 19 Oct
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.

7. 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, (268 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$774
includes taxes & fees
9 Nov - 10 Nov
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
A two-story house with a front porch, a garage, and a small deck.

8. 508 A The Shore Break Cottage

508 A The Shore Break Cottage
3.0 star property
Northeast Virginia Beach
The price is AU$4,099
includes taxes & fees
19 Oct - 20 Oct
508 A The Shore Break Cottage
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

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

8/10 Good
"Our room was very nice and clean. You walked out of the hotel and could be on the boardwalk or the strip for shopping and eating. It was a perfect location."
Christine 2-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
600
Accommodation
151 Cottages
Lowest Price
AU$499
Highest Price
AU$4,099

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.