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Places to stay in Chesapeake Bay

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10861 Best places to stay in Chesapeake Bay

Bethpage Hewick One-bedroom Cottage 25 - Chesapeake Bay
9.0 24 reviews
Chesapeake Bay
2 1
SG$192/nighttotal: SG$768 (4 )

Bethpage Hewick One-bedroom Cottage 25

house - Urbanna
Bethpage Hewick One-Bedroom Cottage 25 is situated in the Bethpage area of Urbanna, approximately 68 kilometres from Newport News/Williamsburg International Airport.
This self-contained cottage offers 37 square metres of space, comprising a bedroom, separate living room, fully equipped kitchen, patio, and access to on-site amenities including a snack bar, children's playground, and bicycle rental.
King Bed Smoking - Chesapeake Bay
9.6 52 reviews
Chesapeake Bay
2 1
SG$149/nightfor 1 night

King Bed Smoking

apartment - Newport News
This Newport News flat is located less than 5 kilometres from Fort Eustis and just minutes from Newport News / Williamsburg International Airport, placing guests close to attractions such as Busch Gardens Europe and the Mariners' Museum.
This 14 square metre apartment offers accommodation for two guests with air conditioning and parking, with select units featuring kitchenettes and whirlpool bathtubs, and on-site coin-operated laundry facilities available for convenience.
Holiday Inn Hotel & Suites Gateway By Ihg - Chesapeake Bay
8.9 1367 reviews
Chesapeake Bay
2 1
SG$139/nightfor 1 night

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.
The Perfect View Virginia Tiny Home - Chesapeake Bay
10 38 reviews
Chesapeake Bay
2 1
SG$272/nighttotal: SG$544 (2 )

The Perfect View Virginia Tiny Home

apartment - Urbanna
This unique tiny home, situated on the Rappahannock River in Urbanna, offers waterfront access and peaceful seclusion, ideal for exploring the historic town.
The 300 sq ft (28 sq m) self-catering property features a king-size bed (convertible twin-over-twin daybed), an XXL cot, a full kitchen, jacuzzi, private beach access, kayaks, and on-site chef services, accommodating up to two guests.
The Nichols House Cottage - Chesapeake Bay
9.8 143 reviews
Chesapeake Bay
2 1
SG$215/nighttotal: SG$430 (2 )

The Nichols House Cottage

house - Oxford
This Oxford guest cottage, situated in the historic district, offers easy walking access to five restaurants, an ice cream shop, Oxford Market, and is within proximity of the Custom House.
The self-contained property sleeps two, features a kitchenette with microwave, mini-fridge, and coffee machine, a dedicated parking space, and free Wi-Fi access.
Private Waterfront Cottage With Pool And Poolhouse - Chesapeake Bay
9.8 44 reviews
Chesapeake Bay
4 2
SG$353/nighttotal: SG$1412 (4 )

Private Waterfront Cottage With Pool And Poolhouse

apartment - Cambridge
This secluded waterfront cottage is located between Easton and Cambridge, offering convenient access to nearby towns such as Trappe, Oxford, and St. Michaels, approximately 10 kilometres away.
This two-bedroom apartment, accommodating up to four guests, features a gourmet kitchen, a wood-burning fireplace, a screened-in porch with water views, and access to an exclusive 60-foot lap pool and pool house with an outdoor kitchen.
4 Bdrm, 3 Bath, 2,700 Sqft Whole House On 1 Acre - Chesapeake Bay
9.9 98 reviews
Chesapeake Bay
7 4
SG$555/nighttotal: SG$1665 (3 )

4 Bdrm, 3 Bath, 2,700 Sqft Whole House On 1 Acre

house - Easton
This spacious Easton property, situated just outside the town centre, offers a tranquil retreat whilst remaining within easy reach of Easton's attractions.
The four-bedroom, three-bathroom dwelling boasts a king-size and queen-size beds, a private in-law suite, a fenced one-acre garden with fresh eggs from backyard chickens, plus a high-quality water system and Merry Maids-cleaned kitchen and bathrooms; sleeping up to eight guests.
Waterfront W/floating Dock, Kayaks~family Home - Chesapeake Bay
10 102 reviews
Chesapeake Bay
7 3
SG$711/nighttotal: SG$2133 (3 )

