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Chesapeake Bay accommodation
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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

Botanical Garden Escape On The River - With A Pool - Chesapeake Bay
9.9 28 reviews
Chesapeake Bay
21/08 – 28/08
NZ$1543/nighttotal: NZ$10801 (7 )

Botanical Garden Escape On The River - With A Pool

4 4
apartment , Lancaster
This spacious apartment is located on the Corrotoman River, just 15 kilometres from Kilmarnock, offering a peaceful retreat with river views. The accommodation has consistently received excellent ratings for location, cleanliness and user experience.
The apartment has four bedrooms and three bathrooms, comfortably accommodating up to 12 guests. Enjoy a range of amenities including a swimming pool, a spa, a fitness centre, a garden, parking, and Sonos speakers, perfect for relaxing and enjoying the beautiful surroundings.
Luxury Condo, Rooftop Pool & Dock, 3 To Downtown - Chesapeake Bay
10 1 review
Chesapeake Bay
29/08 – 05/09
NZ$1320/nighttotal: NZ$9240 (7 )

Luxury Condo, Rooftop Pool & Dock, 3 To Downtown

2 2
house , Annapolis
This luxury condominium in Annapolis is located a 13-minute walk from Annapolis Harbour and 41.8 kilometres from Baltimore's Inner Harbour.
This air-conditioned holiday home offers 49 square metres of living space with two bedrooms, accommodating up to seven guests, and features a rooftop pool with sea views, private dock access, a well-equipped kitchen, and a fireplace.
Cottage With Harbor And Chesapeake Bay View In Rock Hall, Md - Chesapeake Bay
9.7 105 reviews
Chesapeake Bay
30/07 – 05/08
NZ$669/nighttotal: NZ$4014 (6 )

Cottage With Harbor And Chesapeake Bay View In Rock Hall, Md

2 6
apartment , Rock Hall
This charming cottage is situated on Bayside Avenue in Rock Hall, Maryland, just a short stroll from the town beach and swimming pool. It has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The two-bedroom cottage, spanning 93 square metres, comfortably accommodates up to six guests. It offers a range of amenities including a fully equipped kitchen, air conditioning, a screened back deck, and a pet-friendly policy.
Cape Charles Home With Pool And Golf Cart 5 Minutes From The Beach! - Chesapeake Bay
8.8 23 reviews
Chesapeake Bay
14/10 – 18/10
NZ$609/nighttotal: NZ$2436 (4 )

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

3 4
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.

Best family friendly Chesapeake Bay accommodations

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

Salisbury Hideaway - Chesapeake Bay
9.9 16 reviews
Chesapeake Bay
30/07 – 05/08
NZ$536/nighttotal: NZ$3216 (6 )

Salisbury Hideaway

2 6
house , Salisbury
Salisbury Hideaway is located in Salisbury, just 10km from Salisbury-Ocean City Wicomico Regional Airport, offering easy access to the local area.
This 135 square metre home features two bedrooms, one bathroom, and a fully equipped kitchen, comfortably accommodating up to 11 guests, with a garden, terrace, and fitness room for relaxation and recreation.
Hilton Vacation Club The Historic Powhatan Williamsburg - Chesapeake Bay
9.0 5804 reviews
Chesapeake Bay
23/08 – 28/08
NZ$230/nighttotal: NZ$1150 (5 )

Hilton Vacation Club The Historic Powhatan Williamsburg

1 2
resort , Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg is located just outside of Historic Williamsburg, a short drive from the historic district and close to other attractions like WakeMed Soccer Park and the College of William and Mary. This resort has received very good user ratings, with excellent scores for location and cleanliness.
The resort offers spacious suites on the grounds of a restored Manor House, providing a unique and historic ambiance. Guests can enjoy a range of amenities and activities, including a swimming pool, a jacuzzi, a tennis court, and a fitness centre, as well as on-site dining options and a children's playground.
Tiny House At St. George Island - Chesapeake Bay
8.0 4 reviews
Chesapeake Bay
29/08 – 05/09
NZ$264/nighttotal: NZ$1848 (7 )

Tiny House At St. George Island

2 2
cottage , Piney Point
This cottage, a cosy tiny house, is located in Piney Point, a short distance from the historic Piney Point Lighthouse and Cecil's Old Mill, and close to St. Mary's River State Park.
This accommodation sleeps up to five guests across two bedrooms and offers internet, air conditioning, a kitchen with a fridge and microwave, and exclusive access to a private sandy beach for fishing, crabbing, and picnicking.
Lovely Condo With Water & Golf Course View - Chesapeake Bay
9.6 11 reviews
Chesapeake Bay
20/07 – 27/07
NZ$423/nighttotal: NZ$2961 (7 )

Lovely Condo With Water & Golf Course View

1 4
apartment , Williamsburg
This one-bedroom condominium in the Kingsmill district of Williamsburg offers waterfront and golf course views, situated within a 5-kilometre drive of Busch Gardens Williamsburg, Water Country USA, and Colonial Williamsburg.
This family-friendly apartment, ideal for up to four guests, features a private balcony with serene views, air conditioning, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, and access to a swimming pool and garden, all within an award-winning resort.

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

Riverfront Paradise With Hot Tub And Pool In Kinsale! - Chesapeake Bay
9.7 50 reviews
Chesapeake Bay
29/08 – 05/09
NZ$1776/nighttotal: NZ$12432 (7 )

Riverfront Paradise With Hot Tub And Pool In Kinsale!

