Places to stay in Chesapeake Bay

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Chesapeake Bay place to stay
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10861 Best places to stay in Chesapeake Bay

Best Chesapeake Bay lodgings with a pool

Among the 10861 accommodations in Chesapeake Bay, here are the 4 best ones with a pool

Holiday Inn Hotel & Suites Gateway By Ihg - Chesapeake Bay
8.9 1368 reviews

Holiday Inn Hotel & Suites Gateway By Ihg

resort, Williamsburg
The Holiday Inn Hotel & Suites Gateway, An Ihg Hotel is just two miles from the College of William and Mary and Colonial Williamsburg Historic Area, making it a convenient base for exploring the city's rich history and attractions. The hotel consistently receives very good ratings for cleanliness and overall experience, ensuring a comfortable stay.
The hotel offers a range of amenities and activities to suit all tastes, from a swimming pool and fitness centre to a restaurant and bar. Guests can also enjoy the convenience of room service, a business centre, and a tennis court.
Beautiful 1 Bedroom Condo With A View! - Chesapeake Bay
10 75 reviews

Beautiful 1 Bedroom Condo With A View!

apartment, Williamsburg
This Kingsmill Resort apartment, located near the 9th hole of the River golf course, offers golf course views and is within minutes of Busch Gardens, Water Country USA, Colonial Williamsburg, and Jamestown.
The one-bedroom, one-bathroom property sleeps three guests and features a fully equipped kitchen, two 50-inch smart TVs, a covered balcony, access to an on-site pool (open Memorial Day to Labor Day), and proximity to walking trails, the Mill Cafe, and the Kingsmill Spa.
Kingsbay Dockside Waterfront House - Chesapeake Bay
10 5 reviews

Kingsbay Dockside Waterfront House

apartment, Fairmount
This Fairmount property, Kingsbay Dockside at 5757 Dockside Lane, offers breathtaking panoramic water views of Kingsbay Mansion across the water, the precise distance unspecified.
This four-bedroom, eight-guest house boasts 278 square metres of space, including a newly renovated Swiss country-style interior with a modern kitchen, solarium, private swimming pool, and ample parking.
Minutes From Downtown Easton And St. Michaels | Pool | Private Dock | Luxury - Chesapeake Bay
10 1 review

Minutes From Downtown Easton And St. Michaels | Pool | Private Dock | Luxury

apartment, Oxford
This five-bedroom house, ideal for families, is located in Royal Oak, Maryland, approximately 15km from Saint Michaels Village and its museums, and within 20km of the Chesapeake Bay Maritime Museum and Saint Mary's Square.
The 632 square metre property boasts a private pool, fitness centre, tennis court, and spa, accommodating up to 10 guests and offering a fully equipped kitchen, free Wi-Fi, and ample parking.

Best family friendly Chesapeake Bay lodging

Among the 10861 accommodations in Chesapeake Bay, here are the 4 best for families

Stay By Md's Chesapeake Bay This Father's Day! Walk To Marina, Bar & Restaurant! - Chesapeake Bay
10 42 reviews

Stay By Md's Chesapeake Bay This Father's Day! Walk To Marina, Bar & Restaurant!

apartment, Stevensville
This family-friendly house is situated near the sea in Stevensville, just a short drive from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park. It has consistently received excellent ratings from previous guests, making it a popular choice for families and groups visiting the area.
The property spans 203 square metres and comfortably accommodates up to 14 guests in its five bedrooms and two bathrooms. Guests can enjoy a range of amenities including a fitness centre, spa tub, garden, and tennis court, providing plenty of opportunities for relaxation and recreation.
Bee Humble Cottage W/in 20mins To Public Beaches - Chesapeake Bay
9.8 35 reviews

Bee Humble Cottage W/in 20mins To Public Beaches

cottage, Gloucester Courthouse
This family-friendly cottage is located in a peaceful rural area of Gloucester Courthouse, just 13km from Riverside Walter Reed Hospital and within a 32km radius of Gloucester Point Beach Park and Machicomoco State Park. It has received excellent user ratings, making it a popular choice for travellers seeking a relaxing escape.
The two-bedroom cottage spans 102 square metres and comfortably accommodates up to four guests. It offers a range of amenities, including a fully equipped kitchen, a private garden, a swimming pool, a spa, and access to a nearby water park, ensuring a comfortable and enjoyable stay.
The Colonies At Williamsburg - Chesapeake Bay
8.8 2568 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.
Creek Cottage With Dock - Chesapeake Bay
9.7 157 reviews

Creek Cottage With Dock

apartment, Urbanna
This house is located in Lancaster, Virginia, just 19.1 kilometres from the Mary Ball Washington Museum and Library, and within 32 kilometres of Morattico Waterfront Museum and Good Luck Cellars. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The house can comfortably accommodate four guests in its one bedroom and one bathroom. The property features a fully equipped kitchen, a private garden with barbecue facilities, laundry facilities, and entertainment options like a TV and DVD player.

Frequently asked questions about accommodations in Chesapeake Bay

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

    Renting a car is the best way to explore the region and get to all the different towns and attractions. Public transport isn't as developed, but there are some local bus services in major cities. If you're staying in Annapolis or Baltimore, you can also use ride-sharing apps like Uber and Lyft.
  • 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 outdoor activities and adventures are popular in and around Baie de Chesapeake?

