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

Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina - Chesapeake Bay
8.7 1445 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.
Oceanfront Condo With Indoor Pool - Chesapeake Bay
9.4 135 reviews

Oceanfront Condo With Indoor Pool

apartment, Virginia Beach
This oceanfront condo is situated directly on the Virginia Beach boardwalk, offering immediate access to the beach and attractions.
The two-bedroom, two-bathroom apartment sleeps six guests and boasts a fully equipped kitchen, high-speed Wi-Fi, an indoor pool, fitness centre, and assigned parking (maximum height 1.95 metres).
Beach Luxury Oceanfront - Chesapeake Bay
9.7 132 reviews

Beach Luxury Oceanfront

apartment, Virginia Beach
This apartment is situated in Virginia Beach, just a short distance from the beach and Neptune's Park, making it ideal for exploring the area's attractions. The apartment has received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The apartment is spacious, offering 98 square metres of living space, and comes equipped with a fully fitted kitchen, a private bathroom, and a balcony with stunning ocean views. Guests can enjoy the on-site swimming pool, relax in the garden, and take advantage of the free Wi-Fi and parking.
Spacious One Bedroom Condo - Chesapeake Bay
8.0 5 reviews

Spacious One Bedroom Condo

apartment, Virginia Beach
This one-bedroom apartment in Northeast Virginia Beach is a short walk from the Virginia Beach Boardwalk and Pacific Avenue, offering easy access to the beach and attractions such as the Ocean Breeze Waterpark and First Landing State Park.
The self-catering flat sleeps four, features a kitchen with fridge, microwave, and dishwasher, a pool table, a dedicated workspace, and access to an on-site swimming pool and parking; waterfront activities, including boat tours, are readily available nearby.

Best family friendly Chesapeake Bay lodging

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

Peaceful Historic House Near Water, With Hot Tub! - Chesapeake Bay
9.9 181 reviews

Peaceful Historic House Near Water, With Hot Tub!

apartment, Cambridge
This recently renovated three-bedroom Victorian house is located in Cambridge's Historic West End, a short walk from Long Wharf Park and the Choptank River Lighthouse.
The property offers a spacious layout sleeping up to six guests, boasting a newly renovated kitchen, a bathroom with a clawfoot tub, a jacuzzi, a garden, parking and air conditioning; nearby attractions include downtown Cambridge's restaurants and shops.
Chic & Cozy City Living Enjoy Baltimore In Style - Chesapeake Bay
9.8 112 reviews

Chic & Cozy City Living Enjoy Baltimore In Style

house, Baltimore
This house is located in Baltimore, just outside the Fell's Point neighbourhood, approximately 4.8 kilometres from the Harbor East Marina and Pier Six Concert Pavilion. It has consistently received excellent ratings for location, cleanliness, and overall experience from previous guests.
This three-bedroom property offers a comfortable and well-equipped space for families or groups of up to six. It features a fully equipped kitchen, a terrace, a garden, and private parking, making it ideal for a relaxing stay in Baltimore.
Apartment ∙ 2 Bedrooms ∙ 4 Guests - Chesapeake Bay
No reviews

Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment, Norfolk
This Norfolk apartment, situated in the East Ocean View district, offers direct private beach access.
The two-bedroom, one-bathroom flat sleeps four, features a fully equipped kitchen, 50" Roku TV, high-speed Wi-Fi, and complimentary parking; pet-friendly (additional charges apply).
Cozy Cottage Elkton North East 3bed 2 Bath Patio - Chesapeake Bay
9.7 449 reviews

Cozy Cottage Elkton North East 3bed 2 Bath Patio

apartment, North East
This North East property, a three-bedroom house, is situated 2.7km from the Upper Bay Museum and within 9.7km of both the Elkton Golf and Batting Centre and Roachs Shore.
Sleeping up to nine guests, this self-catering holiday home boasts a fully equipped kitchen, spa, garden, terrace, free Wi-Fi, on-site laundry, and parking, making it ideal for families or groups exploring the local area.

