Places to stay in Chesapeake Bay

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Chesapeake Bay place to stay
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7504 Best places to stay in Chesapeake Bay

Best Chesapeake Bay lodgings with a pool

Among the 7504 accommodations in Chesapeake Bay, here are the 4 best ones with a pool

Secluded, Stunning Water Views 1 Mi From Beach️️ - Chesapeake Bay
9.6 96 reviews
Chesapeake Bay
29/08 – 05/09
SG$599/nighttotal: SG$4193 (7 )

Secluded, Stunning Water Views 1 Mi From Beach️️

2 2
cottage , Virginia Beach
This charming cottage sits on the Great Neck River, just a short five-minute drive from Hilltop restaurants and shopping centres like Trader Joe's, Target, Fresh Market, and Whole Foods. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The cottage features two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a private home office, a swimming pool, a garden, and kayaks for exploring the Great Neck River.
Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment - Chesapeake Bay
9.4 14 reviews
Chesapeake Bay
29/08 – 05/09
SG$229/nighttotal: SG$1603 (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.
Magical Wooded Cottage Pool +Priv Hottub Walk2town - Chesapeake Bay
9.9 206 reviews
Chesapeake Bay
14/10 – 18/10
SG$539/nighttotal: SG$2156 (4 )

Magical Wooded Cottage Pool +Priv Hottub Walk2town

3 4
apartment , Irvington
This charming cottage is located in Irvington, Virginia, just a short drive from the historic town of Kilmarnock and the scenic Tide’s Inn. The accommodation has received excellent ratings for location, cleanliness, and overall experience.
The cottage spans 158 square metres and can accommodate up to 6 guests in its three bedrooms. It offers a range of amenities, including a swimming pool, jacuzzi, fitness centre, and a private hot tub, along with access to local attractions and activities like oyster and wine tasting.
Kings Creek Plantation By Tripforth - Chesapeake Bay
9.1 726 reviews
Chesapeake Bay
30/07 – 05/08
SG$509/nighttotal: SG$3054 (6 )

Kings Creek Plantation By Tripforth

2 6
house , Williamsburg
King's Creek Resort By Endless Resorts is conveniently located just outside Williamsburg's historic district, offering easy access to both theme parks and the historic landmarks of Colonial Williamsburg, which is just 7.2 miles away. The resort has received excellent ratings for its location, cleanliness and overall user experience.
The resort offers a range of accommodation options, including rooms and suites. Guests can enjoy amenities such as a swimming pool, fitness centre, restaurant and spa, as well as activities like mini-golf and a playground for families.

Best family friendly Chesapeake Bay lodging

Among the 7504 accommodations in Chesapeake Bay, here are the 4 best for families

Potomac Rvr Woodland Cottage, Polite Pets Welcomed, Central Air, Stunning Sunset - Chesapeake Bay
9.8 60 reviews
Chesapeake Bay
14/10 – 18/10
SG$420/nighttotal: SG$1680 (4 )

Potomac Rvr Woodland Cottage, Polite Pets Welcomed, Central Air, Stunning Sunset

3 4
cottage , Tall Timbers
This Tall Timbers holiday home enjoys a riverside location, less than 1.5 kilometres from the Potomac River and within a 10-kilometre radius of Piney Point Beach, Piney Point Lighthouse, and St. Mary's River State Park.
The 102-square-metre property offers three bedrooms, one bathroom, and sleeps eight guests, boasting a fully equipped kitchen, a terrace, a garden, a spa, free Wi-Fi, and an arcade/game room.
Relaxing Water Views - Mill Creek Cottage - Chesapeake Bay
9.9 452 reviews
Chesapeake Bay
20/07 – 27/07
SG$308/nighttotal: SG$2156 (7 )

Relaxing Water Views - Mill Creek Cottage

1 4
apartment , Arnold
This charming cottage is situated just a few kilometres from downtown Annapolis and the US Naval Academy, offering a tranquil escape in a wooded setting overlooking Mill Creek. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The cottage features two bedrooms and one bathroom, comfortably accommodating up to four guests. It comes equipped with modern amenities such as a fully equipped kitchen, air conditioning, a garden, and a covered porch with stunning water views, perfect for enjoying the peaceful surroundings.
Deltaville 2br Retreat, Walk To Museum, Boat Parking - Chesapeake Bay
10 70 reviews
Chesapeake Bay
21/08 – 28/08
SG$311/nighttotal: SG$2177 (7 )

Deltaville 2br Retreat, Walk To Museum, Boat Parking

2 4
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.
Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc. - Chesapeake Bay
9.6 49 reviews
Chesapeake Bay
29/08 – 05/09
SG$238/nighttotal: SG$1666 (7 )

Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc.

1 2
cottage , Shady Side
This waterfront cottage in Shady Side, Maryland, is situated on a peninsula on the West River, approximately 32 kilometres from Annapolis and close to Galesville.
The one-bedroom, one-bathroom property sleeps three, offering a private dock, kitchen with fridge and microwave, air conditioning, a terrace, garden, parking, internet access, and proximity to Thanksgiving Farm Wines and South River Golf Links.

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.

