Compare Vacation Rentals & Airbnb in Chesapeake Bay

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Chesapeake Bay vacation rentals
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6706 Rentals and Airbnb in Chesapeake Bay

Best family friendly Chesapeake Bay vacation rentals

Among the 6706 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals

Cozy Modern Apt In The Heart Of Fells Point! - Chesapeake Bay
9.0 22 reviews
Chesapeake Bay
23/08 – 28/08
$245/nighttotal: $1225 (5 )

Cozy Modern Apt In The Heart Of Fells Point!

2 2
apartment , Baltimore
This Fells Point apartment in Baltimore is situated a short 1.8km walk from Harbour East Marina and within 3.2km of the Baltimore Convention Center and The Walters Art Museum.
This 60 square metre flat offers two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen with dishwasher, in-unit laundry, and free Wi-Fi.
Last Weeks Open! Waterfront Retreat W/ Pool, Hot Tub, Dock & Sand Beach - Chesapeake Bay
9.7 74 reviews
Chesapeake Bay
27/06 – 04/07
$1166/nighttotal: $8162 (7 )

Last Weeks Open! Waterfront Retreat W/ Pool, Hot Tub, Dock & Sand Beach

3 3
apartment , Irvington
This four-bedroom apartment is situated on the sandy shores of the Corrotoman River, a short distance from Irvington, Virginia, offering a tranquil escape from the hustle and bustle of city life. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment spans 427 square metres and comfortably accommodates up to 12 guests. Enjoy a range of amenities including a private saltwater pool, hot tub, sandy beach, kayaks, paddleboards, a canoe, and a private dock for fishing and crabbing, all with stunning river views.
Sun Sea And Sand - Chesapeake Bay
10 393 reviews
Chesapeake Bay
23/08 – 28/08
$272/nighttotal: $1360 (5 )

Sun Sea And Sand

1 2
house , Hampton
This waterfront property is situated in Hampton, Virginia, just a short distance from the port of Hampton Roads, offering views of the Chesapeake Bay and the bustling activity of the ships entering and exiting the harbour. The property has consistently received excellent ratings for its cleanliness, location and user experience.
This two-bedroom house can accommodate up to four guests and is perfect for families. It is equipped with a fully fitted kitchen, high-speed Wi-Fi, and a private balcony with stunning views of the Bay. Guests can enjoy direct access to the decking and dock areas, perfect for relaxing or taking a dip in the water.
88 M² Apartment ∙ 1 Bedroom ∙ 4 Guests - Chesapeake Bay
Chesapeake Bay
27/06 – 04/07
$320/nighttotal: $2240 (7 )

88 M² Apartment ∙ 1 Bedroom ∙ 4 Guests

1 3
apartment , Newport News
This two-bedroom apartment is situated in the heart of Newport News, just a short walk from the lively waterfront and a stone's throw from the city's renowned breweries and distilleries.
The 88 square metre apartment offers a modern and stylish living space, comfortably accommodating up to four guests and featuring a fully equipped kitchen with a dishwasher, a comfortable living area, and free Wi-Fi.

Best Chesapeake Bay vacation rentals with a pool

Among the 6706 accommodations in Chesapeake Bay, here are the 4 best rentals with a pool

Rooftop Chesapeake Bay Views! Waterfront Retreat - Chesapeake Bay
Chesapeake Bay
23/08 – 28/08
$300/nighttotal: $1500 (5 )

Rooftop Chesapeake Bay Views! Waterfront Retreat

1 2
apartment , Mathews
This studio apartment offers direct Mobjack Bay waterfront access in Westville, approximately 21 kilometres from Williams Wharf Landing and the Gwynn's Island Museum, with the Gloucester Museum of History and Deltaville Maritime Museum also nearby.
This pet-friendly accommodation provides 60 square metres of living space for up to two guests, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, a private balcony, and access to community amenities including a seasonal swimming pool and kayaks.
Four Sails - Oceanfront And City View Balconies! - Chesapeake Bay
9.7 6 reviews
Chesapeake Bay
27/06 – 04/07
$274/nighttotal: $1918 (7 )

Four Sails - Oceanfront And City View Balconies!

