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

Near Chincoteague & Assateague Island\ncharming 2-bedroom Cottage - Chesapeake Bay
9.6 4 reviews
Chesapeake Bay
01/10 – 05/10
A$296/nighttotal: A$1184 (4 )

Near Chincoteague & Assateague Island\ncharming 2-bedroom Cottage

2 3
cottage , Saxis
This Saxis holiday home is conveniently located near Bloxom Winery and Somers Cove Marina, offering easy access to the Chesapeake Forest – Dunn Swamp Complex and Kegotank Bay for birdwatching and outdoor recreation.
Sleeping up to four guests, the two-bedroom property features a queen and a double bed, a fully equipped kitchen with fridge and microwave, air conditioning, Wi-Fi, in-unit laundry, and a bathroom with a hairdryer; local assistance is available from the owner.
Esva Down By The Sea & Pet Friendly - Chesapeake Bay
9.8 7 reviews
Chesapeake Bay
12/09 – 16/09
A$377/nighttotal: A$1508 (4 )

Esva Down By The Sea & Pet Friendly

2 2
cottage , Savageville
This seaside holiday home in Onancock, Virginia, is situated a short drive (approx. 48km) from Chincoteague Island and 64km from Cape Charles, offering easy access to the Onancock Wharf and Kegotank Bay.
The 93 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen (fridge, microwave), air conditioning, garden, parking, internet access, and is pet-friendly.
Cozy, Unique, Historic Registered Cottage On The Corsica River! - Chesapeake Bay
10 7 reviews
Chesapeake Bay
23/08 – 28/08
A$374/nighttotal: A$1870 (5 )

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

1 2
cottage , Centreville
This Centreville cottage is situated 1.5 km from the Hazel Miner Monument and within 15 km of Cassinelli Winery and Vineyards, Wye Oak State Park, and Queenstown Premium Outlets.
The self-catering property sleeps four guests in one bedroom and one bathroom, boasting a fully equipped kitchen, in-unit laundry, free Wi-Fi, a balcony, and a garden with barbecue facilities.
Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc - Chesapeake Bay
10 20 reviews
Chesapeake Bay
01/10 – 05/10
A$463/nighttotal: A$1852 (4 )

Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc

2 3
cottage , Long Beach
This St. Leonard's cottage, near Long Beach, offers easy access to Flag Ponds Nature Park and Flag Harbour Marina, both within 1.6km, and is less than 1.6km from Long Beach and Matoaka Beach.
This 74 square metre holiday home sleeps five, boasting two bedrooms, two bathrooms, a fully equipped kitchen, swimming pool, jacuzzi, and terrace, plus free Wi-Fi and on-site parking.

Best Chesapeake Bay cottages with a garden

Waterfront River Cottage For 2, Dog-friendly - Chesapeake Bay
9.6 26 reviews
Chesapeake Bay
20/06 – 27/06
A$517/nighttotal: A$3619 (7 )

Waterfront River Cottage For 2, Dog-friendly

1 2
cottage , Severna Park
This charming beachside cottage is located near Severna Park, just nine miles from the B&A Trail, Severna Park Golf Center, and Bay Hills Golf Club. It has received excellent ratings for its location, cleanliness, and overall user experience.
The cottage has one bedroom and one bathroom, offering comfortable accommodation for up to two guests, and it comes equipped with a fully equipped kitchen, a terrace, a garden, a spa, and parking. Enjoy the fresh air and sunshine with the relaxing outdoor space, cook up a meal on the charcoal grill, and take advantage of the arcade/game room for entertainment.
Cozy Getaway - Breezy Point Beach & Marina - Chesapeake Bay
9.9 101 reviews
Chesapeake Bay
20/06 – 27/06
A$509/nighttotal: A$3563 (7 )

Cozy Getaway - Breezy Point Beach & Marina

1 2
cottage , Chesapeake Beach
This charming cottage is situated in Breezy Point Beach, just a stone's throw from the beach and a short distance from a pier, jet ski rentals, a waterpark, and a golf course. It has received excellent ratings for location, cleanliness, and overall user experience.
The cottage spans 56 square metres and comfortably accommodates up to six guests in its two bedrooms and one bathroom. It boasts a range of amenities, including a screened-in porch with a swing, a garden, free parking, and Wi-Fi, making it perfect for a relaxing and enjoyable stay.
Cozy Cottage W/ Hot Tub, Pool Table, Fenced Yard - Chesapeake Bay
9.9 180 reviews
Chesapeake Bay
12/09 – 16/09
A$595/nighttotal: A$2380 (4 )

