Search All Cottages in Chesapeake Bay

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 Savageville shore cottage, near Onancock and Onley, offers easy access to Chincoteague Island (48km) and Cape Charles (64km), providing diverse beach experiences and proximity to the Onancock Wharf for water activities.
The 92 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a garden, parking, Wi-Fi, air conditioning, a kitchen with fridge and microwave, and is suitable for guests aged 21 and over.

This beachfront property is located in Heathsville, just 20km from the Northern Neck Farm Museum, Buzzard's Point Marina, and Rice's Hotel / Hughlett's Tavern, offering a peaceful retreat in a quiet setting. The cottage has received excellent user ratings, making it a popular choice for travellers.
The 4-bedroom home can comfortably accommodate up to 8 guests, ideal for families or groups. The house features a fully equipped kitchen, a private fenced yard, a terrace, and a garden, as well as a barbecue grill and a playground, providing everything you need for a relaxing and enjoyable stay.

This cottage is located in Portsmouth, within 4.8 kilometres of Emanuel AME Church, Commodore Theatre, and Portsmouth Art and Cultural Centre.
This pet-friendly, family-friendly holiday home offers a private patio, a fireplace, and a fully equipped kitchen with a microwave and dishwasher, with free on-site parking and WiFi available in public areas.

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 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.

Oyster Cottage, a self-catering holiday home in Oyster, Virginia's Eastern Shore, is situated a short distance (precise distance unspecified) from Cape Charles, offering easy access to dining, shopping and the beach.
This two-bedroom property boasts 94 square metres of living space, sleeping up to six guests, and includes a fully equipped kitchen, air conditioning, a garden, parking, internet access, and a private porch; kayaking in nearby tidal creeks and marshes is also possible.

This Tall Timbers holiday home enjoys a riverside location, less than 1.5 kilometres from the Potomac River and within a 10-kilometre radius of Piney Point Beach, Piney Point Lighthouse, and St. Mary's River State Park.
The 102-square-metre property offers three bedrooms, one bathroom, and sleeps eight guests, boasting a fully equipped kitchen, a terrace, a garden, a spa, free Wi-Fi, and an arcade/game room.

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.

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 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.

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 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.

This charming cottage is located in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. It boasts excellent user ratings, making it a popular choice for travellers.
The property offers 130 square metres of space, with two bedrooms and three bathrooms, comfortably accommodating up to five guests. The cottage comes equipped with a fully fitted kitchen, a private patio, a fireplace, and a garden, perfect for relaxing and enjoying the outdoors.

This Wittman holiday home offers a convenient base on Tilghman Island, located within a 2.4 to 2.6 kilometre drive of Perry Cabin Park, Back Creek Park, St. Michaels Marina, and the Chesapeake Bay Maritime Museum, with Wittman Park and CL Open Field also easily accessible for nature enthusiasts.
This two-bedroom property accommodates up to four guests, providing essential amenities including Wi-Fi, air conditioning, a dryer, and towels, and is a short drive from cultural sites like the Tilghman Watermen’s Museum and outdoor recreational areas such as Phillips Wharf Environmental Center.

This Smith Island beach house, near Terrapin Sand Point, offers easy access to the beach.
The 137 square metre (1475 square feet) self-catering property sleeps four, boasting two bedrooms, a bathroom, a fully equipped kitchen, Wi-Fi, and on-site parking; plus foosball and games for entertainment.