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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

Beachside Retreat For 4  Walk To Buckroe Beach! - Chesapeake Bay
9.2 180 reviews
Chesapeake Bay
29/08 – 05/09
₹20257/nighttotal: ₹141799 (7 )

Beachside Retreat For 4 Walk To Buckroe Beach!

2 2
apartment , Hampton
This two-bedroom flat is located just 0.4 kilometres from Buckroe Beach, offering easy access to the sand and surf. The apartment is highly rated, with excellent user, location and cleanliness scores.
The flat can comfortably accommodate up to four guests and is equipped with a range of amenities, including a private garden, a terrace, a jacuzzi, a fully equipped kitchen, and a washer and dryer. Guests can enjoy complimentary Wi-Fi, relax in the garden, and take advantage of the close proximity to the beach, playground, and bathhouse.
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.
Cozy 2-bedroom Apartment In Welcoming Baltimore With Wifi, Ac - Chesapeake Bay
9.6 10 reviews
Chesapeake Bay
29/08 – 05/09
₹17168/nighttotal: ₹120176 (7 )

Cozy 2-bedroom Apartment In Welcoming Baltimore With Wifi, Ac

2 2
apartment , Baltimore
This Baltimore Greektown apartment is ideally situated near Patterson Park (4.8km) and Canton Waterfront Park (6.4km), offering easy access to the Inner Harbour, CFG Bank Arena, and various cultural attractions.
The two-bedroom, two-bathroom property sleeps four guests and includes Wi-Fi, air conditioning, and in-unit laundry facilities; nearby activities include concerts at Pier Six Pavilion and exploring the National Aquarium.
Prime Spot Staysimple Comfort, Perfect Location - Chesapeake Bay
10 2 reviews
Chesapeake Bay
30/07 – 05/08
₹35504/nighttotal: ₹213024 (6 )

Prime Spot Staysimple Comfort, Perfect Location

3 6
apartment , Annapolis
This 3-bedroom flat is located a mere 160 metres from historic Downtown Annapolis, providing straightforward walking access to the U.S. Naval Academy, City Dock, and the Maryland State House.
Offering 118 square metres of living space, this accommodation can host up to 8 guests and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus air conditioning and parking.

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

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.
Free Breakfast. Outdoor Pool. 10 Min From University Of Delaware! - Chesapeake Bay
Chesapeake Bay
23/08 – 28/08
₹18033/nighttotal: ₹90165 (5 )

Free Breakfast. Outdoor Pool. 10 Min From University Of Delaware!

1 2
apartment , Brookside
This one-bedroom Brookside apartment, near University Office Plaza Shopping Centre and Christiana Skating Center (within 2km), offers easy access to Lewden Green Park and Christiana Care Health System (within 3km).
The self-catering flat sleeps four, includes a fully equipped kitchen with appliances, in-unit entertainment, and free breakfast, plus limited housekeeping and parking is available.
Bay Creek Retreat Near Beach & Golf + Incl. Bikes - Chesapeake Bay
Chesapeake Bay
14/10 – 18/10
₹53636/nighttotal: ₹214544 (4 )

Bay Creek Retreat Near Beach & Golf + Incl. Bikes

3 4
apartment , Cape Charles
This Bay Creek condo in Cape Charles is situated near community amenities, approximately 3.2 kilometres from the beach and a short drive from downtown Cape Charles' historic district.
This 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and offers complimentary access to Bay Creek Resort amenities, including a junior Olympic-size pool and tennis courts, with four bikes provided for exploring the area.
Walk To Beach, Patio, Pool, Central Downtown Condo - Chesapeake Bay
8.4 23 reviews
Chesapeake Bay
01/10 – 05/10
₹25891/nighttotal: ₹103564 (4 )

Walk To Beach, Patio, Pool, Central Downtown Condo

2 3
apartment , Virginia Beach
This three-bedroom, four-bathroom apartment in Northeast Virginia Beach is a short walk (under 0.8km) from Pacific Avenue and the Virginia Beach Boardwalk, and within 1.6km of the Neptune Statue and Virginia Beach Fishing Pier.
The 263 square metre property boasts a fully equipped kitchen, balcony, swimming pool, parking, and accommodates up to five guests, offering easy access to public transport and a smoke-free environment.

