Cottages in Chesapeake Bay at the best prices

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Chesapeake Bay cottages
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570 Best cottages in Chesapeake Bay

Best family friendly Chesapeake Bay cottage rentals

Among the 570 accommodations in Chesapeake Bay, here are the 4 best family friendly cottage rentals

The Heron's Nest At Atlantic Marina - Chesapeake Bay
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.
Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger - Chesapeake Bay
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.
Artists, Writers & Creative Minds  Imagine Your Getaway At Simplicity Cottage - Chesapeake Bay
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.
Premier St. Michaels Cottage - T. Blades House -  Walk To Everything In Town - Chesapeake Bay
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

Cottage On The Bay - Chesapeake Bay
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.
1 Bedroom Cottage Suite Village In King's Creek Weekly Booking 8days/7nights. - Chesapeake 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.
Now Available For Usna Commissioning Week!  16-22 May.  Easy Walk To Stadium. <Br>your Annapolis Waterfront Retreat For A Weekend Getaway. - Chesapeake Bay
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.
Mid-century Rivah Retreat With Dock, Fire Pit & Cozy Fireplace - Chesapeake Bay
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?

    Among the cottage rentals in Chesapeake Bay, Historic Cottage On Ware River Estate, Enchanted Holiday Cottage and Cottage On A Private Island In The York River are the most popular ones.

  • 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

Waterfront Gloucester Cottage W/ Private Boat Dock - Chesapeake Bay
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.
Cozy Cottage - Chesapeake Bay
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.
Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok - Chesapeake Bay
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.
3 Br Bay Home W Private Dock & All The Amenities - 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

Eastern Shore Beach Cottage Get-away - Chesapeake Bay
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.
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Chesapeake Bay
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.
Esva Down By The Sea & Pet Friendly - Chesapeake Bay
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.
Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md. - Chesapeake Bay
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.
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