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Chesapeake Bay accommodation
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10861 Best accommodations in Chesapeake Bay

Find Accommodations by the Sea in Chesapeake Bay

Open your living room doors directly onto the shore at accommodation by the sea in Chesapeake Bay.

Adorable Two-bedroom Retreat Close To Easton, Denton, Centreville - Chesapeake Bay
10 29 reviews

Adorable Two-bedroom Retreat Close To Easton, Denton, Centreville

apartment, Queen Anne
This Queen Anne holiday home is situated 1.1km from Tuckahoe State Park and within 14.5km of Adkins Arboretum, Triple Creek Winery, Daniel Crouse Memorial Park, and Caroline Public Library.
The two-bedroom, one-bathroom property sleeps four guests and boasts a fully equipped kitchen, private balcony, garden, spa, parking, and free Wi-Fi; nearby activities include exploring Tuckahoe State Park and visiting local wineries.

Find City Centre Accommodations in Chesapeake Bay

Stay right where the coastal dining meets the local nightlife strips at accommodation in the heart of Chesapeake Bay.

Kimary Cove - Waterfront Relaxation And No Cleaning Fee - Chesapeake Bay
9.6 28 reviews

Kimary Cove - Waterfront Relaxation And No Cleaning Fee

apartment, Gwynn
This waterfront apartment is situated just 7.7km from Mathews and 22.5km from Gloucester, offering a peaceful retreat with easy access to nearby attractions. The property has received excellent guest reviews, highlighting its comfortable and well-equipped nature.
The self-catering apartment provides accommodation for up to four guests across two bedrooms and one bathroom. Guests can enjoy a private dock, a gazebo, a spacious deck, a cornhole game, a grill, and a pool table, alongside a fully equipped kitchen and three Roku televisions.
The Little House At Waveland - Chesapeake Bay
9.7 196 reviews

The Little House At Waveland

apartment, Deltaville
This Deltaville cottage sits at the confluence of Jackson Creek and the Rappahannock River, offering easy access to the Chesapeake Bay and is less than 1km from a coffee shop with Wi-Fi and the Middlesex County Library.
The three-bedroom property, sleeping five, includes a private dock, small beach, outdoor shower, charcoal grill, and cornhole; guests can also enjoy the screened porch and nearby family-friendly amenities.
1891 Coastal Charmer: Fully Renovated Farmhouse - Chesapeake Bay
10 141 reviews

1891 Coastal Charmer: Fully Renovated Farmhouse

apartment, White Stone
This charming farmhouse is located in White Stone, just a short distance from the bay, offering easy access to water activities. The property boasts excellent user, location, and cleanliness ratings, making it a great choice for travellers.
This two-bedroom, one-bathroom property can accommodate up to five guests. It comes equipped with a well-stocked kitchen, a relaxing screened porch, a fire pit, and a garden shed with games, along with access to kayaks for an additional fee.
Riverfront Cottage: Fire Pit & Kayaks - Chesapeake Bay
9.7 124 reviews

Riverfront Cottage: Fire Pit & Kayaks

house, Deltaville
The Riverfront Cottage Fire Pit and Kayaks is located in Deltaville, Virginia, just 67km from the historic town of Williamsburg. The cottage has received excellent ratings from previous guests for its cleanliness, location and overall experience.
The property has two bedrooms, three living rooms and a fully equipped kitchen, covering a total of 117 square meters. Enjoy amenities like air conditioning, a dishwasher, a coffee machine, a fireplace, a hair dryer, a fire pit, kayaks, free Wi-Fi, and on-site parking.

Frequently asked questions about accommodations in Chesapeake Bay

  • What are the top attractions and must-see sites in Baie de Chesapeake?

    You absolutely must visit the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. They have a great collection of historic boats and exhibits on the region's maritime history. Another must-see is the Assateague Island National Seashore, where you can see wild horses roaming the beach.
  • 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.