Waterfront W/floating Dock, Kayaks~family Home

apartment - Deltaville
Cove Place is a waterfront cottage located in Cobbs Creek, Virginia, just a short drive from the charming town of Mathews and within easy reach of Deltaville. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage is ideal for families or groups of up to seven people, offering three bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a screened porch, a private dock, a fire pit, and a spacious garden, perfect for relaxing and enjoying the outdoors.
Bull Neck Cottage - Chesapeake Bay
9.9 160 reviews
Chesapeake Bay
2 3
SG$162/nighttotal: SG$1782 (11 )

Bull Neck Cottage

apartment - Kilmarnock
This charming cottage is located just a short distance from the centre of Reedville, within easy reach of the Chesapeake Bay and the Watermen's Museum. The property has received excellent ratings for its location, cleanliness and overall experience.
The cottage can accommodate up to 6 guests and features a well-equipped kitchen, a comfortable living area, and a private garden. You'll also benefit from free Wi-Fi, air conditioning, a washing machine and dryer, and a dedicated parking space.
Luxury Home 5 Br 3 Ba Near Beaches And Venues - Chesapeake Bay
9.7 422 reviews
Chesapeake Bay
7 5
SG$575/nighttotal: SG$1725 (3 )

Luxury Home 5 Br 3 Ba Near Beaches And Venues

house - Hampton
This five-bedroom house in Hampton is just 23 miles from Busch Gardens & Water Country and 7.7 miles from the Virginia Living Museum, offering a peaceful retreat on a quiet street. The property has received excellent ratings for its location, cleanliness, and overall experience.
This spacious home, with its 223 square metres of floor space, comfortably accommodates large groups or families. Guests can enjoy a fully equipped kitchen, free Wi-Fi, a terrace, garden, and private parking, as well as explore nearby cycling and hiking trails.
Cambridge Apt In Walkable Neighborhood - Chesapeake Bay
9.3 14 reviews
Chesapeake Bay
2 1
SG$178/nighttotal: SG$1958 (11 )

Cambridge Apt In Walkable Neighborhood

apartment - Cambridge
This Cambridge, Maryland waterfront flat is conveniently located near the Choptank River and within easy reach of local restaurants and historical sites.
The one-bedroom apartment sleeps four, features a fully equipped kitchen, free Wi-Fi, keyless entry, and parking for up to four vehicles, offering board games and a dining table.
Right On Main St!  Shops, Arts, Dining And More! - Chesapeake Bay
9.9 178 reviews
Chesapeake Bay
2 1
SG$221/nighttotal: SG$884 (4 )

Right On Main St! Shops, Arts, Dining And More!

apartment - Gloucester Courthouse
This apartment is located in Gloucester, just 1.8 kilometres from Riverside Walter Reed Hospital and 13.7 kilometres from Machicomoco State Park. The surrounding area offers a peaceful and scenic setting, with easy access to both healthcare facilities and outdoor recreation. The apartment has received excellent ratings for user experience, location, and cleanliness.
The flat is a one-bedroom apartment with one bathroom, covering 79 square metres and accommodating up to four guests. It includes a fully equipped kitchen, a washing machine, a sofa bed, free Wi-Fi, a balcony, a garden, and parking.

Best Chesapeake Bay lodgings with a pool

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

Spacious One Bedroom Condo - Chesapeake Bay
8.0 5 reviews
Chesapeake Bay
2 1
SG$220/nighttotal: SG$880 (4 )

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.
Clearview - Chesapeake Bay
Chesapeake Bay
4 1
SG$1349/nighttotal: SG$5396 (4 )

Clearview

house - Tilghman Island
Clearview, a holiday home on Tilghman Island, Maryland, is situated 39 kilometres from the Academy Art Museum and 121 kilometres from Baltimore/Washington International Thurgood Marshall Airport.
This three-bedroom, three-bathroom property boasts 191 square metres of floor space, sleeps up to 11 guests, and includes a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and free private parking.
One Bedroom Condo With Marina View - Chesapeake Bay
10 1 review
Chesapeake Bay
2 1
SG$293/nighttotal: SG$586 (2 )

One Bedroom Condo With Marina View

apartment - Virginia Beach
This Ocean Key Resort apartment is situated on the South End of Virginia Beach's boardwalk, offering sunrise ocean views and proximity to Rudee Inlet, approximately 8km from Virginia Beach Town Center.
This two-bedroom, one-bathroom condo sleeps four guests and boasts a fully equipped kitchenette, a shared swimming pool, parking, and air conditioning; nearby attractions include the Veterans United Home Loans Amphitheatre and the Virginia Beach Sportsplex.
Wyjek Stays - Riverside Haven - Chesapeake Bay
Chesapeake Bay
7 3
SG$674/nighttotal: SG$2022 (3 )

