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Chesapeake Bay cottages
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546 Best cottages in Chesapeake Bay

Best Family-Friendly Cottages in Chesapeake Bay

Family vacations in a cottage near the water in Chesapeake Bay thrive with extra space, and room for the whole family to relax.

Steps To The Ocean! Family And Dog Friendly North End Cottage W/ Rsrv Parking - Chesapeake Bay
9.8 266 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 960 square foot vacation rental sleeps up to 6 guests with 3 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, free Wi-Fi, and a garden with outdoor furniture.
Secluded Cozy Cottage In Historic Downtown - Chesapeake Bay
9.6 22 reviews

Secluded Cozy Cottage In Historic Downtown

cottage, Annapolis
This charming cottage, in the Historic District of Annapolis, offers immediate access to the city's iconic landmarks and attractions. The restored 1930s cottage has an open and airy interior with vaulted ceilings and an open floor plan.
The cottage has 2 bedrooms, 1 bathroom, and can accommodate up to 8 guests. It features a fully equipped gourmet kitchen, a comfortable living area with a large couch, chaise lounge chairs, a 55" Roku TV, and an electric fireplace. The cottage also has a private entrance and patio, and is pet-friendly.
Eastern Shore Beachfront Cottage With Stunning Sunset Views! - Chesapeake Bay
10 13 reviews

Eastern Shore Beachfront Cottage With Stunning Sunset Views!

cottage, Butlertown
This three-bedroom, three-bathroom vacation home in Worton, Maryland, near Still Pond Creek, is two miles from the Old Coast Guard Station beach and Betterton Historic District.
The 1910-square-foot house features a private beach access with kayak and bike rentals, a well-equipped kitchen, and multiple indoor/outdoor relaxation areas, accommodating up to six guests.
Tiny House At St. George Island - Chesapeake Bay
8.4 5 reviews

Tiny House At St. George Island

cottage, Piney Point
This two-bedroom cottage in Piney Point is located near the Piney Point Lighthouse and Cecil's Old Mill, with St. Mary's River State Park and Salem State Forest also nearby.
This family-friendly rental accommodates up to five guests and includes a kitchen with a fridge and microwave, air conditioning, and internet access, plus full access to a private, fenced beach at 16431 Thomas Road, St. George Island Beach for fishing, crabbing, and picnicking.

Best Chesapeake Bay cottages with a garden

Historic Ware River Cottage At Glebefield - Chesapeake Bay
10 521 reviews

Historic Ware River Cottage At Glebefield

apartment, Gloucester Courthouse
This charming cottage sits on a river, just 5.4 miles from Riverside Walter Reed Hospital and 12 miles from Machicomoco State Park. It's a great option for those looking to explore Gloucester Courthouse and its surrounding area. Guests consistently rate this rental as excellent for its location, cleanliness, and overall experience.
The one-bedroom cottage comfortably sleeps up to four guests and features a fully equipped kitchen, a spa tub, a fireplace, and a patio. Enjoy outdoor activities like grilling, relaxing in the garden, or taking advantage of the riverfront location for fishing or kayaking.
Modern Beachfront Cottage With Endless Bay Views - Chesapeake Bay
9.9 275 reviews

Modern Beachfront Cottage With Endless Bay Views

apartment, Mathews
This beach house is located in Port Haywood, just a short drive from Bethel Beach Natural Area Preserve, Deltaville Marina, and Gwynn's Island Museum. This peaceful and serene location offers a relaxing escape from the hustle and bustle of everyday life. The cottage has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This two-bedroom, one-bathroom vacation rental has a floor area of 680 square feet and comfortably accommodates up to six guests. Enjoy convenient amenities like a fully equipped kitchen, a private patio, a garden, and direct beach access, perfect for relaxing and enjoying the beautiful surroundings.
North End Cottage One Block From Beach - Chesapeake Bay
9.8 57 reviews

North End Cottage One Block From Beach

apartment, Virginia Beach
This charming cottage is located in Northeast Virginia Beach, just a short distance from both First Landing State Park and the Virginia Beach Boardwalk, offering a peaceful escape with easy access to attractions. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The cottage features three bedrooms and two bathrooms, accommodating up to six guests comfortably within its 2,090 square feet. Guests can enjoy amenities like a private garden, a swimming pool, a spa, and a fully equipped kitchen, making it ideal for families and groups seeking a relaxing and enjoyable vacation.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, On The Sands Of The 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘 - Chesapeake Bay
10 136 reviews

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, On The Sands Of The 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

cottage, Piney Point
This 3-bedroom, 1-bathroom cottage is located on a private beach in the Point Lookout neighborhood of Scotland, Maryland, just 8 miles from St. Mary's College and less than 2 hours from Washington, D.C., with excellent user ratings.
The cottage has a fully stocked kitchen, a screened-in porch, a deck, a garden, a parking lot, and air conditioning. It also has a Jacuzzi, a terrace, a balcony, and a private beach with direct access to the Chesapeake Bay. The cottage can accommodate up to 8 guests and has two kayaks and life jackets for guest use.

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Guest-Favorite Cottages with Jacuzzi in Chesapeake Bay

These cottages in Chesapeake Bay feature private hot tubs and jacuzzis, perfect for a relaxing soak after a day by the water.

Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc - Chesapeake Bay
10 22 reviews

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

cottage, Long Beach
This Long Beach, St. Leonard's cottage offers easy beach access, a short walk from Flag Ponds Nature Park and Flag Harbor Marina, and less than 1.2 miles from Long Beach and Matoaka Beach.
This 800-square-foot vacation home sleeps five, boasting two bedrooms, two bathrooms, a full kitchen, a private patio, plus on-site amenities including a swimming pool, hot tub, and barbecue grills.
Waterfront Cottage@chesapeakeparadise Hot Tub/dogs - Chesapeake Bay
9.7 290 reviews

Waterfront Cottage@chesapeakeparadise Hot Tub/dogs

apartment, Deale
This charming cottage sits on the western shore of the Chesapeake Bay, just a short drive from Washington, D.C., Annapolis, and Baltimore, offering a serene escape from the city. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The vacation home features three bedrooms and two bathrooms, spanning 1190 square feet and comfortably accommodating up to eight guests. The cottage boasts a private pier, a fenced-in yard, a swimming pool, kayaks, a canoe, a fire pit, swings, and a BBQ grill, ensuring a fun-filled and relaxing stay.
Beachfront Hideaway - Pet Friendly, Hot Tub, Ev - Chesapeake Bay
9.6 23 reviews

Beachfront Hideaway - Pet Friendly, Hot Tub, Ev

cottage, Heathsville
This waterfront home in Lottsburg, Virginia, offers 100+ feet of private beach access (tide dependent) and is located about two hours from Washington, D.C., and a short drive from Reedville and Kilmarnock, placing you near the Compass entertainment center and several Virginia State Parks.
This 1,100-square-foot vacation rental boasts two bedrooms, one bathroom, sleeps five, includes a fully equipped kitchen, a 7-person Marquis Crown Collection hot tub with a privacy wall, kayaks for exploring the Potomac River and Chesapeake Bay, blazing-fast broadband internet, and a ChargePoint Level 2 EV charger.
902 Ch Historic Carriage House 20 Steps To Beach + Hot Tub, Kayaks, Beachfront Grilling - Chesapeake Bay
No reviews

902 Ch Historic Carriage House 20 Steps To Beach + Hot Tub, Kayaks, Beachfront Grilling

cottage, Norfolk
This historic carriage house offers a true beachfront location on the Chesapeake Bay in Norfolk's Willoughby Spit, just 0.3 miles from Ocean View Beach Park and within 6.0 miles of the Chrysler Museum of Art, Nauticus & Battleship Wisconsin, and the Virginia Zoo.
This family-friendly cottage accommodates two guests with one bedroom and one bathroom, featuring a fully equipped kitchen with stainless steel appliances, air conditioning, a jacuzzi, a terrace, and on-site shared amenities including a hot tub and grilling area, with kayaks and paddleboards available for rent.

Browse Pet-Friendly Cottages in Chesapeake Bay

Traveling with a pet to Chesapeake Bay is simple at these cottages, featuring dog-friendly facilities.

Hosta Cottage | Creekfront Nature Escape W/ Kayaks, Fire Pit + Resort Access, Pet Friendly - Chesapeake Bay
9.2 7 reviews

Hosta Cottage | Creekfront Nature Escape W/ Kayaks, Fire Pit + Resort Access, Pet Friendly

cottage, Sanford
This waterfront cottage near the Eastern Shore of Virginia is conveniently located within 12 miles of the Virginia Welcome Center at New Church, Bloxom Winery, and the Wallops Flight Facility.
This pet-friendly, one-bedroom, one-bathroom vacation rental sleeps two guests and boasts a fully equipped kitchen, private balcony, swimming pool, and access to outdoor grills; limited housekeeping is available.
Comfortable & Private 2 Bedrm Cottage W/ King Bed. - Chesapeake Bay
9.6 25 reviews

Comfortable & Private 2 Bedrm Cottage W/ King Bed.

cottage, Portsmouth
This charming cottage is located in Portsmouth, just a short distance from Rivers Casino Portsmouth and Portsmouth City Park. It has earned excellent ratings from previous guests.
The cozy home offers 2 bedrooms and 1 bathroom, with enough space to accommodate up to 5 guests. Enjoy a fully equipped kitchen, free Wi-Fi, a DVD player, and a private garden with a terrace.
Sunrise Waterfront Cottage In Beautiful Hoopers Island - Chesapeake Bay
10 88 reviews

Sunrise Waterfront Cottage In Beautiful Hoopers Island

cottage, Chesapeake Ranch Estates
This waterfront cottage in Chesapeake Ranch Estates offers stunning views of the Chesapeake Bay and is just a short distance from popular attractions like Middle Hooper Island and Lower Hooper Island. It has received excellent user ratings for its comfortable and well-equipped interior.
The cottage has two bedrooms, one bathroom, and can accommodate up to five guests. It features a fully equipped kitchen, a cozy living room with a fireplace, and a private terrace or balcony. Guests can also enjoy the outdoor amenities, including a garden, barbecue grills, and a fire pit.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Chesapeake Bay
9.6 138 reviews

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

cottage, Easton
This charming cottage is located in St. Michaels, just a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. It has received excellent ratings from previous guests.
The 1400 square foot home has two bedrooms and three bathrooms, comfortably accommodating up to five guests. Enjoy modern amenities like air conditioning, a swimming pool, a patio, a fireplace, and a fully equipped kitchen.
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