Cottages in Chesapeake Bay

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Chesapeake Bay cottages
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546 Best cottages in Chesapeake Bay

Best Chesapeake Bay cottages with a garden

Potomac Rvr Woodland Cottage, Polite Pets Welcomed, Central Air, Stunning Sunset - Chesapeake Bay
9.8 64 reviews

Potomac Rvr Woodland Cottage, Polite Pets Welcomed, Central Air, Stunning Sunset

cottage, Tall Timbers
This Tall Timbers holiday home enjoys a riverside location, less than 1.5 kilometres from the Potomac River and within a 10-kilometre radius of Piney Point Beach, Piney Point Lighthouse, and St. Mary's River State Park.
The 102-square-metre property offers three bedrooms, one bathroom, and sleeps eight guests, boasting a fully equipped kitchen, a terrace, a garden, a spa, free Wi-Fi, and an arcade/game room.
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland - Chesapeake Bay
9.6 17 reviews

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland

cottage, Piney Point
This Piney Point waterfront holiday home boasts stunning Chesapeake Bay views, is situated in Point Lookout, Southern Maryland, and is a short 3.2km drive from Point Lookout State Park and the Smith Island Ferry.
The 95 square metre property offers two bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, Wi-Fi, air conditioning, a garden, parking, and on-site amenities such as a fire pit, kayaks, and fishing/crabbing equipment.
Cozy Bay View - Beachside, Pet Friendly, Wi-fi - Chesapeake Bay
8.6 51 reviews

Cozy Bay View - Beachside, Pet Friendly, Wi-fi

cottage, Norfolk
This charming beach house is situated in Willoughby Spit, just a short drive from Norfolk Beaches, Ocean View Beach, and Oceanview Fishing Pier, offering easy access to the region's attractions. It has consistently received very good ratings from previous guests.
The cottage has one bedroom and one bathroom, accommodating up to five guests comfortably across its 88 square metres. Guests can enjoy a fully equipped kitchen, a private patio, free Wi-Fi, and access to a playground and barbecue grills on-site.
Adorable Chesapeake Bay Beach Cottage A Just 1 Block From The Sand! - Chesapeake Bay
9.6 28 reviews

Adorable Chesapeake Bay Beach Cottage A Just 1 Block From The Sand!

cottage, Virginia Beach
This family-friendly holiday home is located in Virginia Beach, just a mile from First Landing State Park and Marina Shores Marina, with Chesapeake Beach and Sylvan Beach within a three-mile radius. It has received excellent reviews from previous guests.
The cottage has three bedrooms and three bathrooms, providing ample space for up to six guests. It features a fully equipped kitchen, a private swimming pool, a terrace, a garden, and a spa, ensuring a comfortable and enjoyable stay.

Superior Family-Friendly Cottages in Chesapeake Bay

Give the family a spacious seaside basecamp steps from the waves at family island cottages in Chesapeake Bay.

Family And Pet-friendly, Waterfront With Pier - Chesapeake Bay
10 271 reviews

Family And Pet-friendly, Waterfront With Pier

cottage, Madison
This waterfront property is situated just a short drive from Cambridge, Maryland, offering easy access to nearby towns like Easton, St. Michaels, Salisbury, and Ocean City. The cottage enjoys an excellent user rating, reflecting its high standards and appeal to travellers.
This four-bedroom, two-bathroom home spans 174 square metres and comfortably accommodates up to eight guests. The property offers a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, perfect for families and groups seeking a relaxing and enjoyable stay.
Centrally Located Hampton Roads Home W/ Game Room! - Chesapeake Bay
No reviews

Centrally Located Hampton Roads Home W/ Game Room!

cottage, Portsmouth
This cottage is located in Portsmouth, within 4.8 kilometres of Emanuel AME Church, Commodore Theatre, and Portsmouth Art and Cultural Centre.
This pet-friendly, family-friendly holiday home offers a private patio, a fireplace, and a fully equipped kitchen with a microwave and dishwasher, with free on-site parking and WiFi available in public areas.
Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay - Chesapeake Bay
9.8 68 reviews

Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay

cottage, Cecilton
This charming cottage is located in Cecilton, Maryland, just 40 kilometres from Bohemia Vista Marina, Crow Farm and Vineyard, and the C and D Canal Museum. It has received excellent user ratings, making it a popular choice for travellers.
The cottage has two bedrooms and one bathroom, offering comfortable accommodation for up to six guests. It features a well-equipped kitchen, a private garden, a balcony, and a jacuzzi, providing everything you need for a relaxing and enjoyable stay.
Private 1300 Sq Ft Cottage In Historic Yorktown-w/ Trolley Access - Chesapeake Bay
10 172 reviews

Private 1300 Sq Ft Cottage In Historic Yorktown-w/ Trolley Access

cottage, Yorktown
This charming cottage is situated in Yorktown's historic district, just a short walk from Main Street and the Yorktown Beach. It has received excellent user ratings and is a popular choice for travellers seeking a comfortable and convenient stay.
This one-bedroom cottage sleeps up to four guests and features a spacious living area, a fully equipped kitchen, and two bathrooms. Guests can enjoy modern amenities like air conditioning, Wi-Fi, and a private garden, making it ideal for a relaxing getaway.

