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Chesapeake Bay accommodation
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10861 Best accommodations in Chesapeake Bay

Best Chesapeake Bay accommodations with a pool

Among the 10861 accommodations in the area, here is the list of the 4 best ones with a pool

Bay Creek Meets Historic Cape Charles! Pool Access! New Outdoor Shower! - Chesapeake Bay
9.9 121 reviews

Bay Creek Meets Historic Cape Charles! Pool Access! New Outdoor Shower!

apartment, Cape Charles
This three-bedroom apartment, located in the Marina East neighbourhood of the gated Bay Creek community, is just a short walk from the historic centre of Cape Charles and its many restaurants, shops, and attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment spans 242 square metres and comfortably accommodates up to eight guests. It offers a range of amenities, including access to a private beach, a swimming pool, tennis courts, nature trails, and kayaks and paddle boards for exploring the nearby waters.
Cape Charles Home With Pool And Golf Cart 5 Minutes From The Beach! - Chesapeake Bay
8.8 25 reviews

Cape Charles Home With Pool And Golf Cart 5 Minutes From The Beach!

apartment, Cape Charles
Sunshine Baydream, a three-bedroom holiday home in Cape Charles' Kings Creek Landing neighbourhood, offers easy access to the Eastern Shore of Virginia National Wildlife Refuge and Savage Neck Dunes Natural Area Preserve (distances unspecified).
This 158-square-metre (1700 sq ft) property features three master suites, an open-plan layout ideal for entertaining, a private terrace, swimming pool access, and parking; it sleeps nine guests and includes a fully equipped kitchen and grilling facilities.
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.
Waterfront Getaway W/ Pool, Firepit, Kayaks, Dock - Chesapeake Bay
10 34 reviews

Waterfront Getaway W/ Pool, Firepit, Kayaks, Dock

apartment, White Stone
This waterfront property, situated on the Chesapeake Bay near White Stone, Virginia, offers easy access to Kilmarnock and Irvington, and is minutes from the Compass family entertainment centre.
This four-bedroom, 2.5-bathroom holiday home sleeps up to ten guests and boasts a fully equipped kitchen, a saltwater pool (seasonal), two kayaks, 65” and 75” TVs with YouTube TV, an electric vehicle charging station, and a private boat ramp and dock providing direct access to the Chesapeake Bay.

Best family friendly Chesapeake Bay accommodations

Among the 10861 accommodations in the area, here is the list of the 4 best family friendly ones

Charles Village 1-br, Walk To Johns Hopkins - Chesapeake Bay
9.8 7 reviews

Charles Village 1-br, Walk To Johns Hopkins

apartment, Baltimore
This Charles Village apartment in Baltimore is situated a 15-minute walk from both MedStar Union Memorial Hospital and Johns Hopkins University, and within 4.8km of the National Aquarium and Baltimore Convention Centre.
The one-bedroom flat sleeps three, offering a full kitchen with oven, stovetop, microwave and fridge, plus a washer, sofa bed, Smart TV, and games; nearby public transport includes North Avenue and Baltimore Penn Stations within a 30-minute walk.
Walk To Everything Rock Hall From This 1st Floor Apartment. Sleeps 4! - Chesapeake Bay
10 30 reviews

Walk To Everything Rock Hall From This 1st Floor Apartment. Sleeps 4!

apartment, Rock Hall
This Rock Hall apartment is conveniently located less than 1.6km from Rock Hall Harbour, within a 10-minute walk of The Mainstay, and under 1.6km from Waterman's Museum and Ferry Park.
The one-bedroom, one-bathroom flat sleeps four guests and boasts a fully equipped kitchen with appliances including a microwave and dishwasher, in-unit laundry, free Wi-Fi, a Smart TV, and a terrace/balcony plus access to a shared garden with barbecue grills.
Willoughby 4br Coastal Home  Steps To Shore - Chesapeake Bay
9.6 163 reviews

Willoughby 4br Coastal Home Steps To Shore

apartment, Norfolk
This Norfolk house is located in Willoughby Spit, just 3km from Norfolk Beaches, Sarah Constant Shrine Beach, and Oceanview Fishing Pier, offering easy access to the waterfront and local attractions. It has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This 4-bedroom, 2-bathroom property can comfortably accommodate up to 8 guests. The house features a fully equipped kitchen, a terrace, a garden, parking, air conditioning, and a washing machine, making it an ideal choice for families and groups looking for a comfortable and convenient stay.
The Oak - Short Stays On Market - Chesapeake Bay
10 2 reviews

The Oak - Short Stays On Market

apartment, Onancock
This apartment is located in the historic Lilliston Building in downtown Onancock, within a 100-meter walk of the Onancock Wharf and a short distance from the Tangier Island Ferry.
This 65-square-meter flat offers accommodation for up to four guests with one bedroom, a king-size bed, a queen sofa bed, a fully equipped kitchen with full-size appliances, and an in-unit washer/dryer.

Frequently asked questions about accommodations in Chesapeake Bay

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

    Kayaking and paddleboarding are great ways to enjoy the water, and you can find plenty of boat tours and fishing charters. If you're looking for something more adventurous, try hiking in Assateague Island National Seashore or exploring the Blackwater National Wildlife Refuge.
  • 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 types of accommodations are available in Baie de Chesapeake?

