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 37 reviews
Chesapeake Bay
20/07 – 27/07
223 €/nighttotal: 1561 € (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.
10 43 reviews
Chesapeake Bay
23/08 – 28/08
184 €/nighttotal: 920 € (5 )
Unique Cottage Built In The 1800s, Granite Cliffs Of Port Deposit Maryland.
1 2
cottage , Port Deposit
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.
8.8 3 reviews
Chesapeake Bay
01/10 – 05/10
217 €/nighttotal: 868 € (4 )
Cottage On The Bay
2 3
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.
9.0 286 reviews
Chesapeake Bay
01/10 – 05/10
234 €/nighttotal: 936 € (4 )
Norfolk Beach Cottage Rental
3 3
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 29 reviews
Chesapeake Bay
20/07 – 27/07
155 €/nighttotal: 1085 € (7 )
Relax And Renew On Your Private Deck Overlooking The Chesapeake Bay
2 4
cottage , Nassawadox
This charming cottage is located just a short drive from Northampton Shopping Centre and Holly Grove Vineyards, offering a peaceful retreat on the beautiful Nassawadox coastline. The property enjoys an excellent user rating, reflecting its comfortable and well-equipped nature. This two-bedroom holiday home comfortably accommodates up to four guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private garden, and a terrace with barbecue facilities, perfect for relaxing evenings or al fresco dining.
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
20/06 – 27/06
315 €/nighttotal: 2205 € (7 )
Sandy Mutts At The Beach By Redawning
1 2
cottage , Norfolk
This Norfolk beachfront cottage, situated in East Ocean View, is just a short walk from the beach and within 10km of Ocean View Beach, Sarah Constant Shrine Beach, Little Creek Beach, and Ocean View Fishing Pier. Sleeping four guests, this two-bedroom holiday home boasts a fully equipped kitchen, Smart TV, patio, garden, parking, and pet-friendly accommodation.
8.0 4 reviews
Chesapeake Bay
23/08 – 28/08
164 €/nighttotal: 820 € (5 )
Tiny House At St. George Island
2 2
cottage , Piney Point
This cottage, a cosy tiny house, is located in Piney Point, a short distance from the historic Piney Point Lighthouse and Cecil's Old Mill, and close to St. Mary's River State Park. This accommodation sleeps up to five guests across two bedrooms and offers internet, air conditioning, a kitchen with a fridge and microwave, and exclusive access to a private sandy beach for fishing, crabbing, and picnicking.
9.9 68 reviews
Chesapeake Bay
01/10 – 05/10
286 €/nighttotal: 1144 € (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.
9.8 33 reviews
Chesapeake Bay
01/10 – 05/10
149 €/nighttotal: 596 € (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 51 reviews
Chesapeake Bay
20/07 – 27/07
255 €/nighttotal: 1785 € (7 )
Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md.
1 4
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.
Best family friendly Chesapeake Bay cottages
Among the 570 accommodations in Chesapeake Bay, here are the 4 best family friendly cottages
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.
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.
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.
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
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.
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.
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.
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.
Frequently asked questions about cottages in Chesapeake Bay
When is the best time to rent a cottage in Baie de Chesapeake?
The best time to visit is during the shoulder seasons, from April to May or September to October. You'll enjoy pleasant weather and fewer crowds compared to the summer months. The Bay is beautiful in the autumn with the changing colours of the leaves.
What are the can't-miss sights in Baie de Chesapeake?
You must visit the Chesapeake Bay Maritime Museum in St. Michaels, which showcases the history of the Bay and its maritime traditions. Also, take a scenic drive along the Chesapeake Bay Bridge, a 29-km bridge connecting the Eastern Shore to the mainland. You can also visit the historic town of Annapolis, with its cobblestone streets and charming architecture.
What are the best cottages with a pool in Chesapeake Bay?
Why consider renting a cottage in Baie de Chesapeake for your stay?
Renting a cottage on the Chesapeake Bay offers a unique and relaxing experience. You'll enjoy privacy and a peaceful setting, often with direct access to the water for swimming, fishing, or kayaking. Many cottages are located in quiet, picturesque locations, providing a tranquil escape from the hustle and bustle of city life.
What are the best cottages with a jacuzzi in Chesapeake Bay?
Can you easily explore Baie de Chesapeake on foot or by bike?
Exploring the Chesapeake Bay on foot or by bike can be challenging as there are no dedicated paths or trails along the entire Bay. However, many towns and villages on the Eastern Shore have bike paths and walking trails, making it possible to explore these areas on foot or by bike.
What are the best cottages for families and kids in Chesapeake Bay?
What are the best restaurants in Baie de Chesapeake with nature views?
For a beautiful view of the Bay, try The Chart House in Annapolis. It's located right on the water and offers stunning views of the harbour and city skyline. Another option is The Inn at Perry Cabin in St. Michaels, with its waterfront location and elegant dining experience.
What are the best pet friendly cottages in Chesapeake Bay?
What family-friendly activities are available in Baie de Chesapeake?
Chesapeake Bay offers plenty of family-friendly activities. You can visit the Maryland Science Center in Baltimore, take a boat tour of the Bay, or go crabbing or fishing. The Chesapeake Bay Maritime Museum in St. Michaels also has interactive exhibits and activities for children.
What are the best cottages with parking in Chesapeake Bay?
Among the 570 accommodations in Chesapeake Bay, here are the 4 best cottages with a jacuzzi
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.
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.
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.
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
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.
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.
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.
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.