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

Kingsmill 1bed/1ba On Golf Course 9th Fairway - Chesapeake Bay
9.9 485 reviews

Kingsmill 1bed/1ba On Golf Course 9th Fairway

apartment, Williamsburg
This Williamsburg apartment is located just 1.6 kilometers from Busch Gardens Williamsburg, a short drive from the popular theme park, and within walking distance of the Kingsmill Plantation Golf Course and Kingsmill Beach. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment is 130 square meters in size and is suitable for families, offering a comfortable and spacious living space. The apartment is equipped with a range of amenities, including a swimming pool, tennis court, and garden, providing plenty of opportunities for relaxation and recreation.
Vacation Village At Williamsburg - Chesapeake Bay
8.6 6066 reviews

Vacation Village At Williamsburg

resort, Williamsburg
The Vacation Village at Williamsburg is conveniently located just a short drive from Jamestown Settlement, Colonial Williamsburg, and the College of William and Mary, offering easy access to the area's rich history and culture. The resort has received very good ratings for its cleanliness and overall experience, making it a popular choice for travellers.
These self-catering units are spacious and comfortable, perfect for families or groups. Guests can enjoy a range of amenities, including swimming pools, a fitness centre, a spa, and tennis courts, as well as a bar and restaurant.
Virginia Beach Oceanfront/boardwalk, Beach, Pool & Balcony - Chesapeake Bay
9.8 71 reviews

Virginia Beach Oceanfront/boardwalk, Beach, Pool & Balcony

apartment, Virginia Beach
This apartment is located in Northeast Virginia Beach, just a short walk from the beach and the Virginia Beach Boardwalk, with Sandbridge Beach a short 4.3 kilometres away. The apartment has received excellent reviews from previous guests, highlighting its convenient location and comfortable amenities.
This one-bedroom flat provides 28 square metres of space, comfortably accommodating up to three guests. It offers a fully equipped kitchen, a balcony, and a washing machine, as well as free Wi-Fi and access to a swimming pool and garden.
Beach Luxury Oceanfront - Chesapeake Bay
9.8 134 reviews

Beach Luxury Oceanfront

apartment, Virginia Beach
This apartment is situated in Virginia Beach, just a short distance from the beach and Neptune's Park, making it ideal for exploring the area's attractions. The apartment has received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The apartment is spacious, offering 98 square metres of living space, and comes equipped with a fully fitted kitchen, a private bathroom, and a balcony with stunning ocean views. Guests can enjoy the on-site swimming pool, relax in the garden, and take advantage of the free Wi-Fi and parking.

Best family friendly Chesapeake Bay lodging

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

Entire Private 2 Bedrooms House, Nice Neighborhood - Chesapeake Bay
9.4 83 reviews

Entire Private 2 Bedrooms House, Nice Neighborhood

apartment, Arnold
This two-bedroom home is situated in Arnold, a peaceful neighbourhood just 10 miles from Annapolis Harbor and 14 miles from Baltimore-Washington International Airport. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious apartment, spanning 111 square metres, comfortably accommodates up to 5 guests. Enjoy a range of amenities including a private hot tub, a peaceful garden, a fully equipped kitchen, air conditioning, free Wi-Fi and private parking.
"Heron's Nest" Charming Tiny House On Chesapeake Bay-boat Launch/slip Included - Chesapeake Bay
9.6 56 reviews

"Heron's Nest" Charming Tiny House On Chesapeake Bay-boat Launch/slip Included

apartment, Kilmarnock
This charming apartment is situated in Heathsville, a peaceful waterfront location just 10km from Kilmarnock, offering a tranquil escape from the hustle and bustle. The accommodation has received excellent ratings from previous guests, highlighting its comfortable and convenient features.
This well-appointed flat spans 35 square metres and comfortably sleeps up to four guests. Enjoy access to a range of amenities including a fully equipped kitchen, a relaxing jacuzzi, a private terrace, a garden, and parking.
Beautiful Colonial Home On The Choptank River - Chesapeake Bay
10 51 reviews

Beautiful Colonial Home On The Choptank River

house, Cambridge
This Colonial-style property is situated on the Choptank River in Cambridge, Maryland, offering scenic riverfront views and is approximately 34 kilometres from Federalsburg Marina and 24 kilometres from the Academy of the Arts.
This 167 square metre house boasts four bedrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, a private spa, free Wi-Fi, and free bikes for exploring the local area, comfortably accommodating larger families or groups.
Holiday Inn Club Vacations Williamsburg Resort - Chesapeake Bay
9.0 1077 reviews

Holiday Inn Club Vacations Williamsburg Resort

resort, Williamsburg
Holiday Inn Club Vacations Williamsburg Resort, An Ihg Hotel, is situated just 10km from Camp Peary and within 20km of Water Country USA and Busch Gardens amusement park, making it a great base for exploring Williamsburg's attractions. The resort has received very good ratings for user experience, location and cleanliness.
The resort offers spacious one-bedroom villas with well-equipped kitchens, fireplaces, balconies and comfortable furnishings, ideal for families or groups. Guests can enjoy amenities such as a gym, concierge service, barbecue facilities and an outdoor pool.

