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Chesapeake Bay apartments
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5236 Holiday apartments in Chesapeake Bay

Best family friendly Chesapeake Bay Holiday Apartments

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

Beach Combing & Relaxation - Chesapeake Bay
9.7 100 reviews
Chesapeake Bay
01/10 – 05/10
A$329/nighttotal: A$1316 (4 )

Beach Combing & Relaxation

3 3
apartment , Calvert Beach
This apartment is located in a private community in Calvert Beach, Maryland, just a 1.6 kilometre walk from a beautiful stretch of beach. The apartment has excellent ratings for cleanliness, location and user experience.
The apartment has three bedrooms and one bathroom, covering 111 square metres and comfortably accommodating up to six guests. It features a fully equipped kitchen, a spacious deck with a fire pit, and a range of amenities for a relaxing beach getaway, including private beach access, a beach cart, and a high chair for families.
Artsy Homey Rowhouse, 3bdrm & Office, Quiet Urban Area, Free Parking, Fast Wifi - Chesapeake Bay
9.7 164 reviews
Chesapeake Bay
30/07 – 05/08
A$436/nighttotal: A$2616 (6 )

Artsy Homey Rowhouse, 3bdrm & Office, Quiet Urban Area, Free Parking, Fast Wifi

3 6
apartment , Baltimore
This charming bed and breakfast is situated in a peaceful residential neighbourhood, just a short walk from Johns Hopkins University, Union Memorial Hospital, and the vibrant Hampden district. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The house, built in the 1920s, offers a spacious 121 square metres of living space with a Tudor-style design and original features. Guests have access to a fully equipped kitchen, laundry facilities, a private garden, a terrace, and a fitness centre, as well as a shared Jacuzzi and a nearby YMCA with an Olympic-sized pool.
Cozy Modern Micro Apt In The Heart Of Fells Point! - Chesapeake Bay
9.0 33 reviews
Chesapeake Bay
23/08 – 28/08
A$224/nighttotal: A$1120 (5 )

Cozy Modern Micro Apt In The Heart Of Fells Point!

2 2
apartment , Baltimore
This Baltimore waterfront apartment, less than 1.6km from the Inner Harbour and attractions such as the National Aquarium and Johns Hopkins Hospital, offers easy access to public transport and scenic views.
This 60 square metre, two-bedroom flat sleeps four guests and boasts a fully equipped kitchen, swimming pool, spa, parking, and free Wi-Fi; on-site amenities include a water park and barbecue grills.
The Quarter Deck/spacious Home With Water Views! - Chesapeake Bay
9.8 44 reviews
Chesapeake Bay
27/06 – 04/07
A$589/nighttotal: A$4123 (7 )

The Quarter Deck/spacious Home With Water Views!

5 3
apartment , Onancock
This East Point property, a 10-minute (approx. 6.4 km) drive from Onancock town, offers stunning sunset views over Onancock Creek and the Chesapeake Bay.
Sleeping up to 14 guests in 5 bedrooms and 3 bathrooms, this spacious house boasts a fully equipped kitchen, large porches, kayaks for exploring the creek, and provision of bikes, beach toys, and children's equipment; enjoy private beach access and peaceful woodland views.

Best Holiday Apartments in Chesapeake Bay with a pool

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

Seas The Day At Bay Creek | Luxury Resort Townhome W/ Pool, Fenced Yard, Fireplace & Pet Friendly - Chesapeake Bay
9.6 11 reviews
Chesapeake Bay
14/10 – 18/10
A$686/nighttotal: A$2744 (4 )

Seas The Day At Bay Creek | Luxury Resort Townhome W/ Pool, Fenced Yard, Fireplace & Pet Friendly

2 4
apartment , Cape Charles
This Cape Charles holiday home is situated 1.4 km from Bay Creek Golf Club and 2.7 km from Cape Charles Beach, with Kiptopeke State Park and Eastern Shore National Wildlife Refuge within a 19 km radius.
The two-bedroom property, sleeping up to eight guests, boasts a fully equipped kitchen, private patio, swimming pool, and barbecue facilities; nearby activities include golfing and exploring the wildlife refuge.
Modern Federal Hill Retreat Prime Location - Chesapeake Bay
10 1 review
Chesapeake Bay
23/08 – 28/08
A$294/nighttotal: A$1470 (5 )

Modern Federal Hill Retreat Prime Location

1 2
apartment , Baltimore
This Federal Hill flat is located in Baltimore, offering proximity to the historic Fell's Point, a 1.8 kilometre walk away, and is 1.8 kilometres from the Inner Harbour.
This 520 square metre apartment accommodates up to three guests and features air conditioning, a private balcony, and a fully equipped kitchen, with free WiFi available throughout.
Day Dream Believer | Luxury Bay Creek Golf + Pools - Chesapeake Bay
10 1 review
Chesapeake Bay
27/06 – 04/07
A$1577/nighttotal: A$11039 (7 )

Day Dream Believer | Luxury Bay Creek Golf + Pools

4 3
apartment , Cape Charles
Day Dream Believer, a luxury four-bedroom house in the Bay Creek Resort community of Cape Charles, Virginia, offers proximity to pristine beaches and the town centre.
This New Home, sleeping up to 10 guests, boasts a 48" Wolf stove/oven, quartz countertops, two primary suites, a two-car garage, and access to Bay Creek Resort amenities (additional fee applies), including golf courses and pools.
One Bedroom Condo With Marina View - Chesapeake Bay
10 1 review
Chesapeake Bay
01/10 – 05/10
A$318/nighttotal: A$1272 (4 )

One Bedroom Condo With Marina View

1 3
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.

