Places to stay in Chesapeake Bay

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Chesapeake Bay place to stay
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10861 Best places to stay in Chesapeake Bay

Best Chesapeake Bay lodgings with a pool

Among the 10861 accommodations in Chesapeake Bay, here are the 4 best ones with a pool

Stylish 3br Retreat| Patterson Park| Pet Friendly! - Chesapeake Bay
10 11 reviews

Stylish 3br Retreat| Patterson Park| Pet Friendly!

apartment, Baltimore
This charming row house is situated in the Patterson Park neighbourhood, a short walk from the park itself and within easy reach of attractions like the Inner Harbor, Fell's Point, and downtown Baltimore. The property has consistently received excellent user ratings, reflecting its appeal to families and groups of friends.
The house is spread over 186 square metres, offering 3 bedrooms, 2 bathrooms, and enough space to comfortably accommodate up to 10 guests. Amenities include a fully equipped kitchen, a spacious patio, and a finished basement with multiple areas for socialising, along with a host of other features like air conditioning, a garden, and parking.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Chesapeake Bay
No reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

house, Trappe
This substantial Trappe dwelling is located within the district, offering straightforward access to the Academy of the Arts, 8.9 kilometres away, and within driving distance of Federalsburg Marina, 40.2 kilometres away, and the Chesapeake Exploration Centre, 48.3 kilometres away.
This property spans 204 square metres and features four bedrooms, three bathrooms, and accommodates up to 15 guests, with amenities including air conditioning, WiFi, a private swimming pool, a terrace, and on-site parking, alongside a strict no-party policy.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Chesapeake Bay
No reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

cottage, Trappe
This charming cottage is located in Trappe, just 6 kilometres from The Third Haven Friends Meeting House, Academy Art Museum, and Academy of the Arts. The cottage is situated in a peaceful and historic area, offering a tranquil retreat from the hustle and bustle of everyday life.
The cottage is well-equipped with a kitchen featuring a microwave, dishwasher, and a patio for outdoor dining. Guests can enjoy the on-site swimming pool, barbecue grills, and a ceiling fan for added comfort.
Lovely Condo With Water & Golf Course View - Chesapeake Bay
9.0 16 reviews

Lovely Condo With Water & Golf Course View

apartment, Williamsburg
This one-bedroom condominium in the Kingsmill district of Williamsburg offers waterfront and golf course views, situated within a 5-kilometre drive of Busch Gardens Williamsburg, Water Country USA, and Colonial Williamsburg.
This family-friendly apartment, ideal for up to four guests, features a private balcony with serene views, air conditioning, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, and access to a swimming pool and garden, all within an award-winning resort.

Best family friendly Chesapeake Bay lodging

Among the 10861 accommodations in Chesapeake Bay, here are the 4 best for families

Waterfront~peaceful~weemsva~nnk~kayaks~views - Chesapeake Bay
10 59 reviews

Waterfront~peaceful~weemsva~nnk~kayaks~views

apartment, Irvington
This peaceful house on Carters Cove in Irvington offers direct kayak access and serene water views, with proximity to nearby towns (distances unspecified).
The three-bedroom, two-bathroom property sleeps six, boasting an open-plan living/dining/kitchen area, a furnished deck, and a fully equipped kitchen including a dishwasher; kayaking is available directly from the private backyard dock.
The Colonies At Williamsburg - Chesapeake Bay
8.8 2531 reviews

The Colonies At Williamsburg

resort, Williamsburg
The Colonies At Williamsburg is located in the Williamsburg area, just a short drive from Jamestown and Busch Gardens Williamsburg. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
The resort offers a range of self-catering apartments, each with a kitchen, spa tub, and patio. Guests can enjoy a swimming pool with a slide, a game room, a tennis court, a fitness centre, and a spa, as well as free Wi-Fi throughout the resort.
Waterfront 3br/3ba Getaway: Beach, Dock, Firepit! - Chesapeake Bay
9.7 129 reviews

Waterfront 3br/3ba Getaway: Beach, Dock, Firepit!

