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

Private Yard & Water Views: Cozy Urbanna Cottage - Chesapeake Bay
10 23 reviews

Private Yard & Water Views: Cozy Urbanna Cottage

cottage, Urbanna
This family-friendly cottage is located in Urbanna, just 8.4 kilometres from the Middlesex County Museum and within 32 kilometres of several other attractions including the Steamboat Era Museum and Deltaville Maritime Museum. The cottage is highly rated by previous guests and enjoys a peaceful setting.
The 139 square metre cottage has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It offers a well-equipped kitchen, a garden, a patio, barbecue facilities, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Cottage On The Creek - Chesapeake Bay
10 108 reviews

Cottage On The Creek

cottage, California
This Southern Maryland holiday home in Hollywood, Maryland, is situated near Sotterley Plantation and Greenwell State Park.
The three-bedroom, two-bathroom property sleeps seven, boasting a full kitchen, garden, and private dock on Cuckold Creek with access to canoes and kayaks for exploring the Chesapeake Bay area.
Last Minute Cancellation. Key Cottage Is Available This Weekend! - Chesapeake Bay
10 318 reviews

Last Minute Cancellation. Key Cottage Is Available This Weekend!

cottage, Irvington
This charming cottage is located just a short distance from the Steamboat Era Museum and Historic Christ Church, offering a tranquil escape from the hustle and bustle of the city. Guests consistently rate this property as excellent, highlighting its peaceful setting and comfortable amenities.
The cottage provides spacious accommodation for up to four guests, with two bedrooms and two bathrooms spread across 158 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private garden, a spa, a tennis court, and a barbecue grill, making it ideal for families or groups seeking a relaxing retreat.
Firefly Cottage At The Cape, Hot Tub, Community Beach, Boat Show, Usna Football. - Chesapeake Bay
10 121 reviews

Firefly Cottage At The Cape, Hot Tub, Community Beach, Boat Show, Usna Football.

cottage, Arnold
This charming cottage is located in Cape Saint Claire, just a short drive from Arnold's attractions, including Sandy Point State Park and Sandy Point Beach. The cottage has received excellent user ratings, making it a popular choice for travellers.
This holiday home offers 61 square metres of space, comfortably accommodating up to 5 guests in its one bedroom and one bathroom. The cottage is equipped with a range of amenities, including a fully fitted kitchen, a spa, a terrace, a garden, parking and Wi-Fi, ensuring a comfortable and enjoyable stay.

Best Chesapeake Bay cottages with a garden

Comfortable & Private 2 Bedrm Cottage W/ King Bed. - Chesapeake Bay
9.2 27 reviews

Comfortable & Private 2 Bedrm Cottage W/ King Bed.

cottage, Portsmouth
This charming cottage is situated just 1.6 kilometres from Rivers Casino Portsmouth and Portsmouth City Park, making it a great base for exploring the city. It has received excellent reviews from previous guests.
This cosy home has two bedrooms and a bathroom, covering 76 square metres, and can accommodate up to 5 guests. The property offers a fully equipped kitchen, a terrace, a garden, parking, free Wi-Fi, and a range of entertainment options.
Life Is Better At The River!--cozy Waterfront Cottage - Chesapeake Bay
10 122 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.
Waterfront Maryland Retreat W/ Dock & Bay View! - Chesapeake Bay
9.4 12 reviews

Waterfront Maryland Retreat W/ Dock & Bay View!

cottage, Chance
This Chance waterfront holiday home is situated 2.6km from Shark Fin Shoal and 3.9km from Rock Island, within a 32km radius of Whitehaven Historic District and Mount Vernon Park.
The 201 square metre property boasts four bedrooms, two bathrooms, sleeps nine, and includes a fully equipped kitchen, laundry facilities, patio, barbecue, and parking.
Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Chesapeake Bay
10 71 reviews

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

cottage, Stevensville
This Stevensville, Maryland holiday home is conveniently located near several Kent Island wedding venues, within an hour's drive (approx. 80km) of Annapolis, Washington D.C., and Baltimore.
The 111-square-metre property boasts two bedrooms, two bathrooms, sleeping up to six guests, and features a screened-in porch, private sauna, and accessibility features; guests can also hire a chef or artist.

