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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.

Water Front Estate On Farm Cidery.  Pet Friendly With Inviting Private Beach. - Chesapeake Bay
Chesapeake Bay
07/20 – 07/27
$468/nighttotal: $3276 (7 )

Water Front Estate On Farm Cidery. Pet Friendly With Inviting Private Beach.

3 4
cottage , Kilmarnock
This pet-friendly waterfront cottage in Kilmarnock is situated on 100 ft of shoreline, offering a private retreat near the Steamboat Era Museum and the Mary Ball Washington Museum and Library, with Good Luck Cellars and the Compass Entertainment Complex also within convenient reach.
This 1440 sq ft dwelling accommodates up to 6 guests, featuring 4 bedrooms and 2 bathrooms, and includes amenities such as a microwave, dishwasher, air conditioning, a terrace, garden, and parking, with complimentary stand-up paddleboards available for exploring the water.
Sandy Hill Sunsets - Chesapeake Bay
10 74 reviews
Chesapeake Bay
09/12 – 09/16
$278/nighttotal: $1112 (4 )

Sandy Hill Sunsets

1 2
cottage , Nassawadox
This charming cottage is located in Exmore, right on the beach, near the Savage Neck Dunes Natural Area Preserve and Bethel Beach Natural Area Preserve. The cottage has received excellent user ratings, making it a popular choice for travelers seeking a peaceful and relaxing getaway.
This one-bedroom, one-bathroom cottage offers 260 square feet of space and can comfortably accommodate up to 4 guests. The cottage features a fully equipped kitchenette, a private garden, air conditioning, parking, and internet access, ensuring a comfortable stay for all.
Rock Creek Cottage, Waterfront, Serene Views - Chesapeake Bay
10 13 reviews
Chesapeake Bay
07/20 – 07/27
$322/nighttotal: $2254 (7 )

Rock Creek Cottage, Waterfront, Serene Views

2 4
cottage , Riviera Beach
This charming cottage is located in Riviera Beach, Pasadena, close to the Patapsco River and Chesapeake Bay, making it a great base for exploring the area. You’ll also be within easy reach of Baltimore, Annapolis, and Washington D.C.
The cottage provides 990 square feet of space with 2 bedrooms and 2 bathrooms, accommodating up to 4 guests. You’ll enjoy access to a private deck and dock with water views, along with amenities such as a fully equipped kitchen, a spa, and a garden.
Cozy Getaway - Breezy Point Beach & Marina - Chesapeake Bay
9.9 101 reviews
Chesapeake Bay
06/20 – 06/27
$358/nighttotal: $2506 (7 )

Cozy Getaway - Breezy Point Beach & Marina

1 2
cottage , Chesapeake Beach
This Chesapeake Beach cottage is a beachfront haven with a screened-in porch and pier access, offering a relaxing retreat just steps from Breezy Point Beach. With excellent user, location, and cleanliness ratings, this wheelchair-accessible cottage provides a comfortable and convenient stay for families and groups of up to six guests.
The cottage features a 600-square-foot layout with two bedrooms, one bathroom, and a fully equipped kitchen. Guests can enjoy air conditioning, free Wi-Fi, and parking, as well as a garden and porch swing. The nearby attractions include jet skiing, waterparks, and a golf course.

Best Chesapeake Bay cottages with a garden

Norfolk Beach Cottage Rental - Chesapeake Bay
9.0 286 reviews
Chesapeake Bay
10/01 – 10/05
$271/nighttotal: $1084 (4 )

Norfolk Beach Cottage Rental

3 3
cottage , Norfolk
This family-friendly cottage is located just 3 miles from Norfolk Beaches and Ocean View Beach and within 6 miles of Nauticus and Little Creek Beach. It offers an excellent location for exploring the area's attractions and enjoying the beautiful coastline. The cottage has received excellent user ratings, making it a popular choice for travelers.
This charming 3-bedroom vacation rental sleeps up to 6 guests and is perfect for families. The cottage offers a variety of amenities, including a private swimming pool, a barbecue grill, and a spacious garden, allowing you to relax and enjoy your stay.
Cozy Virginia Potomac Riverfront Cottage - Chesapeake Bay
9.6 47 reviews
Chesapeake Bay
08/23 – 08/28
$218/nighttotal: $1090 (5 )