1 3
apartment , Virginia Beach
This oceanfront apartment is located at the northern end of Virginia Beach's boardwalk, near numerous restaurants and a 16km drive from Ocean Breeze Water Park, with Colonial Williamsburg, Yorktown, and Jamestown also within easy reach.
This one-bedroom, one-bathroom condo offers a king-sized bed, a pull-out queen-sized sofa bed sleeping four, a fully equipped kitchen, and access to resort amenities including an indoor heated pool, fitness centre with sauna, and free bikes for exploring the 5km boardwalk; daily housekeeping is provided.
Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc. - Chesapeake Bay
10 51 reviews
Chesapeake Bay
29/08 – 05/09
$361/nighttotal: $2527 (7 )

Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc.

2 2
cottage , Dunkirk
This charming cottage is situated just a short distance from Fridays Creek Winery and the Patuxent River, offering a peaceful escape in the heart of Dunkirk, Maryland. It has received excellent reviews from previous guests, making it a popular choice for travellers seeking a relaxing getaway.
The cottage spans 84 square metres and comfortably accommodates up to four guests in its two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private outdoor pool, barbecue grills, and a spacious garden, as well as the convenience of a fully equipped kitchen, free Wi-Fi and a private patio.
Bethpage Hewick Three-bedroom Cottage 30 - Chesapeake Bay
9.2 19 reviews
Chesapeake Bay
30/07 – 05/08
$977/nighttotal: $5862 (6 )

Bethpage Hewick Three-bedroom Cottage 30

6 6
house , Urbanna
Bethpage Hewick One-Bedroom Cottage 25 is situated in the Bethpage area of Urbanna, approximately 68 kilometres from Newport News/Williamsburg International Airport.
This self-contained cottage offers 37 square metres of space, comprising a bedroom, separate living room, fully equipped kitchen, patio, and access to on-site amenities including a snack bar, children's playground, and bicycle rental.

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.

Destinations nearby

Best Chesapeake Bay vacation rentals with a balcony

Barclay Towers Resort Oceanfront Unit With Full Oceanfront Balcony - Chesapeake Bay
10 1 review
Chesapeake Bay
27/06 – 04/07
$289/nighttotal: $2023 (7 )

Barclay Towers Resort Oceanfront Unit With Full Oceanfront Balcony

1 3
resort , Virginia Beach
Barclay Towers Resort, situated in the Northeast Virginia Beach district directly on the Virginia Beach Boardwalk, offers oceanfront accommodation with easy access to the beach and attractions such as the Veterans United Home Loans Amphitheatre.
The Barclay Towers Resort Oceanfront Unit With Full Oceanfront Balcony features a one-bedroom suite sleeping up to four guests, complete with a fully equipped kitchen, an indoor pool, hot tub, fitness centre, and free parking across the street.
Family-friendly Home In Baltimore With Wifi, Ac, Pool Table, Washer & Dryer - Chesapeake Bay
9.8 6 reviews
Chesapeake Bay
23/08 – 28/08
$191/nighttotal: $955 (5 )

Family-friendly Home In Baltimore With Wifi, Ac, Pool Table, Washer & Dryer

2 2
apartment , Baltimore
This Berea property is conveniently located 2.4km from Johns Hopkins Hospital and 1.8km from the Maryland Institute College of Art, offering easy access to both medical facilities and cultural attractions.
This two-bedroom, two-bathroom house sleeps four guests and features a fully equipped kitchen, free Wi-Fi, on-site parking, and a family-friendly playground nearby, making it ideal for families visiting Baltimore.
Fisher House - Downtown Annapolis! - Chesapeake Bay
Chesapeake Bay
30/07 – 05/08
$810/nighttotal: $4860 (6 )

Fisher House - Downtown Annapolis!

