Vacation Rentals in Chesapeake Bay

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Chesapeake Bay holiday rentals
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6706 Holiday rentals and Airbnb in Chesapeake Bay

Best family friendly Chesapeake Bay holiday rentals

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

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway! - Chesapeake Bay
10 239 reviews
Chesapeake Bay
27/06 – 04/07
A$547/nighttotal: A$3829 (7 )

Your Annapolis Waterfront Retreat For A Weekend Or Any-day Getaway!

1 3
cottage , Annapolis
This charming waterfront cottage is located in West Annapolis, just a short walk from the US Naval Academy and a 1.5-mile stroll from the Annapolis City Dock. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This delightful cottage offers 65 square metres of space and can accommodate up to four guests. The property boasts a fully equipped kitchen, a screened-in porch, a private waterfront backyard with a fire pit, and a private dock with access to Weems Creek, making it ideal for relaxing and enjoying the beautiful surroundings.
Romantic Waterfront Abode With Patio And Dock! - Chesapeake Bay
9.8 65 reviews
Chesapeake Bay
29/08 – 05/09
A$264/nighttotal: A$1848 (7 )

Romantic Waterfront Abode With Patio And Dock!

1 2
house , Deltaville
This waterfront property is situated in Deltaville, a charming town on Virginia's Middle Peninsula, just 67 kilometres from Newport News/Williamsburg International Airport. It has consistently received excellent ratings for its location, cleanliness and overall experience.
The house has one bedroom and one bathroom, covering 70 square metres and accommodating up to two guests. It features a fully equipped kitchen, air conditioning, a private patio and dock, free Wi-Fi, and a garden with a spa.
The Atrium Resort, Virginia Beach By Vacatia - Chesapeake Bay
8.3 2880 reviews
Chesapeake Bay
01/10 – 05/10
A$203/nighttotal: A$812 (4 )

The Atrium Resort, Virginia Beach By Vacatia

1 3
resort , Virginia Beach
The Atrium Resort by VSA Resorts is located directly on the Virginia Beach Boardwalk, just a short walk from the beach and a couple of minutes' drive from attractions like Jungle Golf and the Old Coast Guard Station Museum. The resort has consistently received very good ratings for its location, cleanliness, and overall experience.
The accommodation offers spacious suites with full kitchens and living rooms, ideal for families or groups. Guests can enjoy a range of facilities, including a swimming pool, hot tub, fitness centre, and free Wi-Fi.
* Private Suite Full Of Style & Comfort * - Chesapeake Bay
9.0 47 reviews
Chesapeake Bay
23/08 – 28/08
A$176/nighttotal: A$880 (5 )

* Private Suite Full Of Style & Comfort *

1 2
apartment , Lutherville
This one-bedroom apartment is situated in Lutherville Timonium, just 5km from Goucher College, Loch Raven Reservoir, and Towson Town Center, offering easy access to a range of attractions and amenities. It has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The apartment comfortably accommodates up to four guests and features a fully equipped kitchen, a washing machine, a terrace, a garden, and parking. Enjoy a relaxing stay with access to a range of amenities, including a Smart TV, DVD player, and air conditioning.

Best Chesapeake Bay holiday rentals with a pool

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

Bethpage Two-bedroom Cottage 4 - Chesapeake Bay
8.5 4 reviews
Chesapeake Bay
29/08 – 05/09
A$473/nighttotal: A$3311 (7 )

Bethpage Two-bedroom Cottage 4

2 2
house , Urbanna
Bethpage Two-Bedroom Cottage 4 is located in Urbanna, Virginia, approximately 67km from Newport News/Williamsburg International Airport.
This 37-square-metre self-catering cottage sleeps seven, boasting two bedrooms, one bathroom, a private patio, a fully equipped kitchen, free Wi-Fi, on-site parking, and access to a seasonal outdoor swimming pool with water slides and a children's playground.
Beach Without The Bustle - Chesapeake Bay
10 37 reviews
Chesapeake Bay
27/06 – 04/07
A$408/nighttotal: A$2856 (7 )

Beach Without The Bustle

2 3
apartment , Betterton
This Betterton waterfront apartment, situated just steps from Betterton Beach and within 20km of Washington College, Crow Farm and Vineyard, and Chestertown Dog Park, offers a convenient location for exploring the area.
The 111 square metre property boasts two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, free Wi-Fi, a terrace, swimming pool, and tennis court.
Virginia Beach Oceanfront/boardwalk, Beach, Pool & Balcony - Chesapeake Bay
9.8 64 reviews
Chesapeake Bay
01/10 – 05/10
A$372/nighttotal: A$1488 (4 )

