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Chesapeake Bay apartments
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5236 Best apartments in Chesapeake Bay

Best family friendly Chesapeake Bay Holiday Apartments and Self Catering Accommodations

Among the 5236 accommodations in Chesapeake Bay, here are the 4 best family friendly holiday apartments

Bay View From Calvert Cliffs, Solomons Island & State Park Nearby - Chesapeake Bay
10 69 reviews
Chesapeake Bay
05/07 – 08/07
₹25870/nighttotal: ₹77610 (3 )

Bay View From Calvert Cliffs, Solomons Island & State Park Nearby

3 4
apartment , Chesapeake Ranch Estates
This Chesapeake Ranch Estates lakefront property is situated 9.6km from Calvert Cliffs State Park and 14.5km from Annmarie Sculpture Garden & Arts Centre.
This three-bedroom, two-bathroom holiday home boasts 130 square metres of space, a private terrace, swimming pool, free Wi-Fi, and sleeps up to seven guests, with easy access to on-site water park facilities.
Children's Dream House! Walk To The Beach! - Chesapeake Bay
9.0 18 reviews
Chesapeake Bay
30/07 – 05/08
₹40753/nighttotal: ₹244518 (6 )

Children's Dream House! Walk To The Beach!

3 6
apartment , Hampton
This three-bedroom Hampton house is located just 0.5 kilometres from Buckroe Beach and Park, offering easy access to the sandy shores and recreational activities.
The property features a fully equipped kitchen, laundry facilities, and parking, and can accommodate up to six guests, making it ideal for families or groups visiting Hampton.
Castle Creek - Chesapeake Bay
10 14 reviews
Chesapeake Bay
30/07 – 03/08
₹70830/nighttotal: ₹283320 (4 )

Castle Creek

1 10
apartment , Lancaster
Castle Creek, a magnificent property in Lancaster County, Virginia, boasts a private 75' dock on Lowery Creek, offering access to the Rappahannock and Corrotoman Rivers and the Chesapeake Bay.
This five-bedroom, four-bathroom dwelling sleeps ten guests and features a fully equipped kitchen, a large garden, and on-site watercraft including a canoe, kayak, and paddleboard, alongside a 23-acre estate with a half-mile nature walk.
Lakefront A-frame: Private Dock, Kayaks & Sauna  Sleeps 12, Chesapeake Bay - Chesapeake Bay
9.6 12 reviews
Chesapeake Bay
30/07 – 03/08
₹60205/nighttotal: ₹240820 (4 )

Lakefront A-frame: Private Dock, Kayaks & Sauna Sleeps 12, Chesapeake Bay

4 10
apartment , Chesapeake Ranch Estates
This four-bedroom, three-bathroom house in Lusby, Maryland, is a four-minute drive from Seahorse Beach and six minutes from Drum Point Lake, offering easy access to Annmarie Sculpture Garden and Arts Centre and Calvert Marine Museum.
The 279-square-metre (approximately 3000 square feet) property sleeps twelve guests and includes a fully equipped kitchen, laundry facilities, air conditioning, Wi-Fi, and parking; barbecue facilities are also available on-site.

Best Holiday Apartments and Self Catering Accommodations in Chesapeake Bay with a pool

Among the 5236 accommodations in Chesapeake Bay, here are the 4 best apartments with a pool

Spacious 7-bedroom House In Tranquil Fallston With Fitness Room, Ac - Chesapeake Bay
Chesapeake Bay
02/07 – 05/07
₹1605276/nighttotal: ₹4815828 (3 )

Spacious 7-bedroom House In Tranquil Fallston With Fitness Room, Ac

7 2
apartment , Fallston
This seven-bedroom, nine-bathroom detached house in Fallston is situated a mere 640 metres from Ladew Topiary Gardens and 1.1 kilometres from Gunpowder Falls State Park.
This spacious accommodation, which permits pets, offers Wi-Fi, air conditioning, a swimming pool, barbecue facilities, a fitness centre, on-site parking, and a fully equipped kitchen, catering for up to 30 guests.
2-br 1.5 Blocks From Beach W Pool! - Chesapeake Bay
9.8 7 reviews
Chesapeake Bay
30/07 – 05/08
₹58575/nighttotal: ₹351450 (6 )

2-br 1.5 Blocks From Beach W Pool!

