Cottages in Chesapeake Bay

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Chesapeake Bay cottages
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570 Best cottages in Chesapeake Bay

Best family friendly Chesapeake Bay cottages

Among the 570 accommodations in Chesapeake Bay, here are the 4 best family friendly cottages

Beach Cottage By The Sea.... - Chesapeake Bay
10 32 reviews
Chesapeake Bay
29/08 – 05/09
A$359/nighttotal: A$2513 (7 )

Beach Cottage By The Sea....

2 2
cottage , Kilmarnock
This charming cottage is situated just 15km from the Reedville Fishermen's Museum, Smith Point Marina, and Buzzard's Point Marina, with the Northern Neck Farm Museum a short 16.4km drive away. It enjoys a peaceful location near the beach, making it a perfect escape for those seeking a relaxing getaway. The property has received excellent reviews from previous guests.
This two-bedroom holiday home can comfortably accommodate up to six guests. It comes equipped with a fully fitted kitchen, a terrace, a garden, and parking, as well as air conditioning, Wi-Fi, a dishwasher, and a microwave.
Waterfront Cottage In Beautiful Hoopers Island - Chesapeake Bay
10 84 reviews
Chesapeake Bay
29/08 – 05/09
A$344/nighttotal: A$2408 (7 )

Waterfront Cottage In Beautiful Hoopers Island

2 2
cottage , Chesapeake Ranch Estates
This waterfront cottage is located in Chesapeake Ranch Estates, just 5km from Middle Hooper Island and 8km from Lower Hooper Island, offering a peaceful escape in a picturesque setting. It has received excellent user reviews, making it a popular choice for travellers.
The cottage spans 54 square metres and comfortably accommodates up to 5 guests in its two bedrooms and one bathroom. It includes a fully equipped kitchen, a garden, a terrace, and free Wi-Fi, allowing you to enjoy both indoor and outdoor relaxation, as well as easy access to the surrounding natural beauty.
The Little Blue Cottage - Topping : Waterfront! - Chesapeake Bay
9.9 130 reviews
Chesapeake Bay
30/07 – 05/08
A$717/nighttotal: A$4302 (6 )

The Little Blue Cottage - Topping : Waterfront!

3 6
cottage , White Stone
This waterfront cottage is situated in White Stone, Virginia, just a short drive from award-winning restaurants and a marina. The cottage has consistently received excellent reviews for its location, cleanliness, and overall experience.
The cottage spans 126 square metres and comfortably accommodates up to six guests in its three bedrooms and two bathrooms. Enjoy stunning views of the bay and creek from the porch swings, take advantage of the high-speed internet, and explore the area by kayak, launching from the floating dock or nearby community boat ramp.
Be Persuaded To Experience This Vintage Cottage By The Sassa - Chesapeake Bay
9.2 11 reviews
Chesapeake Bay
30/07 – 05/08
A$565/nighttotal: A$3390 (6 )

Be Persuaded To Experience This Vintage Cottage By The Sassa

4 6
cottage , Galena
This charming cottage is located on the banks of a river, just 20 kilometres from attractions like Dutch Country Farmers Market, Betterton Beach, and Washington College. It has received excellent reviews from previous guests.
This four-bedroom property comfortably sleeps eight guests and includes two bathrooms. The cottage offers a fully-equipped kitchen, a garden, barbecue facilities, a terrace, free Wi-Fi, and parking.

Best Chesapeake Bay cottages with a garden

Summertime Where The Livin Is Easy At The Rivah In Irvington! - Chesapeake Bay
10 308 reviews
Chesapeake Bay
29/08 – 05/09
A$384/nighttotal: A$2688 (7 )

Summertime Where The Livin Is Easy At The Rivah In Irvington!

2 2
cottage , Irvington
This charming cottage is located just a short distance from the Steamboat Era Museum and Historic Christ Church, offering a tranquil escape from the hustle and bustle of the city. Guests consistently rate this property as excellent, highlighting its peaceful setting and comfortable amenities.
The cottage provides spacious accommodation for up to four guests, with two bedrooms and two bathrooms spread across 158 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private garden, a spa, a tennis court, and a barbecue grill, making it ideal for families or groups seeking a relaxing retreat.
Discover Onancock... "A Little Slice Of Nowhere Else." - Chesapeake Bay
Chesapeake Bay
29/08 – 05/09
A$230/nighttotal: A$1610 (7 )

Discover Onancock... "A Little Slice Of Nowhere Else."

1 2
cottage , Onancock
This 1950s waterside bungalow is located in Historic Downtown Onancock, offering views of Onancock Creek and walking access to dining, shopping, and cultural attractions such as the North Street Playhouse and Red Queen Gallery.
This one-bedroom holiday home sleeps two guests and features a private dock for kayaking and relaxation, with amenities including internet and air conditioning.
Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch. - Chesapeake Bay
9.0 8 reviews
Chesapeake Bay
01/10 – 05/10
A$367/nighttotal: A$1468 (4 )

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

1 3
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.
Comfortable & Private 2 Bedrm Cottage W/ King Bed. - Chesapeake Bay
9.4 20 reviews
Chesapeake Bay
01/10 – 05/10
A$317/nighttotal: A$1268 (4 )

Comfortable & Private 2 Bedrm Cottage W/ King Bed.