1 6
house , Annapolis
House listing. Your accommodation will be based in Annapolis.
Facilities and services include a washing machine, a kitchen and a fridge. Take advantage of the terrace in this house in Annapolis.
1br Apartment With Rooftop Deck &  City Views - Chesapeake Bay
8.0 1 review
Chesapeake Bay
27/06 – 04/07
$329/nighttotal: $2303 (7 )

1br Apartment With Rooftop Deck & City Views

1 3
apartment , Baltimore
This Baltimore flat is located in the Inner Harbour district, offering walking distance to transit and attractions such as the National Aquarium.
This 93 square meter flat accommodates up to four guests with two bedrooms and one bathroom, featuring a fully equipped kitchen, air conditioning, a terrace, and access to a rooftop swimming pool and a converted bank vault lounge.

Best Chesapeake Bay vacation rentals with parking

Holiday Inn Express & Suites Williamsburg By Ihg - Chesapeake Bay
8.4 1481 reviews
Chesapeake Bay
27/06 – 04/07
$287/nighttotal: $2009 (7 )

Holiday Inn Express & Suites Williamsburg By Ihg

1 3
resort , Williamsburg
The Holiday Inn Express & Suites Williamsburg is situated close to Colonial Williamsburg and a short drive from Busch Gardens theme park, making it a convenient base for exploring the area. The hotel has consistently received very good ratings for location, cleanliness and overall experience.
The hotel offers a range of modern and comfortable rooms, all featuring convenient in-room amenities. Guests can enjoy a complimentary hot breakfast buffet, relax in the indoor pool or exercise room, and make use of the on-site restaurant, bar, and tennis court.
Cottage On A Private Island In The York River - Chesapeake Bay
10 370 reviews
Chesapeake Bay
29/08 – 05/09
$321/nighttotal: $2247 (7 )

Cottage On A Private Island In The York River

3 2
cottage , Gloucester Point
This charming waterfront cottage is located in Gloucester Point, just 9 kilometres from Machicomoco State Park, Yorktown Beach, and Yorktown Farmers Market, offering easy access to a variety of attractions and activities. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
This 3-bedroom property spans 139 square metres and can accommodate up to 8 guests, making it ideal for families or groups. The cottage features a fully equipped kitchen, a private garden, a swimming pool, a spa, and a terrace, ensuring a relaxing and enjoyable stay.
Home Away - Chesapeake Bay
9.6 87 reviews
Chesapeake Bay
23/08 – 28/08
$123/nighttotal: $615 (5 )

Home Away

1 2
apartment , Fort Meade
This Hanover apartment, situated approximately 23-24 km from Baltimore attractions such as Carroll Park, the Sports Legends Museum at Camden Yards, and the Baltimore Convention Center, and 9 km from Baltimore/Washington International Thurgood Marshall Airport, offers convenient access to Fort Meade and wider Baltimore.
The 70-square-metre one-bedroom flat provides comfortable accommodation for two guests, featuring a fully equipped kitchenette, free Wi-Fi, on-site parking, and a private entrance; nearby attractions include the Inner Harbor and Federal Hill.
Cozy 1 Bdrm/1 Bath Charles Village/hopkins Apartment - Chesapeake Bay
9.0 2 reviews
Chesapeake Bay
27/06 – 04/07
$201/nighttotal: $1407 (7 )

Cozy 1 Bdrm/1 Bath Charles Village/hopkins Apartment

1 3
apartment , Baltimore
This Charles Village apartment in Baltimore is situated a 15-minute walk from both MedStar Union Memorial Hospital and Johns Hopkins University, and within 4.8km of the National Aquarium and Baltimore Convention Centre.
The one-bedroom flat sleeps three, offering a full kitchen with oven, stovetop, microwave and fridge, plus a washer, sofa bed, Smart TV, and games; nearby public transport includes North Avenue and Baltimore Penn Stations within a 30-minute walk.
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