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

Charming, Oversees Pool, Walk To Beach And Restaurants In 3 Minutes - Chesapeake Bay
8.2 21 reviews

Charming, Oversees Pool, Walk To Beach And Restaurants In 3 Minutes

apartment, Virginia Beach
This one-bedroom house is a short walk from Pacific Avenue and the Virginia Beach Boardwalk, offering easy access to the beach, restaurants, and shops. It's rated very good by previous guests and is located in a lively area close to both the beach and the city centre.
The 60 square metre house has a kitchen with a fridge and microwave, a terrace, a garden, and parking. It also has a swimming pool and air conditioning, making it a perfect choice for a relaxing and enjoyable stay in Virginia Beach.
Holiday Inn Club Vacations Williamsburg Resort - Chesapeake Bay
9.0 1053 reviews

Holiday Inn Club Vacations Williamsburg Resort

resort, Williamsburg
Holiday Inn Club Vacations Williamsburg Resort, An Ihg Hotel, is situated just 10km from Camp Peary and within 20km of Water Country USA and Busch Gardens amusement park, making it a great base for exploring Williamsburg's attractions. The resort has received very good ratings for user experience, location and cleanliness.
The resort offers spacious one-bedroom villas with well-equipped kitchens, fireplaces, balconies and comfortable furnishings, ideal for families or groups. Guests can enjoy amenities such as a gym, concierge service, barbecue facilities and an outdoor pool.
3 Mi To Washington College! Updated Home W/ Patio - Chesapeake Bay
No reviews

3 Mi To Washington College! Updated Home W/ Patio

house, Kingstown
This property is located 77 kilometres from Newcastle Airport.
This detached house offers accommodation for seven guests, featuring three bedrooms, air conditioning, a garden, and a kitchen equipped with a fridge, microwave, and dishwasher, plus complimentary WiFi and on-site parking.
Private Riverfront Retreat - Chesapeake Bay
10 2 reviews

Private Riverfront Retreat

house, Montross
This three-bedroom house, perfect for families or groups of up to 13, enjoys a private riverfront location in Hague, Virginia, approximately 40 kilometres from both the George Washington Birthplace National Monument and its Memorial House.
The 102-square-metre property boasts a fully equipped kitchen, terrace, garden, free Wi-Fi, parking, and a washing machine, offering a tranquil escape with easy access to local attractions.

Best Chesapeake Bay accommodations with a kitchen

Historic Old Towne Southern Charm - Chesapeake Bay
9.4 40 reviews

Historic Old Towne Southern Charm

apartment, Portsmouth
This charming 2-bedroom flat is located in Old Towne Portsmouth, just a short walk from the city's restaurants, shops, and attractions. The area is known for its historic architecture and lively atmosphere, making it a great base for exploring the city. The apartment has a very good user rating, indicating a positive experience for previous guests.
This spacious home can comfortably accommodate up to 7 guests. It features a well-equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a terrace, and a garden. Guests can also enjoy free Wi-Fi and the convenience of a washing machine and dryer.
Sunkissed Cottage-private, Natural Waterfront Home - Chesapeake Bay
9.9 181 reviews

Sunkissed Cottage-private, Natural Waterfront Home

apartment, Heathsville
This two-bedroom cottage is located near Heathsville, Virginia, just 3.2 kilometres from Smith Point Marina, offering easy access to the Little Wicomico River.
The property features a private setting with a garden, a fire pit, cornhole boards, a comfortable deck, and modern amenities including high-speed internet, smart TVs, and a well-equipped kitchen, perfect for families or groups of up to six.
Egrets Point On The Creek - Chesapeake Bay
10 110 reviews

Egrets Point On The Creek

apartment, Onancock
Egrets Point on the Creek, a renovated mid-1950s ranch duplex in Onancock, offers a peaceful creekside setting close to the historic district and within easy reach of Chincoteague and Cape Charles.
This two-bedroom, one-bathroom property sleeps four, boasting a well-equipped kitchen, screened porch, sunporch, access to canoes, bicycles, and a golf cart (seasonal), a fire pit, and hammocks in the large garden; internet and air conditioning are also included.
Waterfront Island Retreat - Chesapeake Bay
9.5 57 reviews

Waterfront Island Retreat

apartment, Piney Point
This St. George Island retreat, situated in St. Mary's County near the confluence of the Potomac and St. Mary's Rivers, offers a unique island escape a short distance from Piney Point.
The single-storey, three-bedroom property sleeps eight, boasting a fully accessible layout, waterfront access with a 30-metre pier, and amenities including a kitchen with dishwasher, air conditioning, and a garden; kayaking and boating on the rivers are readily available.
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