Virginia Beach Oceanfront/boardwalk, Beach, Pool & Balcony

1 3
apartment , Virginia Beach
This apartment is located in Northeast Virginia Beach, just a short walk from the beach and the Virginia Beach Boardwalk, with Sandbridge Beach a short 4.3 kilometres away. The apartment has received excellent reviews from previous guests, highlighting its convenient location and comfortable amenities.
This one-bedroom flat provides 28 square metres of space, comfortably accommodating up to three guests. It offers a fully equipped kitchen, a balcony, and a washing machine, as well as free Wi-Fi and access to a swimming pool and garden.
Kings Creek Plantation By Tripforth - Chesapeake Bay
9.1 726 reviews
Chesapeake Bay
30/07 – 05/08
A$563/nighttotal: A$3378 (6 )

Kings Creek Plantation By Tripforth

2 6
house , Williamsburg
King's Creek Resort By Endless Resorts is conveniently located just outside Williamsburg's historic district, offering easy access to both theme parks and the historic landmarks of Colonial Williamsburg, which is just 7.2 miles away. The resort has received excellent ratings for its location, cleanliness and overall user experience.
The resort offers a range of accommodation options, including rooms and suites. Guests can enjoy amenities such as a swimming pool, fitness centre, restaurant and spa, as well as activities like mini-golf and a playground for families.

Frequently asked questions about holiday rentals in Chesapeake Bay

  • What should a first-time visitor not miss in Baie de Chesapeake?

    For a first-time visit, you can't go wrong with a trip to Annapolis. It's the state capital and is full of history, with the United States Naval Academy and the historic district. You can also enjoy a boat trip to see the Chesapeake Bay Bridge, a truly iconic sight.
  • What are the best Airbnb and holiday rentals in Chesapeake Bay?

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

    If you're looking for a more relaxed atmosphere, try Ocean City. It's a popular seaside resort with a long stretch of beach and a lively boardwalk. For something more historic, Annapolis is a good choice, with plenty of charming bed and breakfasts and historic houses to choose from.
  • What are the most popular Airbnbs in Chesapeake Bay?

    Among the Airbnbs in Chesapeake Bay, Dune Cottage Sea Suite, Gem In The Heart Of The Fan #1 and Beautiful 1-bdrm Carytown - Fan - Vmfa are the most popular ones.

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

    For families, the National Aquarium in Baltimore is a must-see, with a huge variety of marine life. The Maryland Science Center is also great for kids, with interactive exhibits and a planetarium. You can also enjoy a day out at Assateague Island National Seashore, where you can see wild horses roaming the beach.
  • What are the best holiday rentals with a pool in Chesapeake Bay?

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

    To get the best deals, book your vacation rental in the shoulder seasons, April-May or September-October. You'll avoid the crowds and the prices will be lower. If you're looking for warm weather and sunshine, July and August are the busiest months.
  • 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 beach at Ocean City or Assateague Island. You can also take a walk or cycle along the Chesapeake Bay Trail, which stretches over 300 km and offers stunning views of the bay. You can also find free concerts and events in many of the towns and cities in the region.
  • 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 local seafood, try The Chart House in Annapolis, which has a great view of the harbour. In Baltimore, you can't go wrong with Faidley's Seafood, known for their delicious crab cakes. If you're looking for something a little more casual, try The Crab Claw in Ocean City, which offers a relaxed atmosphere and fresh seafood.
  • What are the best walking or cycling routes in Baie de Chesapeake?

    The Chesapeake Bay Trail is a great option for walking or cycling, offering a scenic route along the bay. In Annapolis, you can enjoy a walk around the historic district, taking in the beautiful architecture. The Baltimore Inner Harbor is also a great place for a stroll, with plenty of shops and restaurants to explore.
  • Are there pet-friendly attractions in Baie de Chesapeake?

    Many beaches in the Chesapeake Bay region are dog-friendly, including Ocean City and Assateague Island. You can also find pet-friendly restaurants and hotels in many towns and cities.
  • What are the benefits of choosing a vacation rental in Baie de Chesapeake?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Baie de Chesapeake?

    The Chesapeake Bay region is home to a number of sports attractions, including the M&T Bank Stadium, home to the Baltimore Ravens, and Camden Yards, home to the Baltimore Orioles. The region also has a number of golf courses, marinas, and fishing spots.