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

3 2
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.
Secluded Waterfront Cottage On 200 Acre Farm Near Queenstown - Chesapeake Bay
10 107 reviews
Chesapeake Bay
01/10 – 05/10
A$410/nighttotal: A$1640 (4 )

Secluded Waterfront Cottage On 200 Acre Farm Near Queenstown

4 3
cottage , Queenstown
This waterfront property is situated just 15 km from Queenstown Premium Outlets, Hazel Miner Monument, and Queenstown Harbor Golf Links, offering a peaceful retreat close to popular attractions. It has received excellent user ratings, making it a popular choice for travellers.
The cottage has three bedrooms, accommodating up to eight guests, and provides a fully equipped kitchen, a fireplace, a terrace, a garden, a spa, and parking. Guests can enjoy the stunning views, relax by the fireplace, prepare their own meals, and make the most of the outdoor amenities.

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
12/09 – 16/09
A$624/nighttotal: A$2496 (4 )

Beachfront Hideaway - Pet Friendly, Hot Tub, Ev

2 2
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.
Cozy Cottage - Chesapeake Bay
10 1 review
Chesapeake Bay
23/08 – 28/08
A$1069/nighttotal: A$5345 (5 )

Cozy Cottage

4 2
cottage , Dundalk
This Dundalk holiday home is situated within 9.6km of Johns Hopkins Bayview Medical Center, the Baltimore Cruise Terminal, and Johns Hopkins Hospital, offering convenient access to these key locations.
Sleeping eight guests, the four-bedroom, two-bathroom property boasts a fully equipped kitchen with dishwasher, a jacuzzi, private garden, parking, and air conditioning, plus a washing machine and dryer for added convenience.
Hays Beach House - Hot Tub - Private Beach - Chesapeake Bay
9.8 16 reviews
Chesapeake Bay
20/07 – 27/07
A$1550/nighttotal: A$10850 (7 )

Hays Beach House - Hot Tub - Private Beach

5 4
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
10 4 reviews
Chesapeake Bay
23/08 – 28/08
A$483/nighttotal: A$2415 (5 )

Smith Beach Cottage W/ Private Sunset

2 2
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.

Best pet friendly Chesapeake Bay cottages

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

Sandy Mutts At The Beach By Redawning - Chesapeake Bay
Chesapeake Bay
20/06 – 27/06
A$518/nighttotal: A$3626 (7 )

Sandy Mutts At The Beach By Redawning

1 2
cottage , Norfolk
This Norfolk beachfront cottage, situated in East Ocean View, is just a short walk from the beach and within 10km of Ocean View Beach, Sarah Constant Shrine Beach, Little Creek Beach, and Ocean View Fishing Pier.
Sleeping four guests, this two-bedroom holiday home boasts a fully equipped kitchen, Smart TV, patio, garden, parking, and pet-friendly accommodation.
The Little Blue Cottage - Topping : Waterfront! - Chesapeake Bay
9.9 126 reviews
Chesapeake Bay
01/10 – 05/10
A$622/nighttotal: A$2488 (4 )

The Little Blue Cottage - Topping : Waterfront!

3 3
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.
Eastern Shore Beach Cottage Get-away - Chesapeake Bay
10 139 reviews
Chesapeake Bay
23/08 – 28/08
A$691/nighttotal: A$3455 (5 )

Eastern Shore Beach Cottage Get-away

2 2
cottage , Rock Hall
This charming cottage is situated just a short drive from the Eastern Neck Island Wildlife Refuge and 10km from Chestertown, home to Washington College, offering a peaceful escape from the hustle and bustle. It has received excellent reviews from previous guests, making it a popular choice for those looking for a relaxing getaway.
The cottage is spacious, spanning 93 square meters and comfortably accommodating up to five guests. It boasts a fully equipped kitchen, a private garden, a swimming pool, and a spa, as well as direct access to a sandy beach, perfect for families and water sports enthusiasts.
Family And Pet-friendly, Waterfront With Pier - Chesapeake Bay
10 268 reviews
Chesapeake Bay
01/10 – 05/10
A$590/nighttotal: A$2360 (4 )

Family And Pet-friendly, Waterfront With Pier

4 3
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.
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