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

Best family friendly Chesapeake Bay cottages

Among the 546 accommodations in Chesapeake Bay, here are the 4 best family friendly cottages

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.
Steps To The Ocean! Family And Dog Friendly North End Cottage W/ Rsrv Parking - Chesapeake Bay
9.8 265 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.
Relax & Renew In A Waterfront Cottage , Private Pier, Kayaks, Fishing, Wineries. - Chesapeake Bay
10 71 reviews

Relax & Renew In A Waterfront Cottage , Private Pier, Kayaks, Fishing, Wineries.

cottage, Heathsville
This three-bedroom Heathsville waterfront cottage, ideal for families, is centrally located in Lottsburg, offering easy access (within a few kilometres) to marinas, breweries, antique shops, and wineries on the Chesapeake Bay Wine Trail, plus Bush Mill Stream Natural Area Preserve and Sandy Point Beach.
Sleeping up to nine guests, this self-catering holiday home boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a garden, tennis court, parking, internet access, and two bathrooms; enjoy water views and proximity to the Kinsale Museum and Northern Neck Farm Museum.
Be Persuaded To Experience This Vintage Cottage By The Sassa - Chesapeake Bay
9.4 13 reviews

Be Persuaded To Experience This Vintage Cottage By The Sassa

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

Charming 2-bedroom Cottage In Tranquil Reedville - Chesapeake Bay
10 1 review

Charming 2-bedroom Cottage In Tranquil Reedville

cottage, Heathsville
This cottage in Reedville, situated 1.5 kilometres from Bush Mill Stream Natural Area Preserve and Hughlett Point Natural Area, offers convenient access to the Reedville Fishermen's Museum and Northern Neck Farm Museum.
This two-bedroom, two-bathroom holiday home accommodates up to five guests, featuring a fireplace in the living room and a river room with a sofa bed, with pets welcome and parking available.
240 Degree Waterviews And Gorgeous Sunsets! - Chesapeake Bay
10 5 reviews

240 Degree Waterviews And Gorgeous Sunsets!

cottage, Heathsville
This waterfront holiday home in Lottsburg is located 1.2 kilometers from Bush Mill Stream Natural Area Preserve and Protected Bird Sanctuary, with Kinsale Museum and Northern Neck Farm Museum nearby.
This 93 square meter cottage accommodates up to five guests with two bedrooms and one bathroom, offering direct waterfront access with a private dock for fishing and swimming, alongside a garden, terrace, and gazebo for outdoor relaxation.
Serenity Cottage: Central To State Parks, Historic Towns, Md & Va Beaches - Chesapeake Bay
10 20 reviews

Serenity Cottage: Central To State Parks, Historic Towns, Md & Va Beaches

cottage, Pocomoke City
Serenity Cottage, a two-bedroom self-catering property near Pocomoke City, Maryland, offers easy access (within a few kilometres) to Pocomoke River State Park and the Delmarva Discovery Museum.
This octagonal house sleeps five, features a fully equipped kitchen with vintage touches, a unique second-floor cupola room, and allows pets; nearby activities include kayaking, canoeing, hiking, and exploring historical towns on the Eastern Shore.
Private Yard & Water Views: Cozy Urbanna Cottage - Chesapeake Bay
10 22 reviews

Private Yard & Water Views: Cozy Urbanna Cottage

cottage, Urbanna
This family-friendly cottage is located in Urbanna, just 8.4 kilometres from the Middlesex County Museum and within 32 kilometres of several other attractions including the Steamboat Era Museum and Deltaville Maritime Museum. The cottage is highly rated by previous guests and enjoys a peaceful setting.
The 139 square metre cottage has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It offers a well-equipped kitchen, a garden, a patio, barbecue facilities, and free Wi-Fi, ensuring a comfortable and enjoyable stay.

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Best Chesapeake Bay cottages with a jacuzzi

Among the 546 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

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

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.
Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc - Chesapeake Bay
10 21 reviews

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

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.
3 Br Bay Home W Private Dock & All The Amenities - Chesapeake Bay
10 27 reviews

3 Br Bay Home W Private Dock & All The Amenities

cottage, Mathews
This Mathews County waterfront holiday home in Onemo, Virginia, is situated 4.5km from Bethel Beach Natural Area Preserve and within 51km of the Deltaville Maritime Museum and White Stone Beach.
The four-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen, Jacuzzi, terrace, garden, free Wi-Fi, and on-site amenities including a hot tub, arcade, and barbecue grills.
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.

Best pet friendly Chesapeake Bay cottages

Among the 546 accommodations in Chesapeake Bay, here are the 4 best pet friendly cottages

Quarry Landing - Center Of Town & River View - 3 Bedroom - Chesapeake Bay
10 14 reviews

Quarry Landing - Center Of Town & River View - 3 Bedroom

cottage, Port Deposit
This Port Deposit holiday home is situated 0.6km from the Susquehanna River, within 9.6km of Hollywood Casino and Garrett Island Beach, and under 14.5km from Perry Point VA Medical Center and Conowingo Dam.
Sleeping up to nine guests, this three-bedroom property boasts a fully equipped kitchen, air conditioning, a swimming pool, a terrace, free Wi-Fi, and on-site laundry facilities; plus, it's conveniently located near a water park.
Charming Waterfront Cottage With Boat Ramp And Boat Docking - Pet Friendly - Chesapeake Bay
9.6 22 reviews

Charming Waterfront Cottage With Boat Ramp And Boat Docking - Pet Friendly

cottage, Lee Mont
This Lee Mont waterfront holiday home is situated near Parksley, approximately 10km from Parksley Town Park and the Eastern Shore Railway Museum, and 14km from Bloxom Winery and the Accomac Historic District.
The 74 square metre property offers one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, Wi-Fi, patio, garden, parking, and air conditioning.
Captains Quarters By The Bay By Redawning - Chesapeake Bay
8.0 10 reviews

Captains Quarters By The Bay By Redawning

cottage, Norfolk
Captains Quarters by the Bay, a Norfolk cottage, is situated a one-minute walk from Willoughby Beach and within 16-42 km of various attractions including the King Neptune Statue, Busch Gardens Williamsburg, and Norfolk International Airport.
This four-bedroom holiday home offers 204 square metres of space, boasting a fully equipped kitchen with dishwasher, free Wi-Fi, and parking, suitable for groups of guests aged 25 and over.
Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md. - Chesapeake Bay
10 52 reviews

Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md.

cottage, Chesapeake Ranch Estates
This waterfront cottage is located in Fishing Creek, Chesapeake Ranch Estates, just 9 kilometres from Middle Hooper Island and within a 32-kilometre radius of Lower Hooper Island and Blackwater National Wildlife Refuge.
The 65 square metre property offers one bedroom, one bathroom and can accommodate up to four guests, with amenities including a fully equipped kitchen, a terrace, a garden and parking.
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