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

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.
$307 nightly
The price is $356
Oct 7 - Oct 8
Total with taxes and fees
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.

2. 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
$750 nightly
The price is $858
Oct 25 - Oct 26
Total with taxes and fees
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.

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

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Willoughby Spit
$743 nightly
The price is $850
Oct 25 - Oct 26
Total with taxes and fees
900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
A two-story house with a white porch and a mailbox.

4. Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (304 reviews)
"Great host! We had a great time!"
United States
Jessie m.
$351 nightly
The price is $407
Oct 7 - Oct 8
Total with taxes and fees
Norfolk Beach Cottage Rental
A beachside seating area with a wooden deck and a view of the ocean.

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
$747 nightly
The price is $855
Oct 27 - Oct 28
Total with taxes and fees
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.

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, (267 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
A two-story house with a front porch, a garage, and a small deck.

7. 508 A The Shore Break Cottage

508 A The Shore Break Cottage
3.0 star property
Northeast Virginia Beach
$2,582 nightly
The price is $2,971
Oct 19 - Oct 20
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

Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

10/10 Excellent
"Excellent Felicia at the front desk is awesome"
Melthres 1-night trip
Posted 7 hours ago
Crowne Plaza Virginia Beach Town Center by IHG

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
598
Accommodation
144 Cottages
Lowest Price
$356
Highest Price
$2,971

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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