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Chesapeake Bay cottages
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570 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.

Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok - Chesapeake Bay
9.7 275 reviews
Chesapeake Bay
10/01 – 10/05
$412/nighttotal: $1648 (4 )

Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok

3 3
cottage , 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.
Manor And Mutts #2 - Beach Front, Pet Friendly, Wi-fi, Parking, W/d, King Bed - Chesapeake Bay
8.6 39 reviews
Chesapeake Bay
07/30 – 08/05
$519/nighttotal: $3114 (6 )

Manor And Mutts #2 - Beach Front, Pet Friendly, Wi-fi, Parking, W/d, King Bed

3 6
cottage , Norfolk
This Willoughby Spit cottage is located directly on the beach, just a short distance from Norfolk Beaches, Sarah Constant Shrine Beach, and Ocean View Beach. The cottage has received a very good user rating, making it a popular choice for travelers.
This 3-bedroom home comfortably sleeps up to 8 guests and features a fully equipped kitchen, a fireplace, and a patio. Enjoy the convenience of on-site amenities like a playground, barbecue grills, and free WiFi, along with easy access to the nearby Oceanview Fishing Pier.
Idle Hour, A Tranquil 3 Bedroom 1.5 Bath Cottage With Dock & Golf Cart Rental - Chesapeake Bay
10 79 reviews
Chesapeake Bay
07/30 – 08/05
$197/nighttotal: $1182 (6 )

Idle Hour, A Tranquil 3 Bedroom 1.5 Bath Cottage With Dock & Golf Cart Rental

3 6
cottage , Smith Island
This waterfront cottage on Terrapin Sand Point is only 0.1 miles from the point and 2.5 miles from Smith Island. It is highly rated for its location, cleanliness, and user experience.
The cottage has 3 bedrooms and can accommodate up to 6 guests. It features a kitchen with a refrigerator, oven, stovetop, and microwave, as well as free WiFi, air conditioning, and a terrace or balcony. Guests can also enjoy the barbecue grills and garden.
Cottage On A Private Island In The York River - Chesapeake Bay
10 370 reviews
Chesapeake Bay
08/29 – 09/05
$229/nighttotal: $1603 (7 )

Cottage On A Private Island In The York River

3 2
cottage , Gloucester Point
This waterfront cottage in Gloucester Point is conveniently located within 9 miles of popular attractions like Machicomoco State Park, Yorktown Beach, and Yorktown Farmers Market, making it a great base for exploring the area. The property has earned excellent user ratings, suggesting a high level of satisfaction among previous guests.
The 1500 square foot cottage comfortably sleeps up to 8 guests in its 3 bedrooms. Enjoy amenities like a private pool, a spa, a terrace, and a fully equipped kitchen, along with access to a garden, a barbecue grill, and a water park.

Best Chesapeake Bay cottages with a garden

Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills - Chesapeake Bay
9.2 7 reviews
Chesapeake Bay
10/01 – 10/05
$183/nighttotal: $732 (4 )

Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills

2 3
cottage , Queenstown
This Queenstown, Maryland cottage is conveniently located near the Avalon Theatre and The Third Haven Friends Meeting House, offering easy access to area attractions like the Hazel Miner Monument and Adkins Arboretum.
This two-bedroom, one-bathroom house sleeps four guests and features a fully equipped kitchen (fridge, microwave), air conditioning, Wi-Fi, a terrace, garden, parking, and a washer/dryer; pets are welcome.
The Heron's Nest At Atlantic Marina - Chesapeake Bay
9.8 315 reviews
Chesapeake Bay
07/20 – 07/27
$380/nighttotal: $2660 (7 )

The Heron's Nest At Atlantic Marina

1 4
cottage , Lake Shore
This charming cottage is located in Pasadena, just steps from the beach on the Patapsco River, offering breathtaking water views and a peaceful escape. The cottage has consistently received excellent reviews from previous guests.
The cottage has a spacious layout with 580 square feet of living space, one bedroom, one bathroom, and can accommodate up to four guests. It features a fully equipped kitchen, a comfortable living area, a private porch, and access to a swimming pool, making it perfect for families and groups seeking a relaxing getaway.
Private Yard & Water Views: Cozy Urbanna Cottage - Chesapeake Bay
10 21 reviews
Chesapeake Bay
07/30 – 08/05
$343/nighttotal: $2058 (6 )

Private Yard & Water Views: Cozy Urbanna Cottage

3 6
cottage , Urbanna
This family-friendly cottage is located in Urbanna, just a short drive from the Middlesex County Museum and other attractions within a 20-mile radius. It's a great option for those looking for a peaceful getaway close to local history and entertainment. This highly rated vacation rental boasts an excellent user rating, making it a popular choice among travelers.
The cottage is spacious with 3 bedrooms, 2 bathrooms, and a floor area of 1500 square feet, comfortably accommodating up to 6 guests. The cottage includes a fully equipped kitchen, a cozy garden, and a patio for outdoor relaxation, as well as amenities like air conditioning, internet, and parking.
Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay\n\n\n\n\n\n\n\n - Chesapeake Bay
9.8 61 reviews
Chesapeake Bay
08/29 – 09/05
$225/nighttotal: $1575 (7 )

Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay\n\n\n\n\n\n\n\n

2 2
cottage , Cecilton
This two-bedroom, one-bathroom cottage is located in Cecilton, just a short drive from the beach. It has an excellent user rating and can accommodate up to six guests. The cottage has a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace or balcony, a garden, and parking.
The cottage is also pet-friendly and family-friendly, and it has free WiFi. It is situated near the beach and has a garden with barbecue grills. The cottage is within 16 miles of Bohemia Vista Marina and Crow Farm and Vineyard, and within 20 miles of C and D Canal Museum and Back Creek Golf Club.

