Vacation Rentals in Chesapeake Bay

6706 available vacation rental offers

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Chesapeake Bay vacation rentals
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6706 Vacation 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

Luxury Home 5 Br 3 Ba Near Beaches And Venues - Chesapeake Bay
9.7 411 reviews
Chesapeake Bay
30/07 – 05/08
₹61803/nighttotal: ₹370818 (6 )

Luxury Home 5 Br 3 Ba Near Beaches And Venues

5 6
house , Hampton
This five-bedroom house in Hampton is just 23 miles from Busch Gardens & Water Country and 7.7 miles from the Virginia Living Museum, offering a peaceful retreat on a quiet street. The property has received excellent ratings for its location, cleanliness, and overall experience.
This spacious home, with its 223 square metres of floor space, comfortably accommodates large groups or families. Guests can enjoy a fully equipped kitchen, free Wi-Fi, a terrace, garden, and private parking, as well as explore nearby cycling and hiking trails.
New, Chic River Bungalow In Historic District - Chesapeake Bay
9.7 7 reviews
Chesapeake Bay
29/08 – 05/09
₹20114/nighttotal: ₹140798 (7 )

New, Chic River Bungalow In Historic District

1 2
bungalow , Cambridge
This renovated bungalow offers a prime location in Cambridge's historic district, situated just 100 meters from the river and a 5-minute walk to downtown galleries, shops, and dining, with convenient access to Gerry Boyle Park and the Choptank River for watersports.
This family-friendly property accommodates four guests with two en-suite bedrooms, a fully equipped chef's kitchen, air conditioning, and a private garden, complemented by a private driveway providing parking for two cars.
Cozy Portsmouth Retreat 2br 1ba - Chesapeake Bay
9.8 7 reviews
Chesapeake Bay
29/08 – 05/09
₹19070/nighttotal: ₹133490 (7 )

Cozy Portsmouth Retreat 2br 1ba

2 2
house , Portsmouth
This charming house in Portsmouth is conveniently located just 14 km from Mount Trashmore Park, 20 km from Virginia Beach National Golf Club, and 11 km from Topgolf Virginia Beach, making it easy to explore the area's attractions. The property has received excellent user ratings for cleanliness and is situated in a good location.
The house spans 102 square metres and comfortably accommodates up to 6 guests in its two bedrooms and one bathroom. It features a fully equipped kitchen, a washing machine, air conditioning, a garden, and free Wi-Fi, ensuring a relaxing and comfortable stay.
Perfect Beach Getaway For 5! Steps To The Sand! - Chesapeake Bay
9.4 26 reviews
Chesapeake Bay
20/07 – 27/07
₹22641/nighttotal: ₹158487 (7 )

Perfect Beach Getaway For 5! Steps To The Sand!

2 4
apartment , Hampton
This two-bedroom Hampton house is situated just 0.5 kilometres from Buckroe Beach and Park, offering easy access to the beautiful sandy shores and refreshing ocean waters. The property features a fully equipped kitchen, a terrace, parking, and can comfortably accommodate up to five guests.

Best Chesapeake Bay vacation rentals with a pool

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

Cottage With Harbor And Chesapeake Bay View In Rock Hall, Md - Chesapeake Bay
9.7 105 reviews
Chesapeake Bay
20/07 – 27/07
₹32400/nighttotal: ₹226800 (7 )

Cottage With Harbor And Chesapeake Bay View In Rock Hall, Md

2 4
apartment , Rock Hall
This charming cottage is situated on Bayside Avenue in Rock Hall, Maryland, just a short stroll from the town beach and swimming pool. It has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The two-bedroom cottage, spanning 93 square metres, comfortably accommodates up to six guests. It offers a range of amenities including a fully equipped kitchen, air conditioning, a screened back deck, and a pet-friendly policy.
Diamond Resorts Turtle Cay Resort - 2 Bedroom Lockoff - Chesapeake Bay
10 1 review
Chesapeake Bay
29/08 – 05/09
₹60745/nighttotal: ₹425215 (7 )

Diamond Resorts Turtle Cay Resort - 2 Bedroom Lockoff

2 2
house , Virginia Beach
This Virginia Beach property is situated in a quiet South End location, approximately 32 kilometres from Norfolk International Airport and close to False Cape, First Landing, and Cape Henry Memorial State Parks.
The self-catering apartment offers 121 square metres of space, sleeping up to eight guests in two bedrooms and two bathrooms, and includes a swimming pool, jacuzzi, and concierge service.
Charming Cottage With Pool Access And Wifi In Lovely Rock Hall - Chesapeake Bay
10 4 reviews
Chesapeake Bay
29/08 – 05/09
₹21303/nighttotal: ₹149121 (7 )

