A golf course, a large building complex, and a marina by a river.

Search Chesapeake Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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
2.0 star property
Chesapeake
$552 nightly
The price is $637
Nov 9 - Nov 10
Total with taxes and fees
Entire Home in Chesapeake, Virginia
A patio with a wooden table and chairs, a red door, and a wooden fence with string lights.

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, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
$297 nightly
The price is $345
Oct 28 - Oct 29
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. 900 A Seaside 2BR Duplex Steps to Bay w/ Veranda

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Willoughby Spit
$765 nightly
The price is $875
Nov 9 - Nov 10
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, (306 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
$364 nightly
The price is $422
Nov 3 - Nov 4
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
$756 nightly
The price is $865
Nov 4 - Nov 5
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake Hotel Reviews

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

10/10 Excellent
"I wish the breakfast menu could be improved a bit."
Dong 1-night trip
Posted 1 hour ago
Hyatt Place Virginia Beach / Oceanfront

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
333
Accommodation
144 Cottages
Lowest Price
$345
Highest Price
$875

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.

Explore a world of travel with Expedia