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

Gaia House - Chesapeake Bay
9.1 58 reviews

Gaia House

house, Annapolis
Gaia House, in Annapolis, is situated 6 kilometres from Annapolis Harbour and within a 32-48 kilometre radius of Baltimore attractions including the Inner Harbour and Historic Ships in Baltimore.
This two-bedroom property, offering 9 square metres of floor space, sleeps seven guests and features a fully equipped kitchen, private parking, Wi-Fi, air conditioning, and a patio with quiet street views.
Sojourn The Ocean Breeze In Virginia Beach - Chesapeake Bay
9.7 135 reviews

Sojourn The Ocean Breeze In Virginia Beach

house, Virginia Beach
This charming house is located in Northeast Virginia Beach, just a 1.6 km walk from Pacific Avenue and the Virginia Beach Boardwalk, offering easy access to the beach and local attractions. It has consistently received excellent ratings for location, cleanliness, and user experience.
The house has two bedrooms and can comfortably accommodate up to nine guests. It includes a fully equipped kitchen, a balcony, internet access, and a garden, providing everything you need for a relaxing and enjoyable stay.
Restful River House With Water & Golf-course View - Chesapeake Bay
9.9 66 reviews

Restful River House With Water & Golf-course View

cottage, Kilmarnock
This yacht is located in the Indian Creek Yacht & Country Club neighbourhood in Kilmarnock, just minutes from the town centre and its attractions. It enjoys a peaceful setting on a quiet cul-de-sac, adjacent to the 16th hole of the golf course. It has received excellent ratings for user experience, location, and cleanliness.
The yacht features three bedrooms, two bathrooms, a spacious living area, and two decks. It offers a range of amenities including a fully equipped kitchen, air conditioning, internet access, a garden, parking, and a boat dock.
The Garden Estate: Historic Town Center Home - Chesapeake Bay
10 327 reviews

The Garden Estate: Historic Town Center Home

apartment, Chestertown
This charming 19th-century house is located in Chestertown's historic district, just 0.3 kilometres from Washington College and the waterfront. The accommodation consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The property offers five bedrooms, sleeping up to 10 guests, and features a spacious garden and a fenced yard. Guests can enjoy modern conveniences like fast internet, a fully equipped kitchen, and a comfortable living space, as well as access to the expansive gardens located just outside the back gate.

Best Chesapeake Bay accommodations with a kitchen

Vibe District 4br Walk To Beach + Sleeps 8 - Chesapeake Bay
9.8 516 reviews

Vibe District 4br Walk To Beach + Sleeps 8

apartment, Virginia Beach
This family-friendly holiday home is located just a 10-minute walk from Pacific Avenue and the Virginia Beach Boardwalk, offering easy access to the beach, restaurants, and shops. The property has received excellent ratings for location, cleanliness, and overall user experience.
The house has four bedrooms, comfortably accommodating up to 10 guests. It comes equipped with modern amenities, including a fully equipped kitchen, free Wi-Fi, a fireplace, and a terrace or balcony, ensuring a relaxing and enjoyable stay.
Walking Distance To Marinas & Main St! - Chesapeake Bay
9.8 131 reviews

Walking Distance To Marinas & Main St!

house, Rock Hall
This waterfront property is a 15-minute walk from Rock Hall Harbour, The Mainstay, and Waterman’s Museum, offering a peaceful setting close to the town’s attractions. The property has received excellent ratings for its cleanliness, location, and overall user experience.
This three-bedroom house comfortably accommodates eight guests. Enjoy the convenience of a fully equipped kitchen, a fireplace, and a spacious garden with barbecue grills, perfect for relaxing evenings.
*Escape To The Tangerine Dream* - Chesapeake Bay
9.8 127 reviews

*Escape To The Tangerine Dream*

apartment, Norfolk
This Norfolk beachfront property, near Captain's Quarters Park, offers stunning ocean views and is ideally situated for exploring the area.
Sleeping up to eight guests, this three-bedroom, two-bathroom holiday home boasts a spacious open-plan living area, a fully equipped kitchen including dishwasher, air conditioning, a garden, parking, and two balconies; enjoy direct beach access and excellent user ratings.
Waterfront Romantic Studio - Chesapeake Bay
9.9 74 reviews

Waterfront Romantic Studio

apartment
This Dundalk studio apartment, near Baltimore, offers convenient access to waterfront views and nearby state parks, located approximately 32 kilometres from the city.
The self-contained unit sleeps two, features a fully equipped kitchen with dishwasher, a private garden, parking, and boasts a shared deck with stunning water views, a fire pit, and proximity to scenic hiking trails.
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