Destinations nearby

Best Chesapeake Bay holiday rentals with a balcony

Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay - Chesapeake Bay
9.8 61 reviews
Chesapeake Bay
29/08 – 05/09
A$320/nighttotal: A$2240 (7 )

Waterview Cottage With Amazing Sunsets Overlooking The Chesapeake Bay

2 2
cottage , Cecilton
This charming cottage is located in Cecilton, Maryland, just 40 kilometres from Bohemia Vista Marina, Crow Farm and Vineyard, and the C and D Canal Museum. It has received excellent user ratings, making it a popular choice for travellers.
The cottage has two bedrooms and one bathroom, offering comfortable accommodation for up to six guests. It features a well-equipped kitchen, a private garden, a balcony, and a jacuzzi, providing everything you need for a relaxing and enjoyable stay.
Sojourn's Harborage Pet-friendly - Chesapeake Bay
9.0 6 reviews
Chesapeake Bay
23/08 – 28/08
A$281/nighttotal: A$1405 (5 )

Sojourn's Harborage Pet-friendly

1 2
apartment , Norfolk
This East Ocean View flat is less than 0.8km from Norfolk's beaches and within 4.8km of Community Beach and Ocean View Beach.
The 74 square metre self-catering apartment sleeps two, boasting a balcony, garden, free parking, Wi-Fi, and a fully equipped kitchen including a washing machine.
The Carraige House Of Mount Vernon - Chesapeake Bay
10 2 reviews
Chesapeake Bay
30/07 – 05/08
A$526/nighttotal: A$3156 (6 )

The Carraige House Of Mount Vernon

3 6
house , Baltimore
The Carriage House in Baltimore offers convenient access to Penn Station, a short walk from the Walters Art Museum, and within 2.4km of the Inner Harbour and Baltimore Convention Centre.
This three-bedroom, three-bathroom villa boasts 125 square metres of space, sleeping up to 11 guests and featuring a fully equipped kitchen, Wi-Fi, air conditioning, a jacuzzi, and a private balcony.
The Heron's Nest At Atlantic Marina - Chesapeake Bay
9.8 315 reviews
Chesapeake Bay
23/08 – 28/08
A$243/nighttotal: A$1215 (5 )

The Heron's Nest At Atlantic Marina

1 2
cottage , Lake Shore
This charming lakeside retreat is located in Pasadena, Maryland, just a short drive from historical landmarks and art galleries. It has received excellent reviews from previous guests.
The cottage offers 54 square metres of living space, accommodating up to four guests in a comfortable layout with one bedroom and one bathroom. You can enjoy a range of amenities including a swimming pool, a terrace, and a garden, and the property is perfect for enjoying water activities like fishing and boating.

Best Chesapeake Bay holiday rentals with parking

️The Speakeasy️downtown Newport News! - Chesapeake Bay
9.3 129 reviews
Chesapeake Bay
01/10 – 05/10
A$271/nighttotal: A$1084 (4 )

️The Speakeasy️downtown Newport News!

1 3
apartment , Newport News
This apartment is ideally located in Newport News, just 0.3 kilometres from City Hall and within a 5 kilometre radius of The Newsome House Museum and Cultural Center and King-Lincoln Park. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers visiting Newport News.
The flat offers one bedroom and one bathroom, spanning 88 square metres and comfortably accommodating up to four guests. It features a modern kitchen with a fridge, freezer, microwave, and dishwasher, as well as a washing machine, sofa bed, TV, hair dryer, iron/ironing board, and a desk, providing everything you need for a comfortable and convenient stay.
Salisbury Hideaway - Chesapeake Bay
9.9 16 reviews
Chesapeake Bay
30/07 – 05/08
A$443/nighttotal: A$2658 (6 )

Salisbury Hideaway

2 6
house , Salisbury
Salisbury Hideaway is located in Salisbury, just 10km from Salisbury-Ocean City Wicomico Regional Airport, offering easy access to the local area.
This 135 square metre home features two bedrooms, one bathroom, and a fully equipped kitchen, comfortably accommodating up to 11 guests, with a garden, terrace, and fitness room for relaxation and recreation.
1br Apartment With Rooftop Deck &  City Views - Chesapeake Bay
8.0 1 review
Chesapeake Bay
27/06 – 04/07
A$335/nighttotal: A$2345 (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.
Cozy Home Away From Home Just Minutes From The Beach - Chesapeake Bay
9.7 177 reviews
Chesapeake Bay
01/10 – 05/10
A$289/nighttotal: A$1156 (4 )

Cozy Home Away From Home Just Minutes From The Beach

1 3
apartment , Virginia Beach
This one-bedroom apartment is located just 500 metres from Pacific Avenue and the Virginia Beach Boardwalk, with Sandbridge Beach and the Virginia Beach Fishing Pier within a 24 kilometre radius. It has been highly rated by previous guests, receiving excellent reviews for its location, cleanliness, and overall experience.
The apartment is 46 square metres in size and comfortably accommodates up to four guests. It comes equipped with a kitchen, a bathroom, a swimming pool, a spa, parking, and internet access, as well as a water park within the building.
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