Search Chesapeake Bay accommodations

7504 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Chesapeake Bay accommodation
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

7504 Best accommodations in Chesapeake Bay

Best Chesapeake Bay accommodations with a pool

Among the 7504 accommodations in the area, here is the list of the 4 best ones with a pool

Wake Up To Picturesque Views Of The Ocean, Beach And Boardwalk - Chesapeake Bay
9.0 8 reviews
Chesapeake Bay
20/06 – 27/06
NZ$883/nighttotal: NZ$6181 (7 )

Wake Up To Picturesque Views Of The Ocean, Beach And Boardwalk

2 2
apartment , Virginia Beach
This oceanfront apartment in Northeast Virginia Beach boasts spectacular ocean views from every window, situated close to the Cape Henry Lighthouse and Virginia Beach Town Centre.
The two-bedroom, two-bathroom condo sleeps four, offering amenities including a saltwater indoor pool, private garage parking, and proximity to JT's Grommet Island Park and Atlantic Fun Park, with monthly off-season rentals available (September to May).
Deluxe 2br Cottage W/ Whirlpool Tub + Deck Near Williamsburg Hotspots - Chesapeake Bay
8.8 3 reviews
Chesapeake Bay
12/09 – 16/09
NZ$310/nighttotal: NZ$1240 (4 )

Deluxe 2br Cottage W/ Whirlpool Tub + Deck Near Williamsburg Hotspots

2 2
resort , Williamsburg
This resort in Williamsburg offers a "Deluxe 2br Cottage W/ Whirlpool Tub + Deck Near Williamsburg Hotspots" with a prime location just a few kilometres from Busch Gardens and Colonial Williamsburg, and within easy reach of Water Country USA and Historic Jamestowne.
The spacious 500 sq. ft. cottages accommodate up to six guests and feature a kitchen, 50-inch television, complimentary toiletries, daily cleaning, and access to on-site amenities including tennis, miniature golf, a fitness centre, and a shared outdoor swimming pool, with complimentary parking also provided.
Rooftop Chesapeake Bay Views! Waterfront Retreat - Chesapeake Bay
Chesapeake Bay
20/08 – 29/08
NZ$299/nighttotal: NZ$2691 (9 )

Rooftop Chesapeake Bay Views! Waterfront Retreat

1 2
studio , Mathews
This waterside apartment offers direct access to the Chesapeake Bay from Bohannon on Virginia's Middle Peninsula, providing bay views ideal for morning coffee and a community boat dock for aquatic pursuits.
This studio sleeps two guests, features a private balcony and rooftop deck, offers a seasonal community swimming pool and kayaks, and includes a fully equipped kitchen, air conditioning, and Wi-Fi, with a spiral staircase leading to the sleeping area.
Baydream Believer - Chesapeake Bay
10 1 review
Chesapeake Bay
20/06 – 27/06
NZ$3745/nighttotal: NZ$26215 (7 )

Baydream Believer

5 2
house , Tilghman Island
Baydream Believer, a five-bedroom house in Saint Michaels, Maryland, is situated approximately 24 kilometres from the Academy of the Arts and 106 kilometres from Salisbury-Ocean City Wicomico Regional Airport, offering convenient access to Tilghman Island.
This 465-square-metre property sleeps up to 15 guests and boasts a private pool, Jacuzzi, tennis court, and fully equipped kitchen; additional features include a terrace, garden, and free Wi-Fi.

