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.

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
This Riva apartment, located within 10km of Annapolis Harbour Center and Westfield Annapolis Mall, offers easy access to Annapolis's key attractions.
The 41-square-metre self-catering flat features one bedroom, one bathroom, sleeps four, and includes a terrace, garden, parking, WiFi, and a barbecue.

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.

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.
Luxury 2 Bedroom Basement - Chesapeake Bay
9.7 20 reviews

Luxury 2 Bedroom Basement

apartment, Bowie
This one-bedroom, one-bathroom apartment in Bowie, Maryland, is situated approximately 29 kilometres from Washington, D.C. landmarks including the Supreme Court and the US Capitol.
The self-catering flat offers free Wi-Fi, air conditioning, a flat-screen TV, and sleeps up to five guests, with easy access to Addison Road-Seat Pleasant station (24 km) and local amenities.
Living On Island Time - Chesapeake Bay
10 166 reviews

Living On Island Time

apartment, Piney Point
This apartment is situated on St. George Island, just a short distance from Piney Point, offering a peaceful retreat in a tranquil setting. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The accommodation features two bedrooms and two bathrooms, comfortably sleeping up to four guests. Guests can enjoy a range of amenities, including a private pier, paddle boards, a fire pit, a full bar setup, and a spacious kitchen with a large island, perfect for preparing meals and socialising.
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.

Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth - Chesapeake Bay
8.6 11 reviews

Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth

apartment, Portsmouth
This one-bedroom flat in Portsmouth is situated a 19-minute drive from Town Point Park and 40 minutes from Chesapeake Bay, offering convenient access to the Chrysler Museum of Art and the Children's Museum of Virginia.
This pet-friendly apartment accommodates up to three guests and includes on-site parking, complimentary Wi-Fi, air conditioning, and essential amenities such as towels, linens, and soap, with a check-out time of 12:00.
Luxurious 3 Bedroom Condo Sleeps 8! Brand New Full Size Washer And Dryer..!! - Chesapeake Bay
9.8 149 reviews

Luxurious 3 Bedroom Condo Sleeps 8! Brand New Full Size Washer And Dryer..!!

apartment, Williamsburg
This 3-bedroom house is located in the Kingsmill Resort community, just 5km from Busch Gardens and a short drive from other attractions like Water Country USA, Colonial Williamsburg, Jamestown, and Yorktown. The property enjoys excellent ratings for location, cleanliness, and user experience.
The house spans 149 square metres and comfortably sleeps 8 guests. It offers a fully equipped kitchen, a washer and dryer, a swimming pool, a terrace, parking, and access to tennis courts, playgrounds, and walking paths in the community.
Private Pool & Stunning Bay Views On Kent Island - Chesapeake Bay
9.2 62 reviews

Private Pool & Stunning Bay Views On Kent Island

apartment, Stevensville
This Stevensville holiday home is ideally situated within 14.5km of Matapeake State Park, Romancoke Wharf County Park, and Paul Reed Smith Guitars.
This 185 square metre property boasts three bedrooms, a sofa bed, three bathrooms, a fully equipped kitchen, private pool, barbecue facilities, on-site laundry, and accommodates up to twelve guests.
Eclectic Apartment- 2-4 Friends- Family Centered. Safe Neighborhood - Chesapeake Bay
10 6 reviews

Eclectic Apartment- 2-4 Friends- Family Centered. Safe Neighborhood

apartment, Gloucester Courthouse
This Gloucester Courthouse apartment, situated within 9.6km of Beaverdam Park and the Captain John Smith National Historic Trail, offers easy access to local attractions and Riverside Walter Reed Hospital.
The one-bedroom, one-bathroom flat sleeps four guests and boasts a private pool, private yard, and access to a swimming pool and parking; it's a smoke-free property.

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.

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.
Bayberry - Awesome Solo Stove Fire Pit - Chesapeake Bay
9.8 80 reviews

Bayberry - Awesome Solo Stove Fire Pit

apartment, Kilmarnock
This charming cottage is located in Reedville, Virginia, a coastal town on the Chesapeake Bay, just a short drive from the Northern Neck Wine Trail and Belle Isle State Park. The property has received excellent ratings for location, cleanliness, and overall user experience.
The three-bedroom home comfortably sleeps six guests and features a spacious sunporch and a private outdoor area with a fire pit, deck, and patio. Guests can enjoy a range of amenities, including a well-equipped kitchen, air conditioning, and a private garden.
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).
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.

Water View Cottage - Chesapeake Bay
9.9 169 reviews

Water View Cottage

apartment, Deal Island
1 Mi To Boardwalk: Convenient North Beach Apt! - Chesapeake Bay
8.8 5 reviews

1 Mi To Boardwalk: Convenient North Beach Apt!

apartment, North Beach
A Little Serenity- A Cozy One Bedroom Escape In Quant Onancock,mid-eastern Shore - Chesapeake Bay
9.8 13 reviews

A Little Serenity- A Cozy One Bedroom Escape In Quant Onancock,mid-eastern Shore

apartment, Onancock
Woodland Hideaway: Cozy 1 Bedroom Apartment Tucked Away In A Quiet Neighborhood. - Chesapeake Bay
9.8 10 reviews

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

apartment, Dover

Best Chesapeake Bay holiday apartments with air conditioning

Pet-friendly Smith Island Cottage W/ Golf Cart! - Chesapeake Bay
9.9 38 reviews

Pet-friendly Smith Island Cottage W/ Golf Cart!

apartment, Smith Island
2 Full Beds Non-smoking - Chesapeake Bay
9.5 81 reviews

2 Full Beds Non-smoking

apartment, Newport News
King Bed Non-smoking - Chesapeake Bay
9.6 82 reviews

King Bed Non-smoking

apartment, Newport News
Spacious Riverfront Loft Close To Downtown And Dining - Chesapeake Bay
9.0 13 reviews

Spacious Riverfront Loft Close To Downtown And Dining

apartment, Salisbury

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.

Beachfront Home On The River - 01 - Chesapeake Bay
9.9 27 reviews

Beachfront Home On The River - 01

apartment, Piney Point
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