Private 1300 Sq Ft Cottage In Historic Yorktown-w/ Trolley Access
1 4
cottage , Yorktown
This charming cottage is situated in Yorktown's historic district, just a short walk from Main Street and the Yorktown Beach. It has received excellent user ratings and is a popular choice for travellers seeking a comfortable and convenient stay. This one-bedroom cottage sleeps up to four guests and features a spacious living area, a fully equipped kitchen, and two bathrooms. Guests can enjoy modern amenities like air conditioning, Wi-Fi, and a private garden, making it ideal for a relaxing getaway.
9.9 101 reviews
Chesapeake Bay
20/06 – 27/06
$500/nighttotal: $3500 (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.
10 16 reviews
Chesapeake Bay
20/07 – 27/07
$507/nighttotal: $3549 (7 )
Cozy Cottage With Private Dock- Chesapeake Bay/ Cambridge (Pet-friendly)
2 4
cottage , Madison
This charming waterfront cottage is located just a short drive from the historic town of Cambridge, Maryland, offering a peaceful escape from the bustle of Madison. The nearby Blackwater National Wildlife Refuge provides ample opportunities for nature lovers to explore. The cottage features two bedrooms, comfortably accommodating up to six guests, and a fully equipped kitchen with modern appliances. Guests can enjoy the private dock, kayaks, and scenic views, or relax by the fire pit, unwind on the porch or deck, and take advantage of the spa and other amenities.
10 1 review
Chesapeake Bay
12/09 – 16/09
$237/nighttotal: $948 (4 )
Ruscincys Rest "Minutes Drive To Orioles Stadium"
1 2
cottage , Baltimore
Ruscincy's Rest, a one-bedroom cottage in Arcadia, Baltimore, is located a short drive (approximately 2-3km) from Oriole Park at Camden Yards and offers easy access to Baltimore's Inner Harbour. This self-catering property sleeps two, features air-conditioned rooms with ironing boards, and includes a shower and hairdryer in the bathroom; nearby attractions include the National Aquarium and Port Discovery Children's Museum.
9.9 180 reviews
Chesapeake Bay
23/08 – 28/08
$570/nighttotal: $2850 (5 )
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.
9.0 286 reviews
Chesapeake Bay
12/09 – 16/09
$379/nighttotal: $1516 (4 )
Norfolk Beach Cottage Rental
3 2
cottage , Norfolk
This charming cottage is located just 3 miles from Norfolk Beaches and Ocean View Beach, offering easy access to the stunning Norfolk coastline. It has received excellent reviews from previous guests, highlighting its family-friendly atmosphere and comfortable accommodation. The property spans 116 square metres and comfortably sleeps 6 guests across 3 bedrooms. You'll enjoy a fully equipped kitchen, a private patio, a swimming pool, and a water park, perfect for a relaxing and fun-filled family holiday.
9.8 33 reviews
Chesapeake Bay
01/10 – 05/10
$240/nighttotal: $960 (4 )
Bee Humble Cottage W/in 20mins To Public Beaches
2 3
cottage , Gloucester Courthouse
This family-friendly cottage is located in a peaceful rural area of Gloucester Courthouse, just 13km from Riverside Walter Reed Hospital and within a 32km radius of Gloucester Point Beach Park and Machicomoco State Park. It has received excellent user ratings, making it a popular choice for travellers seeking a relaxing escape. The two-bedroom cottage spans 102 square metres and comfortably accommodates up to four guests. It offers a range of amenities, including a fully equipped kitchen, a private garden, a swimming pool, a spa, and access to a nearby water park, ensuring a comfortable and enjoyable stay.
10 37 reviews
Chesapeake Bay
20/07 – 27/07
$360/nighttotal: $2520 (7 )
Pet Friendly Water View Cottage
2 4
cottage , Riviera Beach
This charming cottage is located in Pasadena, Maryland, a picturesque waterfront neighbourhood just 20 kilometres from both Annapolis and Baltimore, offering easy access to a range of attractions. The cottage has received excellent reviews from previous guests, highlighting its comfortable and welcoming atmosphere. The cottage spans 111 square metres and comfortably accommodates up to four guests in its two bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a private garden, and a host of amenities including air conditioning, laundry facilities, and free parking. The cottage is also pet-friendly, allowing guests to bring their furry companions along.
9.8 16 reviews
Chesapeake Bay
20/06 – 27/06
$1523/nighttotal: $10661 (7 )
Hays Beach House - Hot Tub - Private Beach
5 2
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.
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.
Chesapeake Bay
20/07 – 27/07
$296/nighttotal: $2072 (7 )
93 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests
2 4
cottage , Savageville
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.
