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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chesapeake cottages

A two-story house with a front porch and a wooden fence.

1. Hike, Beach & Explore! Family Home in Chesapeake

Hike, Beach & Explore! Family Home in Chesapeake
2.0 star property
Chesapeake
$579 nightly
The price is $668
Oct 17 - Oct 18
Total with taxes and fees
Hike, Beach & Explore! Family Home in Chesapeake
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.
$301 nightly
The price is $349
Oct 17 - Oct 18
Total with taxes and fees
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
A wooden deck with a white railing, a wicker sofa with cushions, and a glass-top table.

3. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
$536 nightly
The price is $619
Nov 5 - Nov 6
Total with taxes and fees
Centrally Located Hampton Roads Home w/ Game Room!
A beachside seating area with a wooden pergola, a blue and green slide, and a view of the beach and ocean.

4. 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
$755 nightly
The price is $864
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.

5. 900 A Seaside 2BR Duplex Steps to Bay w/ Veranda

900 A Seaside 2BR Duplex Steps to Bay w/ Veranda
Willoughby Spit
$758 nightly
The price is $867
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.

6. Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (305 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
Oct 18 - Oct 19
Total with taxes and fees
Norfolk Beach Cottage Rental
A single-story house with a front porch, a garage, and a well-maintained lawn.

7. 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, (268 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.
$414 nightly
The price is $478
Nov 15 - Nov 16
Total with taxes and fees
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
A beachside seating area with a wooden deck and a view of the ocean.

8. 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
$745 nightly
The price is $852
Oct 18 - Oct 19
Total with taxes and fees
902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & Kayaks
A two-story house with a front porch, a garage, and a small deck.

9. 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

Hyatt Studios Chesapeake

Hyatt Studios Chesapeake

10/10 Excellent
"Excellent rooms and hotel. Brand new so everything is as good as it can be. If you are looking for a longer stay it is geared up with everything you need to cook and eat even with washing up bowl with sponges and washing up liquid. They have a large laundry room with plenty of washers and dryers even a laundry basket in the room. Very geared to longer stays. It states that breakfast was included but the only offerings were sweet muffins and apples and bananas neither of which I eat. Don’t think it would hurt to have some bagels or bread to toast with cream cheese and jams or little cheese portions and boiled eggs. It wasn’t particularly cheap so a little more offerings should be included. I know you can buy fridge sandwiches but the price was enough without spending more. Didn’t like to awful smell of pot in the hallways. Don’t think it should be allowed even though it’s legal in Va. It wasn’t particularly cheap but a great facility and we would stay again."
Raymond 1-night trip
Posted 1 hour ago
Hyatt Studios Chesapeake

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
600
Accommodation
144 Cottages
Lowest Price
$349
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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