Wyjek Stays - Riverside Haven

apartment - Cambridge
This spacious 3-bedroom residence in Cambridge is situated 24 kilometres from the Academy Of The Arts and 34 kilometres from Federalsburg Marina, offering riverside views from a private balcony and convenient access to Salisbury-Ocean City Wicomico Regional Airport, 59 kilometres away.
This family-friendly apartment boasts a generous 204 square metres of floor area, accommodating up to 15 guests with four bathrooms, a fully equipped kitchen featuring a fridge and dishwasher, air conditioning, a seasonal outdoor swimming pool, a fitness centre, private parking with an electric vehicle charging station, and an on-site coffee shop, with opportunities for cycling nearby.

Best family friendly Chesapeake Bay lodging

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

Hilton Vacation Club Greensprings Williamsburg - Chesapeake Bay
8.9 3894 reviews
Chesapeake Bay
2 1
SG$155/nightfor 1 night

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.
Delta Hotels By Marriott™ Virginia Beach Waterfront Suites - Chesapeake Bay
8.5 5153 reviews
Chesapeake Bay
2 1
SG$170/nighttotal: SG$680 (4 )

Delta Hotels By Marriott™ Virginia Beach Waterfront Suites

resort - Virginia Beach
The Delta Hotels by Marriott Virginia Beach Waterfront is situated on the Chesapeake Bay, a short distance from Seashore State Park and 9.6 miles from the Virginia Marine Science Museum. This resort has received very good ratings for location, cleanliness, and overall user experience.
The hotel offers spacious guest rooms with separate sleeping and living areas, perfect for families or groups. Guests can enjoy a variety of amenities, including a private beach, an outdoor pool, a fitness centre, and a restaurant and bar.
Deltaville 2br Retreat, Walk To Museum, Boat Parking - Chesapeake Bay
10 71 reviews
Chesapeake Bay
2 2
SG$273/nighttotal: SG$3003 (11 )

Deltaville 2br Retreat, Walk To Museum, Boat Parking

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.
Kimary Cove - Waterfront Relaxation And No Cleaning Fee - Chesapeake Bay
9.6 28 reviews
Chesapeake Bay
2 2
SG$205/nighttotal: SG$410 (2 )

Kimary Cove - Waterfront Relaxation And No Cleaning Fee

apartment - Gwynn
This waterfront apartment is situated just 7.7km from Mathews and 22.5km from Gloucester, offering a peaceful retreat with easy access to nearby attractions. The property has received excellent guest reviews, highlighting its comfortable and well-equipped nature.
The self-catering apartment provides accommodation for up to four guests across two bedrooms and one bathroom. Guests can enjoy a private dock, a gazebo, a spacious deck, a cornhole game, a grill, and a pool table, alongside a fully equipped kitchen and three Roku televisions.

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

El  Camino - Chesapeake Bay
10 59 reviews
Chesapeake Bay
2 1
SG$170/nighttotal: SG$680 (4 )

El Camino

cabin - Piney Point
This Piney Point waterfront lodge is situated approximately 1.6km from Cardinal Gibbons Park and First District Community Park, and 4.7km from Saint Inigoes State Forest, offering easy access to local recreation and nature.
Sleeping up to three guests, this one-bedroom, one-bathroom self-catering cottage boasts a fully equipped kitchen, smart TV, terrace, barbecue, and parking, perfect for exploring the surrounding area.
The Dollhouse In Central Historic St Michaels - Chesapeake Bay
9.6 125 reviews
Chesapeake Bay
2 2
SG$398/nighttotal: SG$4378 (11 )

The Dollhouse In Central Historic St Michaels

apartment - Easton
This charming house is located in St. Michaels, a picturesque town on Maryland's Eastern Shore, just 1 kilometre from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. The property enjoys excellent ratings for location, cleanliness, and user experience.
The house has two bedrooms, accommodating up to four guests, and features a fully equipped kitchen, two bathrooms, a washing machine, and a Smart TV. Guests can enjoy a spa tub, garden, barbecue grills, and a terrace, making it ideal for relaxation and outdoor dining.
Pet-friendly Home W/ Gazebo: Minutes To Beach! - Chesapeake Bay
9.6 76 reviews
Chesapeake Bay
4 5
SG$599/nighttotal: SG$2396 (4 )