  • Which cultural festivals and seasonal events should visitors attend in Baie de Chesapeake?

    The annual Chesapeake Bay Blues Festival in Annapolis is a big one, attracting top blues musicians. In the autumn, the annual Oyster Festival in St. Michaels is a great event for trying local seafood and enjoying live music.
  • What are the best accommodations with a pool in Chesapeake Bay?

    The Laughing King Retreat - Cobb Island Suite, Refuge Inn and The Jefferson Hotel are the best accommodations with a pool in Chesapeake Bay.

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

    The best way to get around the Chesapeake Bay region is by car, as it gives you the flexibility to explore the different towns and attractions at your own pace. You can also use the ferry services that run between some of the islands and mainland towns.
  • What are the best accommodations with a jacuzzi in Chesapeake Bay?

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

    You can go kayaking or canoeing in the calm waters of the Bay, or try your hand at fishing. If you're feeling adventurous, you can even go sailing or windsurfing. In the summer, there's also great swimming and sunbathing on the beaches.
  • 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, The Jefferson Hotel and Comfort Suites Chincoteague Island Bayfront Resort.

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

    There's a wide variety of accommodation options in the Chesapeake Bay area, from budget-friendly motels and campgrounds to luxury hotels and waterfront resorts. You can also find charming bed and breakfasts in many of the towns.
  • What are the best pet friendly accommodations in Chesapeake Bay?

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

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

    The best time to visit the Chesapeake Bay is during the spring or autumn, when the weather is mild and the crowds are smaller. Summer is also popular, but can be hot and humid.
  • 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.

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

    You have to try the fresh seafood, especially crab cakes and oysters. There are also lots of great restaurants serving traditional Chesapeake Bay cuisine, like crab soup and steamed crabs. And don't forget the local craft beers!
  • In which part of Baie de Chesapeake should you consider renting accommodation?

    It really depends on what you want to see and do. If you're interested in history and maritime culture, St. Michaels is a great choice. If you want to be close to the beach and enjoy some outdoor activities, Ocean City is a good option. Annapolis is also a great choice if you want to be in a bustling city with lots of restaurants and bars.

Popular destinations

Your Guide to the Finest High-End Stays in Chesapeake Bay

Find luxury beach accommodation in Chesapeake Bay for an indulgent tropical escape.

Cozy Modern Micro Apt In The Heart Of Fells Point! - Chesapeake Bay
9.0 38 reviews

Cozy Modern Micro Apt In The Heart Of Fells Point!

apartment, Baltimore
This Baltimore waterfront apartment, less than 1.6km from the Inner Harbour and attractions such as the National Aquarium and Johns Hopkins Hospital, offers easy access to public transport and scenic views.
This 60 square metre, two-bedroom flat sleeps four guests and boasts a fully equipped kitchen, swimming pool, spa, parking, and free Wi-Fi; on-site amenities include a water park and barbecue grills.

Find the Best Accommodations with a Swimming Pool in Chesapeake Bay

Alternate between a refreshing freshwater plunge and an ocean swim at beach accommodation with a pool in Chesapeake Bay.

Chesapeake Waterfront - 7br 5ba - Beach Pool Dock - Chesapeake Bay
No reviews

Chesapeake Waterfront - 7br 5ba - Beach Pool Dock

house, Madison
This Chesapeake Bay waterfront property, situated in Woolford, Maryland, is 43km from the Academy of the Arts and 77km from Salisbury-Ocean City Wicomico Regional Airport.
This seven-bedroom, five-bathroom house boasts 374 square metres of floor space, a private pool and dock, accommodating up to 25 guests and offering amenities including a fully equipped kitchen, Wi-Fi, and a fireplace.
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.
Clearview - Chesapeake Bay
No reviews