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 should definitely visit the Chesapeake Bay Maritime Museum in St. Michaels. It's a great place to learn about the history of the Bay. You could also take a day trip to Annapolis, the state capital, and explore its historic district and Naval Academy.
  • What are the best apartments in Chesapeake Bay?

  • Which neighborhoods in Baie de Chesapeake are best for renting an apartment?

    It really depends on what you're looking for. If you want to be close to the action, Annapolis is a good choice. But if you prefer a quieter, more relaxed atmosphere, you might want to consider St. Michaels or Easton. There are also some great waterfront communities on the Eastern Shore, like Ocean City and Rehoboth Beach.
  • What are the best apartments with a pool in Chesapeake Bay?

  • What are the top cultural and historical sites in Baie de Chesapeake?

    There are many! The Chesapeake Bay Maritime Museum in St. Michaels is a must-see. You could also visit the National Museum of the American Sailor in Annapolis, or the Harriet Tubman Underground Railroad Byway, which runs through several towns on the Eastern Shore.
  • What are the best apartments with a jacuzzi in Chesapeake Bay?

  • What makes Baie de Chesapeake unique or famous?

    The Chesapeake Bay is known for its beautiful scenery, diverse wildlife, and rich history. It's also a popular destination for boating, fishing, and crabbing. The Bay is home to a variety of ecosystems, from salt marshes to forested islands. The Bay's unique geography and history have made it a special place for generations.
  • What are the best apartments for families and kids in Chesapeake Bay?

  • Where can you find the best local markets and street food in Baie de Chesapeake?

    There are lots of great places to find local produce and street food. The Easton Farmers' Market is a great option, and the Annapolis City Dock is a popular spot for seafood vendors. The Chesapeake Bay region is known for its blue crabs, oysters, and other seafood. You can also find plenty of local produce, like tomatoes, corn, and peaches.
  • What are the best pet friendly apartments in Chesapeake Bay?

    The best pet friendly apartments in Chesapeake Bay are Walk To Beach By Busch Gardens - Lovely Room, Dune Cottage Sea Suite and Lucy's Downtown Apartment.

  • How is the public transportation system in Baie de Chesapeake?

    Public transportation in the Chesapeake Bay region is limited. It's best to have a car if you want to explore the area. However, there are some bus routes in Annapolis and Baltimore. You can also find ferries that connect some of the islands and towns on the Bay.
  • What are the best apartments with parking in Chesapeake Bay?

  • Which seasonal events or festivals should apartment renters look forward to in Baie de Chesapeake?

    There are many festivals throughout the year! The Annapolis Maritime Festival is a big one, and the St. Michaels Crab & Maritime Festival is another popular event. There are also many smaller festivals and events happening all over the Bay.
  • What amenities are typically included in apartments in Baie de Chesapeake?

    Apartments in the Chesapeake Bay region vary in amenities. Many include basic appliances like a refrigerator, stove, and oven. Some might also offer laundry facilities, parking, and a swimming pool. It really depends on the specific apartment complex and location.
  • What leisure activities are available for relaxation in Baie de Chesapeake?

    The Chesapeake Bay is a great place to relax and enjoy the outdoors. You can go boating, fishing, crabbing, kayaking, or swimming. You can also go hiking, biking, or birdwatching. There are also many parks and beaches in the area.

Destinations nearby

Best Chesapeake Bay holiday apartments with air conditioning

3-bedroom House In Soothing Saint Leonard With Ac For Relaxing Stays - Chesapeake Bay
Chesapeake Bay
27/06 – 04/07
A$268/nighttotal: A$1876 (7 )

3-bedroom House In Soothing Saint Leonard With Ac For Relaxing Stays

3 3
apartment , Long Beach
This apartment in St. Leonard is located just 200 metres from Long Beach, offering easy access to Calvert Cliffs, a popular site for shark tooth and fossil discovery, and convenient for those working at the Calvert Cliffs Power Plant, Cove Point LNG plant, or Patuxent Naval Air Station.
This property sleeps up to seven guests, featuring three bedrooms and one bathroom, with amenities including air conditioning, Wi-Fi, and a kitchen equipped with a microwave oven and dishwasher, all within proximity to the CalvART Gallery, Calvert Marine Museum, Flag Harbor Marina, and Perigeaux Vineyards and Winery.
Relaxation Haven On The Shore Near Choptank River - Chesapeake Bay
9.4 9 reviews
Chesapeake Bay
14/10 – 18/10
A$417/nighttotal: A$1668 (4 )