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

Private Beach And Inviting Hot Tub - Charming Coastal Oasis - Chesapeake Bay
No reviews

Private Beach And Inviting Hot Tub - Charming Coastal Oasis

cottage, Piney Point
This spacious five-bedroom, three-bathroom holiday home in Piney Point offers direct access to a private beach on the Chesapeake Bay and features a gourmet kitchen, air conditioning, and a hot tub with bay views.
Guests can enjoy provided kayaks and paddleboards, a private deck, a top-floor balcony with expansive bay vistas, and a Tesla charging station, with accommodation for up to twelve people and pet-friendly options available.
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.
Bungalow W/ Large Yard: 8 Mi To Cape Charles Beach - Chesapeake Bay
10 3 reviews

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

cottage, Cheriton
This Cheriton cottage, situated 13km from Cape Charles' historic district and beaches, provides easy access to Bay Creek Resort (14km) and Kiptopeke State Park (19km).
The 37 square metre self-catering property sleeps four, boasting two bedrooms, one bathroom, a Jacuzzi, a terrace, a garden, parking, and a well-equipped kitchen including a dishwasher and a Keurig coffee machine, plus on-site hot tub and gas grill.
Cozy Cottage, Hot Tub, Blocktobeach, 1hr To Dc - Chesapeake Bay
9.9 194 reviews

Cozy Cottage, Hot Tub, Blocktobeach, 1hr To Dc

cottage, Long Beach
This renovated cottage is located just 4 kilometres from a larger public beach and offers a tranquil retreat near a private community beach on the Chesapeake Bay. It has received excellent ratings for cleanliness, location and user experience.
The property can accommodate up to 5 guests and features 2 bedrooms and 1 bathroom. The cottage offers a range of amenities including a fully equipped kitchen, a private hot tub, a fire pit, a screened deck with Chesapeake Bay views, laundry facilities, and a guidebook with local tips.

Best pet friendly Chesapeake Bay cottage rentals

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

Cottage On A Private Island In The York River - Chesapeake Bay
10 381 reviews

Cottage On A Private Island In The York River

cottage, Gloucester Point
This charming waterfront cottage is located in Gloucester Point, just 9 kilometres from Machicomoco State Park, Yorktown Beach, and Yorktown Farmers Market, offering easy access to a variety of attractions and activities. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
This 3-bedroom property spans 139 square metres and can accommodate up to 8 guests, making it ideal for families or groups. The cottage features a fully equipped kitchen, a private garden, a swimming pool, a spa, and a terrace, ensuring a relaxing and enjoyable stay.
2 Bedroom Cottage At Coles Point Marina - Chesapeake Bay
No reviews

2 Bedroom Cottage At Coles Point Marina

cottage, Montross
This Montross cottage is situated in Hague, a 5-minute walk from Coles Point Marina and a 14-minute drive from The Hague Winery, with Sandy Point Beach 39 kilometres and Cedar Island 77 kilometres away.
This 2-bedroom, 2-bathroom holiday home accommodates up to six guests, offering air conditioning, internet, and a dryer, with nearby access to Kinsale Museum, Westmoreland County Museum, Saint Mary's Fairground, and Michael P. O'Brien Athletics and Recreation Center.
Steps To The Ocean! Family And Dog Friendly North End Cottage W/ Rsrv Parking - Chesapeake Bay
9.8 266 reviews

Steps To The Ocean! Family And Dog Friendly North End Cottage W/ Rsrv Parking

cottage, Virginia Beach
This pet-friendly cottage is located in Northeast Virginia Beach, a short walk from First Landing State Park and a 4-minute drive to the Chesapeake Bay.
This 89 square metre holiday home accommodates up to six guests and features three bedrooms, a full kitchen, a private garden, and is equipped with air conditioning and Wi-Fi.
Oyster Cottage  - Walk To Shops , Mainstay Music Venue And The Bay! - Chesapeake Bay
9.6 14 reviews

Oyster Cottage - Walk To Shops , Mainstay Music Venue And The Bay!

cottage, Rock Hall
Oyster Cottage is a charming holiday home situated just a short walk from the waterfront in Rock Hall, offering easy access to shops, restaurants, and entertainment. The cottage consistently receives excellent reviews from guests, highlighting its comfortable and convenient location.
The property features two bedrooms, accommodating up to seven guests, making it ideal for families or groups of friends. The cottage offers a range of amenities including a fully equipped kitchen, a private garden, and a patio for outdoor dining, ensuring a relaxing and enjoyable stay.
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