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

Pool Access! Cozy Couple's Getaway In Kilmarnock - Chesapeake Bay
No reviews

Pool Access! Cozy Couple's Getaway In Kilmarnock

apartment, Kilmarnock
This studio flat in Kilmarnock offers views of the Chesapeake Bay, situated 6.4 kilometres from Main Street and within driving distance of Williamsburg.
This 46 square metre studio apartment accommodates two guests and features a kitchen with a fridge and microwave, air conditioning, Wi-Fi, a swimming pool, and parking, with bicycles provided for exploring nearby attractions such as Ditchley Cider Works (3.2 kilometres) and Good Luck Cellars (8 kilometres).
1st Floor Condo In Annapolis - Chesapeake Bay
9.9 163 reviews

1st Floor Condo In Annapolis

apartment, Annapolis
This newly renovated studio flat is situated in Eastport, a quiet neighbourhood directly across Spa Creek from historic Annapolis, within a 1.6 km walk of the city centre and the US Naval Academy.
This pet-free apartment offers a fully equipped kitchen, high-speed Wi-Fi, free onsite parking, a secure building entrance, and a rooftop patio with a seasonal pool, with stunning views of the city.
Blake House Historic Estate With Private Inn - Chesapeake Bay
10 2 reviews

Blake House Historic Estate With Private Inn

house, Centreville
Blake House Historic Estate, a six-bedroom villa in Centreville, Maryland, is situated 34km from the Academy of the Arts and 39km from Sandy Point State Park.
This 465-square-metre property offers ample space for up to 20 guests, boasting a private pool, fitness centre, fully equipped kitchen, and laundry facilities.
Bethpage Two-bedroom Cottage 4 - Chesapeake Bay
9.0 3 reviews

Bethpage Two-bedroom Cottage 4

house, Urbanna
Bethpage Two-Bedroom Cottage 4 is located in Urbanna, Virginia, approximately 67km from Newport News/Williamsburg International Airport.
This 37-square-metre self-catering cottage sleeps seven, boasting two bedrooms, one bathroom, a private patio, a fully equipped kitchen, free Wi-Fi, on-site parking, and access to a seasonal outdoor swimming pool with water slides and a children's playground.

Best family friendly Chesapeake Bay lodging

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

Charming 3-bedroom House With Wifi, Ac& Heat In Peaceful Reedville - Chesapeake Bay
8.6 15 reviews

Charming 3-bedroom House With Wifi, Ac& Heat In Peaceful Reedville

apartment, Heathsville
This beachfront property in Reedville, a rural area near Heathsville, offers convenient access to Buzzard's Point Marina and Smith Point Marina, and is also close to Bush Mill Stream Natural Area Preserve and Hughlett Point Natural Area.
The 130-square-metre (1,400 sq ft) house sleeps six, featuring three bedrooms, two bathrooms (each with a shower and bath), a fully equipped kitchen (including fridge, microwave, and dishwasher), Wi-Fi, air conditioning, and a swimming pool; birdwatching and nature walks are readily available nearby.
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.
Heaven On Baltimore Downtown Fully Furnished Apartments - Chesapeake Bay
8.9 239 reviews

Heaven On Baltimore Downtown Fully Furnished Apartments

apartment, Baltimore
This apartment is ideally located in downtown Baltimore, just a short walk from the Sports Legends Museum at Camden Yards and the Baltimore Convention Center, making it perfect for exploring the city's attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment is well-equipped with a fully equipped kitchen, a comfortable living space, and a terrace for enjoying the fresh air. Guests can enjoy a range of amenities, including a fitness centre, swimming pool, and parking, as well as access to a restaurant and bar on-site.
New Hot Tub~1st Floor King Bed~fire Pit~bunk Room! - Chesapeake Bay
9.7 53 reviews

New Hot Tub~1st Floor King Bed~fire Pit~bunk Room!

apartment, Cape Charles
This family-friendly holiday home is located just 3.2 kilometres from Cape Charles Beach and the Cape Charles Museum & Welcome Center, offering easy access to the town's attractions and a peaceful setting. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The 279 square metre home features four bedrooms, comfortably accommodating up to eleven guests. It offers a range of amenities, including a swimming pool, a terrace, a garden, parking, and a fully equipped kitchen.

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

Oceanfront White Stone Cottage W/ Private Beach! - Chesapeake Bay
No reviews

Oceanfront White Stone Cottage W/ Private Beach!

house, White Stone
Vacation rental. You will stay in White Stone.
Services and facilities include air conditioning, an iron and a barbecue. Take advantage of the Free Parking with this accommodation.
Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment - Chesapeake Bay
9.4 14 reviews

Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment

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.
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.
Holiday Inn Express Annapolis East-kent Island By Ihg - Chesapeake Bay
9.2 1256 reviews

Holiday Inn Express Annapolis East-kent Island By Ihg

resort, Kent Narrows
The Holiday Inn Express Annapolis East-Kent Island is situated in Grasonville, just 20 miles from Annapolis Harbor and 30 miles from Baltimore-Washington International Airport, offering easy access to both bustling city life and the tranquil beauty of Kent Narrows. The hotel has received very good user ratings for cleanliness and an excellent rating for its location.
The hotel features 25 square metre rooms with one bedroom and one bathroom, each with a range of modern amenities. Guests can enjoy a variety of activities, including swimming in the seasonal outdoor pool, relaxing in the garden, and dining at the on-site restaurant and bar, as well as taking advantage of the fitness centre and tennis court.

Best Chesapeake Bay accommodations with a kitchen

Entire Private 2 Bedrooms House, Nice Neighborhood - Chesapeake Bay
9.4 84 reviews

Entire Private 2 Bedrooms House, Nice Neighborhood

apartment, Arnold
This two-bedroom home is situated in Arnold, a peaceful neighbourhood just 10 miles from Annapolis Harbor and 14 miles from Baltimore-Washington International Airport. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious apartment, spanning 111 square metres, comfortably accommodates up to 5 guests. Enjoy a range of amenities including a private hot tub, a peaceful garden, a fully equipped kitchen, air conditioning, free Wi-Fi and private parking.
Summer Breeze Waterfront New Home-private Beach - Chesapeake Bay
9.9 81 reviews

Summer Breeze Waterfront New Home-private Beach

apartment, Kilmarnock
Summer Breeze, a three-bedroom waterfront house in Reedville, offers private beach access and is situated 30.6km from Kilmarnock, close to the Reedville Fisherman's Museum.
This self-catering property sleeps six, boasts a private pier, canoe, screened porch, and access to a neighbourhood boat ramp, plus a dishwasher, fridge, freezer, microwave, air conditioning, Wi-Fi, and parking.
Salisbury Hideaway - Chesapeake Bay
9.9 16 reviews

Salisbury Hideaway

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.
Coastal Hideaway Near Calvertcliffs  Beach Access - Chesapeake Bay
9.8 12 reviews

Coastal Hideaway Near Calvertcliffs Beach Access

apartment, Chesapeake Ranch Estates
This private, lower-level flat in Chesapeake Ranch Estates offers a peaceful retreat with its own entrance, located a short drive from Solomons Island's waterfront dining, marinas, and museums, and within easy reach of Calvert Cliffs State Park and Flag Ponds Nature Park.
This self-contained unit accommodates up to four guests, featuring a kitchenette, living area, full private bathroom, and air conditioning, with driveway parking and access to community beaches and a neighbourhood lake for outdoor pursuits.
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