Frequently Asked Questions about cottages in Chesapeake Bay

Destinations nearby

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.

Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach - Chesapeake Bay
10 3 reviews
Chesapeake Bay
08/29 – 09/05
$323/nighttotal: $2261 (7 )

Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach

1 2
cottage , Cheriton
This Cape Charles cottage, located near Brockenberry Bay and eight miles from the Cape Charles Historic District and beaches, offers easy access to Kiptopeke State Park (12 miles) and Bay Creek Resort & Golf Club (9 miles).
This 400-square-foot vacation home sleeps four with two bedrooms, one bathroom, a full kitchen including a dishwasher, a Jacuzzi, and a private terrace, plus a spacious yard with a fire pit and hammocks.
Firefly Cottage At The Cape, Community Beach, Spring  Adventures, Hot Tub, Usna - Chesapeake Bay
10 108 reviews
Chesapeake Bay
08/23 – 08/28
$293/nighttotal: $1465 (5 )

Firefly Cottage At The Cape, Community Beach, Spring Adventures, Hot Tub, Usna

1 2
cottage , Arnold
This charming cottage is located in the peaceful neighborhood of Cape Saint Claire, just 3.1 miles from Sandy Point State Park and within 6 miles of both Sandy Point Beach and Bay Hills Golf Club. Guests consistently rate this cottage as excellent, making it a popular choice for travelers seeking a comfortable and convenient stay.
The cottage offers 660 square feet of space, accommodating up to 5 guests in a single bedroom and bathroom. Enjoy modern conveniences like air conditioning, a Jacuzzi, a terrace, a garden, and a spa, as well as a fully equipped kitchen and free Wi-Fi.
Smith Beach Cottage W/ Private Sunset - Chesapeake Bay
10 4 reviews
Chesapeake Bay
08/23 – 08/28
$339/nighttotal: $1695 (5 )

Smith Beach Cottage W/ Private Sunset

2 2
cottage , Eastville
This Eastville cottage offers private beach access and is located near the Chesapeake Bay and Cape Charles Beach.
This 2-bedroom, 1-bathroom rental accommodates up to 4 guests and features a private hot tub, air conditioning, and internet.
Cozy Cottage - Chesapeake Bay
10 1 review
Chesapeake Bay
10/01 – 10/05
$761/nighttotal: $3044 (4 )

Cozy Cottage

4 3
cottage , Dundalk
This Dundalk cottage rental is conveniently located within 6 miles of Johns Hopkins Bayview Medical Center, the Baltimore Cruise Terminal, and Johns Hopkins Hospital, offering easy access to medical facilities and cruise departures.
This four-bedroom, two-bathroom vacation home sleeps eight guests and boasts a fully equipped kitchen, in-unit laundry, a Jacuzzi, and a private garden with parking; nearby attractions include the Inner Harbor and Fort McHenry.

Browse Pet-Friendly Cottages in Chesapeake Bay

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

Manor And Mutts #1 - Beach Front, Pet Friendly, High Speed Wifi, Private - Chesapeake Bay
8.6 16 reviews
Chesapeake Bay
07/30 – 08/05
$522/nighttotal: $3132 (6 )

Manor And Mutts #1 - Beach Front, Pet Friendly, High Speed Wifi, Private

4 6
cottage , Norfolk
This charming beach house in Willoughby Spit is located just a short distance from Norfolk Beaches, Sarah Constant Shrine Beach, and Ocean View Beach. It's a great option for travelers looking for a relaxing getaway close to the beach and local attractions. Guests have rated this cottage "very good" for its comfortable accommodations and convenient location.
This 4-bedroom home comfortably sleeps 8 guests, providing plenty of space for families or groups of friends. The cottage features a fully equipped kitchen, a fireplace, a private fenced yard, and a terrace or balcony, making it perfect for enjoying the beautiful Norfolk weather.
"Dragonfly" Waterfront Cottage On Chesapeake Bay - Chesapeake Bay
10 4 reviews
Chesapeake Bay
10/01 – 10/05
$266/nighttotal: $1064 (4 )

"Dragonfly" Waterfront Cottage On Chesapeake Bay

3 3
cottage , Kilmarnock
This Chesapeake Bayfront cottage rental in Reedville, a short drive from Kilmarnock, offers direct bay frontage with a private cove perfect for swimming, kayaking, and fishing, and is near attractions like the Reedville Fishermen's Museum and Compass Entertainment Complex.
The one-bedroom, one-bathroom house sleeps four with a queen bed and fold-out couch, features a small kitchen, air conditioning, Wi-Fi, a garden, and access to 30 acres of waterfront property including two outdoor soaking tubs and water toys.
Relax & Renew In A Waterfront Cottage , Private Pier, Kayaks, Fishing, Wineries. - Chesapeake Bay
10 65 reviews
Chesapeake Bay
08/29 – 09/05
$317/nighttotal: $2219 (7 )

Relax & Renew In A Waterfront Cottage , Private Pier, Kayaks, Fishing, Wineries.

3 2
cottage , Heathsville
This waterfront Heathsville cottage, located in Lottsburg, offers easy access to the Chesapeake Bay Wine Trail, Bush Mill Stream Natural Area Preserve, and Sandy Point Beach, with nearby marinas, breweries, antique shops, and wineries.
The three-bedroom, two-bathroom home sleeps nine guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, a tennis court, and on-site parking, plus excellent internet access.
Secluded Cozy Cottage In Historic Downtown - Chesapeake Bay
9.6 20 reviews
Chesapeake Bay
07/30 – 08/05
$678/nighttotal: $4068 (6 )

Secluded Cozy Cottage In Historic Downtown

2 6
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.
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