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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 £476
includes taxes & fees
9 Nov - 10 Nov
Entire Home in Chesapeake, Virginia
A patio with a wooden table and chairs, a red door, and a wooden fence with string lights.

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, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is £281
includes taxes & fees
29 Nov - 30 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. 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 £654
includes taxes & fees
10 Nov - 11 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.

4. 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 £651
includes taxes & fees
4 Nov - 5 Nov
902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & Kayaks
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, (306 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 £320
includes taxes & fees
9 Nov - 10 Nov
Norfolk Beach Cottage Rental
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, (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.
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

Hilton Vacation Club Oceanaire Virginia Beach

Hilton Vacation Club Oceanaire Virginia Beach

10/10 Excellent
"Great hotel"
Shawn 1-night trip
Posted less than an hour ago
Hilton Vacation Club Oceanaire Virginia Beach

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
601
Accommodation
146 Cottages
Lowest Price
£281
Highest Price
£654

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.