Charming Cottage With Pool Access And Wifi In Lovely Rock Hall

1 2
cottage , Rock Hall
This Rock Hall cottage, ideally situated near the Waterman's Museum and The Mainstay, offers convenient access to Rock Hall Harbour and Rolph's Wharf Marina, all within walking distance (exact distances unspecified).
The 56-square-metre (approximately 600 square feet) self-catering property features a two-story layout with a king-size bedroom upstairs, a downstairs living area, and accommodates two guests; amenities include air conditioning, Wi-Fi, a mini-refrigerator, and a private pool (accessible May 1st to September 21st, 11 am to 5 pm).
One Bedroom Condo With Marina View - Chesapeake Bay
10 1 review
Chesapeake Bay
01/10 – 05/10
₹21350/nighttotal: ₹85400 (4 )

One Bedroom Condo With Marina View

1 3
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.

Frequently asked questions about holiday rentals in Chesapeake Bay

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

    The Maryland Science Center in Baltimore is a fantastic place for kids of all ages, and the National Aquarium is another great option. For a more outdoorsy experience, Assateague Island National Seashore is a beautiful beach with wild horses.
  • 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.

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

    You'll want to book your vacation rental well in advance, especially if you're travelling during peak season, which is typically from June to August. This will give you the best choice of properties and ensure you get the dates you want.
  • What are the most popular Airbnbs in Chesapeake Bay?

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

    The Chesapeake Bay Wine Festival in Stevensville is a great event for wine lovers, and the National Folk Festival in Salisbury is a fantastic celebration of music and culture. You can also check out the annual Oyster Festival in St. Michaels.
  • What are the best vacation rentals with a pool in Chesapeake Bay?

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

    Take a walk along the Chesapeake Bay Trail, it's a scenic path that stretches for miles, and it's completely free. You can also visit one of the many state parks in the area, such as Assateague Island National Seashore, for a day of hiking, swimming, or just relaxing.
  • What are the best rentals for families and kids in Chesapeake Bay?

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

    For a taste of the Chesapeake Bay, try the crab cakes at The Chart House in Annapolis. If you're looking for something a bit more casual, The Crab Claw in Cambridge is a great option for fresh seafood.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesapeake Bay?

  • What are the best walking or cycling routes in Baie de Chesapeake?

    The Chesapeake Bay Trail is a great option for both walking and cycling, it offers stunning views of the Bay. For a shorter ride, check out the scenic loop around the town of St. Michaels.
  • Are there pet-friendly attractions in Baie de Chesapeake?

    Many of the beaches in the area are dog-friendly, including Assateague Island National Seashore. You can also find plenty of pet-friendly restaurants and cafes.
  • What are the benefits of choosing a vacation rental in Baie de Chesapeake?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities like kitchens and laundry facilities, which can be very convenient for families. They also tend to be more affordable than hotels, especially if you're travelling with a large group.
  • What are the top sports attractions and facilities in Baie de Chesapeake?

    The M&T Bank Stadium in Baltimore is home to the Baltimore Ravens, and the Camden Yards is home to the Baltimore Orioles. If you're interested in sailing, the Annapolis Yacht Club is a great place to watch races.

Destinations nearby

Best Chesapeake Bay holiday rentals with a balcony

Adorable Chesapeake Bay Beach Cottage B Just 1 Block From The Sand! - Chesapeake Bay
9.4 16 reviews
Chesapeake Bay
30/07 – 05/08
₹54293/nighttotal: ₹325758 (6 )

Adorable Chesapeake Bay Beach Cottage B Just 1 Block From The Sand!

3 6
cottage , Virginia Beach
This charming three-bedroom cottage is located in Northeast Virginia Beach, just a mile from First Landing State Park and Marina Shores Marina, and within three miles of Chesapeake Beach and Sylvan Beach. The cottage has received excellent reviews from previous guests, highlighting its comfortable and convenient location.
The 167 square metre cottage comfortably sleeps six guests and offers three bathrooms, a fully equipped kitchen, and a private water park. Guests can enjoy a range of amenities including a terrace, garden, spa, and parking, as well as access to free WiFi, a Smart TV, and a washing machine.
Dollhouse In Central Historic St Michaels - Chesapeake Bay
9.6 119 reviews
Chesapeake Bay
20/07 – 27/07
₹33293/nighttotal: ₹233051 (7 )

