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Cottages in Chesapeake

Our top choices for Chesapeake cottages

Cozy Bay View Oceanside 1 Bedroom Cottage by RedAwning
Cottage, 1 Bedroom | Beach | Beach nearby

Cozy Bay View Oceanside 1 Bedroom Cottage by RedAwning

3.0 star property
Cozy Bay View Oceanside 1 Bedroom Cottage by RedAwning
Lakefront Newport News Home, 6 Mi to City Center!
House (4 Bedrooms) | Interior

Lakefront Newport News Home, 6 Mi to City Center!

3.0 star property
8.0 out of 10, Very Good, (1)
Lakefront Newport News Home, 6 Mi to City Center!
Waterfront Home w/ Dock & Yard in Hampton!
House (3 Bedrooms) | Interior

Waterfront Home w/ Dock & Yard in Hampton!

3.0 star property
Waterfront Home w/ Dock & Yard in Hampton!
Hampton Home w/ Fireplace + Close to Beaches!
House (3 Bedrooms) | Interior

Hampton Home w/ Fireplace + Close to Beaches!

3.0 star property
6.0 out of 10, (2)
"I traveled with my family from pennsylvania check in was held up with no one called about Dirty dishes dirty towels ripped up towels barely any wash cloths barely parking old food and rippers behind the beds major dust just horrible "
Hampton Home w/ Fireplace + Close to Beaches!
Old Time Beach Front Cottage - The Beach Is Your Backyard! 3 Bedroom Cottage by RedAwning
Cottage, 3 Bedrooms | Beach | On the beach

Old Time Beach Front Cottage - The Beach Is Your Backyard! 3 Bedroom Cottage by RedAwning

3.5 star property
Old Time Beach Front Cottage - The Beach Is Your Backyard! 3 Bedroom Cottage by RedAwning
Mariners Cove 4 Bedroom Cottage by RedAwning
Cottage, 4 Bedrooms | Interior

Mariners Cove 4 Bedroom Cottage by RedAwning

3.0 star property
8.0 out of 10, Very Good, (1)
"Great location right on the water with lots of space inside and out. The host was very helpful and easy to work with. "
Mariners Cove 4 Bedroom Cottage by RedAwning
4 Mi to Hampton Coliseum: Home w/ Yard!
House (3 Bedrooms) | Interior

4 Mi to Hampton Coliseum: Home w/ Yard!

3.0 star property
4 Mi to Hampton Coliseum: Home w/ Yard!
Historic Beach Side Getaway - Pet Friendly, Wifi 3 Bedroom Cottage by RedAwning
Cottage, 3 Bedrooms | Beach | Beach nearby

Historic Beach Side Getaway - Pet Friendly, Wifi 3 Bedroom Cottage by RedAwning

3.0 star property
Historic Beach Side Getaway - Pet Friendly, Wifi 3 Bedroom Cottage by RedAwning
Pet-friendly Norfolk Retreat ~ 7 Mi to Beach!
House (3 Bedrooms) | Interior

Pet-friendly Norfolk Retreat ~ 7 Mi to Beach!

3.0 star property
Pet-friendly Norfolk Retreat ~ 7 Mi to Beach!
Walk to Waterfront: Downtown Elizabeth City Home!
House (4 Bedrooms) | Interior

Walk to Waterfront: Downtown Elizabeth City Home!

3.0 star property
10.0 out of 10, Exceptional, (1)
"My family And I truly enjoyed this property. Such a great house in a beautiful historic community. Thank you"
Walk to Waterfront: Downtown Elizabeth City Home!
Pink Flamingo At The Beach 2 Bedroom Cottage by RedAwning
Cottage, 2 Bedrooms | Exterior

Pink Flamingo At The Beach 2 Bedroom Cottage by RedAwning

3.0 star property
Pink Flamingo At The Beach 2 Bedroom Cottage by RedAwning
Walk to Dining: Sleek Hampton Home w/ Deck!
House (3 Bedrooms) | Interior

Walk to Dining: Sleek Hampton Home w/ Deck!

3.0 star property
Walk to Dining: Sleek Hampton Home w/ Deck!
Walk to Beach: Hampton Home w/ Grill!
House (2 Bedrooms) | Interior

Walk to Beach: Hampton Home w/ Grill!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful communication with property owner, comfortable beds and amenities like a welcome basket with snacks/bottle water/juice was an added bonus. Very clean throughout and easy to follow check-in and out instructions. Only minor complaint is that the air conditioner for the upstairs room was off upon arrival, so the room was quite hot when we arrived near 8pm at night. Would definitely stay again as we were close walk to the beach and local food spots. "
Walk to Beach: Hampton Home w/ Grill!
Manor And Mutts #1 4 Bedroom Cottage by RedAwning
Cottage, 4 Bedrooms | Balcony

Manor And Mutts #1 4 Bedroom Cottage by RedAwning

3.5 star property
Manor And Mutts #1 4 Bedroom Cottage by RedAwning
Elizabeth City Vacation Rental: Gazebo w/ Hot Tub!
House (3 Bedrooms) | Interior

Elizabeth City Vacation Rental: Gazebo w/ Hot Tub!

3.0 star property
Elizabeth City Vacation Rental: Gazebo w/ Hot Tub!
3 Mi to Huntington Beach: Hampton Family Home!
House (3 Bedrooms) | Interior

3 Mi to Huntington Beach: Hampton Family Home!

3.0 star property
3 Mi to Huntington Beach: Hampton Family Home!
Cozy Currituck Home w/ Fire Pit Near Ferry!
House (3 Bedrooms) | Interior

Cozy Currituck Home w/ Fire Pit Near Ferry!

3.0 star property
8.0 out of 10, Very Good, (1)
"Everything was great except there were ants in the kitchen and bathroom. Place needs to be visited by an exterminator. "
Cozy Currituck Home w/ Fire Pit Near Ferry!
Charming Hampton Home Near Downtown & Beaches!
House (2 Bedrooms) | Interior

Charming Hampton Home Near Downtown & Beaches!

3.0 star property
Charming Hampton Home Near Downtown & Beaches!
Inviting Norfolk Family Retreat: 1 Block to Beach!
House (4 Bedrooms) | Interior

Inviting Norfolk Family Retreat: 1 Block to Beach!

3.0 star property
Inviting Norfolk Family Retreat: 1 Block to Beach!
Walk to River & Downtown: Portsmouth Apartment!
House (2 Bedrooms) | Interior

Walk to River & Downtown: Portsmouth Apartment!

3.0 star property
Walk to River & Downtown: Portsmouth Apartment!
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
"The staff was friendly and helpful. "
Christie 2-night trip
Posted 21 hours ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Find out more about Chesapeake

Find out more about Chesapeake

Chesapeake Cottages information

Number of reviews
7
Accommodation
65 Cottages
Lowest Price
Highest Price

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

Explore a world of travel with Expedia