4 2
house , Heathsville
This riverfront property in Kinsale, Virginia, offers stunning views and is approximately 50 kilometres from the George Washington Birthplace National Monument and Memorial House.
This spacious 307-square-metre house boasts four bedrooms, three bathrooms, a private hot tub, swimming pool, and free bicycle use for exploring the Kinsale area, alongside a fully equipped kitchen and free Wi-Fi.
Pet Friendly Water View Cottage - Chesapeake Bay
10 37 reviews
Chesapeake Bay
20/07 – 27/07
NZ$443/nighttotal: NZ$3101 (7 )

Pet Friendly Water View Cottage

2 4
cottage , Riviera Beach
This charming cottage is located in Pasadena, Maryland, a picturesque waterfront neighbourhood just 20 kilometres from both Annapolis and Baltimore, offering easy access to a range of attractions. The cottage has received excellent reviews from previous guests, highlighting its comfortable and welcoming atmosphere.
The cottage spans 111 square metres and comfortably accommodates up to four guests in its two bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a private garden, and a host of amenities including air conditioning, laundry facilities, and free parking. The cottage is also pet-friendly, allowing guests to bring their furry companions along.
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! - Chesapeake Bay
9.6 90 reviews
Chesapeake Bay
01/10 – 05/10
NZ$266/nighttotal: NZ$1064 (4 )

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

1 3
apartment , Annapolis
This apartment is located in Annapolis, just half a mile from Anne Arundel Medical Center and 2.7 miles from the U.S. Naval Academy, offering a peaceful retreat from the city centre. The accommodation has been rated excellent by previous guests.
The flat has one bedroom and one bathroom, comfortably sleeping up to three guests. It comes with a range of amenities including free Wi-Fi, a balcony, a fully equipped kitchen, parking and a relaxing reading nook.
8 Mi To Dover Motor Speedway! Dog-friendly Retreat - Chesapeake Bay
9.2 7 reviews
Chesapeake Bay
29/08 – 05/09
NZ$468/nighttotal: NZ$3276 (7 )

8 Mi To Dover Motor Speedway! Dog-friendly Retreat

3 2
house , Wyoming
Eternal Sunshine is a spacious house in Dover, Delaware, situated just 11.4 kilometres from Dover International Speedway and 21 kilometres from Killens Pond Water Park. It has received excellent ratings for location, cleanliness, and user experience.
The property has three bedrooms and three bathrooms, covering 142 square metres and accommodating up to six guests. It offers a fully equipped kitchen, a washing machine, air conditioning, a fireplace, a garden, and free Wi-Fi.

Best Chesapeake Bay accommodations with a kitchen

Sleek And Cozy Micro Fells Point Residence! - Chesapeake Bay
8.8 40 reviews
Chesapeake Bay
01/10 – 05/10
NZ$281/nighttotal: NZ$1124 (4 )

Sleek And Cozy Micro Fells Point Residence!

2 3
apartment , Baltimore
This Fells Point apartment in Baltimore is less than 2 kilometres from the Inner Harbour, National Aquarium, and Baltimore Convention Centre, offering easy access to public transport and historical sites such as Frederick Douglass-Isaac Myers Maritime Park.
The two-bedroom, one-bathroom flat sleeps four guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, free Wi-Fi, and a Smart TV.
Guesthouse In Ideal Location With Private Entrance - Chesapeake Bay
9.8 123 reviews
Chesapeake Bay
23/08 – 28/08
NZ$279/nighttotal: NZ$1395 (5 )

Guesthouse In Ideal Location With Private Entrance

1 2
apartment , Suffolk
This Suffolk apartment is conveniently located within 5km of Riverfront Golf Club and local medical facilities, including Bon Secours Health Center At Harbour View and Sentara BelleHarbour, and within 14km of Chesapeake Square Mall and Portsmouth City Park.
This self-catering flat offers one bedroom, one bathroom, sleeping up to two guests, and features free Wi-Fi, a Smart TV, in-unit laundry, and convenient on-site parking.
Affordable Furnished Luxurytownhouse Near Stadiums In Baltimore Pig Town. - Chesapeake Bay
9.5 490 reviews
Chesapeake Bay
01/10 – 05/10
NZ$276/nighttotal: NZ$1104 (4 )

Affordable Furnished Luxurytownhouse Near Stadiums In Baltimore Pig Town.

2 3
apartment , Baltimore
This charming Baltimore house is located in the Pigtown neighbourhood, just a 15-minute walk from the Charm'tastic Mile, Oriole Park at Camden Yards, and M&T Bank Stadium. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house has two bedrooms and can accommodate up to five guests. It offers a fully equipped kitchen, two bathrooms, a washing machine, a coffee/tea maker, and a Smart TV, as well as a garden with barbecue facilities.
Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment - Chesapeake Bay
9.4 14 reviews
Chesapeake Bay
29/08 – 05/09
NZ$306/nighttotal: NZ$2142 (7 )

Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment

1 2
house , Brock Hall
This Brock Hall house, near Addison Road-Seat Pleasant Station (22km) and approximately 32km from both the Supreme Court and the US Capitol, offers a convenient base for exploring the area.
The 223-square-metre property boasts a private pool, garden, terrace, fitness centre, and parking, accommodating up to six guests in its one-bedroom, one-bathroom layout with a fully equipped kitchenette.
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