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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Cottages in Chesapeake

Property grounds
900. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks

Cottage in Willoughby Spit

2.0 star property
$916 nightly
The price is $1,049
Dec 11 - Dec 12
Total with taxes and fees
900. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks
Property grounds
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Cottage in Portsmouth

10.0 out of 10, Exceptional, (15)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
$284 nightly
The price is $330
Dec 14 - Dec 15
Total with taxes and fees
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Exterior
Norfolk Beach Cottage Rental

Cottage in East Ocean View

9.0 out of 10, Wonderful, (277)
"Held my daughter’s sweet 16 slumber party here the girls loved it awesome time and the host family is awesome!"
United States
Merinda F.
$345 nightly
The price is $400
Dec 8 - Dec 9
Total with taxes and fees
Norfolk Beach Cottage Rental
Exterior
Cozy Bay Cottage private backyard blocks from beach!

Cottage in Bayview

9.0 out of 10, Wonderful, (43)
"Beautiful home! Spacious and very clean! Short walk to the beach! And very close to Virginia Beach board walk! Highly recommend for all!"
United States
Elizabeth B.
$337 nightly
The price is $391
Dec 22 - Dec 23
Total with taxes and fees
Cozy Bay Cottage private backyard blocks from beach!
Property grounds
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda

Cottage in Willoughby Spit

2.0 star property
$919 nightly
The price is $1,052
Dec 11 - Dec 12
Total with taxes and fees
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Interior
Centrally Located Hampton Roads Home w/ Game Room!

Cottage in Portsmouth

3.0 star property
$535 nightly
The price is $614
Dec 8 - Dec 9
Total with taxes and fees
Centrally Located Hampton Roads Home w/ Game Room!
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

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

10/10 Excellent
"Great hotel and great staff! Rooms are modern, clean and with fantastic ocean views. Central location and good breakfast too. The staff in all areas goes above and beyond. "
Alexandra 2-night trip
Posted 4 days ago
Hyatt Place Virginia Beach / Oceanfront

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
334
Accommodation
152 Cottages
Lowest Price
$330
Highest Price
$1,052

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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