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Chesapeake Bay cottages
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570 Cottages at the best price in Chesapeake Bay

Best family friendly Chesapeake Bay cottages

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

Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc - Chesapeake Bay
10 20 reviews
Chesapeake Bay
12/09 – 16/09
274 €/nighttotal: 1096 € (4 )

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

2 2
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.
Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc. - Chesapeake Bay
9.6 49 reviews
Chesapeake Bay
23/08 – 28/08
189 €/nighttotal: 945 € (5 )

Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc.

1 2
cottage , Shady Side
This waterfront cottage in Shady Side, Maryland, is situated on a peninsula on the West River, approximately 32 kilometres from Annapolis and close to Galesville.
The one-bedroom, one-bathroom property sleeps three, offering a private dock, kitchen with fridge and microwave, air conditioning, a terrace, garden, parking, internet access, and proximity to Thanksgiving Farm Wines and South River Golf Links.
Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway! - Chesapeake Bay
10 239 reviews
Chesapeake Bay
23/08 – 28/08
335 €/nighttotal: 1675 € (5 )

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!

1 2
cottage , Annapolis
This charming waterfront cottage is located in West Annapolis, just a short walk from the US Naval Academy and a 1.5-mile stroll from the Annapolis City Dock. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This delightful cottage offers 65 square metres of space and can accommodate up to four guests. The property boasts a fully equipped kitchen, a screened-in porch, a private waterfront backyard with a fire pit, and a private dock with access to Weems Creek, making it ideal for relaxing and enjoying the beautiful surroundings.
Hays Beach House - Hot Tub - Private Beach - Chesapeake Bay
9.8 16 reviews
Chesapeake Bay
20/07 – 27/07
942 €/nighttotal: 6594 € (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.

Best Chesapeake Bay cottages with a garden

Walk To Beach: Pet-friendly Gem In Scotland! - Chesapeake Bay
9.8 7 reviews
Chesapeake Bay
12/09 – 16/09
201 €/nighttotal: 804 € (4 )

Walk To Beach: Pet-friendly Gem In Scotland!

1 2
cottage , Piney Point
This Piney Point holiday home is situated near Point Lookout State Park (1.6 km), Buzz's and Drury's Marinas (6.4 km), and Piney Point Lighthouse (43.5 km), offering easy access to Chesapeake Bay beaches.
The 39 square metre self-catering property sleeps three, features a sunroom, fully equipped kitchen with a Keurig coffee machine, a furnished deck with charcoal grill, driveway parking for three vehicles, and allows one pet for a fee.
Charming 2-bedroom 1 Bath Cottage With Ac, Wifi In Peaceful North Beach, Md. - Chesapeake Bay
9.6 4 reviews
Chesapeake Bay
01/10 – 05/10
209 €/nighttotal: 836 € (4 )

Charming 2-bedroom 1 Bath Cottage With Ac, Wifi In Peaceful North Beach, Md.

2 3
cottage , North Beach
This holiday let in North Beach is located 800 metres from the Chesapeake Bay and 800 metres from the Bayside History Museum.
This holiday let offers Wi-Fi, air conditioning, a dishwasher, and a microwave oven, with parking and laundry facilities available on site.
Cozy Getaway - Breezy Point Beach & Marina - Chesapeake Bay
9.9 101 reviews
Chesapeake Bay
20/06 – 27/06
309 €/nighttotal: 2163 € (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.
Cottage Located On The Patuxent River! - Chesapeake Bay
9.8 62 reviews
Chesapeake Bay
20/06 – 27/06
299 €/nighttotal: 2093 € (7 )

Cottage Located On The Patuxent River!

1 2
cottage , Golden Beach
This charming cottage is situated just a short distance from the Patuxent River, offering a peaceful retreat close to Running Hare Vineyard and Battle Creek Cypress Swamp Sanctuary. The cottage boasts excellent ratings for location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay.
The cottage comprises one bedroom and one bathroom, providing a cosy space for two guests. It features a private garden, a fireplace for cosy evenings, and modern amenities such as a coffee maker and a TV, making it ideal for a relaxing getaway.