9.9 126 reviews
Chesapeake Bay
20/06 – 27/06
$574/nighttotal: $4018 (7 )
The Little Blue Cottage - Topping : Waterfront!
1 2
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.
Best family friendly Chesapeake Bay cottage rentals
Among the 570 accommodations in Chesapeake Bay, here are the 4 best family friendly cottage rentals
9.8 315 reviews
Chesapeake Bay
20/07 – 27/07
$531/nighttotal: $3717 (7 )
The Heron's Nest At Atlantic Marina
1 4
cottage , Lake Shore
This charming lakeside retreat is located in Pasadena, Maryland, just a short drive from historical landmarks and art galleries. It has received excellent reviews from previous guests. The cottage offers 54 square metres of living space, accommodating up to four guests in a comfortable layout with one bedroom and one bathroom. You can enjoy a range of amenities including a swimming pool, a terrace, and a garden, and the property is perfect for enjoying water activities like fishing and boating.
9.9 68 reviews
Chesapeake Bay
01/10 – 05/10
$462/nighttotal: $1848 (4 )
Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger
3 3
cottage , Piney Point
This charming cottage is located in Piney Point, Maryland, just a short distance from the Chesapeake Bay. It benefits from excellent user, location and cleanliness ratings. The cottage has three bedrooms, accommodating up to eight guests, and offers a range of amenities, including private beach access, a fishing pier, kayaks and stand-up paddle boards, a Tesla charger, and contactless check-in.
10 15 reviews
Chesapeake Bay
20/07 – 27/07
$598/nighttotal: $4186 (7 )
Artists, Writers & Creative Minds Imagine Your Getaway At Simplicity Cottage
2 4
cottage , Tilghman Island
Simplicity Cottage is situated on Tilghman Island, a short distance from the Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum, offering a peaceful retreat surrounded by the scenic Chesapeake Bay. This charming holiday home is perfect for a small family or group of friends seeking a relaxing getaway. The cottage has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It features a waterfront location with a substantial dock, air conditioning, internet access, and a spacious lot perfect for outdoor activities and entertaining.
9.6 285 reviews
Chesapeake Bay
01/10 – 05/10
$641/nighttotal: $2564 (4 )
Premier St. Michaels Cottage - T. Blades House - Walk To Everything In Town
2 3
cottage , Easton
This charming cottage is located in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it ideal for exploring this historic town. The cottage has received excellent ratings for its location, cleanliness and overall experience. The cottage has two bedrooms and can accommodate up to five guests, making it perfect for families or groups of friends. Guests can enjoy a range of amenities including a swimming pool, terrace, garden, and a fully equipped kitchen.
Best Chesapeake Bay cottages with a garden
8.8 3 reviews
Chesapeake Bay
23/08 – 28/08
$345/nighttotal: $1725 (5 )
Cottage On The Bay
2 2
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.
8.8 5 reviews
Chesapeake Bay
20/06 – 27/06
$298/nighttotal: $2086 (7 )
1 Bedroom Cottage Suite Village In King's Creek Weekly Booking 8days/7nights.
1 2
cottage , Williamsburg
This Williamsburg self-catering property is situated 2.6 kilometres from Colonial National Historical Park and within 9.7 kilometres of Busch Gardens Williamsburg and Water Country USA. The 40-square-metre cottage offers one bedroom, one bathroom, sleeps four guests, and features a fully equipped kitchen, fireplace, jetted tub, two swimming pools (indoor and outdoor), barbecue grills, and a balcony.
10 239 reviews
Chesapeake Bay
23/08 – 28/08
$542/nighttotal: $2710 (5 )
Now Available For Usna Commissioning Week! 16-22 May. Easy Walk To Stadium. <Br>your Annapolis Waterfront Retreat For A Weekend 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.
Chesapeake Bay
20/07 – 27/07
$395/nighttotal: $2765 (7 )
Mid-century Rivah Retreat With Dock, Fire Pit & Cozy Fireplace
2 4
cottage , Saluda
This Saluda waterfront holiday home is situated near Thousand Trails Dog Park and Beach Park (under 5km), and approximately 19km from Main Street Centre and Walter Reed Plaza. Sleeping up to five guests, this two-bedroom, one-bathroom cottage boasts a fully equipped kitchen, terrace, garden, Wi-Fi, air conditioning, and is within easy reach of local amenities and outdoor activities.
Frequently Asked Questions about cottages in Chesapeake Bay
What would be a good 2-days itinerary for visiting Baie de Chesapeake?
For a two-day trip, you could spend the first day exploring Annapolis, the state capital of Maryland. Visit the historic Naval Academy and the charming downtown area. On the second day, head to the Eastern Shore, perhaps visiting St. Michaels, a beautiful town with a maritime museum. You can also enjoy a scenic boat tour on the bay.
