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

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.
Unique Tangier Cottage W/ Chesapeake Bay Views! - Chesapeake Bay
10 17 reviews

Unique Tangier Cottage W/ Chesapeake Bay Views!

cottage, Tangier
This family-friendly Tangier holiday home is situated less than 1 kilometre from both the Tangier Museum of History and Tangier Island Beach.
The 167 square metre property boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, terrace, garden, parking, and Wi-Fi.
Secluded Cozy Cottage In Historic Downtown - Chesapeake Bay
9.6 22 reviews

Secluded Cozy Cottage In Historic Downtown

cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
3-bedroom Water-front Cottage On 2 1/2 Secluded Acres Near Reedville,va - Chesapeake Bay
10 13 reviews

3-bedroom Water-front Cottage On 2 1/2 Secluded Acres Near Reedville,va

cottage, Kilmarnock
This Kilmarnock beach house, situated 3.7 kilometres from both the Reedville Fishermen's Museum and the Reedville Historic District, offers easy access to Fleeton Beach and Smith Point Marina within a 9.7 kilometre radius.
The 135 square metre property sleeps eight guests in three bedrooms and two bathrooms, boasting a fully equipped kitchen, Wi-Fi, a Smart TV, laundry facilities, and an outdoor barbecue; enjoy direct beach access.

Best Chesapeake Bay cottages with a garden

Lake Access, Tranquil Acreage: Farnham Cottage - Chesapeake Bay
No reviews

Lake Access, Tranquil Acreage: Farnham Cottage

cottage, Lancaster
This waterfront lodge in Farnham, Virginia, is located on a lake that feeds into the Rappahannock River, offering proximity to Belle Isle State Park (16 kilometres) and the Lancaster Virginia Historical Society (24 kilometres).
This 120 square metre holiday home accommodates up to five guests with two bedrooms, two bathrooms, and a sleeping loft, featuring direct lake access with a canoe and fishing dock, a spacious garden and deck, and is equipped with air conditioning, central heating, and a washer/dryer.
Manor And Mutts #2 - Beach Front, Pet Friendly, Wi-fi, Parking, W/d, King Bed - Chesapeake Bay
8.6 39 reviews

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

cottage, Norfolk
This charming beach house is situated in Willoughby Spit, just a short distance from Norfolk Beaches, Sarah Constant Shrine Beach, and Ocean View Beach. The cottage is rated very good by previous guests.
This comfortable holiday home has three bedrooms and can accommodate up to eight guests. The property includes a fully equipped kitchen, a fireplace, a patio, a garden, and free Wi-Fi, as well as a playground and barbecue grills for guests to enjoy.
Historic Beach Side Getaway - Pet Friendly, Wi-fi, Just Steps To The Beach - Chesapeake Bay
8.8 111 reviews

Historic Beach Side Getaway - Pet Friendly, Wi-fi, Just Steps To The Beach

cottage, Norfolk
This family-friendly cottage is located in Norfolk, just a short distance from the beautiful beaches, including Norfolk Beaches, Sarah Constant Shrine Beach, and Oceanview Fishing Pier. It has received excellent user ratings, making it a popular choice for travellers.
The cottage has three bedrooms and two bathrooms, offering ample space for up to ten guests. It features a fully equipped kitchen, a comfortable living area, a patio, a garden, and parking, providing everything you need for a relaxing and enjoyable stay.
Charming 2-bedroom 1 Bath Cottage With Ac, Wifi In Peaceful North Beach, Md. - Chesapeake Bay
9.0 7 reviews

Charming 2-bedroom 1 Bath Cottage With Ac, Wifi In Peaceful North Beach, Md.

cottage, North Beach
This holiday let in North Beach is located 800 metres from the Chesapeake Bay and 800 metres from the Bayside History Museum.
This holiday let offers Wi-Fi, air conditioning, a dishwasher, and a microwave oven, with parking and laundry facilities available on site.

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 4 best cottage rentals with a jacuzzi

Smith Beach Cottage W/ Private Sunset - Chesapeake Bay
9.8 10 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.
Waterfront Gloucester Cottage W/ Private Boat Dock - Chesapeake Bay
9.8 12 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.
Cottage On The Bay - Chesapeake Bay
8.8 3 reviews

Cottage On The Bay

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.
3 Br Bay Home W Private Dock & All The Amenities - Chesapeake Bay
10 25 reviews

3 Br Bay Home W Private Dock & All The Amenities

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

Charming Beach Cottage On Fishing Bay - Chesapeake Bay
10 8 reviews

Charming Beach Cottage On Fishing Bay

cottage, Deltaville
This Deltaville beachfront property, "Charming Beach Cottage on Fishing Bay", is situated on Fishing Bay and offers easy access to the Holyhead Maritime Museum and Christ Church.
The 186 square metre holiday home sleeps eight guests in three bedrooms and three bathrooms, boasting a fully equipped kitchen, laundry facilities, terrace, garden, and air conditioning, plus proximity to the Middlesex County Museum, Rosewell Ruins, Steamboat Era Museum and Compass Entertainment Complex.
Family Hideaway ,Family Friendly And Pet Friendly. - Chesapeake Bay
No reviews

Family Hideaway ,Family Friendly And Pet Friendly.

cottage, Virginia Beach
This three-bedroom Virginia Beach holiday home is situated in Northeast Virginia Beach, a short walk (less than 1.6km) from Pacific Avenue, the Virginia Beach Boardwalk, and the Virginia Beach Station.
Sleeping up to nine guests, the self-catering property boasts two bathrooms, in-cottage laundry facilities, and is within easy reach of the Naval Aviation Monument Park and the Virginia Museum of Contemporary Art.
Kiptopeke Drive Cozy Cottage Right Up The Road From Kiptopeke State Park. - Chesapeake Bay
9.6 99 reviews

Kiptopeke Drive Cozy Cottage Right Up The Road From Kiptopeke State Park.

cottage, Cape Charles
This charming cottage is situated just over 1.6 kilometres from Kiptopeke State Park and 4.8 kilometres from the Eastern Shore of Virginia National Wildlife Refuge, offering easy access to scenic natural landscapes. The cottage has received excellent reviews from previous guests.
The two-bedroom property can accommodate up to six guests and features a fully equipped kitchen, a patio for outdoor dining, and a barbecue grill. Enjoy the fresh air and scenic views while exploring the nearby parks and wildlife refuges.
Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch - Chesapeake Bay
9.8 206 reviews

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch

cottage, Easton
This charming cottage is situated in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it ideal for exploring the town's rich maritime history and vibrant culture. The cottage has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
The two-bedroom cottage spans 130 square metres and comfortably accommodates up to five guests. It offers a fully equipped kitchen, a private garden, a swimming pool, and a spa, providing everything you need for a relaxing and enjoyable stay.
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