Destinations nearby

Best Chesapeake Bay accommodations with a balcony

4br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12 - Chesapeake Bay
10 1 review
Chesapeake Bay
30/07 – 05/08
SG$730/nighttotal: SG$4380 (6 )

4br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12

4 6
house , Arnold
This four-bedroom property in Annapolis is situated 12.7 kilometres from Annapolis Harbour and 37 kilometres from Baltimore's Inner Harbour.
This spacious residence accommodates up to 12 guests, offering a fully equipped kitchen with a dishwasher, an on-site bar, a garden, and private parking, with a floor area of 17 square metres.
Peach Perfect - Chesapeake Properties - Chesapeake Bay
9.7 45 reviews
Chesapeake Bay
14/10 – 18/10
SG$656/nighttotal: SG$2624 (4 )

Peach Perfect - Chesapeake Properties

2 4
apartment , Cape Charles
This holiday home is located in Cape Charles, just 2.4 kilometres from Cape Charles Beach and the Cape Charles Museum & Welcome Center, and 3.2 kilometres from Bay Creek Golf Club. It offers a peaceful retreat close to the town's main attractions and amenities, with excellent user, location, and cleanliness ratings.
The property features two bedrooms and can accommodate up to six guests, making it ideal for families or small groups. It offers a range of amenities, including a fully equipped kitchen, a terrace, a garden, and a tennis court, ensuring a comfortable and enjoyable stay.
Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia - Chesapeake Bay
8.2 3026 reviews
Chesapeake Bay
01/10 – 05/10
SG$213/nighttotal: SG$852 (4 )

Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia

1 3
resort , Virginia Beach
Ocean Sands Resort by VSA Resorts is situated on the oceanfront in Virginia Beach, just half a mile from the amusement park and one mile from the convention centre. The resort consistently receives excellent ratings for its location and cleanliness, as well as very good reviews for its overall experience.
The resort offers a range of self-catering suites with Caribbean-style decor, each with a private balcony or terrace. Guests have access to a variety of on-site amenities, including a swimming pool, hot tub, sauna, fitness centre, tennis court, restaurant, bar, and spa, ensuring a relaxing and enjoyable stay.
2-bedroom Apartmt In Awesome Baltimore With Easy Access To Restaurants And Sites - Chesapeake Bay
9.8 10 reviews
Chesapeake Bay
01/10 – 05/10
SG$296/nighttotal: SG$1184 (4 )

2-bedroom Apartmt In Awesome Baltimore With Easy Access To Restaurants And Sites

2 3
apartment , Baltimore
This Downtown Baltimore flat is located minutes from the Inner Harbour, M&T Bank Stadium, and Baltimore/Washington International Thurgood Marshall Airport (BWI), offering easy access to major attractions.
This two-bedroom, two-bathroom apartment sleeps six guests, features a kitchenette with microwave and dishwasher, in-unit laundry, a smart TV, Wi-Fi, and is within walking distance of numerous restaurants.

Best Chesapeake Bay accommodations with a kitchen

Retreat At Fenwick - Chesapeake Bay
9.7 28 reviews
Chesapeake Bay
20/07 – 27/07
SG$207/nighttotal: SG$1449 (7 )

Retreat At Fenwick

1 4
apartment , Leonardtown
The Retreat at Fenwick apartment is situated in Leonardtown, Maryland, just 18 km from the Calvert Marine Museum and 19 km from Cape Saint Marys Marina, offering easy access to local attractions. The apartment has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
This one-bedroom apartment spans 56 square metres and comfortably accommodates up to 7 guests. The apartment offers a fully equipped kitchen with a dishwasher, a fireplace for a cosy atmosphere, free Wi-Fi, on-site parking, and towels and bed linen for a hassle-free stay.
3 Mi To Washington College! Updated Home W/ Patio - Chesapeake Bay
Chesapeake Bay
30/07 – 05/08
SG$333/nighttotal: SG$1998 (6 )

3 Mi To Washington College! Updated Home W/ Patio

3 6
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.
Cottage On A Private Island In The York River - Chesapeake Bay
10 370 reviews
Chesapeake Bay
14/10 – 18/10
SG$367/nighttotal: SG$1468 (4 )

Cottage On A Private Island In The York River

3 4
cottage , Gloucester Point
This charming waterfront cottage is located in Gloucester Point, just 9 kilometres from Machicomoco State Park, Yorktown Beach, and Yorktown Farmers Market, offering easy access to a variety of attractions and activities. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
This 3-bedroom property spans 139 square metres and can accommodate up to 8 guests, making it ideal for families or groups. The cottage features a fully equipped kitchen, a private garden, a swimming pool, a spa, and a terrace, ensuring a relaxing and enjoyable stay.
3 Bedroom/2.5 Bath Smith Island Bungalow With Dock - Chesapeake Bay
9.9 142 reviews
Chesapeake Bay
20/07 – 27/07
SG$189/nighttotal: SG$1323 (7 )

3 Bedroom/2.5 Bath Smith Island Bungalow With Dock

1 4
apartment , Smith Island
This three-bedroom Smith Island cottage is located in Tylerton, a short walk from the main dock and Drum Point Market.
Offering direct harbour access with a private dock, two kayaks, a fully equipped kitchen, and sleeping up to six guests, this restored 1860s home provides a unique island experience with Verizon Wi-Fi and air conditioning.
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