Search All Cottages in Chesapeake Bay

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.

This charming cottage is located in Cecilton, Maryland, just 40 kilometres from Bohemia Vista Marina, Crow Farm and Vineyard, and the C and D Canal Museum. It has received excellent user ratings, making it a popular choice for travellers.
The cottage has two bedrooms and one bathroom, offering comfortable accommodation for up to six guests. It features a well-equipped kitchen, a private garden, a balcony, and a jacuzzi, providing everything you need for a relaxing and enjoyable stay.

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.

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.

This charming cottage is situated on a picturesque river, just 8.7 kilometres from Riverside Walter Reed Hospital and 19.3 kilometres from Machicomoco State Park, offering a peaceful retreat for those seeking tranquility. The property consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The self-catering property has one bedroom and one bathroom, comfortably accommodating up to four guests. The cottage provides a range of amenities, including a fully equipped kitchen, a private patio, a hot tub, and a garden, offering everything you need for a relaxing and enjoyable getaway.

The Yellow Cottage is located on Harness Creek in Hillsmere, a peaceful residential neighbourhood in Annapolis, just a short distance from Jonas Green State Park and the Smithsonian Environmental Research Center. This charming property has received excellent user ratings, making it a popular choice for travellers.
The cottage offers 88 square metres of living space, comfortably accommodating up to six guests in two bedrooms and a living room with a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, and parking, as well as activities such as fishing, crabbing, and kayaking on the creek.

This charming cottage is located in Cecil County, Maryland, just 2 kilometres from the Susquehanna River and 33 kilometres from Elk Neck State Park, offering a peaceful retreat surrounded by natural beauty. The property has received excellent user ratings, highlighting its appeal for travellers seeking a comfortable and convenient stay.
This one-bedroom cottage spans 139 square metres and comfortably accommodates up to four guests. Guests will enjoy access to a well-equipped kitchen with a fridge and microwave, a garden, air conditioning, and complimentary Wi-Fi, making it ideal for both relaxing and exploring the surrounding area.

Dragonfly Cottage, a self-catering property near Reedville on the Chesapeake Bay, offers stunning bay views and is a short drive (distance unspecified) from Kilmarnock and its attractions, including the Reedville Fishermen's Museum.
This one-bedroom holiday home sleeps four, boasting a small kitchen, a garden, air conditioning, Wi-Fi, pet-friendliness, and access to water toys, plus two private outdoor soaking tubs and 30 acres of waterfront property with a shared beach.

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.

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.

This charming cottage is located in Cape Saint Claire, just a short drive from Arnold's attractions, including Sandy Point State Park and Sandy Point Beach. The cottage has received excellent user ratings, making it a popular choice for travellers.
This holiday home offers 61 square metres of space, comfortably accommodating up to 5 guests in its one bedroom and one bathroom. The cottage is equipped with a range of amenities, including a fully fitted kitchen, a spa, a terrace, a garden, parking and Wi-Fi, ensuring a comfortable and enjoyable stay.

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.

This Chance waterfront holiday home is situated 2.6km from Shark Fin Shoal and 3.9km from Rock Island, within a 32km radius of Whitehaven Historic District and Mount Vernon Park.
The 201 square metre property boasts four bedrooms, two bathrooms, sleeps nine, and includes a fully equipped kitchen, laundry facilities, patio, barbecue, and parking.

This charming cottage is located on Deal Island in Maryland's Eastern Shore, just a short walk or drive from a Chesapeake Bay beach, offering a tranquil escape from the hustle and bustle of everyday life. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The 3-bedroom, 2-bathroom home spans 144 square metres and comfortably accommodates up to 8 guests. The cottage is fully equipped with modern amenities, including a kitchen with a fridge, freezer, microwave, and dishwasher, as well as a terrace, garden, and parking. Guests can enjoy breathtaking sunrises from the dining room or screened-in porch, explore the beautiful Tangier Sound by kayak, or go crabbing in secret local spots.

This rural holiday let in Jarrettsville is situated near cultural sites such as Monkton Railroad Station and Harford Artists Gallery, and attractions including Ladew Topiary Gardens and Liriodendron Mansion, offering an exceptional stay experience.
This two-bedroom, non-smoking cottage accommodates up to six guests, features on-site laundry facilities, and is conveniently located for access to family-friendly entertainment like Maize Quest Fun Park and Guppy Gulch Quarry.

This charming waterfront cottage is located in Gloucester Point, just 9 kilometres from Machicomoco State Park, Yorktown Beach, and Yorktown Farmers Market, offering easy access to a variety of attractions and activities. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
This 3-bedroom property spans 139 square metres and can accommodate up to 8 guests, making it ideal for families or groups. The cottage features a fully equipped kitchen, a private garden, a swimming pool, a spa, and a terrace, ensuring a relaxing and enjoyable stay.