What are the best cottage rentals in Chesapeake Bay?
What part of Baie de Chesapeake is ideal for renting a cottage?
The Eastern Shore is a popular choice for renting cottages. The towns of St. Michaels, Easton, and Oxford are particularly charming and offer a range of options, from quaint waterfront cottages to larger family homes. You'll find plenty of beautiful scenery and a peaceful atmosphere.
What are the best cottage rentals with a pool in Chesapeake Bay?
When is the best time to rent a cottage in Baie de Chesapeake?
The best time to visit Chesapeake Bay is during the spring and autumn. The weather is pleasant, and you can enjoy a variety of activities, including boating, fishing, and hiking. Summer can be hot and humid, but it's a great time for swimming and enjoying the beach.
What are the best cottage rentals with a jacuzzi in Chesapeake Bay?
What are the can't-miss sights in Baie de Chesapeake?
Some can't-miss sights include the Chesapeake Bay Bridge, the US Naval Academy in Annapolis, the Chesapeake Bay Maritime Museum in St. Michaels, and Assateague Island National Seashore. You can also enjoy the charming towns of Annapolis, St. Michaels, and Easton, each with its own unique character.
What are the best cottage rentals for families and kids in Chesapeake Bay?
Why consider renting a cottage in Baie de Chesapeake for your stay?
Renting a cottage offers a more intimate and relaxing experience compared to staying in a hotel. You can enjoy privacy, a home-like atmosphere, and often stunning views of the bay. Many cottages also come with amenities like private docks and outdoor spaces, perfect for enjoying the beautiful surroundings.
What are the best pet friendly cottage rentals in Chesapeake Bay?
Can you easily explore Baie de Chesapeake on foot or by bike?
While some areas are walkable, it's best to have a car to explore the Chesapeake Bay region. The towns are spread out, and you'll want the flexibility to visit different attractions and enjoy the scenic drives along the bay.
What are the best cottage rentals with parking in Chesapeake Bay?
What are the best restaurants in Baie de Chesapeake with nature views?
The Chart Room in St. Michaels offers stunning views of the harbour from its waterfront location. The restaurant serves fresh seafood and has a lively atmosphere. The Inn at Perry Cabin in St. Michaels also has a beautiful restaurant with outdoor seating overlooking the bay.
What family-friendly activities are available in Baie de Chesapeake?
There are plenty of family-friendly activities in the Chesapeake Bay area. You can visit the Chesapeake Bay Maritime Museum in St. Michaels, explore the Assateague Island National Seashore, or go crabbing or fishing. Many towns also have parks, playgrounds, and beaches for kids to enjoy.
Destinations nearby
Best Chesapeake Bay cottage rentals with jacuzzi
Among the 570 accommodations in Chesapeake Bay, here are the 4 best cottage rentals with a jacuzzi
9.8 12 reviews
Chesapeake Bay
01/10 – 05/10
$725/nighttotal: $2900 (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.
10 1 review
Chesapeake Bay
01/10 – 05/10
$1064/nighttotal: $4256 (4 )
Cozy Cottage
4 3
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.
9.7 275 reviews
Chesapeake Bay
23/08 – 28/08
$539/nighttotal: $2695 (5 )
Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok
3 2
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.
10 21 reviews
Chesapeake Bay
01/10 – 05/10
$569/nighttotal: $2276 (4 )
3 Br Bay Home W Private Dock & All The Amenities
3 3
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.
Best pet friendly Chesapeake Bay cottage rentals
Among the 570 accommodations in Chesapeake Bay, here are the 4 best pet friendly cottage rentals
10 139 reviews
Chesapeake Bay
23/08 – 28/08
$679/nighttotal: $3395 (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.
9.6 128 reviews
Chesapeake Bay
01/10 – 05/10
$641/nighttotal: $2564 (4 )
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!
2 3
cottage , Easton
This charming cottage is situated in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, offering easy access to the town's historical attractions. It has received excellent reviews from previous guests, highlighting its family-friendly atmosphere and comfortable amenities. The property spans 130 square metres and comfortably accommodates up to five guests in its two bedrooms and three bathrooms. Guests can enjoy a range of facilities including a private swimming pool, a tennis court, and a spa, as well as a fully equipped kitchen, a garden, and a terrace.
9.8 7 reviews
Chesapeake Bay
20/07 – 27/07
$368/nighttotal: $2576 (7 )
Esva Down By The Sea & Pet Friendly
2 4
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.
10 51 reviews
Chesapeake Bay
23/08 – 28/08
$447/nighttotal: $2235 (5 )
Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md.
1 2
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.