Best apartment offers in Chesapeake Bay

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Chesapeake Bay apartments
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7757 Holiday apartments in Chesapeake Bay

Top-Rated Apartments near the Ocean in Chesapeake Bay

Walk straight out of your building onto the soft, powdery sand at apartments near the sea in Chesapeake Bay.

Designer Owned Coastal Getaway Retreat - Chesapeake Bay
10 419 reviews

Designer Owned Coastal Getaway Retreat

apartment, Drum Point
This private apartment is situated in Drum Point, a waterfront community just 5km from beaches, 10km from Solomons, and close to Calvert Cliffs. The property has received excellent ratings for its location, cleanliness, and overall experience.
The self-catering apartment has one bedroom and one bathroom, comfortably accommodating two guests. The well-equipped kitchen features a range of appliances, while the garden provides a relaxing outdoor space with a fire pit and grill. Guests can also enjoy access to a fitness centre and a range of local activities, including hiking, fishing, kayaking, and exploring nearby attractions.

Guests’ Favourite Family Apartments in Chesapeake Bay

Give the family a spacious seaside base camp with a full kitchen steps from the waves at family island apartments in Chesapeake Bay.

Cozy Modern Micro Apt In The Heart Of Fells Point! - Chesapeake Bay
9.0 39 reviews

Cozy Modern Micro Apt In The Heart Of Fells Point!

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.
Walk To Usna, Main St W Parking Historic Wisteria - Chesapeake Bay
9.8 113 reviews

Walk To Usna, Main St W Parking Historic Wisteria

apartment, Annapolis
This charming house is situated in Annapolis' Historic District, just a kilometre from The Colonial Players and the U.S. Naval Academy, making it a great base for exploring the city’s rich history and culture. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The house has four bedrooms and can accommodate up to eight guests, making it ideal for families or groups of friends. Guests can enjoy the fully equipped kitchen, a comfortable living space, a dedicated library, a terrace, a garden, a spa, and private parking.
The Glick - Short Stays On Market - Chesapeake Bay
10 2 reviews

The Glick - Short Stays On Market

apartment, Onancock
This apartment is located in downtown Onancock, within the historic Lilliston Building, just steps from the Onancock Wharf, Tangier Island Ferry, and local shops and eateries.
This 65 square metre flat accommodates up to four guests, featuring a king bedroom, a queen sleeper sofa, a fully equipped kitchen with full-size appliances, in-unit laundry, and entertainment options, with easy access to water activities and cycling.
The Harbour - Short Stays On Market - Chesapeake Bay
10 2 reviews

The Harbour - Short Stays On Market

apartment, Onancock
This one-bedroom flat is located in the centre of Onancock, a short walk from the waterfront attractions including the wharf and Tangier Island Ferry, with restaurants, shops and galleries also within easy reach.
This 65 square metre apartment accommodates up to four guests with a king-size bed and a queen sofa bed, and features a fully equipped kitchen with full-size appliances, an in-unit washer/dryer, and high-speed Wi-Fi.

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.

Popular destinations

Top-Rated Apartments with a Pool in Chesapeake Bay

Walk out of your door and jump straight into a crystal-clear swimming pool at island apartments in Chesapeake Bay.

Historic Waterfront Estate With Pool & Pet-friendly   Perfect For Fall Getaways - Chesapeake Bay
9.9 46 reviews

Historic Waterfront Estate With Pool & Pet-friendly Perfect For Fall Getaways

apartment, Oxford
Combsberry, a beautifully restored 1730s historic estate in Talbot County, Maryland (note: this listing incorrectly states Oxford as the destination), is situated on a 30-acre waterfront property on Island Creek, offering proximity to acclaimed restaurants.
This five-bedroom, six-bathroom property, sleeping up to ten guests, boasts a gourmet kitchen, waterfront pool, terrace, and extensive gardens, along with on-site caretakers and access to local insider tips.
Oceanfront Condo On Boardwalk/indoor Pool/hot Tub - Chesapeake Bay
9.0 4 reviews

Oceanfront Condo On Boardwalk/indoor Pool/hot Tub

apartment, Virginia Beach
This beachfront condo in Northeast Virginia Beach offers direct access to the beach and boardwalk, with panoramic ocean views from a private balcony, and is near attractions such as the Ocean Breeze Waterpark and the Veterans United Home Loans Amphitheatre.
This 46-square-metre (495-square-foot) apartment features a king-size bed, a sleeper sofa, a fully equipped kitchen, and access to an indoor pool, hot tub, and exercise room; it sleeps four guests and includes high-speed Wi-Fi and a designated parking space.
Rooftop Chesapeake Bay Views! Waterfront Retreat - Chesapeake Bay
No reviews

Rooftop Chesapeake Bay Views! Waterfront Retreat

apartment, Mathews
This Westville flat is situated within 25 kilometres of cultural landmarks such as the Bay School Community Arts Centre and Ware Parish Church.
This apartment offers a fully equipped kitchen with a microwave and dishwasher, air conditioning, a private balcony, free Wi-Fi in common areas, and on-site barbecue facilities, with pets welcome and parking provided.
"Endless Summer" Waterfront On The Chesapeake Bay! - Chesapeake Bay
9.8 13 reviews

"Endless Summer" Waterfront On The Chesapeake Bay!

apartment, Madison
This Woolford holiday home is situated within 19 kilometres of Blackwater National Wildlife Refuge, the Harriet Tubman State Park Visitor Centre, and the Harriet Tubman Underground Railroad National Historical Park.
This four-bedroom, three-bathroom property sleeps twelve guests and boasts a private indoor pool, fully equipped kitchen, barbecue grills, smart TV, laundry facilities, and a patio area; enjoy easy self-catering and proximity to local attractions.

