Explore the wonders of Chesapeake Bay, a vibrant destination in North Carolina. With 4,410 different cottages available, your dream vacation is within reach.

Chesapeake Bay offers cottages that cater to a variety of tastes and budgets. With prices ranging from $39 to $5,899, you can customize your experience to match your lifestyle. Look forward to amenities such as Internet / Wifi, ensuring a memorable stay.

Top Features: Internet / Wifi, Air conditioner, Kitchen / Kitchenette, Parking and TV

Local Highlights: Yorktown Battlefield, American Revolution Museum at Yorktown, Newport News Park, Water Country USA and Barrier Islands Center

Begin your journey in Chesapeake Bay today! Reserve your cottages and dive into the beauty and culture of North Carolina.

Top Cottages in Chesapeake Bay

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Interior
Cottage
 in Lusby
Waterfront Lusby Retreat w/ Deep-water Dock & Slip
Pets allowed · Kitchen / Kitchenette · Air conditioner

Experience the best of Chesapeake Bay with this Cottage available for $376. This property is equipped with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

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Exterior
4.9
Outstanding(306 Reviews)
Cottage
 in Gloucester Point
Cottage on a Private Island in the York River
8 guests · 3 bedrooms · 2 baths
Garden · Pool · Pets allowed

Looking for the perfect place to call home during your trip to Chesapeake Bay? This Cottage offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.

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Cottage
 in Dameron
Bay Estate by Avantstay Waterfront, Private Pond
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Discover the beauty of Chesapeake Bay with a stay at Bay Estate by Avantstay Waterfront, Private Pond, a top rated Cottage with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

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Exterior
4.9
Outstanding(268 Reviews)
Cottage
 in Pasadena
The Heron's Nest at Atlantic Marina
4 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

Discover the beauty of Chesapeake Bay with a stay at The Heron's Nest at Atlantic Marina, a top rated Cottage with amenities such as Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.

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Cottage
 in Dameron
Bay Cottage by Avantstay Waterfront, Pier, Pond
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

The best choice in Chesapeake Bay for Cottage, for $303 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Property grounds
5.0
Outstanding(267 Reviews)
Cottage
 in Irvington
Have you made your summer vacay plans yet at the Rivah in Irvington?
4 guests · 2 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

This attractive Cottage in Chesapeake Bay, $251 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Cottage
 in Hampton
Charming Hampton Home w/ Yard: 2 Mi to Beach!
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Soak up the beauty of Chesapeake Bay in our Cottage, Charming Hampton Home w/ Yard: 2 Mi to Beach!. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

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Outdoor dining
5.0
Outstanding(235 Reviews)
Cottage
 in Cambridge
Family and Pet-Friendly, Waterfront with Pier
8 guests · 4 bedrooms · 2 baths
Garden · Pool · Pets allowed

This inviting Cottage in Chesapeake Bay can fit your needs for many types of vacations, at $275 per night.

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Cottage
 in Newport News
Centrally Located Hampton Home: 6 Mi to Downtown!
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This inviting Cottage in Chesapeake Bay can fit your needs for many types of vacations, at $343 per night.

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Property grounds
5.0
Outstanding(238 Reviews)
Cottage
 in Gloucester
Historic Cottage on Ware River Estate
4 guests · 1 bedroom · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

Cottage in Chesapeake Bay, for $195 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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Cottage
 in Norfolk
Stately Norfolk Home w/ Fenced Yard: Walk to Beach
Garden · Pets allowed · Kitchen / Kitchenette

The best choice in Chesapeake Bay for Cottage, for $268 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Exterior
5.0
Outstanding(189 Reviews)
Cottage
 in Edgewater
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
11 guests · 3 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA for $387 for your next trip.

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Vacation rentals with internet & wifi in Chesapeake Bay

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Cottage
 in Norfolk
Norfolk Beach House Rental w/ Private Pool!
Pool · Pets allowed · Kitchen / Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Norfolk Beach House Rental w/ Private Pool! for $263 for your next trip.

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Exterior
5.0
Outstanding(210 Reviews)
Cottage
 in Annapolis
Annapolis waterfront \"tiny house\" in garden setting
4 guests · 1 bedroom · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our Cottage in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Annapolis waterfront \"tiny house\" in garden setting's exceptional amenities, such as Air conditioner, Internet / Wifi and Balcony / Patio.

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Cottage
 in Hampton
Hampton Home w/ Grill < 1 Mi to Beach!
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Nestled in Chesapeake Bay, this Cottage is perfect for your next vacation. Enjoy Hampton Home w/ Grill < 1 Mi to Beach!'s top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property grounds
4.9
Outstanding(177 Reviews)
Cottage
 in Yorktown
Private 2,000 Sq Ft Cottage in Historic Yorktown (at Yorktown Cottages)
5 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Experience the best of Chesapeake Bay with this Cottage available for $364. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Cottage
 in Hampton
Hampton Sanctuary w/ Fire Pit & Fenced Yard!
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Nestled in Chesapeake Bay, this Cottage is perfect for your next vacation. Enjoy Hampton Sanctuary w/ Fire Pit & Fenced Yard!'s top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Exterior
4.8
Outstanding(201 Reviews)
Cottage
 in Wittman
Relaxing Waterfront Cottage Near St Michaels, Maryland
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

This attractive Cottage in Chesapeake Bay, $274 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Cottage
 in Hampton
Updated Hampton Home w/ Grill: Walk to Beach!
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This Cottage in Chesapeake Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Property grounds
5.0
Outstanding(177 Reviews)
Cottage
 in Grimstead
Waterfront Cottage with Private Beach, Pet Friendly, Sunsets Over the Water
4 guests · 2 bedrooms · 1 bath
Garden · Pool · Pets allowed

Enjoy the best of Chesapeake Bay in our Cottage, Waterfront Cottage with Private Beach, Pet Friendly, Sunsets Over the Water. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Cottage
 in Norfolk
Inviting Norfolk Family Retreat: 1 Block to Beach!
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Experience the best of Chesapeake Bay with this Cottage available for $290. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property grounds
4.9
Outstanding(155 Reviews)
Cottage
 in Saint Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
5 guests · 2 bedrooms · 2 baths
Garden · Pool · Pets allowed

Are you ready to indulge in a relaxing getaway? Our Cottage in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
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Cottage, 3 Bedrooms | Balcony
Cottage
 in Norfolk
Manor And Mutts #2 3 Bedroom Cottage by RedAwning
Pets allowed · Kitchen / Kitchenette · Internet / Wifi

Cottage in Chesapeake Bay, for $420 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Sun loungers, beach towels
4.5
Excellent(234 Reviews)
Cottage
 in Norfolk
Norfolk Beach Cottage Rental
6 guests · 3 bedrooms · 1 bath
Pool · Pets allowed · Kitchen / Kitchenette
Most favorited

Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Norfolk Beach Cottage Rental for $394 for your next trip.

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