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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Chesapeake cottages

Interior

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.4 out of 10, Exceptional, (19 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
$270 nightly
The price is $314
May 5 - May 6
Total with taxes and fees
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Exterior

Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (283 reviews)
"Great place loved it cozy beach house "
United States
JaLiylah M.
$345 nightly
The price is $400
May 3 - May 4
Total with taxes and fees
Norfolk Beach Cottage Rental
House (4 Bedrooms) | Interior

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
$535 nightly
The price is $618
May 31 - Jun 1
Total with taxes and fees
Centrally Located Hampton Roads Home w/ Game Room!
Property grounds

Wild Horses - 4x4 Beach - Quiet & Cozy

Wild Horses - 4x4 Beach - Quiet & Cozy
Corolla
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at The Salty Dog. The space was very clean and well-kept, which made it easy to settle in and feel comfortable right away. Communication with the host was excellent—quick, clear, and helpful throughout our stay.One of the highlights was the location. It’s back in a quiet wooded area and just a short, easy walk to the beach, which made our trip even more relaxing and convenient.It had all the amenities anyone could ask for. Even for our K9. Overall, a wonderful place to stay....
United States
Branden S.
$395 nightly
The price is $445
May 4 - May 5
Total with taxes and fees
Wild Horses - 4x4 Beach - Quiet & Cozy
Exterior

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, (263 reviews)
"Clean well taken care of property. Process to rent is easy and the owner was extremely accommodating. Thanks for a great stay"
United States
Kevin P.
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
Interior

508 A The Shore Break Cottage

508 A The Shore Break Cottage
3.0 star property
Northeast Virginia Beach
$2,534 nightly
The price is $2,917
May 6 - May 7
Total with taxes and fees
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

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

10/10 Excellent
"This was my first time staying here. It won't be my last. The staff was extremely friendly and helpful. My room was nice and the view was awesome."
Knekesha 3-night trip
Posted 5 hours ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
567
Accommodation
162 Cottages
Lowest Price
$314
Highest Price
$2,917

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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