Best apartment offers in Chesapeake Bay

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Chesapeake Bay apartments
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5236 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.

Family Vacation Retreat W/ In-ground Pool With Private Chesapeake Bay Access! - Chesapeake Bay
9.6 126 reviews

Family Vacation Retreat W/ In-ground Pool With Private Chesapeake Bay Access!

apartment, Cape Charles
This Cape Charles, Virginia holiday home is situated near Kiptopeke State Park, less than 0.8 kilometres from a private community beach and offers easy access to the town of Cape Charles and Williamsburg (driving distance).
The 300 square metre property boasts five bedrooms, three bathrooms, sleeping up to ten adults, and features a saltwater swimming pool, kayaks, a BBQ, and a well-equipped kitchen.

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.

Entire Private 2 Bedrooms House, Nice Neighborhood - Chesapeake Bay
9.4 83 reviews

Entire Private 2 Bedrooms House, Nice Neighborhood

apartment, Arnold
This two-bedroom home is situated in Arnold, a peaceful neighbourhood just 10 miles from Annapolis Harbor and 14 miles from Baltimore-Washington International Airport. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious apartment, spanning 111 square metres, comfortably accommodates up to 5 guests. Enjoy a range of amenities including a private hot tub, a peaceful garden, a fully equipped kitchen, air conditioning, free Wi-Fi and private parking.
Sojourn's Harborage | Pet-friendly - Chesapeake Bay
8.0 1 review

Sojourn's Harborage | Pet-friendly

apartment, Norfolk
This Norfolk apartment, situated in East Ocean View, is less than 0.6km from Norfolk Beaches and within a short drive of Community Beach and Ocean View Beach.
The 74 square metre flat offers one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private balcony, free Wi-Fi, and on-site parking.
Amazing Waterfront House With Expansive Views Of The Chesapeake Bay And Sunsets - Chesapeake Bay
10 9 reviews

Amazing Waterfront House With Expansive Views Of The Chesapeake Bay And Sunsets

apartment, Tolchester
This Rock Hall holiday home, sleeping up to 12 guests, is situated within 10km of The Mainstay, Rock Hall Harbour, and the Waterman's Museum, and within 19km of Ferry Park and Eastern Neck National Wildlife Refuge.
The four-bedroom property boasts three bathrooms, a fully equipped kitchen with microwave and dishwasher, a terrace, garden, parking, internet access, a playground, and a smart TV; enjoy a smoke-free environment and explore the local attractions.
Downings Farmhouse - Historic 6 Bedroom Home - Chesapeake Bay
9.7 22 reviews

Downings Farmhouse - Historic 6 Bedroom Home

apartment, Heathsville
Downings Farmhouse, a historic 1830s general store and post office conversion, is situated in Virginia's Northern Neck, approximately 24-32 km from Belle Isle State Park and local amenities.
This six-bedroom farmhouse sleeps up to 17 guests, boasting multiple living areas, a gourmet kitchen with a 48-inch Wolf range, a games room with pinball and air hockey, and three acres of private grounds including a fire pit and various outdoor games.

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 42 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.
One Bedroom Condo With Marina View - Chesapeake Bay
10 1 review

One Bedroom Condo With Marina View

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.
Walk To Main St: Condo W/ Pool Access In Crisfield - Chesapeake Bay
9.4 8 reviews

Walk To Main St: Condo W/ Pool Access In Crisfield

apartment, Crisfield
This Crisfield waterfront apartment, a short walk from the ferry terminal and shops, offers stunning Daugherty Creek views from its private screened balcony and is located approximately 1.6km from Wellington Beach.
The 133 square metre, three-bedroom property sleeps six guests, boasting two bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, air conditioning, and access to a communal swimming pool and on-site marina.
Oceanfront Beach Condo, Pool, Gym, Fishing Surfing - Chesapeake Bay
9.5 125 reviews

Oceanfront Beach Condo, Pool, Gym, Fishing Surfing

apartment, Virginia Beach
This oceanfront condo is situated directly on the Virginia Beach boardwalk, offering immediate access to the beach and attractions.
The two-bedroom, two-bathroom apartment sleeps six guests and boasts a fully equipped kitchen, high-speed Wi-Fi, an indoor pool, fitness centre, and assigned parking (maximum height 1.95 metres).