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Best Chesapeake Bay cottages with a jacuzzi

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

Charming 3-bedroom Villa With Wifi, And  Jaccuzzi , Just Minutes From Yorktown - Chesapeake Bay
8.4 5 reviews
Chesapeake Bay
12/09 – 16/09
591 €/nighttotal: 2364 € (4 )

Charming 3-bedroom Villa With Wifi, And Jaccuzzi , Just Minutes From Yorktown

3 2
cottage , Gloucester Point
This Gloucester Point holiday home is situated near Yorktown, a short drive (approximately 8km) from the Yorktown Victory Center and Gloucester Museum of History, offering easy access to the York River.
Sleeping up to 10 guests, the property features three queen beds, one double bed, and a bunk bed, alongside a spacious living area, two bathrooms (one with an outdoor shower, an indoor shower is coming soon), and Wi-Fi; a marina and boat ramp are directly opposite.
Waterfront Gloucester Cottage W/ Private Boat Dock - Chesapeake Bay
9.8 12 reviews
Chesapeake Bay
01/10 – 05/10
449 €/nighttotal: 1796 € (4 )

Waterfront Gloucester Cottage W/ Private Boat Dock

3 3
cottage , Gloucester Point
This Gloucester Point seaside holiday home is situated 1.9km from Rosewell Ruins and 2.1km from Middle Peninsula State Park, offering stunning water views.
The 139 square metre property boasts four bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, jacuzzi, terrace, garden, and parking.
Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok - Chesapeake Bay
9.7 275 reviews
Chesapeake Bay
01/10 – 05/10
356 €/nighttotal: 1424 € (4 )

Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok

3 3
cottage , Deale
This charming cottage is situated just 16km from Deale, on the western shore of the Chesapeake Bay, offering a peaceful retreat close to the vibrant city of Annapolis. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage spans 111 square metres and comfortably accommodates up to 8 guests. It boasts a fully equipped kitchen, a private garden with a fire pit and a pier, and access to kayaks and other watercraft for exploring the nearby creek and Chesapeake Bay.
Cozy Cottage - Chesapeake Bay
10 1 review
Chesapeake Bay
23/08 – 28/08
650 €/nighttotal: 3250 € (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.

Best pet friendly Chesapeake Bay cottages

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

Waterfront Cottage In Beautiful Hoopers Island - Chesapeake Bay
10 84 reviews
Chesapeake Bay
12/09 – 16/09
240 €/nighttotal: 960 € (4 )

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.
Cozy Beach Cottage - Walking Distance To The Beach!! - Chesapeake Bay
9.8 89 reviews
Chesapeake Bay
12/09 – 16/09
378 €/nighttotal: 1512 € (4 )

Cozy Beach Cottage - Walking Distance To The Beach!!

3 2
cottage , Virginia Beach
This charming cottage is situated in Northeast Virginia Beach, just a mile from First Landing State Park and Marina Shores Marina, with Chesapeake Beach and Sylvan Beach within a 3-mile radius. It has received excellent user ratings, making it a popular choice for travellers.
The cottage has three bedrooms and two bathrooms, offering comfortable accommodation for up to six guests. It features a fully equipped kitchen, a private garden, a terrace, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
3b/1fb/kitchen, Center Of Town, The Cottage @ The Manor - Chesapeake Bay
9.6 45 reviews
Chesapeake Bay
12/09 – 16/09
265 €/nighttotal: 1060 € (4 )

3b/1fb/kitchen, Center Of Town, The Cottage @ The Manor

3 2
cottage , Port Deposit
This charming cottage is located just nine miles from Hollywood Casino, Garrett Island Beach, and Perry Point VA Medical Center, offering a peaceful retreat in a scenic riverside location. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The three-bedroom property spans 177 square metres and is ideal for families or groups of friends. It comes equipped with a modern kitchen, a private fenced garden, a fitness centre, a spa tub, and a barbecue grill, providing everything you need for a comfortable and enjoyable stay.
2 Bedroom Cottage At Coles Point Marina - Chesapeake Bay
Chesapeake Bay
20/07 – 27/07
366 €/nighttotal: 2562 € (7 )

2 Bedroom Cottage At Coles Point Marina

2 4
cottage , Montross
This Montross cottage is situated in Hague, a 5-minute walk from Coles Point Marina and a 14-minute drive from The Hague Winery, with Sandy Point Beach 39 kilometres and Cedar Island 77 kilometres away.
This 2-bedroom, 2-bathroom holiday home accommodates up to six guests, offering air conditioning, internet, and a dryer, with nearby access to Kinsale Museum, Westmoreland County Museum, Saint Mary's Fairground, and Michael P. O'Brien Athletics and Recreation Center.
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