Cottages in Chesapeake Bay at the best prices

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Chesapeake Bay cottages
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546 Best cottages in Chesapeake Bay

Best family friendly Chesapeake Bay cottage rentals

Among the 546 accommodations in Chesapeake Bay, here are the 4 best family friendly cottage rentals

Artists, Writers & Creative Minds  Imagine Your Getaway At Simplicity Cottage - Chesapeake Bay
10 19 reviews

Artists, Writers & Creative Minds Imagine Your Getaway At Simplicity Cottage

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.
Sunrise And Sunset At The Bay - Chesapeake Bay
10 23 reviews

Sunrise And Sunset At The Bay

cottage, Heathsville
This beachfront property is located in Heathsville, just 20km from the Northern Neck Farm Museum, Buzzard's Point Marina, and Rice's Hotel / Hughlett's Tavern, offering a peaceful retreat in a quiet setting. The cottage has received excellent user ratings, making it a popular choice for travellers.
The 4-bedroom home can comfortably accommodate up to 8 guests, ideal for families or groups. The house features a fully equipped kitchen, a private fenced yard, a terrace, and a garden, as well as a barbecue grill and a playground, providing everything you need for a relaxing and enjoyable stay.
Cheery Waterfront Cottage W/boat Dock - Chesapeake Bay
9.2 10 reviews

Cheery Waterfront Cottage W/boat Dock

cottage, Kilmarnock
This charming cottage is situated just seven miles from Kilmarnock, a quaint town on the Chesapeake Bay, offering a peaceful retreat in a rural setting. The property boasts excellent user ratings, indicating a positive experience for previous guests.
The self-catering property accommodates up to five guests in two bedrooms and one bathroom. Enjoy a range of amenities including a fully equipped kitchen, air conditioning, a private garden, and parking, as well as direct access to the water for fishing, boating, and kayaking.
Quarry Landing - Center Of Town & River View - 3 Bedroom - Chesapeake Bay
10 14 reviews

Quarry Landing - Center Of Town & River View - 3 Bedroom

cottage, Port Deposit
This Port Deposit holiday home is situated 0.6km from the Susquehanna River, within 9.6km of Hollywood Casino and Garrett Island Beach, and under 14.5km from Perry Point VA Medical Center and Conowingo Dam.
Sleeping up to nine guests, this three-bedroom property boasts a fully equipped kitchen, air conditioning, a swimming pool, a terrace, free Wi-Fi, and on-site laundry facilities; plus, it's conveniently located near a water park.

Best Chesapeake Bay cottages with a garden

Life Is Better At The River!--cozy Waterfront Cottage - Chesapeake Bay
10 118 reviews

Life Is Better At The River!--cozy Waterfront Cottage

cottage, Galena
This riverside lodge in Galena, Maryland, offers direct access to the Sassafras River, a tributary of the Chesapeake Bay, and is located near the Middletown and Betterton Historic Districts.
This 77-square-meter holiday home sleeps five guests across three bedrooms, featuring a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a garden, parking, and kayaks and bikes for guest use, with an option to dock a boat for an additional fee.
Rustic Beach Front Apartment - Cozy, Rustic And On The Beach! - 2 Br/1 Bath - Chesapeake Bay
8.4 46 reviews

Rustic Beach Front Apartment - Cozy, Rustic And On The Beach! - 2 Br/1 Bath

cottage, Norfolk
This charming Norfolk cottage is ideally situated just a short distance from a selection of beautiful beaches, including Norfolk Beaches, Community Beach, and Ocean View Beach, offering the perfect base for a seaside getaway. It has received very good user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay.
The cottage boasts two bedrooms and two bathrooms, comfortably accommodating up to five guests, and spans 87 square metres. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, parking, and free WiFi, ensuring a relaxing and enjoyable stay.
Charming 3-bedroom Villa With Wifi, And  Jaccuzzi , Just Minutes From Yorktown - Chesapeake Bay
8.4 5 reviews

Charming 3-bedroom Villa With Wifi, And Jaccuzzi , Just Minutes From Yorktown

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.
Smith Beach Cottage W/ Private Sunset - Chesapeake Bay
9.8 11 reviews

Smith Beach Cottage W/ Private Sunset

cottage, Eastville
This two-bedroom holiday home in Eastville offers private beach access for sunset viewing and is situated approximately 5.6 kilometres from Chesapeake Bay and 7.2 kilometres from Cape Charles Beach.
This Eastville holiday home accommodates up to four guests, featuring a king and a queen bedroom, a private hot tub, air conditioning, and Wi-Fi, with a check-out time of 12:00 PM.

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.

Popular destinations

Best Chesapeake Bay cottage rentals with jacuzzi

Among the 546 accommodations in Chesapeake Bay, here are the 1 best cottage rentals with a jacuzzi

Waterfront Gloucester Cottage W/ Private Boat Dock - Chesapeake Bay
9.6 14 reviews

Waterfront Gloucester Cottage W/ Private Boat Dock

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.

Best pet friendly Chesapeake Bay cottage rentals

Among the 546 accommodations in Chesapeake Bay, here are the 4 best pet friendly cottage rentals

Water Front Estate On Farm Cidery.  Pet Friendly With Inviting Private Beach. - Chesapeake Bay
10 1 review

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

cottage, Kilmarnock
This waterfront holiday home in Kilmarnock offers a private 30-meter pier and a small sandy beach, located a short drive from the Steamboat Era Museum and the Mary Ball Washington Museum and Library.
This spacious 134 square meter cottage accommodates up to six guests across four bedrooms and two bathrooms, featuring a microwave, dishwasher, air conditioning, a terrace, garden, and parking, with complimentary use of SUPs for exploring the shoreline.
Waterfront Cottage In Beautiful Hoopers Island - Chesapeake Bay
10 86 reviews

Waterfront Cottage In Beautiful Hoopers Island

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.
Cozy Beach Cottage - Walking Distance To The Beach!! - Chesapeake Bay
9.8 94 reviews

Cozy Beach Cottage - Walking Distance To The Beach!!

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.
Pink Flamingo At The Beach - Chesapeake Bay
8.4 17 reviews

Pink Flamingo At The Beach

cottage, Norfolk
This vintage cottage in East Ocean View, Norfolk, offers direct access to the Chesapeake Bay beaches via a 0.1-kilometre boardwalk, with no streets to cross, and is a short drive from the Waterside District and Greenbrier Mall.
This pet-friendly holiday home, covering 116 square meters and accommodating up to five guests, features a fully equipped kitchen with a gas stove, a Large Smart TV, High Speed WiFi, off-street parking, and a small back deck with a charcoal barbecue grill.
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