    You'll find a range of accommodation options, from charming bed and breakfasts to luxury hotels. There are also plenty of campgrounds and vacation rentals available if you're looking for a more budget-friendly option.
  • What are the best accommodations with a pool in Chesapeake Bay?

    The Laughing King Retreat - Cobb Island Suite, Refuge Inn and Walk To Beach By Busch Gardens - Lovely Room are the best accommodations with a pool in Chesapeake Bay.

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

    The best time to visit is during the spring and autumn, when the weather is mild and the crowds are smaller. Summer can be hot and humid, but it's a great time to enjoy the beaches and outdoor activities.
  • What are the best accommodations with a jacuzzi in Chesapeake Bay?

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

    You have to try the Chesapeake Bay blue crabs, they're a local delicacy. And don't forget to sample the fresh oysters, which are a staple of the region. There are also plenty of great seafood restaurants serving up delicious dishes like crab cakes and shrimp.
  • 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 By Busch Gardens - Lovely Room and The Jefferson Hotel.

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

    It really depends on what you want to do. If you're interested in history and culture, Annapolis is a great choice. If you're looking for a more relaxed atmosphere, St. Michaels is a good option. And if you want to be close to the beach, Ocean City is a popular destination.
  • What are the best pet friendly accommodations in Chesapeake Bay?

    The best pet friendly accommodations in Chesapeake Bay are Walk To Beach By Busch Gardens - Lovely Room, The Jefferson Hotel and Wedmore Place.

  • 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

Sojourn The Ocean Breeze In Virginia Beach - Chesapeake Bay
9.7 135 reviews

Sojourn The Ocean Breeze In Virginia Beach

apartment, 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.
Wild Blue Cottage, Steps From The Beach - Chesapeake Bay
9.4 35 reviews

Wild Blue Cottage, Steps From The Beach

apartment, Cape Charles
This Cape Charles house is located just 1.6 kilometres from Cape Charles Beach and the Cape Charles Museum & Welcome Center, offering a peaceful retreat near the sea. It has received excellent ratings for its cleanliness, location, and overall experience.
This three-bedroom property can comfortably accommodate up to six guests, making it ideal for families or groups of friends. The house features a fully equipped kitchen, a private garden, a terrace, a tennis court, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Rooftop Chesapeake Bay Views! Waterfront Retreat - Chesapeake Bay
10 1 review

Rooftop Chesapeake Bay Views! Waterfront Retreat

apartment, Mathews
This studio apartment offers direct Mobjack Bay waterfront access in Westville, approximately 21 kilometres from Williams Wharf Landing and the Gwynn's Island Museum, with the Gloucester Museum of History and Deltaville Maritime Museum also nearby.
This pet-friendly accommodation provides 60 square metres of living space for up to two guests, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, a private balcony, and access to community amenities including a seasonal swimming pool and kayaks.
Hot Tub + Private Beach: Waterfront Urbanna Escape - Chesapeake Bay
9.9 150 reviews

Hot Tub + Private Beach: Waterfront Urbanna Escape

house, Urbanna
This beachfront property in Urbanna, Virginia, boasts stunning sea views and is situated 50km from the Tradition at Stonehouse Golf Club in West Irvington and 70km from Newport News/Williamsburg International Airport.
This 415-square-metre house offers three bedrooms, a fully equipped kitchen with dishwasher, a jacuzzi, a private balcony, on-site bar, and free bicycle use, ideal for exploring Urbanna and enjoying its amenities.

Best Chesapeake Bay accommodations with a kitchen

Bush River Waterfront Retreat - Chesapeake Bay
10 5 reviews

Bush River Waterfront Retreat

apartment, Perryman
This Aberdeen flat is located 46 kilometres from Towson University and Clifton Park, offering waterfront views and convenient access to Baltimore attractions.
This one-bedroom flat accommodates up to seven guests and features a private parking space, complimentary WiFi, air conditioning, and a fully equipped kitchen, along with a jacuzzi for relaxation.
Bluegreen Vacations Parkside Williamsburg, An Ascend Collection Resort - Chesapeake Bay
9.1 1302 reviews

Bluegreen Vacations Parkside Williamsburg, An Ascend Collection Resort

resort, Williamsburg
Bluegreen Parkside Williamsburg, Ascend Resort Collection is conveniently located near Busch Gardens, just a short drive from other attractions like Golden Horseshoe Golf Club and Abby Aldrich Rockefeller Folk Art Museum. The resort is highly rated by guests, earning excellent scores for location, cleanliness, and overall experience.
The resort offers a variety of self-catering apartments with modern furnishings and spacious living areas. You can enjoy a range of amenities including a swimming pool, jacuzzi, tennis court, fitness centre, and restaurant, as well as a garden and a terrace or balcony with scenic views.
Harbor Hideaway - Chesapeake Bay
10 6 reviews

Harbor Hideaway

apartment, Montross
This 3-bedroom, 2-bathroom flat in Montross offers a peaceful waterfront community setting with direct access to the Rappahannock River, just a short drive from the town's amenities.
This accommodation, suitable for up to 6 guests and allowing pets, boasts nearly 0.4 hectares of land, private beach access, a communal swimming pool, and a boat launch for exploring the waterways.
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.
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