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

Spacious 3br In Phoebus - Great Monthly Rates - Chesapeake Bay
9.4 60 reviews
Chesapeake Bay
30/07 – 05/08
₹41266/nighttotal: ₹247596 (6 )

Spacious 3br In Phoebus - Great Monthly Rates

3 6
apartment , Hampton
This Hampton property is located just 1.5 kilometres from The American Theatre and Hampton University, offering easy access to cultural attractions and educational institutions. It's also within 3.2 kilometres of Hampton University Museum and Fort Monroe, providing a chance to explore the region's rich history. This home has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
This 3-bedroom home can accommodate up to 6 guests, making it ideal for families or groups of friends. The property comes with a fully equipped kitchen, two bathrooms, a washing machine, a coffee/tea maker, a Smart TV, and a private garden, ensuring a comfortable and enjoyable stay.
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.
Beautiful Peaceful, Scenic, Enjoy Crabs N Fish Memorable, Free Tour Of Area! - Chesapeake Bay
9.9 136 reviews
Chesapeake Bay
30/07 – 05/08
₹36764/nighttotal: ₹220584 (6 )

Beautiful Peaceful, Scenic, Enjoy Crabs N Fish Memorable, Free Tour Of Area!

4 6
apartment , Chesapeake Ranch Estates
This apartment is situated on Hoopers Island, a short distance from the Chesapeake Bay and its abundance of seafood. It has received excellent ratings for its cleanliness, location, and overall experience.
The property is a spacious four-bedroom dwelling, spanning 102 square metres and comfortably accommodating up to 10 guests. This home offers a range of amenities, including a garden, a fire pit, a BBQ, and fishing and crabbing equipment, making it ideal for families and groups seeking a relaxing and enjoyable stay.
Irvington Country Getaway House - Chesapeake Bay
10 155 reviews
Chesapeake Bay
30/07 – 05/08
₹29405/nighttotal: ₹176430 (6 )

Irvington Country Getaway House

3 6
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.

Best pet-friendly Chesapeake Bay holiday apartments

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

Set Sail To The Rusty Anchor! Your Perfect Getaway On Deal Island, Md - Chesapeake Bay
9.8 11 reviews
Chesapeake Bay
01/10 – 05/10
₹17170/nighttotal: ₹68680 (4 )

Set Sail To The Rusty Anchor! Your Perfect Getaway On Deal Island, Md

3 3
apartment , Deal Island Historic District
This Deal Island holiday home, situated near Shark Fin Shoal (3.2km) and Rock Island (4.5km), offers convenient access to the Deal Island Historic District and is within 32km of Whitehaven Historic District and Mount Vernon Park.
The 108 square metre property sleeps eight guests in three bedrooms and one bathroom, boasting a fully equipped kitchen, in-unit laundry, a terrace, and barbecue facilities.
Heart Of Irvington W/fireplace Walk To Tides Inn &  Restaurants - Dog Friendly! - Chesapeake Bay
9.6 344 reviews
Chesapeake Bay
29/08 – 05/09
₹21009/nighttotal: ₹147063 (7 )

Heart Of Irvington W/fireplace Walk To Tides Inn & Restaurants - Dog Friendly!

2 2
apartment , Irvington
This charming house is situated in Irvington, just 0.6 kilometres from the Steamboat Era Museum and within 5 kilometres of Historic Christ Church and Compass Entertainment Complex, offering a peaceful escape close to local attractions. It enjoys excellent ratings for location, cleanliness and user experience.
The 2-bedroom house spans 121 square metres and comfortably accommodates up to 4 guests. Amenities include a fully equipped kitchen, a private patio, a garden, a jacuzzi, a tennis court, and free Wi-Fi, providing everything you need for a relaxing and enjoyable stay.
Blue House In Hampden - Chesapeake Bay
9.4 10 reviews
Chesapeake Bay
29/08 – 05/09
₹14848/nighttotal: ₹103936 (7 )

Blue House In Hampden

1 2
apartment , Baltimore
This one-bedroom flat is located in Wyman Park, a neighbourhood in Baltimore, within walking distance of Johns Hopkins Hospital and a short drive to downtown Baltimore, Oriole Park at Camden Yards and M&T Bank Stadium. It has been highly rated by previous guests, making it an excellent choice for travellers.
The flat can comfortably accommodate up to 3 guests and has a fully equipped kitchen with a fridge, microwave oven, and dishwasher. Guests can also enjoy features such as air conditioning, parking, internet access and the option to bring pets.
Woodland Hideaway: Cozy 1 Bedroom Apartment Tucked Away In A Quiet Neighborhood. - Chesapeake Bay
10 2 reviews
Chesapeake Bay
23/08 – 28/08
₹13080/nighttotal: ₹65400 (5 )

Woodland Hideaway: Cozy 1 Bedroom Apartment Tucked Away In A Quiet Neighborhood.

1 2
apartment , Dover
This private one-bedroom flat in Dover is situated just over 3 kilometres from key attractions including Greentree Village and Gateway West shopping centres, Dover Downs, NASCAR, and Delaware State University, with views of a golf course and convenient access to coastal beaches.
This accommodation offers space for up to four guests, featuring a full kitchen, in-unit laundry, two Smart TVs with streaming services, and complimentary WiFi, and is conveniently located approximately 1.6 kilometres from Fork Branch Nature Preserve and Killens Pond State Park.
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