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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

Peaceful 1br Retreat In Gated Estate Near History + Local Parks - Chesapeake Bay
No reviews

Peaceful 1br Retreat In Gated Estate Near History + Local Parks

resort, Williamsburg
The "Peaceful 1br Retreat In Gated Estate Near History + Local Parks" holiday apartment is located in Williamsburg, a short drive from Busch Gardens Williamsburg and Colonial Williamsburg, and approximately 10 kilometres from Newport News/Williamsburg Airport, with convenient access to Water Country USA and Historic Jamestowne.
This 56 square metre, one-bedroom, two-bathroom holiday apartment accommodates up to four guests and offers amenities such as air conditioning, a kitchen, a 50-inch television, complimentary toiletries, daily cleaning, a fitness centre, a shared outdoor swimming pool, tennis, and miniature golf.
Pristine Townhouse With Rooftop Deck Near Canton! - Chesapeake Bay
9.8 21 reviews

Pristine Townhouse With Rooftop Deck Near Canton!

apartment, Baltimore
This Patterson Park holiday home in Baltimore is less than 2 kilometres from Patterson Park and within 5 kilometres of the National Aquarium and Baltimore's Inner Harbour.
The 139 square metre property boasts two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, patio, garden, parking, and free Wi-Fi.
Artist Windmill Pt Condo Sunset Pool Relaxation - Chesapeake Bay
9.8 24 reviews

Artist Windmill Pt Condo Sunset Pool Relaxation

apartment, Deltaville
This Deltaville waterfront apartment, located at Windmill Point, offers direct access to the Windmill Point Marina and is a short walk from a tiki bar.
The two-bedroom, two-bathroom property sleeps four, boasts a fully equipped kitchen, private balcony with sunset views, and proximity to planned public fishing pier and beach (opening 2025), plus original artwork.
Oyster Haven - Chesapeake Bay
No reviews

Oyster Haven

house, Madison
Oyster Haven, a spacious eight-bedroom house in Madison, is located 47 kilometres from the Academy of the Arts and 80 kilometres from Salisbury-Ocean City Wicomico Regional Airport.
This 353-square-metre property boasts a private pool, five bathrooms, free Wi-Fi, and parking, comfortably accommodating up to 31 guests.

Best family friendly Chesapeake Bay accommodations

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

Waterfront Lux Cottage With Amazing Views Near Dc - Chesapeake Bay
9.7 15 reviews

Waterfront Lux Cottage With Amazing Views Near Dc

house, North Beach
This waterfront cottage is situated in North Beach, Maryland, 1.9 kilometres from the town centre and approximately 45-61 kilometres from Annapolis, Washington, D.C., and Ronald Reagan Washington National Airport.
This self-catering property boasts 149 square metres of floor space, comprising a spacious living room, one bedroom, two bathrooms, and can accommodate up to 11 guests, offering a private garden, free parking, and Wi-Fi.
Near Chincoteague & Assateague Island Charming 2-bedroom Cottage - Chesapeake Bay
9.8 10 reviews

Near Chincoteague & Assateague Island Charming 2-bedroom Cottage

cottage, Saxis
This Saxis holiday home is conveniently located near Bloxom Winery and Somers Cove Marina, offering easy access to the Chesapeake Forest – Dunn Swamp Complex and Kegotank Bay for birdwatching and outdoor recreation.
Sleeping up to four guests, the two-bedroom property features a queen and a double bed, a fully equipped kitchen with fridge and microwave, air conditioning, Wi-Fi, in-unit laundry, and a bathroom with a hairdryer; local assistance is available from the owner.
Waterfront Wicomico Bay Compound In Reedville, Va - Chesapeake Bay
No reviews

Waterfront Wicomico Bay Compound In Reedville, Va

house, Heathsville
This holiday home in Reedville, Virginia, offers waterfront accommodation on Wicomico Bay, approximately 112 kilometres from Newport News/Williamsburg International Airport.
The 135 square metre property accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, a games room, an outdoor fireplace, and barbecue facilities, with opportunities for fishing, canoeing, and hiking nearby.
Relax & Renew In A Waterfront Cottage , Private Pier, Kayaks, Fishing, Wineries. - Chesapeake Bay
10 71 reviews

Relax & Renew In A Waterfront Cottage , Private Pier, Kayaks, Fishing, Wineries.

cottage, Heathsville
This three-bedroom Heathsville waterfront cottage, ideal for families, is centrally located in Lottsburg, offering easy access (within a few kilometres) to marinas, breweries, antique shops, and wineries on the Chesapeake Bay Wine Trail, plus Bush Mill Stream Natural Area Preserve and Sandy Point Beach.
Sleeping up to nine guests, this self-catering holiday home boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a garden, tennis court, parking, internet access, and two bathrooms; enjoy water views and proximity to the Kinsale Museum and Northern Neck Farm Museum.