Top-Rated Apartments in the CBD in Chesapeake Bay

Stay steps away from local fish markets, surf rentals, and seashore dining at central island apartments in Chesapeake Bay.

Room On River With Sunset Views And Private Beach! - Chesapeake Bay
10 42 reviews

Room On River With Sunset Views And Private Beach!

apartment, Deltaville
This Deltaville apartment is situated approximately 10km from the Deltaville Maritime Museum and Holly Point Nature Park, offering a riverside location with scenic views.
The self-catering flat sleeps two guests, features a private patio, barbecue facilities, free Wi-Fi, and a kitchen equipped with a fridge and microwave, perfect for exploring the nearby Piankatank River Golf Club (19km).
Monthly Discount- Beautiful House, Gloucester Va - Chesapeake Bay
10 31 reviews

Monthly Discount- Beautiful House, Gloucester Va

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.
The Moore Cottage - Chesapeake Bay
9.8 403 reviews

The Moore Cottage

apartment, White Stone
The Moore Cottage is a charming fisherman's retreat situated on the Northern Neck, just 1.6km from Windmill Point Marina and 8km from the town of White Stone. This cosy cottage has received excellent ratings for its location, cleanliness and overall experience.
The cottage has one bedroom and one bathroom, comfortably accommodating two guests. It boasts a fully equipped kitchen, a private garden, a back porch with stunning views and a propane grill, as well as kayaks and a paddleboard for exploring the tranquil waters of Little Bay and Antipoison Creek.
Kimary Cove - Waterfront Relaxation And No Cleaning Fee - Chesapeake Bay
9.6 30 reviews

Kimary Cove - Waterfront Relaxation And No Cleaning Fee

apartment, Gwynn
This waterfront apartment is situated just 7.7km from Mathews and 22.5km from Gloucester, offering a peaceful retreat with easy access to nearby attractions. The property has received excellent guest reviews, highlighting its comfortable and well-equipped nature.
The self-catering apartment provides accommodation for up to four guests across two bedrooms and one bathroom. Guests can enjoy a private dock, a gazebo, a spacious deck, a cornhole game, a grill, and a pool table, alongside a fully equipped kitchen and three Roku televisions.

Top-Rated Pet-Friendly Apartments in Chesapeake Bay

Let your dog doze in the warm sea breeze on a private terrace at pet-friendly island apartments in Chesapeake Bay.

* Beautiful Oasis W/ No Detail Spared * - Chesapeake Bay
9.8 56 reviews

* Beautiful Oasis W/ No Detail Spared *

apartment, Lutherville
Stylish 2 Bedroom 1 Bath With Riverfront Views Close To Dining And Downtown - Chesapeake Bay
9.8 23 reviews

Stylish 2 Bedroom 1 Bath With Riverfront Views Close To Dining And Downtown

apartment, Salisbury
1 Queen Bed  Ada Ri Shower Nsmk Kitchen - Chesapeake Bay
No reviews

1 Queen Bed Ada Ri Shower Nsmk Kitchen

apartment, Hampton
Waterfront 1br On Working Farm W/ Deck + View - Chesapeake Bay
9.8 42 reviews

Waterfront 1br On Working Farm W/ Deck + View

apartment, Bobtown

Best Chesapeake Bay holiday apartments with air conditioning

Cozy Home W/fenced In Yard-dog Friendly With Pet Fee. 2 Block Walk To Downtown! - Chesapeake Bay
9.8 76 reviews

Cozy Home W/fenced In Yard-dog Friendly With Pet Fee. 2 Block Walk To Downtown!

apartment, Havre de Grace
New Loft W/south River View From Treehouse Deck! - Chesapeake Bay
9.9 173 reviews

New Loft W/south River View From Treehouse Deck!

apartment, Riva
Deal Island Bay Cottage - Chesapeake Bay
9.4 329 reviews

Deal Island Bay Cottage

cottage, Chance
King Bed Non-smoking - Chesapeake Bay
9.6 82 reviews

King Bed Non-smoking

apartment, Newport News

Highly Recommended Luxury Apartments in Chesapeake Bay

Indulge in elite tropical living with high-end architecture and absolute privacy at luxury island apartments in Chesapeake Bay.

2 Full Beds|non-smoking - Chesapeake Bay
10 80 reviews

2 Full Beds|non-smoking

apartment, Newport News
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