2 6
apartment , Virginia Beach
This two-bedroom, two-bathroom apartment in Northeast Virginia Beach is less than 0.24 kilometres from the beach, close to the Cape Henry Lighthouse and Seatack Community.
The property, sleeping up to five guests, boasts a king-size bed, full/twin bunk bed, pull-out sofa, kitchen with fridge, microwave, and dishwasher, plus access to a communal swimming pool and parking; nearby attractions include the Veterans United Home Loans Amphitheatre and Ocean Breeze Waterpark.
Minutes From Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly - Chesapeake Bay
9.6 40 reviews
Chesapeake Bay
29/08 – 05/09
₹74891/nighttotal: ₹524237 (7 )

Minutes From Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

3 2
apartment , Easton
This charming apartment is located in St. Michaels, just a short drive from the Bay Hundred Community Pool, golf courses, and the town centre. It has received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The apartment is spacious, covering 196 square metres and comfortably accommodating up to 6 guests in its 3 bedrooms and 3 bathrooms. You can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, and parking, as well as access to the internet.
Oceanfront 1br Getaway + Heated Pool - Chesapeake Bay
9.1 316 reviews
Chesapeake Bay
27/06 – 04/07
₹46095/nighttotal: ₹322665 (7 )

Oceanfront 1br Getaway + Heated Pool

1 3
apartment , Virginia Beach
This apartment is directly on the beach in Northeast Virginia Beach, just steps from the famous boardwalk and within a mile of Sandbridge Beach and the Virginia Beach Fishing Pier. It has excellent user, location and cleanliness ratings, making it a great choice for a relaxing and enjoyable stay. The apartment is a one-bedroom property with a floor area of 46 square metres, comfortably accommodating up to four guests. It features a fully equipped kitchen, a terrace, a swimming pool, a jacuzzi, a fitness centre, and a garden, offering a wide range of amenities and activities.

Frequently asked questions about apartment rentals in Chesapeake Bay

  • What are the must-see attractions for a 2 days stay in Baie de Chesapeake?

    For a two-day trip, you'd want to visit the Chesapeake Bay Maritime Museum in St. Michaels, explore the historic district of Annapolis, and perhaps take a boat tour to see the wildlife and scenery of the bay.
  • Which neighborhoods in Baie de Chesapeake are best for renting an apartment?

    For a good mix of waterfront views and easy access to the city, you'd probably want to look at apartments in Annapolis, especially the neighbourhoods of Eastport, West Annapolis, and the downtown area.
  • What makes Baie de Chesapeake unique or famous?

    The Chesapeake Bay is famous for its beautiful scenery, its abundance of seafood, and its rich history. The bay is home to a diverse ecosystem, with everything from blue crabs to bald eagles, and it's a popular destination for boating, fishing, and kayaking. It's also known for its charming towns and cities, like Annapolis and St. Michaels.
  • Where can you find the best local markets and street food in Baie de Chesapeake?

    The best local markets are usually found in the towns and cities around the bay. In Annapolis, you can find the Annapolis Farmers Market on Saturdays, while in St. Michaels, you can visit the St. Michaels Farmers Market on Fridays. You can find street food vendors at many of the local festivals and events.
  • How is the public transportation system in Baie de Chesapeake?

    The public transportation system in the Chesapeake Bay area is not as extensive as in larger cities. The best option for getting around is by car, although there are bus services available in some areas. For example, the Annapolis Area Transit (AAT) provides bus service in and around Annapolis.
  • Which seasonal events or festivals should apartment renters look forward to in Baie de Chesapeake?

    There are many festivals and events throughout the year in the Chesapeake Bay area. Some of the most popular include the Annapolis Maritime Festival in May, the St. Michaels Crab & Oyster Festival in October, and the Chesapeake Bay Wine Festival in November.
  • What amenities are typically included in apartments in Baie de Chesapeake?

    Apartments in the Chesapeake Bay area typically include standard amenities such as central heating and air conditioning, laundry facilities, and parking. Some apartments may also offer amenities like swimming pools, fitness centres, and community rooms.
  • What leisure activities are available for relaxation in Baie de Chesapeake?

    The Chesapeake Bay offers a wide range of leisure activities for relaxation. You can go for a swim at one of the many beaches, take a boat tour to see the wildlife, or go for a hike in one of the many parks and nature reserves. You can also simply relax on the beach, enjoy a picnic, or go for a bike ride.