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

Relax On Kent Island In 3 Bedroom Home W/waterview - Chesapeake Bay
10 4 reviews

Relax On Kent Island In 3 Bedroom Home W/waterview

house, Stevensville
This Stevensville holiday home on Kent Island offers a tranquil waterside retreat, situated 35 kilometres from Annapolis Harbour and 51 kilometres from Baltimore-Washington International Airport.
This spacious 138 square metre property accommodates up to 21 guests with four bedrooms, three bathrooms, a fully equipped kitchen, a living room, and outdoor space including a garden and patio, complemented by free private parking and WiFi.
Stunning, Large Historic Annapolis Home, Steps To Downtown, Private Driveway! - Chesapeake Bay
9.9 72 reviews

Stunning, Large Historic Annapolis Home, Steps To Downtown, Private Driveway!

apartment, Annapolis
This apartment is located on King George Street in downtown Annapolis, just 0.16 kilometres from the USNA Gate 3 entrance and 0.64 kilometres from the waterfront. The property has been rated excellent for location, cleanliness and user experience.
The accommodation has four bedrooms, four bathrooms, and a basement recreation area, covering 334 square meters and comfortably sleeping up to 10 guests. The property features a gourmet kitchen, a private driveway, a rooftop deck with views, and a finished basement with a pool table, wet bar, and an entertainment area.
Adorable 2-bedroom Bungalow Near Easton, Denton - Chesapeake Bay
9.9 110 reviews

Adorable 2-bedroom Bungalow Near Easton, Denton

house, Queen Anne
This Queen Anne bungalow is conveniently located near Easton and Denton, Maryland, approximately 21 kilometres from the Academy of the Arts and 43 kilometres from Killens Pond State Park.
This two-bedroom, one-bathroom property offers 98 square metres of living space, including a fully equipped kitchen, free Wi-Fi, private parking, and a garden; guests can enjoy nearby attractions such as Sandy Point State Park.
'River's Edge Retreat’ With Kayaks & River Access! - Chesapeake Bay
9.6 117 reviews

'River's Edge Retreat’ With Kayaks & River Access!

house, Heathsville
Rivers Edge Retreat is situated in Reedville, a charming town on the Northern Neck of Virginia, just 105 kilometres from Newport News/Williamsburg International Airport. The property has received excellent ratings for its location, cleanliness and overall experience.
The five-bedroom house spans 353 square metres and comfortably accommodates up to 12 guests. Enjoy the beautiful river views from the terrace, relax in the garden, or take advantage of the included kayaks for a day out on the water.

Best Chesapeake Bay accommodations with a kitchen

Heathsville Home W/ Sunroom < 10 Mi To Beach! - Chesapeake Bay
9.8 22 reviews

Heathsville Home W/ Sunroom < 10 Mi To Beach!

house, Heathsville
This beachfront property is located in Heathsville, just 16 kilometres from the beach and 114 kilometres from Newport News/Williamsburg International Airport, offering a peaceful escape from the hustle and bustle. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom house spans 97 square metres and comfortably accommodates up to four guests. The house offers a range of amenities, including a fully equipped kitchen, free Wi-Fi, a sunroom, and a garden, ensuring a comfortable and enjoyable stay.
Waterfront Gem < 1 Mi To Dtwn Cambridge! - Chesapeake Bay
No reviews

Waterfront Gem < 1 Mi To Dtwn Cambridge!

apartment, Cambridge
This waterfront flat in Cambridge offers scenic views and is situated just under 1 kilometre from the city centre, 26 kilometres from the Academy of the Arts and 35 kilometres from Federalsburg Marina.
This air-conditioned, 70-square-metre apartment features one bedroom, a living room, a fully equipped kitchen with a fridge and microwave, and private parking, accommodating up to seven guests.
The Colonies At Williamsburg - Chesapeake Bay
8.8 2548 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.
Historic Olde Towne 2 Bedroom 1 Bath 1100sq Ft Vacation Rental - Chesapeake Bay
9.0 53 reviews

Historic Olde Towne 2 Bedroom 1 Bath 1100sq Ft Vacation Rental

apartment, Portsmouth
This Portsmouth apartment, a short walk from the Commodore Theatre and the Virginia Sports Hall of Fame, enjoys a riverfront location offering scenic views and is within 2.4km of the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum.
The two-bedroom, one-bathroom flat sleeps four, features free WiFi, a DVD player, a fully equipped kitchen, on-site parking, and a terrace; board games and books are also provided for guests' entertainment.
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