Frequently asked questions about cottages in Chesapeake Bay

  • What would be a good 2-days itinerary for visiting Baie de Chesapeake?

    You could spend a day exploring Annapolis, the state capital of Maryland, with its charming historic district and waterfront. The next day, head to the Eastern Shore for a taste of small-town life and stunning scenery. You could visit St. Michaels, a picturesque town with a rich maritime history, or explore Assateague Island National Seashore, home to wild horses.
  • What are the best cottages in Chesapeake Bay?

    Among the cottages in Chesapeake Bay, Historic Cottage On Ware River Estate, Enchanted Holiday Cottage and Cottage On A Private Island In The York River are the most popular ones.

  • What part of Baie de Chesapeake is ideal for renting a cottage?

    The Eastern Shore is a popular choice for cottage rentals, offering a peaceful escape from the hustle and bustle of city life. Areas like St. Michaels, Easton, and Ocean City provide a range of options, from quaint waterfront cottages to spacious homes with private docks.
  • What are the best cottages with a pool in Chesapeake Bay?

  • When is the best time to rent a cottage in Baie de Chesapeake?

    The shoulder seasons, spring and autumn, offer the best of both worlds: pleasant weather and fewer crowds. You can enjoy the beauty of the bay without the summer heat and crowds. However, if you prefer warm weather and outdoor activities, summer is also a good time to visit.
  • What are the best cottages with a jacuzzi in Chesapeake Bay?

  • What are the can't-miss sights in Baie de Chesapeake?

    You can't miss the Chesapeake Bay Bridge, a stunning engineering feat that connects the Eastern Shore to the mainland. The National Aquarium in Baltimore is a must-visit for marine life enthusiasts. And for a glimpse of nature's beauty, explore Assateague Island National Seashore, home to wild horses and diverse wildlife.
  • What are the best cottages for families and kids in Chesapeake Bay?

  • Why consider renting a cottage in Baie de Chesapeake for your stay?

    Renting a cottage offers a unique and relaxing experience. It gives you a chance to enjoy the tranquility of the bay, with easy access to local attractions and activities. Many cottages come with amenities like private docks, fire pits, and outdoor spaces, perfect for enjoying the fresh air and scenic views.
  • What are the best pet friendly cottages in Chesapeake Bay?

  • Can you easily explore Baie de Chesapeake on foot or by bike?

    While some areas offer walking and cycling paths, exploring Chesapeake Bay is best done by car. The bay is vast and spread out, with many attractions located a distance apart. Driving allows you to explore the diverse landscapes and towns that make up the region.
  • What are the best cottages with parking in Chesapeake Bay?

  • What are the best restaurants in Baie de Chesapeake with nature views?

    The Chart Room in St. Michaels offers breathtaking views of the harbour while you enjoy fresh seafood. The Blackwall Hitch in Annapolis has a waterfront patio with stunning views of the Chesapeake Bay Bridge.
  • What family-friendly activities are available in Baie de Chesapeake?

    The Chesapeake Bay Maritime Museum in St. Michaels offers interactive exhibits and boat tours for all ages. Assateague Island National Seashore is a great place for kids to spot wildlife, explore the beach, and learn about the natural environment. The Maryland Science Center in Baltimore is another excellent option for families with interactive exhibits and educational programs.

Popular destinations

Check Out Cottages with a Hot Tub in Chesapeake Bay

Listen to the ocean waves from the bubbling comfort of your private shoreline hot tub at island cottages with a hot tub in Chesapeake Bay.

Hays Beach House - Hot Tub - Private Beach - Chesapeake Bay
9.8 16 reviews

Hays Beach House - Hot Tub - Private Beach

cottage, Piney Point
This five-bedroom cottage is located in Point Lookout, a rural beachside neighbourhood in Scotland, MD, approximately 24 kilometres from Piney Point. The property has consistently received excellent reviews from guests.
The cottage can accommodate up to 12 guests and features a fully equipped gourmet kitchen, a private hot tub with bay views, and a screened porch. Guests can enjoy direct access to a private beach for crabbing, fishing, kayaking, and stand-up paddle boarding, as well as a Tesla charger and contactless check-in.
Smith Beach Cottage W/ Private Sunset - Chesapeake Bay
9.8 10 reviews

Smith Beach Cottage W/ Private Sunset

cottage, Eastville
This two-bedroom holiday home in Eastville offers private beach access for sunset viewing and is situated approximately 5.6 kilometres from Chesapeake Bay and 7.2 kilometres from Cape Charles Beach.
This Eastville holiday home accommodates up to four guests, featuring a king and a queen bedroom, a private hot tub, air conditioning, and Wi-Fi, with a check-out time of 12:00 PM.
3 Br Bay Home W Private Dock & All The Amenities - Chesapeake Bay
10 25 reviews