Relaxation Haven On The Shore Near Choptank River

2 4
apartment , Greensboro
This Greensboro apartment is ideally situated near Tuckahoe State Park, Olive Branch Lodge Park, Adkins Arboretum, and Martinak State Park, all within a 9-16km radius.
This two-bedroom, one-bathroom property sleeps six guests and boasts a fully equipped kitchen, fireplace, DVD player, terrace, garden, and on-site living plant wall; towel changes are available on request.
Monthly Discount- Beautiful House, Gloucester Va - Chesapeake Bay
10 30 reviews
Chesapeake Bay
23/08 – 28/08
A$242/nighttotal: A$1210 (5 )

Monthly Discount- Beautiful House, Gloucester Va

3 2
apartment , Deltaville
This recently refurbished property is situated in Gloucester, Virginia, just off the Piankatank River, and is within easy driving distance of Mathews Courthouse, Gloucester Main Street Community, Urbanna, and Gwynns Island. The house has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
The 93-square-metre house has three bedrooms, two bathrooms, and can comfortably accommodate six guests. This pet-friendly home offers a range of amenities including a fully equipped kitchen, air conditioning, a terrace, a garden, and parking.
Hidden Fells Point Gem / Private Courtyard Patio - Chesapeake Bay
9.6 95 reviews
Chesapeake Bay
23/08 – 28/08
A$196/nighttotal: A$980 (5 )

Hidden Fells Point Gem / Private Courtyard Patio

1 2
apartment , Baltimore
This one-bedroom flat is located in Fells Point, a historic Baltimore district, within walking distance of Fell's Point Visitor Center and Johns Hopkins Hospital. It has received excellent reviews from previous guests.
The 59 square metre property has two bathrooms and can comfortably accommodate up to three guests. It offers a fully equipped kitchen, a terrace, a garden, a spa, parking, and internet access, as well as a washer and dryer for added convenience.

Best pet-friendly Chesapeake Bay holiday apartments

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

Deluxe Corner Apartment With Riverfront Views Close To Dining And Downtown - Chesapeake Bay
9.7 148 reviews
Chesapeake Bay
23/08 – 28/08
A$352/nighttotal: A$1760 (5 )

Deluxe Corner Apartment With Riverfront Views Close To Dining And Downtown

2 2
apartment , Salisbury
This Salisbury apartment is conveniently located within a mile of both Peninsula Regional Medical Center and Poplar Hill Mansion, making it ideal for those visiting the hospital or exploring local attractions. It has received excellent ratings for cleanliness, location, and user experience.
This two-bedroom, one-bathroom flat comfortably sleeps four guests. The fully equipped kitchen, washing machine, and on-site parking make it a convenient option, while the quiet location provides a peaceful retreat.
Cove Point Beach Cottage With Chesapeake Bay Views - Chesapeake Bay
10 3 reviews
Chesapeake Bay
14/10 – 18/10
A$462/nighttotal: A$1848 (4 )

Cove Point Beach Cottage With Chesapeake Bay Views

3 4
apartment , Lusby
This Lusby seaside holiday home is situated one block (approximately 0.16 km) from Cove Point Beach on the Chesapeake Bay, offering easy access to the Annmarie Sculpture Garden and Arts Centre and Calvert Marine Museum.
Sleeping six guests in three bedrooms and one bathroom, this self-catering property boasts a garden, terrace, parking, Wi-Fi, air conditioning, and a beach wagon for transporting equipment to the beach, where shell and shark tooth hunting is possible; an outdoor shower is also available.
Norfolk Beach Casita / Fenced Yard / Dog Friendly - Chesapeake Bay
9.7 206 reviews
Chesapeake Bay
01/10 – 05/10
A$359/nighttotal: A$1436 (4 )

Norfolk Beach Casita / Fenced Yard / Dog Friendly

2 3
apartment , Norfolk
This Norfolk house is located just 3km from Ocean View Beach, Norfolk Beaches, and Sarah Constant Shrine Beach, offering easy access to the coastline. It has received excellent ratings for its location, cleanliness, and user experience.
The property features two bedrooms and two bathrooms, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, a garden, parking, and a terrace, providing everything you need for a relaxing and enjoyable stay.
Three Blocks From The Beach - Chesapeake Bay
9.8 274 reviews
Chesapeake Bay
01/10 – 05/10
A$421/nighttotal: A$1684 (4 )

Three Blocks From The Beach

2 3
apartment , Hampton
This Hampton apartment is located just a short walk from the beach and within easy reach of the town's main attractions, making it a perfect choice for exploring the area. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The apartment offers two bedrooms and one bathroom, covering 46 square metres and comfortably accommodating up to six guests. It comes fully furnished and equipped with modern appliances, high-speed internet, a washer and dryer, and a fully equipped kitchen.
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