Compare Vacation Rentals & Airbnb in Chesapeake Bay

9615 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Chesapeake Bay vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Chesapeake Bay Vacation rentals: no available offers. Here are other great options for your stay!

King Bed|non-smoking - Chesapeake Bay
10 83 reviews

King Bed|non-smoking

apartment, Newport News
This apartment in North Newport News is situated less than 3 kilometres from Fort Eustis and a short drive from attractions such as Busch Gardens Europe and Water Country USA.
This 14 square meter flat offers accommodation for 2 guests, featuring cable TV with free movies, free high-speed internet, and coin-operated laundry facilities on-site.
King Bed Non-smoking - Chesapeake Bay
9.6 82 reviews

King Bed Non-smoking

apartment, Newport News
This studio flat in Newport News offers convenient access, situated under 5 kilometres from Fort Eustis and a short drive from attractions such as Busch Gardens Europe and the Newport News / Williamsburg International Airport.
This 14 square metre studio apartment accommodates two guests and features air conditioning, parking, and on-site laundry facilities, with some units offering kitchenettes and whirlpool bathtubs.
King Bed Smoking - Chesapeake Bay
9.6 52 reviews

King Bed Smoking

apartment, Newport News
This Newport News flat is located less than 5 kilometres from Fort Eustis and just minutes from Newport News / Williamsburg International Airport, placing guests close to attractions such as Busch Gardens Europe and the Mariners' Museum.
This 14 square metre apartment offers accommodation for two guests with air conditioning and parking, with select units featuring kitchenettes and whirlpool bathtubs, and on-site coin-operated laundry facilities available for convenience.
Adorable Two-bedroom Retreat Close To Easton, Denton, Centreville - Chesapeake Bay
10 29 reviews

Adorable Two-bedroom Retreat Close To Easton, Denton, Centreville

apartment, Queen Anne
This Queen Anne holiday home is situated 1.1km from Tuckahoe State Park and within 14.5km of Adkins Arboretum, Triple Creek Winery, Daniel Crouse Memorial Park, and Caroline Public Library.
The two-bedroom, one-bathroom property sleeps four guests and boasts a fully equipped kitchen, private balcony, garden, spa, parking, and free Wi-Fi; nearby activities include exploring Tuckahoe State Park and visiting local wineries.

Frequently Asked Questions about vacation rentals in Chesapeake Bay

  • Which neighborhood in Baie de Chesapeake should you consider for a vacation rental?

    If you're looking for a great location for a vacation rental, I'd recommend Ocean City. It's a lively seaside town with plenty of shops, restaurants, and attractions. You'll find a wide range of rental options, from cosy beach houses to spacious apartments, to suit your group size and budget.
  • What are the best Airbnb and vacation rentals in Chesapeake Bay?

    Gem In The Heart Of The Fan #1, Lovely Large Room By River In "Kingsmill On The James" and Beautiful 1-bdrm Carytown - Fan - Vmfa are the most popular Airbnb and vacation rentals in Chesapeake Bay among travelers.

  • What are the top family-friendly attractions in Baie de Chesapeake?

    For family fun, you can't beat the National Aquarium in Baltimore. It's home to a wide variety of marine life, including sharks, dolphins, and sea turtles. Another great option is the Maryland Science Center, which has interactive exhibits and a planetarium. And for a day of outdoor adventure, head to Assateague Island National Seashore, where you can spot wild horses roaming the beach.
  • What are the most popular Airbnbs in Chesapeake Bay?

  • When is the best time to book a vacation rental in Baie de Chesapeake?

    To get the best deals and avoid the crowds, it's best to book your vacation rental in the shoulder seasons, like spring or autumn. The weather is still pleasant, but the prices are lower and the crowds are smaller. If you're looking for a summer getaway, book your rental well in advance, as they tend to sell out quickly.
  • What are the best vacation rentals with a pool in Chesapeake Bay?

  • What events or festivals should visitors check out in and around Baie de Chesapeake?

    There are lots of great events to check out in the area, but one of my favourites is the Annapolis Maritime Museum's OysterFest in October. It's a celebration of all things oyster, with live music, food stalls, and oyster shucking competitions. You can also check out the annual Maryland Seafood Festival, which takes place in October in Crisfield. It's a huge festival with a focus on fresh seafood and local culture.
  • What are the best rentals for families and kids in Chesapeake Bay?

  • What are the best budget-friendly activities in Baie de Chesapeake?

    For a budget-friendly day out, head to the Chesapeake Bay Maritime Museum in St. Michaels. It's a great place to learn about the history of the Bay and see historic boats. You can also explore the many parks and nature trails in the area, which are free to access. For a unique experience, take a free ferry ride to Tilghman Island, which is known for its beautiful scenery and charming shops.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesapeake Bay?

  • What are the best restaurants with local dishes in Baie de Chesapeake?

    For a taste of local cuisine, you should try the Chesapeake Inn in Stevensville. They're famous for their crab cakes, which are made with fresh, local crab meat. Another great option is The Chart House in Annapolis, which has stunning views of the Bay and a menu featuring fresh seafood dishes. You'll also find plenty of casual seafood restaurants along the waterfront, where you can enjoy a delicious meal with a view.
  • What are the best walking or cycling routes in Baie de Chesapeake?

    For a scenic walk or bike ride, check out the Bay Trail, which stretches for over 300 kilometres along the shores of the Chesapeake Bay. There are several sections of the trail, so you can choose a route that suits your fitness level and interests. Another great option is the Annapolis Loop Trail, which takes you through the historic streets of Annapolis and along the waterfront. You can also find plenty of shorter trails in local parks and nature reserves.
  • Are there pet-friendly attractions in Baie de Chesapeake?

    Yes, there are plenty of pet-friendly attractions in the area. Many of the beaches allow dogs, and there are also several dog parks where your furry friend can run and play. You can also find pet-friendly restaurants and cafes, where you can enjoy a meal with your dog. For a fun day out, check out the Chesapeake Bay Maritime Museum, which welcomes well-behaved dogs on a leash.
  • What are the benefits of choosing a vacation rental in Baie de Chesapeake?

    Vacation rentals offer a great deal of flexibility and privacy, as you have your own space to relax and unwind. They're also often more spacious and affordable than hotels, especially if you're travelling with a large group or family. Many rentals also have kitchens, which allow you to prepare your own meals and save money on dining out.
  • What are the top sports attractions and facilities in Baie de Chesapeake?

    The Chesapeake Bay area is a great place for sports enthusiasts. You can enjoy water sports like sailing, kayaking, and fishing. There are also several golf courses in the area, including the renowned Bayside Resort Golf Club. For a unique sporting experience, check out the US Naval Academy in Annapolis, which offers tours of its athletic facilities and events.

Popular destinations

©2026 cozycozy.com