2 3
cottage , Portsmouth
This charming cottage is situated just 1.6 kilometres from Rivers Casino Portsmouth and Portsmouth City Park, making it a great base for exploring the city. It has received excellent reviews from previous guests.
This cosy home has two bedrooms and a bathroom, covering 76 square metres, and can accommodate up to 5 guests. The property offers a fully equipped kitchen, a terrace, a garden, parking, free Wi-Fi, and a range of entertainment options.

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.

Destinations nearby

Best Chesapeake Bay cottages with a jacuzzi

Among the 570 accommodations in Chesapeake Bay, here are the 4 best cottages with a jacuzzi

Beachfront Hideaway - Pet Friendly, Hot Tub, Ev - Chesapeake Bay
9.8 16 reviews
Chesapeake Bay
01/10 – 05/10
A$593/nighttotal: A$2372 (4 )

Beachfront Hideaway - Pet Friendly, Hot Tub, Ev

2 3
cottage , Heathsville
This waterfront holiday home in Lottsburg, Virginia, boasts 100+ feet of private beach access (tide dependent) and is situated approximately 320 km from Washington, D.C., and 6.4 km from the Maryland shoreline across the Potomac River.
The 102-square-metre property sleeps five guests in two bedrooms and one bathroom, offering a Jacuzzi, kayaks for exploring the Potomac River and Chesapeake Bay, a fully equipped kitchen with a dishwasher, and blazing-fast broadband internet, plus a ChargePoint Level 2 EV charger.
Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach - Chesapeake Bay
10 3 reviews
Chesapeake Bay
29/08 – 05/09
A$459/nighttotal: A$3213 (7 )

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

1 2
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.
Hays Beach House - Hot Tub - Private Beach - Chesapeake Bay
9.8 16 reviews
Chesapeake Bay
23/08 – 28/08
A$1561/nighttotal: A$7805 (5 )

Hays Beach House - Hot Tub - Private Beach

5 2
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.
Cozy Cottage W/ Hot Tub, Pool Table, Fenced Yard - Chesapeake Bay
9.9 183 reviews
Chesapeake Bay
01/10 – 05/10
A$453/nighttotal: A$1812 (4 )

Cozy Cottage W/ Hot Tub, Pool Table, Fenced Yard

3 3
cottage , Norfolk
This charming cottage is located in Bayview, Norfolk, just 1.8km from Norfolk Beaches and within 5km of Community Beach and Ocean View Beach. It has received excellent ratings for location, cleanliness, and user experience.
The cottage offers 3 bedrooms and 93 square metres of space, comfortably accommodating up to 6 guests. It features a fully equipped kitchen, a private fenced yard, and a terrace, making it perfect for families and groups looking for a relaxing and enjoyable stay.

Best pet friendly Chesapeake Bay cottages

Among the 570 accommodations in Chesapeake Bay, here are the 4 best pet friendly cottages

Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger - Chesapeake Bay
9.9 68 reviews
Chesapeake Bay
29/08 – 05/09
A$1025/nighttotal: A$7175 (7 )

Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger

3 2
cottage , Piney Point
This charming cottage is located in Piney Point, Maryland, just a short distance from the Chesapeake Bay. It benefits from excellent user, location and cleanliness ratings.
The cottage has three bedrooms, accommodating up to eight guests, and offers a range of amenities, including private beach access, a fishing pier, kayaks and stand-up paddle boards, a Tesla charger, and contactless check-in.
Manor And Mutts #1 - Beach Front, Pet Friendly, High Speed Wifi, Private - Chesapeake Bay
8.6 16 reviews
Chesapeake Bay
30/07 – 05/08
A$743/nighttotal: A$4458 (6 )

Manor And Mutts #1 - Beach Front, Pet Friendly, High Speed Wifi, Private

4 6
cottage , Norfolk
This beach house is located in Willoughby Spit, just 3 kilometres from Norfolk Beaches, Sarah Constant Shrine Beach, and Ocean View Beach, offering a peaceful escape from the city bustle. It has received very good ratings from previous guests.
The property has 4 bedrooms and can accommodate up to 8 guests. It comes equipped with a fully fitted kitchen, a terrace, and a private garden, perfect for enjoying the Norfolk sunshine and making the most of the area's attractions.
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Chesapeake Bay
9.6 128 reviews
Chesapeake Bay
01/10 – 05/10
A$653/nighttotal: A$2612 (4 )

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!

2 3
cottage , Easton
This charming cottage is situated in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, offering easy access to the town's historical attractions. It has received excellent reviews from previous guests, highlighting its family-friendly atmosphere and comfortable amenities.
The property spans 130 square metres and comfortably accommodates up to five guests in its two bedrooms and three bathrooms. Guests can enjoy a range of facilities including a private swimming pool, a tennis court, and a spa, as well as a fully equipped kitchen, a garden, and a terrace.
Water Front Estate On Farm Cidery.  Pet Friendly With Inviting Private Beach. - Chesapeake Bay
Chesapeake Bay
30/07 – 05/08
A$739/nighttotal: A$4434 (6 )

Water Front Estate On Farm Cidery. Pet Friendly With Inviting Private Beach.

3 6
cottage , Kilmarnock
This waterfront holiday home in Kilmarnock offers a private 30-meter pier and a small sandy beach, located a short drive from the Steamboat Era Museum and the Mary Ball Washington Museum and Library.
This spacious 134 square meter cottage accommodates up to six guests across four bedrooms and two bathrooms, featuring a microwave, dishwasher, air conditioning, a terrace, garden, and parking, with complimentary use of SUPs for exploring the shoreline.
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