Destinations nearby

Best Chesapeake Bay holiday apartments with air conditioning

Pet-friendly 2br- Near Beach, Bases, & Hospitals - Chesapeake Bay
9.4 28 reviews
Chesapeake Bay
29/08 – 05/09
₹16723/nighttotal: ₹117061 (7 )

Pet-friendly 2br- Near Beach, Bases, & Hospitals

2 2
apartment , Norfolk
This Bayview Norfolk holiday home is situated less than 3.2km from Norfolk Beaches, Ocean View Beach, and Sarah Constant Shrine Beach, and 3.4km from Oceanview Fishing Pier.
The two-bedroom property sleeps six, boasts a fully equipped kitchen including dishwasher, a terrace, garden, parking, and Wi-Fi, plus a family-friendly atmosphere.
Magical Wooded Cottage Pool +Priv Hottub Walk2town - Chesapeake Bay
9.9 206 reviews
Chesapeake Bay
14/10 – 18/10
₹40002/nighttotal: ₹160008 (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.
Stunning Sunsets On Breton Bay, Seaside Apartment - Chesapeake Bay
10 145 reviews
Chesapeake Bay
29/08 – 05/09
₹15914/nighttotal: ₹111398 (7 )

Stunning Sunsets On Breton Bay, Seaside Apartment

1 2
apartment , Leonardtown
This Leonardtown apartment, situated 8km from the town centre and 40km from Solomons Island, offers convenient access to historical sites and the Breton Bay.
The self-contained flat features a king-sized bed, full couch, and loveseat, sleeping two guests, a fully equipped kitchen, private pergola, designated parking, and private pier access for fishing and crabbing.
Working Horse Farm Retreat! Convenient To Wedding Venue! - Chesapeake Bay
9.8 53 reviews
Chesapeake Bay
30/07 – 05/08
₹23411/nighttotal: ₹140466 (6 )

Working Horse Farm Retreat! Convenient To Wedding Venue!

3 6
apartment , Jarrettsville
This apartment is situated in a peaceful rural setting, just 12.5 kilometres from Ladew Topiary Gardens and within 40 kilometres of Liriodendron Mansion and Harford Community College. It has consistently received excellent ratings from previous guests.
The apartment has three bedrooms, two bathrooms, and a spacious 111 square metre floor area, comfortably accommodating up to six guests. Enjoy a range of amenities, including a swimming pool, a spa, a garden, a terrace, and a fully equipped kitchen, perfect for a relaxing and enjoyable stay.

Best pet-friendly Chesapeake Bay holiday apartments

Among the 5236 accommodations in Chesapeake Bay, here are the 4 best pet friendly holiday apartments

Tilghman | Pool | Private Dock | Pet Friendly - Chesapeake Bay
9.4 15 reviews
Chesapeake Bay
27/06 – 04/07
₹89979/nighttotal: ₹629853 (7 )

Tilghman | Pool | Private Dock | Pet Friendly

3 3
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.
Johns Hopkins Inner Harbor Downtown 5 Beds W/deck - Chesapeake Bay
9.6 5 reviews
Chesapeake Bay
14/10 – 18/10
₹24918/nighttotal: ₹99672 (4 )

Johns Hopkins Inner Harbor Downtown 5 Beds W/deck

3 4
apartment , Baltimore
This three-bedroom, three-bathroom Baltimore dwelling is situated in Upper Canton, Greektown, approximately 4.8km from the Inner Harbour and 0.6km from Brewers Hill.
The 134 square metre property boasts a stylish open-plan kitchen, rooftop deck, off-street parking, and accommodates up to seven guests, with amenities including three 4K smart TVs and a washer-dryer.
St George`s Getaway W/ Firepit! - Chesapeake Bay
9.4 3 reviews
Chesapeake Bay
14/10 – 18/10
₹25412/nighttotal: ₹101648 (4 )

St George`s Getaway W/ Firepit!

3 4
apartment , Piney Point
This Piney Point flat is located near the beach, offering proximity to the Piney Point Lighthouse and Cecil's Old Mill.
This 1208 square meter dwelling accommodates up to six guests with three bedrooms and two bathrooms, featuring a fully stocked kitchen, air conditioning, parking, and a backyard with a firepit, all within easy reach of local amenities and outdoor pursuits.
Last Weeks Open! Waterfront Retreat W/ Pool, Hot Tub, Dock & Sand Beach - Chesapeake Bay
9.7 74 reviews
Chesapeake Bay
27/06 – 04/07
₹79639/nighttotal: ₹557473 (7 )

Last Weeks Open! Waterfront Retreat W/ Pool, Hot Tub, Dock & Sand Beach

3 3
apartment , Irvington
This four-bedroom apartment is situated on the sandy shores of the Corrotoman River, a short distance from Irvington, Virginia, offering a tranquil escape from the hustle and bustle of city life. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment spans 427 square metres and comfortably accommodates up to 12 guests. Enjoy a range of amenities including a private saltwater pool, hot tub, sandy beach, kayaks, paddleboards, a canoe, and a private dock for fishing and crabbing, all with stunning river views.
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