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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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
$562 nightly
The price is $648
Nov 29 - Nov 30
Total with taxes and fees
Entire Home in Chesapeake, Virginia
A modern living room with a wooden coffee table, a large white orchid, and a flat-screen TV.

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, (29 reviews)
"We really enjoyed our stay! The house was cozy and the perfect size for the three of us. While we didn't do any cooking, the kitchen appeared to have everything you would need. The shower had great hot water, which was nice after a long day. The neighborhood was quiet and peaceful, and there were several good restaurants nearby, making it easy to grab a meal. We'd definitely stay here again!"
United States
Allan S.
$293 nightly
The price is $340
Nov 13 - Nov 14
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.

3. 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
$728 nightly
The price is $833
Nov 29 - Nov 30
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.

4. 900 A Seaside 2BR Duplex Steps to Bay w/ Veranda

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Willoughby Spit
$716 nightly
The price is $819
Nov 18 - Nov 19
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.

5. Chalet Rental on Norfolk Beach

Chalet Rental on Norfolk Beach
East Ocean View
9.0 out of 10, Wonderful, (308 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 traveler
$351 nightly
The price is $407
Nov 13 - Nov 14
Total with taxes and fees
Chalet Rental on Norfolk Beach
A beachside seating area with a wooden deck and a view of the ocean.

6. 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
902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & Kayaks
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

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

8/10 Good
"ok"
Andrew 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
Accommodation
144 Cottages
Lowest Price
$340
Highest Price
$833

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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