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

Rivers Edge Retreat With Kayaks And River Access! - Chesapeake Bay
9.6 115 reviews
Chesapeake Bay
29/08 – 05/09
A$935/nighttotal: A$6545 (7 )

Rivers Edge Retreat With Kayaks And River Access!

5 2
house , Heathsville
Rivers Edge Retreat is situated in Reedville, a charming town on the Northern Neck of Virginia, just 105 kilometres from Newport News/Williamsburg International Airport. The property has received excellent ratings for its location, cleanliness and overall experience.
The five-bedroom house spans 353 square metres and comfortably accommodates up to 12 guests. Enjoy the beautiful river views from the terrace, relax in the garden, or take advantage of the included kayaks for a day out on the water.
Charming Waterfront Cottage With Private Dock. Close To Annapolis & Usna - Chesapeake Bay
10 225 reviews
Chesapeake Bay
30/07 – 05/08
A$673/nighttotal: A$4038 (6 )

Charming Waterfront Cottage With Private Dock. Close To Annapolis & Usna

3 6
cottage , Mayo
This family-friendly cottage is situated in Edgewater, Mayo, just a short drive from Triton Beach and other local attractions. It enjoys an excellent user rating, making it a popular choice for families seeking a relaxing getaway.
The three-bedroom property, spanning 172 square metres, comfortably accommodates up to 11 guests. Enjoy a fully equipped kitchen, a spacious garden, and a terrace, perfect for al fresco dining and taking in the scenic views.
Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment - Chesapeake Bay
9.4 14 reviews
Chesapeake Bay
29/08 – 05/09
A$253/nighttotal: A$1771 (7 )

Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment

1 2
house , Brock Hall
This Brock Hall house, near Addison Road-Seat Pleasant Station (22km) and approximately 32km from both the Supreme Court and the US Capitol, offers a convenient base for exploring the area.
The 223-square-metre property boasts a private pool, garden, terrace, fitness centre, and parking, accommodating up to six guests in its one-bedroom, one-bathroom layout with a fully equipped kitchenette.
Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger - Chesapeake Bay
9.9 68 reviews
Chesapeake Bay
29/08 – 05/09
A$1025/nighttotal: A$7175 (7 )

Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger

3 2
cottage , Piney Point
This charming cottage is located in Piney Point, Maryland, just a short distance from the Chesapeake Bay. It benefits from excellent user, location and cleanliness ratings.
The cottage has three bedrooms, accommodating up to eight guests, and offers a range of amenities, including private beach access, a fishing pier, kayaks and stand-up paddle boards, a Tesla charger, and contactless check-in.

Best Chesapeake Bay holiday rentals with a pool

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

2br Luxury Apartment Rooftop Pool & Gym - Chesapeake Bay
9.9 6 reviews
Chesapeake Bay
02/07 – 05/07
A$482/nighttotal: A$1446 (3 )

2br Luxury Apartment Rooftop Pool & Gym

2 2
apartment , Baltimore
This 2BR Luxury Apartment is conveniently located in downtown Baltimore, just a short walk from the Inner Harbor and a few blocks from the Historic Ships in Baltimore. The apartment is situated in a lively area with easy access to the city's main attractions.
The 111 square metre flat has two bedrooms and one bathroom, comfortably accommodating up to six guests. The apartment offers a range of amenities, including a rooftop pool, a fitness centre, a private patio, and a fully equipped kitchen with a fridge, microwave oven, and dishwasher.
Holiday Inn Express Williamsburg North By Ihg - Chesapeake Bay
9.0 2280 reviews
Chesapeake Bay
27/06 – 04/07
A$255/nighttotal: A$1785 (7 )

Holiday Inn Express Williamsburg North By Ihg

1 3
resort , Williamsburg
The Holiday Inn Express Williamsburg North is conveniently located just 15 minutes from Busch Gardens and within 10 miles of the College of William and Mary, making it a great base for exploring Williamsburg's historical attractions and entertainment. The hotel consistently receives very good ratings for location, cleanliness, and overall experience.
The hotel offers a range of amenities, including a fitness centre, indoor pool, and complimentary continental breakfast. Guests can also enjoy comfortable rooms with cable TV, free toiletries, and select rooms with sofa beds, as well as a suite with a spa tub.
Newly Renovated, Coastal Themed;  W/ Outdoor Kitchen, Pool & Porch - Chesapeake Bay
8.8 3 reviews
Chesapeake Bay
02/07 – 05/07
A$1032/nighttotal: A$3096 (3 )

Newly Renovated, Coastal Themed; W/ Outdoor Kitchen, Pool & Porch

1 2
apartment , Virginia Beach
This Virginia Beach Oceanfront District flat is a 0.2-kilometre walk from the beach and boardwalk, offering easy access to restaurants and shops.
The 70-square-metre self-catering property sleeps four guests, boasting two bedrooms, one bathroom, a fully equipped kitchen with stainless steel appliances, and free Wi-Fi; on-site parking is also available.
Walnuts - Chesapeake Bay
Chesapeake Bay
29/08 – 05/09
A$311/nighttotal: A$2177 (7 )

Walnuts

3 2
house , Garrison
This detached house in Owings Mills is located between 16 and 21 kilometres from Towson University, the Baltimore Zoo, the Edgar Allan Poe Museum, and Baltimore - Penn Station, MD.
With a floor area of 152 square metres, this property offers accommodation for up to 11 guests, featuring a private terrace, garden, swimming pool, air conditioning, free WiFi, and a kitchen with a dishwasher and microwave.