3 Br Bay Home W Private Dock & All The Amenities

cottage, Mathews
This Mathews County waterfront holiday home in Onemo, Virginia, is situated 4.5km from Bethel Beach Natural Area Preserve and within 51km of the Deltaville Maritime Museum and White Stone Beach.
The four-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen, Jacuzzi, terrace, garden, free Wi-Fi, and on-site amenities including a hot tub, arcade, and barbecue grills.
Firefly Cottage At The Cape, Hot Tub, Community Beach, Boat Show, Usna Games. - Chesapeake Bay
10 114 reviews

Firefly Cottage At The Cape, Hot Tub, Community Beach, Boat Show, Usna Games.

cottage, Arnold
This charming cottage is located in Cape Saint Claire, just a short drive from Arnold's attractions, including Sandy Point State Park and Sandy Point Beach. The cottage has received excellent user ratings, making it a popular choice for travellers.
This holiday home offers 61 square metres of space, comfortably accommodating up to 5 guests in its one bedroom and one bathroom. The cottage is equipped with a range of amenities, including a fully fitted kitchen, a spa, a terrace, a garden, parking and Wi-Fi, ensuring a comfortable and enjoyable stay.

Charming Pet-Friendly Cottages in Chesapeake Bay

Let your pup doze in the sea breeze at these pet-friendly island cottages in Chesapeake Bay.

Chesapeake City Pool Retreat  Waterfront Stay In The Woods - Chesapeake Bay
8.8 15 reviews

Chesapeake City Pool Retreat Waterfront Stay In The Woods

cottage, Elkton
This charming cottage is located just 10 kilometres from Chesapeake Inn, nestled in a peaceful wooded setting on the water in Elkton. It has received very good ratings from previous guests.
The property has two bedrooms and two bathrooms, comfortably accommodating up to seven guests. It features a private waterfront location, a spacious open floor plan, a swimming pool, and a large deck overlooking the water.
Private Beach Front Getaway At The Sunshine Beach Cottage. - Chesapeake Bay
9.8 83 reviews

Private Beach Front Getaway At The Sunshine Beach Cottage.

cottage, Piney Point
This charming beach house is situated just 8 kilometres from Point Lookout State Park and within a 19 kilometre radius of several other attractions, offering easy access to the region's natural beauty and historical sites. It has received excellent user ratings, making it a popular choice for families and groups.
The two-bedroom property spans 91 square metres and comfortably accommodates up to 8 guests. The cottage features a range of amenities, including a fully equipped kitchen, a cosy fireplace, a terrace, and a garden, ensuring a relaxing and enjoyable stay.
Manor And Mutts #1 (4-bedroom Cottage) - Pets Allowed By Redawning - Chesapeake Bay
8.4 19 reviews

Manor And Mutts #1 (4-bedroom Cottage) - Pets Allowed By Redawning

cottage, Norfolk
This beachfront holiday home in Norfolk's Willoughby Spit district offers direct access to the Chesapeake Bay, approximately 15 meters from the sandy dune walk, and is a short drive from the Waterside District.
This 204 square meter holiday home accommodates up to 8 guests, featuring two living areas, a fully equipped kitchen, high-speed WiFi, off-street parking, and a large back deck with a charcoal grill, with Buckroe Beach and Park nearby for outdoor activities.
Restored 1930s Cottage On 1 Acre W/ Fire Pit - Chesapeake Bay
No reviews

Restored 1930s Cottage On 1 Acre W/ Fire Pit

cottage, Gloucester Point
This charming cottage is situated in Hayes, Virginia, just a short drive from the historical Rosewell Ruins and the scenic Machicomoco State Park. The cottage offers a peaceful retreat in a rural setting, perfect for those seeking a relaxing getaway.
The cottage features a well-equipped kitchen with a dishwasher, allowing you to prepare your own meals. You can enjoy the outdoors with barbecue facilities and free parking, making it ideal for a self-catering holiday.

Uncover Charming Luxury Cottages in Chesapeake Bay

Indulge in private seaside exclusivity, high-end architecture, and elite service at luxury island cottages near the sea in Chesapeake Bay.

Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac - Chesapeake Bay
10 7 reviews

Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac

cottage, Piney Point

Seashore Cottages in Chesapeake Bay

Step straight out of a charming, intimate guest property onto the sand at cottages by the sea in Chesapeake Bay.

Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills - Chesapeake Bay
9.2 7 reviews

Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills

cottage, Queenstown

Cottages with a Pool in Chesapeake Bay

Alternate between a refreshing freshwater plunge and an ocean swim at island cottages with a pool in Chesapeake Bay.

The Yellow Cottage On Harness Creek - Chesapeake Bay
10 178 reviews

The Yellow Cottage On Harness Creek

cottage, Annapolis
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