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

Tilghman | Pool | Private Dock | Pet Friendly - Chesapeake Bay
9.4 15 reviews
Chesapeake Bay
07/10 – 11/10
SG$1241/nighttotal: SG$4964 (4 )

Tilghman | Pool | Private Dock | Pet Friendly

3 2
apartment , Tilghman Island
This waterfront property on Tilghman Island is just 0.3 miles from the Tilghman Watermen’s Museum and within easy reach of other attractions like the Chesapeake Bay Maritime Museum and St. Michaels Museum. The house has consistently received excellent ratings for location, cleanliness, and overall experience.
The property offers 191 square metres of space, accommodating up to 6 guests in its 3 bedrooms and 3 bathrooms. Guests can enjoy a private pool, a spa tub, a garden, a terrace, a barbecue, and modern amenities like free Wi-Fi and a fully equipped kitchen.
Boutique By The Bay - Chesapeake Bay
10 299 reviews
Chesapeake Bay
20/08 – 29/08
SG$243/nighttotal: SG$2187 (9 )

Boutique By The Bay

1 2
apartment , Stevensville
This Stevensville apartment is located just 14 kilometres south of the Bay Bridge, offering a convenient base for exploring the area, with easy access to wedding venues like the Chesapeake Bay Beach Club and Swan Cove. The property consistently receives excellent ratings for its cleanliness, location and overall experience.
The self-catering apartment can comfortably accommodate up to four guests and features a private entrance, modern farmhouse décor, a fully equipped kitchen and a spacious walk-in shower. Guests can enjoy access to a shared pool, a 4-person paddle boat, fishing rods, a private garden and parking.
Virginia Beach Oceanfront/boardwalk, Beach, Pool & Balcony - Chesapeake Bay
9.8 64 reviews
Chesapeake Bay
01/10 – 05/10
SG$336/nighttotal: SG$1344 (4 )

Virginia Beach Oceanfront/boardwalk, Beach, Pool & Balcony

1 3
apartment , Virginia Beach
This apartment is located in Northeast Virginia Beach, just a short walk from the beach and the Virginia Beach Boardwalk, with Sandbridge Beach a short 4.3 kilometres away. The apartment has received excellent reviews from previous guests, highlighting its convenient location and comfortable amenities.
This one-bedroom flat provides 28 square metres of space, comfortably accommodating up to three guests. It offers a fully equipped kitchen, a balcony, and a washing machine, as well as free Wi-Fi and access to a swimming pool and garden.
Waterfront Getaway W/ Pool + Beaches+ Hot Tub +Bbq - Chesapeake Bay
9.9 59 reviews
Chesapeake Bay
20/08 – 29/08
SG$293/nighttotal: SG$2637 (9 )

Waterfront Getaway W/ Pool + Beaches+ Hot Tub +Bbq

1 2
house , Grasonville
This Grasonville waterfront apartment offers convenient access to private beaches, a shared heated pool, and a pier, all within easy reach of local attractions.
The one-bedroom, one-bathroom property sleeps three guests and boasts a microwave, air conditioning, kayak and paddleboard access, plus the option of arranging boat trips, fishing excursions, and crabbing expeditions.

Best family friendly Chesapeake Bay lodging

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

Private Riverfront Retreat - Chesapeake Bay
9.6 51 reviews
Chesapeake Bay
20/07 – 27/07
SG$222/nighttotal: SG$1554 (7 )

Private Riverfront Retreat

1 4
apartment , Montross
This three-bedroom, two-bathroom apartment near Montross, Virginia, offers waterfront access with a private dock, approximately 48 kilometres from Westmoreland State Park and 64 kilometres from Colonial Beach.
Sleeping seven guests, the property boasts a fire pit, kayaks, and proximity to The Hague Winery, alongside a stylish interior and amenities including a dishwasher, air conditioning, and parking.
Baydream Believer - Chesapeake Bay
10 1 review
Chesapeake Bay
20/06 – 27/06
SG$2799/nighttotal: SG$19593 (7 )

Baydream Believer

5 2
house , Tilghman Island
Baydream Believer, a five-bedroom house in Saint Michaels, Maryland, is situated approximately 24 kilometres from the Academy of the Arts and 106 kilometres from Salisbury-Ocean City Wicomico Regional Airport, offering convenient access to Tilghman Island.
This 465-square-metre property sleeps up to 15 guests and boasts a private pool, Jacuzzi, tennis court, and fully equipped kitchen; additional features include a terrace, garden, and free Wi-Fi.
Beautfiul 7br Home Minutes From Downtown Annapolis - Chesapeake Bay
10 1 review
Chesapeake Bay
20/06 – 27/06
SG$2305/nighttotal: SG$16135 (7 )

Beautfiul 7br Home Minutes From Downtown Annapolis

1 13
apartment , Arnold
This modern colonial property is situated in Arnold, just a short drive from downtown Annapolis and the Naval Academy, offering easy access to the city's attractions and the Chesapeake Bay. The apartment has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
This spacious seven-bedroom home can accommodate up to 14 guests, making it perfect for large families or groups. The apartment features a fully equipped kitchen, a large garden, and parking, ensuring a comfortable and enjoyable stay.
Charming Lower Level Guest Unit, Fully Equipped Kitchen, Wifi, Free Onsite Park - Chesapeake Bay
9.6 4 reviews
Chesapeake Bay
20/06 – 27/06
SG$220/nighttotal: SG$1540 (7 )

Charming Lower Level Guest Unit, Fully Equipped Kitchen, Wifi, Free Onsite Park

1 2
apartment , Glen Burnie
This Pasadena apartment, minutes from Downs Park and the Baltimore & Annapolis Trail, offers easy access to attractions such as the Baltimore Cruise Terminal and Arundel Mills Mall.
The 111-square-metre (1194 sq ft) self-catering flat features one bedroom, one bathroom, sleeps three, and includes a fully equipped kitchen, in-unit laundry, free parking, and a spa.