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

Annapolis Home | Fenced Yard | Pool Table | 10 Guests - Chesapeake Bay
9.8 11 reviews
Chesapeake Bay
30/07 – 03/08
A$948/nighttotal: A$3792 (4 )

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

3 10
apartment , Arnold
This five-bedroom, two-bathroom house in Annapolis, Maryland, is situated approximately 9.6 kilometers from Sandy Point State Park and Beach, offering easy access to Annapolis attractions.
This spacious 1640 square metre property sleeps ten guests and boasts a fully equipped kitchen, terrace, garden, parking, Wi-Fi, and barbecue facilities, plus proximity to several golf courses.
Spacious North East Home With Fenced Yard And Fire Pit - Chesapeake Bay
Chesapeake Bay
30/07 – 03/08
A$839/nighttotal: A$3356 (4 )

Spacious North East Home With Fenced Yard And Fire Pit

5 10
house , North East
This five-bedroom house in North East, Maryland, is situated 26 kilometres from tennis courts and 27 kilometres from the University of Delaware, offering easy access to local attractions within a 40-kilometre radius.
The 185-square-metre property boasts three bathrooms, a fully equipped kitchen including a dishwasher and microwave, air conditioning, a garden, parking, and accommodates up to 19 guests, perfect for large family gatherings or group getaways.
Beautiful Canton Home W/rooftop Deck +Private Parking - Chesapeake Bay
10 3 reviews
Chesapeake Bay
30/07 – 05/08
A$658/nighttotal: A$3948 (6 )

Beautiful Canton Home W/rooftop Deck +Private Parking

3 6
house , Baltimore
This house is located in the Canton neighbourhood of Baltimore, a short walk from the Korean War Memorial and a short drive from Fell's Point, Historic Ships in Baltimore, and The Walters Art Museum. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The house offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, a private balcony, a rooftop deck with city views, private parking, and free Wi-Fi.
Historic Row Home | Hot Tub - 1 Block From Gate 1! - Chesapeake Bay
9.8 6 reviews
Chesapeake Bay
02/07 – 05/07
A$1297/nighttotal: A$3891 (3 )

Historic Row Home | Hot Tub - 1 Block From Gate 1!

3 2
apartment , Annapolis
This Annapolis holiday home is situated in the Historic District, a short distance from Annapolis City Dock.
This three-bedroom, two-and-a-half-bathroom apartment offers 186 square metres of living space, complete with a fully equipped kitchen, in-unit laundry, private balcony, and access to an outdoor grill; nearby attractions include Jonas Green State Park and Hammond-Harwood House.

Best Chesapeake Bay holiday rentals with parking

Pet-friendly Smith Island Cottage With Golf Cart! - Chesapeake Bay
9.5 2 reviews
Chesapeake Bay
29/08 – 05/09
A$321/nighttotal: A$2247 (7 )

Pet-friendly Smith Island Cottage With Golf Cart!

2 2
house , Smith Island
This Smith Island house, sleeping seven guests, offers a 137 square metre property with two bedrooms and one bathroom; precise location within Smith Island is unspecified, preventing distance calculations to local landmarks.
The self-catering dwelling includes a fully equipped kitchen with fridge and microwave, free Wi-Fi, on-site parking, and free bicycle use, perfect for exploring the island.
The Rene Carr House - Chesapeake Bay
Chesapeake Bay
30/07 – 05/08
A$311/nighttotal: A$1866 (6 )

The Rene Carr House

1 6
house , Elkton
This detached property in Elkton is situated 22 kilometres from New Castle Airport.
This dwelling accommodates up to eleven guests and features two bathrooms, a fully equipped kitchen, complimentary Wi-Fi, and private parking, with a non-smoking policy in effect.
Club Wyndham Kingsgate - Chesapeake Bay
8.9 6556 reviews
Chesapeake Bay
30/07 – 03/08
A$638/nighttotal: A$2552 (4 )

Club Wyndham Kingsgate

3 10
resort , Williamsburg
Club Wyndham Kingsgate is located in Williamsburg, less than a kilometre from the historic area, making it a great base for exploring the town's rich history. This 3-star hotel has consistently received very good user ratings, suggesting a comfortable and enjoyable stay.
The hotel offers a range of amenities and activities, including a swimming pool, jacuzzi, and tennis court, making it suitable for families and those seeking relaxation. Guests can also enjoy a restaurant, bar, and fitness centre, ensuring a convenient and enjoyable stay.
Cozy Baltimore Studio Apts - Chesapeake Bay
Chesapeake Bay
27/06 – 04/07
A$226/nighttotal: A$1582 (7 )

Cozy Baltimore Studio Apts

1 3
studio , Baltimore
This Parkville flat offers proximity to Clifton Park, located 6.28 kilometres away, and is within a 11.27 kilometre radius of Towson University, Johns Hopkins University, and the Baltimore Museum of Art.
This studio apartment accommodates up to five guests and features a kitchenette with a microwave, complimentary WiFi, and private parking, with cycling opportunities available in the surrounding area.
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