Best family friendly Chesapeake Bay accommodations

Among the 7504 accommodations in the area, here is the list of the 4 best family friendly ones

Historic Cottage On Ware River Estate - Chesapeake Bay
10 511 reviews
Chesapeake Bay
07/10 – 11/10
NZ$405/nighttotal: NZ$1620 (4 )

Historic Cottage On Ware River Estate

1 2
cottage , Gloucester Courthouse
This charming cottage is situated on a picturesque river, just 8.7 kilometres from Riverside Walter Reed Hospital and 19.3 kilometres from Machicomoco State Park, offering a peaceful retreat for those seeking tranquility. The property consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The self-catering property has one bedroom and one bathroom, comfortably accommodating up to four guests. The cottage provides a range of amenities, including a fully equipped kitchen, a private patio, a hot tub, and a garden, offering everything you need for a relaxing and enjoyable getaway.
Cozy Clean Apartment In The Heart Of Leonardtown! - Chesapeake Bay
10 14 reviews
Chesapeake Bay
20/07 – 27/07
NZ$296/nighttotal: NZ$2072 (7 )

Cozy Clean Apartment In The Heart Of Leonardtown!

1 4
apartment , Leonardtown
This Leonardtown apartment offers a convenient downtown location, within walking distance of shops and restaurants.
The one-bedroom, one-bathroom flat sleeps five guests and features a full kitchen, Jacuzzi, free parking, and is close to attractions including New Towne Neck State Park and the Patuxent River Naval Air Museum.
Deltaville 2br Retreat, Walk To Museum, Boat Parking - Chesapeake Bay
10 70 reviews
Chesapeake Bay
20/07 – 27/07
NZ$411/nighttotal: NZ$2877 (7 )

Deltaville 2br Retreat, Walk To Museum, Boat Parking

2 4
apartment , Deltaville
This Deltaville seaside house, a 10-minute walk from the Deltaville Maritime Museum, Holly Point Nature Park, and Deltaville Marina, and within 32 kilometres of White Stone Beach and the Middlesex County Museum, offers stunning waterfront views.
This 72-square-metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, private patio, garden, free Wi-Fi, and parking.
The Atrium Resort, Virginia Beach By Vacatia - Chesapeake Bay
8.3 2876 reviews
Chesapeake Bay
01/10 – 05/10
NZ$246/nighttotal: NZ$984 (4 )

The Atrium Resort, Virginia Beach By Vacatia

1 3
resort , Virginia Beach
The Atrium Resort by VSA Resorts is located directly on the Virginia Beach Boardwalk, just a short walk from the beach and a couple of minutes' drive from attractions like Jungle Golf and the Old Coast Guard Station Museum. The resort has consistently received very good ratings for its location, cleanliness, and overall experience.
The accommodation offers spacious suites with full kitchens and living rooms, ideal for families or groups. Guests can enjoy a range of facilities, including a swimming pool, hot tub, fitness centre, and free Wi-Fi.

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.

Destinations nearby

Best Chesapeake Bay accommodations with a balcony

Artistic Abode Close To Mica & Johns Hopkins - Chesapeake Bay
8.4 5 reviews
Chesapeake Bay
20/07 – 27/07
NZ$403/nighttotal: NZ$2821 (7 )

Artistic Abode Close To Mica & Johns Hopkins

1 4
apartment , Baltimore
This one-bedroom flat is located in Madison Park, a quiet residential neighbourhood in Baltimore, within 3km of Maryland Institute College of Art, Oriole Park at Camden Yards, and Johns Hopkins University. The property has received excellent guest reviews.
The flat can accommodate up to four guests and features a fully equipped kitchen, a balcony, and a washing machine. Guests can enjoy free Wi-Fi, parking, and air conditioning.
Book A Piece Of History At Kingsmill Resort In Williamsburg Virginia! - Chesapeake Bay
9.5 180 reviews
Chesapeake Bay
20/07 – 27/07
NZ$523/nighttotal: NZ$3661 (7 )

Book A Piece Of History At Kingsmill Resort In Williamsburg Virginia!