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

Family Retreat At Lansdowne Manor - Chesapeake Bay
10 12 reviews
Chesapeake Bay
12/09 – 16/09
SG$887/nighttotal: SG$3548 (4 )

Family Retreat At Lansdowne Manor

4 2
farm , Centreville
This Centreville farmhouse, a spacious 300 square metre (approx. 325 sq m) self-catering property, is situated in a peaceful rural setting, approximately 14-19 kilometres from landmarks including the Hazel Miner Monument, Tuckahoe State Park, and Adkins Arboretum.
The four-bedroom, three-bathroom holiday home sleeps eight guests and boasts amenities such as air conditioning, Wi-Fi, a fully equipped kitchen with dishwasher, ample parking, and designated smoking areas; a farm stay experience is also offered.
Lavish Luxe 2bd-1ba Apartment In Federal Hill - Chesapeake Bay
Chesapeake Bay
20/07 – 27/07
SG$266/nighttotal: SG$1862 (7 )

Lavish Luxe 2bd-1ba Apartment In Federal Hill

2 4
apartment , Baltimore
This recently renovated 1900s flat in Baltimore's Federal Hill district is 1.8 kilometres from the Inner Harbour and 1.7 kilometres from the Baltimore Convention Centre.
This 135 square metre apartment offers two bedrooms, a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, and a terrace with city views, accommodating up to 11 guests.
This Thoughtfully Styled Home Overlooks The Bay And Is Perfect For Your Annapolis Escape. - Chesapeake Bay
Chesapeake Bay
20/06 – 27/06
SG$2539/nighttotal: SG$17773 (7 )

This Thoughtfully Styled Home Overlooks The Bay And Is Perfect For Your Annapolis Escape.

5 13
apartment , Annapolis
This waterfront property in Annapolis offers direct access to the historic downtown waterfront, sailing, marinas, and Chesapeake Bay views, situated a mere 500 meters from local seafood restaurants, boutiques, and the Naval Academy.
This spacious 550 square meter flat provides accommodation for up to 14 guests across five bedrooms and five bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, and parking.
Camp Chesapeake 50% Off 6 Bedroom Private Waterfront Retreat - Chesapeake Bay
Chesapeake Bay
20/06 – 27/06
SG$1228/nighttotal: SG$8596 (7 )

Camp Chesapeake 50% Off 6 Bedroom Private Waterfront Retreat

6 13
apartment , Savageville
This six-bedroom waterfront holiday home in Onancock offers secluded accommodation on a six-acre property, located approximately 4.8 kilometres from the centre of Savageville and about three hours by car from Washington D.C. and Richmond.
The property accommodates up to sixteen guests and features a hot tub, private dock, movie room, and a children's treehouse, with nearby attractions including the Red Queen Gallery and the Eastern Shore Yacht and Country Club Golf Course.

Best Chesapeake Bay accommodations with a kitchen

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! - Chesapeake Bay
9.6 90 reviews
Chesapeake Bay
07/10 – 11/10
SG$214/nighttotal: SG$856 (4 )

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

1 2
apartment , Annapolis
This apartment is located in Annapolis, just half a mile from Anne Arundel Medical Center and 2.7 miles from the U.S. Naval Academy, offering a peaceful retreat from the city centre. The accommodation has been rated excellent by previous guests.
The flat has one bedroom and one bathroom, comfortably sleeping up to three guests. It comes with a range of amenities including free Wi-Fi, a balcony, a fully equipped kitchen, parking and a relaxing reading nook.
Walkable Baltimore Rowhouse With Fenced-in Patio! - Chesapeake Bay
8.0 3 reviews
Chesapeake Bay
20/06 – 27/06
SG$230/nighttotal: SG$1610 (7 )

Walkable Baltimore Rowhouse With Fenced-in Patio!

2 2
house , Baltimore
This Baltimore row house offers comfortable accommodation for seven guests, situated in a walkable neighbourhood 2.4 kilometres from the Inner Harbour and 1.4 kilometres from the Edgar Allan Poe Museum.
The 93 square metre property features two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, free Wi-Fi, and in-unit laundry facilities, plus a fenced patio.
Rustic Waterfront 5bd Home With 9 Boat Slips! - Chesapeake Bay
9.7 13 reviews
Chesapeake Bay
20/06 – 27/06
SG$1042/nighttotal: SG$7294 (7 )

Rustic Waterfront 5bd Home With 9 Boat Slips!

1 13
apartment , California
This five-bedroom, three-bathroom California waterfront apartment, sleeping fourteen, boasts private deep-water piers ideal for boating and fishing, offering unparalleled access to coastal California's waters.
The property includes kayaks, and its rustic interior features wood panelling and accommodates large groups with ample space for a relaxing getaway focused on outdoor adventure.
Irvington Country Getaway House - Chesapeake Bay
10 155 reviews
Chesapeake Bay
20/07 – 27/07
SG$340/nighttotal: SG$2380 (7 )

Irvington Country Getaway House

3 4
apartment , Irvington
This property is situated in Irvington, just 0.3 kilometres from the Steamboat Era Museum and within 5 kilometres of Historic Christ Church and Compass Entertainment Complex, offering easy access to the town's attractions. This accommodation has received excellent ratings for location, cleanliness, and overall guest experience.
This three-bedroom house comfortably sleeps six guests, providing ample space for families or groups of friends. The property features a fully equipped kitchen, a private garden with barbecue facilities, and free Wi-Fi, making it ideal for both relaxation and entertainment.
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