Clearview

house, Tilghman Island
Clearview, a holiday home on Tilghman Island, Maryland, is situated 39 kilometres from the Academy Art Museum and 121 kilometres from Baltimore/Washington International Thurgood Marshall Airport.
This three-bedroom, three-bathroom property boasts 191 square metres of floor space, sleeps up to 11 guests, and includes a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and free private parking.
Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina - Chesapeake Bay
8.7 1443 reviews

Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina

resort, Cambridge
The Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina is situated in Cambridge, Maryland, just a short drive from the Cambridge - Dorchester Regional Airport and offering easy access to the beautiful Chesapeake Bay. The resort has consistently received very good ratings for its location, cleanliness and overall experience.
The hotel features a range of facilities including a championship golf course, a full-service spa and salon, a marina with 150 slips, three restaurants, three swimming pools, a fitness centre and tennis courts. Guests can also enjoy a variety of activities such as boating, fishing, swimming and spa treatments.

The Best Family-Rated Stays in Chesapeake Bay

Give the family a spacious shoreline base camp steps from the waves at family beach accommodation in Chesapeake Bay.

Near Chincoteague & Assateague Island Charming 2-bedroom Cottage - Chesapeake Bay
9.8 10 reviews

Near Chincoteague & Assateague Island Charming 2-bedroom Cottage

cottage, Saxis
The Tides Inn - Chesapeake Bay
8.9 388 reviews

The Tides Inn

resort, Irvington
Where Peace Is Sitting By The Moonlight - Chesapeake Bay
9.6 100 reviews

Where Peace Is Sitting By The Moonlight

apartment, Heathsville
Kingsmill Resort - Chesapeake Bay
8.7 1296 reviews

Kingsmill Resort

resort, Williamsburg

Leading Dog-Friendly Accommodations in Chesapeake Bay

Let your dog run wild through the sand and surf at these pet-friendly beach accommodations in Chesapeake Bay.

Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay - Chesapeake Bay
9.8 70 reviews

Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay

cottage, Cecilton
Golden Anchor Retreat Lux Living! - Chesapeake Bay
10 3 reviews

Golden Anchor Retreat Lux Living!

house, Mayo
Circa 1700 Chesapeake Colonial Home On The National Register. - Chesapeake Bay
9.8 255 reviews

Circa 1700 Chesapeake Colonial Home On The National Register.

apartment, Stevensville
Waterfront Wicomico Bay Compound In Reedville, Va - Chesapeake Bay
10 3 reviews

Waterfront Wicomico Bay Compound In Reedville, Va

apartment, Heathsville

Find the Best Accommodations with Balconies in Chesapeake Bay

Take in breathtaking, uninterrupted ocean sunsets directly from your personal balcony at beach accommodation in Chesapeake Bay.

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
❤️Charming Coastal/country Home W/3 Acres & Sauna!❤️ - Chesapeake Bay
9.0 3 reviews

❤️Charming Coastal/country Home W/3 Acres & Sauna!❤️

house, Stevensville
Spacious And Luxurious 3 Bed/1.5 Bath Townhome With Free Parking, Sleeps 6 - Chesapeake Bay
9.6 14 reviews

Spacious And Luxurious 3 Bed/1.5 Bath Townhome With Free Parking, Sleeps 6

apartment, Middletown
'River's Edge Retreat’ With Kayaks & River Access! - Chesapeake Bay
9.6 117 reviews

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

house, Heathsville

Best Chesapeake Bay accommodations with a kitchen

Pet-friendly Smith Island Cottage W/ Golf Cart! - Chesapeake Bay
9.5 2 reviews

Pet-friendly Smith Island Cottage W/ Golf Cart!

house, Smith Island
Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia - Chesapeake Bay
8.2 2973 reviews

Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia

resort, Virginia Beach
Affordable Cottage! - Chesapeake Bay
10 3 reviews

Affordable Cottage!

apartment, Deltaville
Charming Townhome In Federal Hill - Chesapeake Bay
9.5 2 reviews

Charming Townhome In Federal Hill

house, Baltimore
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