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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chesapeake cottages

Smart TV, DVD player

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

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.6 out of 10, Exceptional, (25 reviews)
"Great small home would rent again"
United States
Ronnie B.
$293 nightly
The price is $340
Aug 23 - Aug 24
Total with taxes and fees
Comfortable & Private 2 Bedrm Cottage w/ King bed.
House (4 Bedrooms) | Interior

2. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
$536 nightly
The price is $619
Sep 1 - Sep 2
Total with taxes and fees
Centrally Located Hampton Roads Home w/ Game Room!
Property grounds

3. 900 A Seaside 2BR Duplex Steps to Bay w/ Veranda

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Willoughby Spit
$803 nightly
The price is $919
Aug 23 - Aug 24
Total with taxes and fees
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Exterior

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.
$369 nightly
The price is $427
Sep 15 - Sep 16
Total with taxes and fees
Norfolk Beach Cottage Rental
Property grounds

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
$816 nightly
The price is $934
Aug 27 - Aug 28
Total with taxes and fees
902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & Kayaks
Exterior

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.
$526 nightly
The price is $607
Sep 3 - Sep 4
Total with taxes and fees
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

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

10/10 Excellent
"Friendly staff and very attentive to our request"
Derek 2-night trip
Posted 2 hours ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
Accommodation
157 Cottages
Lowest Price
$619
Highest Price
$619

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.

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