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

Waterfront With Private Pier And Tranquil Water Views! - Chesapeake Bay
10 115 reviews

Waterfront With Private Pier And Tranquil Water Views!

cottage, Deltaville
This waterfront property is located in Gloucester, Virginia, just a short drive from Deltaville and its attractions like the Deltaville Marina and Holly Point Nature Park. The cottage has consistently received excellent ratings from previous guests, highlighting its charm and comfort.
The two-bedroom cottage offers 121 square metres of space, comfortably accommodating up to four guests. The property features a fully equipped kitchen, a garden, air conditioning, high-speed internet, and a private dock with stunning waterfront views, perfect for fishing, crabbing, or simply relaxing by the water.
Bay View Bungalow By The Pier - Swimming Pool And Pet Friendly - 30 Day Listing - Chesapeake Bay
No reviews

Bay View Bungalow By The Pier - Swimming Pool And Pet Friendly - 30 Day Listing

cottage, Norfolk
This charming cottage is situated in Willoughby Spit, Norfolk, just a short distance from the Chesapeake Bay beaches and the Ocean View Fishing Pier, offering a peaceful escape with easy access to both the coast and the city. The cottage is located in a quiet residential area, perfect for families and those looking for a relaxing getaway.
The cottage sleeps up to 10 guests in four bedrooms, making it ideal for larger families or groups of friends. The property offers a range of amenities, including a private swimming pool, a spacious garden, a terrace, and parking for several vehicles, ensuring a comfortable and enjoyable stay.
Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc. - Chesapeake Bay
10 53 reviews

Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc.

cottage, Dunkirk
This charming cottage is situated just a short distance from Fridays Creek Winery and the Patuxent River, offering a peaceful escape in the heart of Dunkirk, Maryland. It has received excellent reviews from previous guests, making it a popular choice for travellers seeking a relaxing getaway.
The cottage spans 84 square metres and comfortably accommodates up to four guests in its two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private outdoor pool, barbecue grills, and a spacious garden, as well as the convenience of a fully equipped kitchen, free Wi-Fi and a private patio.
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.

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.

Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch. - Chesapeake Bay
9.2 15 reviews

Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch.

cottage, Benedict
This Benedict beach house is situated near the Dr Samuel A Mudd House Museum and Drum Point Lighthouse, offering private beach access with over 150 metres of shoreline and a 120-metre pier, and is a 15-minute drive (approx. 24km) from local amenities.
Sleeping six, this self-catering property boasts a queen bed, bunk beds, and a sofa bed, plus a fully equipped kitchen, air conditioning, a terrace, garden, spa, and a gas grill; enjoy birdwatching at Walter's Walk sandbar and explore nearby attractions.
Oyster Cottage  - Walk To Shops , Mainstay Music Venue And The Bay! - Chesapeake Bay
9.6 14 reviews

Oyster Cottage - Walk To Shops , Mainstay Music Venue And The Bay!

cottage, Rock Hall
Oyster Cottage is a charming holiday home situated just a short walk from the waterfront in Rock Hall, offering easy access to shops, restaurants, and entertainment. The cottage consistently receives excellent reviews from guests, highlighting its comfortable and convenient location.
The property features two bedrooms, accommodating up to seven guests, making it ideal for families or groups of friends. The cottage offers a range of amenities including a fully equipped kitchen, a private garden, and a patio for outdoor dining, ensuring a relaxing and enjoyable stay.
Rustic Beach Front Apartment - Cozy, Rustic And On The Beach! - 2 Br/1 Bath - Chesapeake Bay
8.4 47 reviews

Rustic Beach Front Apartment - Cozy, Rustic And On The Beach! - 2 Br/1 Bath

cottage, Norfolk
This charming Norfolk cottage is ideally situated just a short distance from a selection of beautiful beaches, including Norfolk Beaches, Community Beach, and Ocean View Beach, offering the perfect base for a seaside getaway. It has received very good user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay.
The cottage boasts two bedrooms and two bathrooms, comfortably accommodating up to five guests, and spans 87 square metres. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, parking, and free WiFi, ensuring a relaxing and enjoyable stay.
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.

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.

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.
Cottage On The Bay - Chesapeake Bay
8.8 3 reviews

Cottage On The Bay

cottage, Long Beach
This family-friendly beach lodge in St. Leonard, Maryland, offers access to three private community beaches and is situated within 160 kilometres of Washington D.C. and Joint Base Andrews, 72 kilometres from Waldorf, and 24 kilometres from Solomons Island.
This two-bedroom holiday home accommodates up to four guests, featuring two smart TVs, a bathroom with a tub, a living area with a pellet stove, a fully equipped kitchen, and on-site laundry facilities, with shared amenities including a fire pit and kayaks for exploring the bay.
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).
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.

Charming Pet-Friendly Cottages in Chesapeake Bay

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

Charming 1-bedroom Cottage With Ac In Cozy Harwood - Chesapeake Bay
10 3 reviews

Charming 1-bedroom Cottage With Ac In Cozy Harwood

cottage, Riva
This Anne Arundel County holiday let is situated approximately 18 kilometres from the Patuxent River and 24 kilometres from the Chesapeake Bay, with London Town and Annapolis Harbour Centre a short 13 to 14 kilometre drive away.
This one-bedroom annex accommodates up to four guests and offers amenities including Wi-Fi, air conditioning, a dryer, and ironing board, with toiletries provided, and is conveniently located for South River Golf Links and Thanksgiving Farm Wines.
Sandy Mutts At The Beach - Chesapeake Bay
8.0 16 reviews

Sandy Mutts At The Beach

cottage, Norfolk
This Norfolk seaside cottage offers immediate beach access, situated in East Ocean View, less than 10km from Ocean View Beach and Sarah Constant Shrine Beach.
The 111 square metre property sleeps four, boasting a fully equipped kitchen, private patio, garden, and in-cottage laundry facilities; barbecue grills are available for outdoor use.
Mariners Cove 4 Bedroom Cottage By Redawning - Chesapeake Bay
No reviews

Mariners Cove 4 Bedroom Cottage By Redawning

cottage, Norfolk
This pet-friendly cottage is located in Norfolk, 13 kilometres from the city centre.
This accommodation offers air conditioning, Wi-Fi, a barbeque area, and parking, with a kitchen equipped with a fridge, microwave oven, and dishwasher, making it suitable for both active and relaxed holidays.
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.

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.

Waterfront Maryland Retreat W/ Dock & Bay View! - Chesapeake Bay
9.4 12 reviews

Waterfront Maryland Retreat W/ Dock & Bay View!

cottage, Chance

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.

Key Lime Cottage - Your Beachside Retreat - Chesapeake Bay
10 58 reviews

Key Lime Cottage - Your Beachside Retreat

cottage, Cape Charles

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.

Beach Cottage By The Sea.... - Chesapeake Bay
9.8 39 reviews

Beach Cottage By The Sea....

cottage, Kilmarnock
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