Cozy Virginia Potomac Riverfront Cottage

4 2
cottage , Montross
This waterfront cottage rental in Hague, Northern Neck, Virginia, offers easy access to nearby wineries like Hague Winery and Vault Field Vineyards, as well as historical sites such as the Kinsale Museum and Piney Point Lighthouse.
The two-bedroom, two-bathroom house sleeps seven, features a fully equipped kitchen with a dishwasher, a 50-foot private dock perfect for fishing and crabbing, and includes free Wi-Fi and air conditioning.
Waterfront River Cottage For 2, Dog-friendly - Chesapeake Bay
9.6 26 reviews
Chesapeake Bay
06/20 – 06/27
$364/nighttotal: $2548 (7 )

Waterfront River Cottage For 2, Dog-friendly

1 2
cottage , Severna Park
This charming beach house is just 9 miles from Severna Park, offering easy access to attractions like the B&A Trail, Severna Park Golf Center, and Bay Hills Golf Club. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The 560 square foot cottage comfortably accommodates two guests in one bedroom and one bathroom. Enjoy the private garden, relax on the balcony, or unwind in the arcade/game room, all while having access to a fully equipped kitchen, free WiFi, and a charcoal grill for outdoor dining.
Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md. - Chesapeake Bay
10 51 reviews
Chesapeake Bay
07/20 – 07/27
$294/nighttotal: $2058 (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 5.5 miles from Middle Hooper Island and within a 12-mile radius of Lower Hooper Island and Blackwater National Wildlife Refuge.
The 700 square foot cottage features one bedroom, one bathroom, and can accommodate up to four guests, with amenities including a fully equipped kitchen, a private garden, and a terrace.

Frequently Asked Questions about cottages in Chesapeake Bay

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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.

Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach - Chesapeake Bay
10 3 reviews
Chesapeake Bay
09/12 – 09/16
$359/nighttotal: $1436 (4 )

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.
Waterfront Gloucester Cottage W/ Private Boat Dock - Chesapeake Bay
9.8 12 reviews
Chesapeake Bay
10/01 – 10/05
$519/nighttotal: $2076 (4 )

Waterfront Gloucester Cottage W/ Private Boat Dock

3 3
cottage , Gloucester Point
This Gloucester Point vacation home sits 1.2 miles from Rosewell Ruins and 1.3 miles from Middle Peninsula State Park, offering easy access to White Marsh Shopping Center and Catlett Islands within a 9-mile radius.
This 1500-square-foot seaside rental boasts four bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, Jacuzzi, private patio, and parking.
Beachfront Hideaway - Pet Friendly, Hot Tub, Ev - Chesapeake Bay
9.8 16 reviews
Chesapeake Bay
08/23 – 08/28
$488/nighttotal: $2440 (5 )

Beachfront Hideaway - Pet Friendly, Hot Tub, Ev

2 2
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.

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
9.6 5 reviews
Chesapeake Bay
08/23 – 08/28
$345/nighttotal: $1725 (5 )

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

1 2
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.
Dog-friendly Westover Cottage W/ River Access! - Chesapeake Bay
10 16 reviews
Chesapeake Bay
09/12 – 09/16
$343/nighttotal: $1372 (4 )

Dog-friendly Westover Cottage W/ River Access!

2 2
cottage , Westover
This Westover cottage offers prime waterfront living on the Big Annemessex River, located 11 miles from the University of Maryland Eastern Shore and Janes Island State Park.
This pet-friendly vacation home spans 1150 square feet, accommodating up to 7 guests in 2 bedrooms and a loft, and features direct river access with provided equipment for water activities.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Chesapeake Bay
9.6 131 reviews
Chesapeake Bay
10/01 – 10/05
$420/nighttotal: $1680 (4 )

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

2 3
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.
Premier St. Michaels Cottage - T. Blades House -  Walk To Everything In Town - Chesapeake Bay
9.6 285 reviews
Chesapeake Bay
10/01 – 10/05
$459/nighttotal: $1836 (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 and other popular attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom cottage provides 1400 square feet of space for up to five guests. Enjoy a relaxing stay with amenities like a private garden, a swimming pool, and a spa, as well as a fully equipped kitchen and modern conveniences like air conditioning and Wi-Fi.
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