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.

Relax & Heal Cottage Near Ocean & Forest Retreat - Chesapeake Bay
9.9 55 reviews

Relax & Heal Cottage Near Ocean & Forest Retreat

apartment, Mathews
This two-bedroom Mathews County cottage, near Davis Creek, is conveniently located approximately a few kilometres from the New Point Comfort Lighthouse and an observation deck offering sunset views.
The self-catering holiday home sleeps six, boasting two living areas, a dedicated workspace with Wi-Fi, a fully equipped kitchen (including fridge and microwave), air conditioning, a garden with barbecue and fire pit, plus private parking and self check-in.
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.
1891 Coastal Charmer: Fully Renovated Farmhouse - Chesapeake Bay
10 141 reviews

1891 Coastal Charmer: Fully Renovated Farmhouse

apartment, White Stone
This charming farmhouse is located in White Stone, just a short distance from the bay, offering easy access to water activities. The property boasts excellent user, location, and cleanliness ratings, making it a great choice for travellers.
This two-bedroom, one-bathroom property can accommodate up to five guests. It comes equipped with a well-stocked kitchen, a relaxing screened porch, a fire pit, and a garden shed with games, along with access to kayaks for an additional fee.
Spacious 4br Coastal Retreat In Bay Creek  Beach & Golf - Chesapeake Bay
10 8 reviews

Spacious 4br Coastal Retreat In Bay Creek Beach & Golf

apartment, Cape Charles
This charming four-bedroom apartment is situated in a peaceful golf cart community in Cape Charles, just a short distance from the beach, bay, and nature trails. It has consistently received excellent reviews from previous guests.
The property comfortably accommodates up to 12 guests and boasts a range of amenities, including air conditioning, internet access, and pet-friendly policies. Enjoy the convenience of a golf cart community, allowing easy access to the nearby Bay Creek Golf Club, biking trails, kayaking opportunities, and fishing spots.

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.

Nyc Style Living - Chesapeake Bay
8.2 18 reviews

Nyc Style Living

apartment, Baltimore
Cozy 2-bedroom Apartment In Welcoming Baltimore With Wifi, Ac - Chesapeake Bay
9.8 13 reviews

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

apartment, Baltimore
Boho Oasis 2 Bed 1 Bath Home In Baltimore City! - Chesapeake Bay
8.6 7 reviews

Boho Oasis 2 Bed 1 Bath Home In Baltimore City!

apartment, Baltimore
Waterfront!! Hot Tub!! 4 Bed/4 Bath Charming Home In The Heart Of Cambridge - Chesapeake Bay
9.0 13 reviews

Waterfront!! Hot Tub!! 4 Bed/4 Bath Charming Home In The Heart Of Cambridge

apartment, Cambridge

Best Chesapeake Bay holiday apartments with air conditioning

Cozy Cedar Cottage-beach Getaway - Chesapeake Bay
10 27 reviews

Cozy Cedar Cottage-beach Getaway

apartment, Long Beach
Quiet Coastal Cottage Escape With Water Views - Chesapeake Bay
9.8 130 reviews

Quiet Coastal Cottage Escape With Water Views

apartment
Lovely 2 Br Condo In 4 Historic Golf Resort - Chesapeake Bay
9.7 113 reviews

Lovely 2 Br Condo In 4 Historic Golf Resort

apartment, Williamsburg
Mid Century Modern 1 Bedroom Apartment - Chesapeake Bay
9.9 126 reviews

Mid Century Modern 1 Bedroom Apartment

apartment, Virginia Beach

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.

5 Bd 3 Bth West Towson Cottage - Chesapeake Bay
9.8 76 reviews

5 Bd 3 Bth West Towson Cottage

apartment, Towson
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