apartment, Heathsville
This Heathsville beachfront property is situated within 3km of the Heathsville Farmers' Market and Rice's Hotel/Hughlett's Tavern, and approximately 12km from the Northern Neck Farm Museum.
This 186 square metre house boasts three bedrooms, three bathrooms, sleeps ten guests, and offers a fully equipped kitchen, private fenced yard, spa, and free WiFi, along with direct beach access and on-site barbecue grills and playground.
Peaceful Historic House Near Water, With Hot Tub! - Chesapeake Bay
9.9 181 reviews

Peaceful Historic House Near Water, With Hot Tub!

apartment, Cambridge
This recently renovated three-bedroom Victorian house is located in Cambridge's Historic West End, a short walk from Long Wharf Park and the Choptank River Lighthouse.
The property offers a spacious layout sleeping up to six guests, boasting a newly renovated kitchen, a bathroom with a clawfoot tub, a jacuzzi, a garden, parking and air conditioning; nearby attractions include downtown Cambridge's restaurants and shops.

Frequently asked questions about accommodations in Chesapeake Bay

  • What are the most convenient modes of transportation within Baie de Chesapeake?

    Renting a car is the best way to explore the region and get to all the different towns and attractions. Public transport isn't as developed, but there are some local bus services in major cities. If you're staying in Annapolis or Baltimore, you can also use ride-sharing apps like Uber and Lyft.
  • What are the best accommodations in Chesapeake Bay?

    Among the accommodations in Chesapeake Bay, The Laughing King Retreat - Cobb Island Suite, Gem In The Heart Of The Fan #1 and Refuge Inn are the most popular ones.

  • What outdoor activities and adventures are popular in and around Baie de Chesapeake?

    Kayaking and paddleboarding are popular activities on the bay. There are many great places to hike in the area, like the Patapsco Valley State Park. And for a more adventurous experience, try sailing or fishing. You could also try a scenic bike ride on the Chesapeake Bay Trail.
  • What are the best accommodations with a pool in Chesapeake Bay?

  • What types of accommodations are available in Baie de Chesapeake?

    You'll find a range of options, from budget-friendly motels to luxury hotels and resorts. If you're looking for a unique experience, try staying in a bed and breakfast or a waterfront cottage. There are also plenty of campgrounds for those who prefer a more rustic experience.
  • What are the best accommodations with a jacuzzi in Chesapeake Bay?

  • When is the best time to visit Baie de Chesapeake?

    Spring and autumn are the most pleasant times to visit, with mild temperatures and fewer crowds. Summer is hot and humid, but it's a great time for water activities. Winter can be cold, but you can enjoy the beauty of the bay with fewer visitors.
  • What are the best accommodations for families and kids in Chesapeake Bay?

    The best accommodations for families and kids in Chesapeake Bay are Refuge Inn, Walk To Beach - Large Lovely Condo By Lake In "Kingsmill On The James" and The Jefferson Hotel.

  • What local dishes and culinary experiences are a must-try in Baie de Chesapeake?

    You have to try the famous Maryland crab cakes, made with fresh blue crabs. Don't forget to sample the local oysters, which are a delicacy in the area. For a sweet treat, try a Smith Island cake, a layered chocolate cake with a unique history.
  • What are the best pet friendly accommodations in Chesapeake Bay?

  • In which part of Baie de Chesapeake should you consider renting accommodation?

    It depends on what you want to see and do. Annapolis is a great choice for history and culture, while Ocean City is perfect for beach lovers. If you're looking for a quieter experience, consider staying on the Eastern Shore in towns like St Michaels or Oxford.
  • What are the best accommodations with parking in Chesapeake Bay?

    The Laughing King Retreat - Cobb Island Suite, Gem In The Heart Of The Fan #1 and Refuge Inn are the best accommodations with parking in Chesapeake Bay.

