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

Grace Creek Cottage, Minutes To St. Michaels, Pool, Dock - Chesapeake Bay
10 3 reviews

Grace Creek Cottage, Minutes To St. Michaels, Pool, Dock

cottage, Tilghman Island
This private coastal lodge in Bozman, a short drive from St. Michaels, offers a secluded retreat on Tilghman Island, with proximity to the Chesapeake Bay Maritime Museum and St. Michaels Museum.
This three-bedroom, two-bathroom holiday home accommodates six guests and features a private pool, a private pier for water access, a waterfront screened porch, and a fireplace, with air conditioning and internet provided.
Pink Flamingo At The Beach - Chesapeake Bay
8.0 18 reviews

Pink Flamingo At The Beach

cottage, Norfolk
This vintage cottage in East Ocean View, Norfolk, offers direct access to the Chesapeake Bay beaches via a 0.1-kilometre boardwalk, with no streets to cross, and is a short drive from the Waterside District and Greenbrier Mall.
This pet-friendly holiday home, covering 116 square meters and accommodating up to five guests, features a fully equipped kitchen with a gas stove, a Large Smart TV, High Speed WiFi, off-street parking, and a small back deck with a charcoal barbecue grill.
Private Beach Front Getaway At The Sunshine Beach Cottage. - Chesapeake Bay
9.8 87 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.
Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Chesapeake Bay
10 71 reviews

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

cottage, Stevensville
This Stevensville, Maryland holiday home is conveniently located near several Kent Island wedding venues, within an hour's drive (approx. 80km) of Annapolis, Washington D.C., and Baltimore.
The 111-square-metre property boasts two bedrooms, two bathrooms, sleeping up to six guests, and features a screened-in porch, private sauna, and accessibility features; guests can also hire a chef or artist.

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.

Charming Beach Cottage Only 100 Yds From The Beach - Chesapeake Bay
9.2 80 reviews

Charming Beach Cottage Only 100 Yds From The Beach

cottage, Virginia Beach
This charming cottage is situated just a short walk from First Landing State Park, Atlantic University, and Edgar Cayce's Association for Research and Enlightenment, offering easy access to both natural beauty and cultural attractions. The property has received excellent user ratings for its location, cleanliness, and overall experience.
The cottage spans 139 square metres and comfortably accommodates families with its three bedrooms and a sofa bed. Guests can enjoy a private spa tub, a garden, a swimming pool, a barbecue grill, and a terrace, perfect for relaxing after a day of exploring the beach or nearby attractions.
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
This Piney Point waterfront holiday home is situated near St Mary's River State Park and the Piney Point Lighthouse, offering tranquil river views.
Sleeping up to six guests, the two-bedroom property boasts a fully equipped kitchen, air conditioning, Wi-Fi, smart TVs, and on-site barbecue facilities, making it ideal for families exploring the local area's attractions including the Patuxent River Naval Air Museum.
Cozy Virginia Potomac Riverfront Cottage - Chesapeake Bay
9.6 54 reviews

Cozy Virginia Potomac Riverfront Cottage

cottage, Montross
This waterfront holiday home in Hague, Northern Neck, Virginia, is situated close to the Kinsale Museum and Piney Point Lighthouse, offering easy access to local wineries.
The two-bedroom, two-bathroom property sleeps seven, boasts a fully equipped kitchen, private 50ft dock, and spectacular Potomac River views, perfect for fishing, crabbing, or simply enjoying the scenery.
902 Ch Historic Carriage House 20 Steps To Beach + Hot Tub, Kayaks, Beachfront Grilling - Chesapeake Bay
9.8 218 reviews

902 Ch Historic Carriage House 20 Steps To Beach + Hot Tub, Kayaks, Beachfront Grilling

cottage, Norfolk
This historic carriage house offers direct bayfront access in Willoughby Spit, Norfolk, featuring private walkways to the Chesapeake Bay and situated 483 metres from Ocean View Beach Park and 644 metres from Willoughby Spit.
This family-friendly cottage accommodates two guests with one bedroom and one bathroom, boasting a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, and complimentary kayaks and paddleboards, with parking available and a 10:00 AM check-out.

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.