Dollhouse In Central Historic St Michaels

2 4
apartment , Easton
This charming house is located in St. Michaels, a picturesque town on Maryland's Eastern Shore, just 1 kilometre from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. The property enjoys excellent ratings for location, cleanliness, and user experience.
The house has two bedrooms, accommodating up to four guests, and features a fully equipped kitchen, two bathrooms, a washing machine, and a Smart TV. Guests can enjoy a spa tub, garden, barbecue grills, and a terrace, making it ideal for relaxation and outdoor dining.
Deal Island Bay Cottage - Chesapeake Bay
9.4 319 reviews
Chesapeake Bay
23/08 – 28/08
₹17892/nighttotal: ₹89460 (5 )

Deal Island Bay Cottage

3 2
cottage , Chance
This charming cottage is located on Deal Island in Maryland's Eastern Shore, just a short walk or drive from a Chesapeake Bay beach, offering a tranquil escape from the hustle and bustle of everyday life. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The 3-bedroom, 2-bathroom home spans 144 square metres and comfortably accommodates up to 8 guests. The cottage is fully equipped with modern amenities, including a kitchen with a fridge, freezer, microwave, and dishwasher, as well as a terrace, garden, and parking. Guests can enjoy breathtaking sunrises from the dining room or screened-in porch, explore the beautiful Tangier Sound by kayak, or go crabbing in secret local spots.
Beautiful Canton Home W/rooftop Deck +Private Parking - Chesapeake Bay
10 3 reviews
Chesapeake Bay
30/07 – 05/08
₹44130/nighttotal: ₹264780 (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.

Best Chesapeake Bay holiday rentals with parking

Exciting Elegance In Vibrant Fells Point! - Chesapeake Bay
Chesapeake Bay
29/08 – 05/09
₹20818/nighttotal: ₹145726 (7 )

Exciting Elegance In Vibrant Fells Point!

3 2
house , Baltimore
This Fells Point holiday home in Baltimore is situated within 2.25 kilometres of the Inner Harbour, placing it less than 1.93 kilometres from the Pier Six Concert Pavilion, Korean War Memorial, and Power Plant, and a short distance from Fell's Point and the Historic Ships in Baltimore.
This 119 square metre property accommodates up to nine guests with three bedrooms, a fully equipped kitchen, air conditioning, and an outdoor dining area, offering free on-site parking and complimentary WiFi.
Cozy Fells Point Gem / In The Heart Of Fells Point - Chesapeake Bay
9.8 479 reviews
Chesapeake Bay
23/08 – 28/08
₹13296/nighttotal: ₹66480 (5 )

Cozy Fells Point Gem / In The Heart Of Fells Point

1 2
apartment , Baltimore
This one-bedroom flat is located in Fells Point, a historic waterfront district in Baltimore, within a mile of Fell's Point Visitor Center and Johns Hopkins Hospital. The apartment has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers.
The flat is 56 square metres and features a fully equipped kitchen with a fridge, oven, microwave, and dishwasher. You can enjoy the on-site spa, relax in the smoke-free environment, and stay connected with free Wi-Fi and a Smart TV.
Riverside Tiny Home Retreat - Chesapeake Bay
9.8 275 reviews
Chesapeake Bay
20/07 – 27/07
₹23181/nighttotal: ₹162267 (7 )

Riverside Tiny Home Retreat

1 4
apartment , Hampton
This Hampton house is ideally situated in the city centre, just a short walk from attractions like Hampton City Hall, Hampton University, Art By Gerome Galleria, and the Virginia Air and Space Center. It has received excellent ratings for location, cleanliness and user experience.
The property has one bedroom and one bathroom, comfortably accommodating up to four guests. It comes equipped with a fully fitted kitchen, laundry facilities, a private patio, a garden, air conditioning, parking and free Wi-Fi.
Club Wyndham Governors Green - Chesapeake Bay
9.4 1692 reviews
Chesapeake Bay
01/10 – 05/10
₹21297/nighttotal: ₹85188 (4 )

Club Wyndham Governors Green

1 3
resort , Williamsburg
Club Wyndham Governors Green is located in Williamsburg, Virginia, just three miles from the College of William and Mary and six miles from Camp Peary, offering easy access to both historical sites and modern conveniences. The resort is a four-star establishment, consistently receiving excellent reviews from guests for its cleanliness, location, and overall experience.
The apartments at Club Wyndham Governors Green are spacious and self-contained, providing guests with kitchens, separate living and dining areas, and in-unit laundry facilities. The resort offers a wide range of amenities, including swimming pools, a fitness centre, tennis courts, a spa, and a restaurant, ensuring there is something for everyone to enjoy.
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