Popular destinations

Best Chesapeake Bay accommodations with a balcony

Weems Creek Cottage, Annapolis  Waterfront - Chesapeake Bay
10 252 reviews

Weems Creek Cottage, Annapolis Waterfront

apartment, 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.
Private Riverfront Retreat - Chesapeake Bay
10 2 reviews

Private Riverfront Retreat

house, Montross
This three-bedroom house, perfect for families or groups of up to 13, enjoys a private riverfront location in Hague, Virginia, approximately 40 kilometres from both the George Washington Birthplace National Monument and its Memorial House.
The 102-square-metre property boasts a fully equipped kitchen, terrace, garden, free Wi-Fi, parking, and a washing machine, offering a tranquil escape with easy access to local attractions.
Water Views - Close To Downtown Annapolis - Chesapeake Bay
10 47 reviews

Water Views - Close To Downtown Annapolis

apartment, Highland Beach
This five-bedroom, three-bathroom Highland Beach house offers stunning waterfront views in Annapolis, situated approximately 5km from the Bay Bridge Market Place Shopping Centre and Historic Mount Moriah AME Church.
Sleeping up to twelve guests, this self-catering property boasts a fully equipped kitchen, free Wi-Fi, a terrace, garden, parking, and an on-site arcade/game room; nearby attractions include the Wild Bird Center and Annapolis Maritime Museum (within 10km).
Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay - Chesapeake Bay
9.8 68 reviews

Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay

cottage, Cecilton
This charming cottage is located in Cecilton, Maryland, just 40 kilometres from Bohemia Vista Marina, Crow Farm and Vineyard, and the C and D Canal Museum. It has received excellent user ratings, making it a popular choice for travellers.
The cottage has two bedrooms and one bathroom, offering comfortable accommodation for up to six guests. It features a well-equipped kitchen, a private garden, a balcony, and a jacuzzi, providing everything you need for a relaxing and enjoyable stay.

Best Chesapeake Bay accommodations with a kitchen

Bull Neck Cottage - Chesapeake Bay
9.9 159 reviews

Bull Neck Cottage

apartment, Kilmarnock
This charming cottage is located just a short distance from the centre of Reedville, within easy reach of the Chesapeake Bay and the Watermen's Museum. The property has received excellent ratings for its location, cleanliness and overall experience.
The cottage can accommodate up to 6 guests and features a well-equipped kitchen, a comfortable living area, and a private garden. You'll also benefit from free Wi-Fi, air conditioning, a washing machine and dryer, and a dedicated parking space.
Tiny House On Maypop Homestead - Chesapeake Bay
10 42 reviews

Tiny House On Maypop Homestead

house, Sharptown
Maypop Homestead, a 14-acre retreat in the historic San Domingo district of Sharptown, offers a peaceful escape near a wildlife-filled pond.
This Sharptown cottage, featuring a queen bed, kitchenette, full bathroom with composting toilet, and meditation loft, sleeps two guests and includes Wi-Fi, a large deck with fire pit, and on-site organic food tours.
Red, White & Waterview 
Studio Apt With Pool - Chesapeake Bay
9.7 300 reviews

Red, White & Waterview Studio Apt With Pool

studio, Kingstown
This apartment is located in Chestertown, a short distance from Washington College and Rolphs Wharf Marina, offering easy access to cultural attractions and scenic waterfront views. The apartment has consistently received excellent ratings for location, cleanliness, and overall experience.
This self-catering home can accommodate up to three guests and offers a comfortable living space with a bedroom, a bathroom, and a fully equipped kitchen. The apartment comes with a range of amenities, including a private pool, a fitness centre, a spa, and a terrace, perfect for relaxing and enjoying the surrounding area.
Fleets Cove Farm *Pets Stay Free* - Chesapeake Bay
10 116 reviews

Fleets Cove Farm *Pets Stay Free*

gîte, Heathsville
This Heathsville apartment, situated on a working farm near the town, offers a secluded rural retreat with ample parking for RVs and campers.
The self-contained flat comprises one bedroom, one bathroom, a full kitchen including a dishwasher, and accommodates up to four guests, featuring a fire pit and opportunities to participate in farm activities.
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