2 4
apartment , Williamsburg
This apartment is situated in Kingsmill, just 0.3 kilometres from the Kingsmill Plantation Golf Course and 2.6 kilometres from Busch Gardens Williamsburg, offering a convenient location close to popular attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has two bedrooms, providing ample space for families or groups of friends, and covers 117 square metres. It offers a range of amenities, including a swimming pool, jacuzzi, terrace, and garden, as well as a fully equipped kitchen, internet access, and parking.
Galloway 118 I Spacious Garden Style Retreat - Chesapeake Bay
Chesapeake Bay
20/06 – 27/06
NZ$245/nighttotal: NZ$1715 (7 )

Galloway 118 I Spacious Garden Style Retreat

1 2
apartment , New Castle
This New Castle apartment is situated within 3.2km of Llangollen Estates Park, Brandywine Valley, and Kirkwood Soccer Complex, and within 4.8km of the New Castle Farmers' Market and Lewden Green Park.
The 79 square metre flat offers one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private balcony, on-site fitness centre, and free Wi-Fi.
Cabin At Holdens Creek On Eastern Shore Of Va - Chesapeake Bay
9.8 187 reviews
Chesapeake Bay
01/10 – 05/10
NZ$276/nighttotal: NZ$1104 (4 )

Cabin At Holdens Creek On Eastern Shore Of Va

1 3
cabin , Sanford
This cabin is located in a peaceful rural setting, just 25 kilometres from Bloxom Winery, Wallops Flight Facility, and the Eastern Shore Railway Museum. It has received excellent user ratings.
The cabin is a one-bedroom, one-bathroom property with a floor area of 74 square metres and a capacity of six guests. It offers a range of amenities including a kitchen with a fridge and microwave oven, air conditioning, a terrace, a garden, parking, and free Wi-Fi.

Best Chesapeake Bay accommodations with a kitchen

Charming Riverside Cottage W/optional Guest House - Chesapeake Bay
9.8 27 reviews
Chesapeake Bay
20/06 – 27/06
NZ$974/nighttotal: NZ$6818 (7 )

Charming Riverside Cottage W/optional Guest House

1 13
apartment , Deltaville
This historic farmhouse, located on the private sandy banks of the Piankatank River in Deltaville, offers direct river access and is situated less than 200 metres from a public beach.
This riverside property accommodates up to 16 guests with its main house and optional guest house, featuring a fully stocked kitchen with an outdoor grill, multiple outdoor living spaces, and included kayaks and fishing equipment.
Hidden Fells Point Gem / Private Courtyard Patio - Chesapeake Bay
9.6 95 reviews
Chesapeake Bay
23/08 – 28/08
NZ$237/nighttotal: NZ$1185 (5 )

Hidden Fells Point Gem / Private Courtyard Patio

1 2
apartment , Baltimore
This one-bedroom flat is located in Fells Point, a historic Baltimore district, within walking distance of Fell's Point Visitor Center and Johns Hopkins Hospital. It has received excellent reviews from previous guests.
The 59 square metre property has two bathrooms and can comfortably accommodate up to three guests. It offers a fully equipped kitchen, a terrace, a garden, a spa, parking, and internet access, as well as a washer and dryer for added convenience.
Gaia House - Chesapeake Bay
9.3 58 reviews
Chesapeake Bay
07/10 – 11/10
NZ$255/nighttotal: NZ$1020 (4 )

Gaia House

2 2
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.
Indoor Soft Hot Tub - Family Friendly Staycation! - Chesapeake Bay
9.6 5 reviews
Chesapeake Bay
20/06 – 27/06
NZ$2216/nighttotal: NZ$15512 (7 )

Indoor Soft Hot Tub - Family Friendly Staycation!

1 13
apartment , Marlboro Meadows
This spacious apartment in Marlboro Meadows is located just a short distance from The Cannon Club and three local golf courses, making it an ideal choice for those seeking a relaxing getaway in a peaceful setting. It has received excellent ratings for user experience, location, and cleanliness.
The apartment features a large, open-plan layout with a two-story cathedral ceiling, accommodating up to 14 guests comfortably. Residents can enjoy access to a community pool, clubhouse, and a garden, as well as a fully equipped kitchen, air conditioning, and a private parking space.
©2026 cozycozy.com