Pet-friendly Home W/ Gazebo: Minutes To Beach!

house - Cape Charles
This charming house is situated just 3.2 kilometres from the stunning beaches of Cape Charles, offering easy access to the area's natural beauty. With excellent user, location, and cleanliness ratings, this property promises a comfortable and enjoyable stay.
This spacious home offers 204 square metres of living space, comfortably accommodating up to eight guests across four bedrooms and two bathrooms. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, a spa, and free Wi-Fi.
Serenity On The Bay-complimentary Sunrise & Sunset Views - Chesapeake Bay
9.6 72 reviews
Chesapeake Bay
7 4
SG$693/nighttotal: SG$2079 (3 )

Serenity On The Bay-complimentary Sunrise & Sunset Views

apartment - Norfolk
This spacious apartment is located in Norfolk, Virginia, just a short drive from the beaches, the Naval Station Norfolk, and Norfolk International Airport. It has received excellent user ratings for its comfort and convenience.
The apartment offers 260 square metres of living space across multiple levels, with a capacity of 10 guests. It comes equipped with a fully fitted kitchen, air conditioning, a jacuzzi, parking, and internet access, ensuring a comfortable and enjoyable stay.

Best Chesapeake Bay accommodations with a kitchen

Holiday Inn Express Williamsburg North By Ihg - Chesapeake Bay
9.0 2285 reviews
Chesapeake Bay
2 1
SG$168/nighttotal: SG$672 (4 )

Holiday Inn Express Williamsburg North By Ihg

resort - Williamsburg
The Holiday Inn Express Williamsburg North is conveniently located just 15 minutes from Busch Gardens and within 10 miles of the College of William and Mary, making it a great base for exploring Williamsburg's historical attractions and entertainment. The hotel consistently receives very good ratings for location, cleanliness, and overall experience.
The hotel offers a range of amenities, including a fitness centre, indoor pool, and complimentary continental breakfast. Guests can also enjoy comfortable rooms with cable TV, free toiletries, and select rooms with sofa beds, as well as a suite with a spa tub.
1 Mi To Boardwalk: Convenient North Beach Apt! - Chesapeake Bay
8.0 1 review
Chesapeake Bay
2 1
SG$214/nighttotal: SG$2354 (11 )

1 Mi To Boardwalk: Convenient North Beach Apt!

apartment - North Beach
This North Beach flat, located approximately 1.6 kilometres from the North Beach Boardwalk, offers easy access to the Bayside History Museum and Chesapeake Beach Railway Museum.
The 46-square-metre self-catering apartment sleeps three, and includes a kitchen with fridge and microwave, laundry facilities, Wi-Fi, and a terrace; nearby attractions include the Chesapeake Beach Water Park and R&J's PlayPark.
Hilton Virginia Beach Oceanfront - Chesapeake Bay
8.3 3650 reviews
Chesapeake Bay
2 1
SG$248/nighttotal: SG$496 (2 )

Hilton Virginia Beach Oceanfront

resort - Virginia Beach
The Hilton Virginia Beach Oceanfront is situated directly on the Virginia Beach Oceanfront, just a short walk from the boardwalk and the Shoppes at 31. This hotel has consistently received very good ratings for cleanliness, user experience, and location.
The hotel offers a range of amenities, including a rooftop infinity pool, a sky bar, and a fitness centre. Guests can enjoy on-site dining at Catch 31 restaurant and take advantage of the complimentary shuttle service to nearby attractions.
Waterfront Historic Gem W/ Kayaks & Fire Pit - Chesapeake Bay
9.8 32 reviews
Chesapeake Bay
7 4
SG$601/nighttotal: SG$1803 (3 )

Waterfront Historic Gem W/ Kayaks & Fire Pit

apartment - Whitehaven
This four-bedroom, two-bathroom flat is located in historic Quantico, Maryland, directly on the Wicomico River, offering a riverside escape within 10 kilometers of Whitehaven.
This pet-friendly property accommodates up to seven guests and features a fenced garden, kayaks, paddleboards, bikes, a furnished deck, a screened porch, a fire pit, and a dedicated workspace.
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