    Kayaking and paddleboarding are popular activities on the bay. There are many great places to hike in the area, like the Patapsco Valley State Park. And for a more adventurous experience, try sailing or fishing. You could also try a scenic bike ride on the Chesapeake Bay Trail.
  • What are the best accommodations with a pool in Chesapeake Bay?

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

    You'll find a range of options, from budget-friendly motels to luxury hotels and resorts. If you're looking for a unique experience, try staying in a bed and breakfast or a waterfront cottage. There are also plenty of campgrounds for those who prefer a more rustic experience.
  • What are the best accommodations with a jacuzzi in Chesapeake Bay?

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

    Spring and autumn are the most pleasant times to visit, with mild temperatures and fewer crowds. Summer is hot and humid, but it's a great time for water activities. Winter can be cold, but you can enjoy the beauty of the bay with fewer visitors.
  • 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 - Large Lovely Condo By Lake In "Kingsmill On The James" and The Jefferson Hotel.

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

    You have to try the famous Maryland crab cakes, made with fresh blue crabs. Don't forget to sample the local oysters, which are a delicacy in the area. For a sweet treat, try a Smith Island cake, a layered chocolate cake with a unique history.
  • What are the best pet friendly accommodations in Chesapeake Bay?

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

    It depends on what you want to see and do. Annapolis is a great choice for history and culture, while Ocean City is perfect for beach lovers. If you're looking for a quieter experience, consider staying on the Eastern Shore in towns like St Michaels or Oxford.
  • 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

Ocean Key Resort - Chesapeake Bay
9.0 11 reviews

Ocean Key Resort

resort, Virginia Beach
Ocean Key Resort, a 3-star hotel in Virginia Beach, is located in a district offering ocean views and potential for integrated balconies or terraces, suggesting proximity to the coast. This family-friendly accommodation provides rooms with separate living areas, in-room entertainment, air conditioning and laundry service in select rooms, alongside a swimming pool, restaurant, bar, fitness centre, room service, and parking.
Hilton Vacation Club Greensprings Williamsburg - Chesapeake Bay
8.9 3945 reviews

Hilton Vacation Club Greensprings Williamsburg

resort, Williamsburg
Greensprings Vacation Resort is located near the Green Springs National Historic Landmark District in Williamsburg, providing easy access to the area's rich history and top attractions. The resort has consistently received very good ratings for its cleanliness and user experience, with an excellent location rating.
The resort offers spacious apartments with fully equipped kitchens and comfortable fireplaces, providing a home-away-from-home feel. Guests can enjoy amenities such as a swimming pool, jacuzzi, fitness centre, tennis court, and a restaurant and bar, ensuring a relaxing and enjoyable stay.
Rooftop Chesapeake Bay Views! Waterfront Retreat - Chesapeake Bay
No reviews

Rooftop Chesapeake Bay Views! Waterfront Retreat

studio, Mathews
This waterfront studio apartment is located in Bohannon, offering Chesapeake Bay views, and is situated approximately 58 kilometres from Newport News/Williamsburg International Airport.
This 60 square metre apartment accommodates up to three guests and features a fully equipped kitchen, air conditioning, free WiFi, a balcony, and access to an outdoor swimming pool and barbecue area, with private parking available.
Charming Waterfront Home With Expansive Views - Chesapeake Bay
9.8 176 reviews

Charming Waterfront Home With Expansive Views

apartment, Heathsville
Mom and Pop's Honest Point Home is a charming cottage located in the historic Northern Neck region of Virginia, just 30 minutes from major amenities, offering a tranquil retreat on 25 acres with deep water access. The property has consistently received excellent ratings for location, cleanliness and overall guest experience.
This two-bedroom dwelling spans 111 square metres and comfortably accommodates up to six guests. The cottage offers a fully equipped kitchen, a private beach, spacious grounds, a terrace, a garden and ample parking, perfect for relaxing and enjoying the beautiful surroundings.

Best Chesapeake Bay accommodations with a kitchen

Walk To Everything Rock Hall From This 1st Floor Apartment. Sleeps 4! - Chesapeake Bay
10 28 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.
Va Beach Zen Studio B - Chesapeake Bay
No reviews

Va Beach Zen Studio B

studio, Virginia Beach
Vacation rental. This accommodation is based in Virginia Beach.
Facilities and services include free parking and a kitchen. This apartment in Virginia Beach also has air conditioning!
Country River Getaway! - Chesapeake Bay
9.3 29 reviews

Country River Getaway!

apartment, Heathsville
This recently renovated three-bedroom house in Heathsville offers convenient access to a neighbourhood swimming pool and boat landing, ideal for water activities.
Sleeping six guests, the property boasts a fully equipped kitchen, air conditioning, and parking, along with a family-friendly atmosphere and all amenities for a comfortable stay.
Walk To Everything House - Chesapeake Bay
9.8 164 reviews

Walk To Everything House

apartment, Easton
This charming house is located in St. Michaels, a short 1-kilometre walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has three bedrooms and can accommodate up to six guests. It includes a fully equipped kitchen, a garden, a spa, and parking, providing everything you need for a comfortable and enjoyable stay.
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