900.a Seaside 2 Br Duplex Wrap-around Porch, Private Beach & Walkways, Beachfront Grilling, Hot Tub & Kayaks - Chesapeake Bay
No reviews

900.a Seaside 2 Br Duplex Wrap-around Porch, Private Beach & Walkways, Beachfront Grilling, Hot Tub & Kayaks

cottage, Norfolk
This 1920s duplex, a beachfront property offering coastal character, is situated in Norfolk's Ocean View district, just 75 feet from the sand and 0.5 kilometres from Ocean View Beach Park.
This family-friendly holiday home accommodates up to six guests across two bedrooms and one bathroom, featuring air conditioning, Wi-Fi, a kitchen with a dishwasher and microwave, a Jacuzzi, and a private deck, with kayaks and paddleboards available for rent to enjoy the Chesapeake Bay.
Year Round Playground - Rare Rustic-modern Getaway - Chesapeake Bay
No reviews

Year Round Playground - Rare Rustic-modern Getaway

cottage, Fairmount
This Fairmount holiday home is situated in Marion Station, Maryland, approximately 16km from Great Hope Golf Course and a supermarket, and around 160km from Ocean City and Assateague Island, near Crisfield and the Coventry Parish Ruins.
The four-bedroom, three-bathroom property sleeps eight guests and boasts a private pool (open Memorial Day to Labor Day), a seven-person hot tub, a fully equipped outdoor kitchen, a spacious recreation room with an 85-inch TV and pool table, and a unique waterfront location on East Creek with a private dock offering bay access.
Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach - Chesapeake Bay
10 3 reviews

Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach

cottage, Cheriton
This Cheriton cottage, situated 13km from Cape Charles' historic district and beaches, provides easy access to Bay Creek Resort (14km) and Kiptopeke State Park (19km).
The 37 square metre self-catering property sleeps four, boasting two bedrooms, one bathroom, a Jacuzzi, a terrace, a garden, parking, and a well-equipped kitchen including a dishwasher and a Keurig coffee machine, plus on-site hot tub and gas grill.
900.b Seaside 2 Br Cottage With Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, Paddle-boards, Kayaks & Beach Umbrellas/chairs - Chesapeake Bay
9.4 188 reviews

900.b Seaside 2 Br Cottage With Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, Paddle-boards, Kayaks & Beach Umbrellas/chairs

cottage, Norfolk
This second-floor holiday home in Ocean View, Norfolk, offers direct bayfront access via private walkways, placing it less than 100 metres from the bay and within 1.1 kilometres of Ocean View Beach Park and Fishing Pier, within a historic 1920s duplex featuring original wood trim and 14-foot ceilings. The accommodation, suitable for up to six guests, boasts two bedrooms, one bathroom, a fully equipped kitchen, air conditioning, a jacuzzi, a terrace with partial bay views, and is conveniently located near attractions such as Norfolk Botanical Garden (10.5 km) and Nauticus & Battleship Wisconsin (15.3 km).

Charming Pet-Friendly Cottages in Chesapeake Bay

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

Secluded Cozy Cottage In Historic Downtown - Chesapeake Bay
9.6 22 reviews

Secluded Cozy Cottage In Historic Downtown

cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
Old Time Beach Front Cottage - The Beach Is Your Backyard! 3 Bedroom Cottage By Redawning - Chesapeake Bay
No reviews

Old Time Beach Front Cottage - The Beach Is Your Backyard! 3 Bedroom Cottage By Redawning

cottage, Norfolk
This cottage offers a secluded holiday experience in Norfolk, situated 12 kilometres from the city centre with direct beach access.
This pet-friendly holiday home accommodates two guests and features air conditioning, a kitchen with a fridge, microwave, and dishwasher, as well as a barbecue area.
Steps To The Ocean! Family And Dog Friendly North End Cottage W/ Rsrv Parking - Chesapeake Bay
9.8 266 reviews

Steps To The Ocean! Family And Dog Friendly North End Cottage W/ Rsrv Parking

cottage, Virginia Beach
This pet-friendly cottage is located in Northeast Virginia Beach, a short walk from First Landing State Park and a 4-minute drive to the Chesapeake Bay.
This 89 square metre holiday home accommodates up to six guests and features three bedrooms, a full kitchen, a private garden, and is equipped with air conditioning and Wi-Fi.
Waterfront Home, Private Dock, A/c, Amazing Views, Boating, Fishing & Kayaking - Chesapeake Bay
10 35 reviews

Waterfront Home, Private Dock, A/c, Amazing Views, Boating, Fishing & Kayaking

cottage, North East
This waterfront holiday home, offering space for four guests, is located on the North East River, a short walk from Main Street and the Nauti Goose, and within easy reach of over 5,000 acres of nature trails.
This two-bedroom, one-bathroom abode features a fully equipped kitchen, air conditioning, a garden with a grill and fire pit, and direct access to a private dock.

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.

Pet-friendly Smith Island Cottage W/ Golf Cart! - Chesapeake Bay
10 23 reviews

Pet-friendly Smith Island Cottage W/ Golf Cart!

cottage, Smith Island

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.

The Heron's Nest At Atlantic Marina - Chesapeake Bay
9.8 322 reviews

The Heron's Nest At Atlantic Marina

cottage, Lake Shore

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.

Cozy, Unique, Historic Registered Cottage On The Corsica River! - Chesapeake Bay
9.0 11 reviews

Cozy, Unique, Historic Registered Cottage On The Corsica River!

cottage, Centreville
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