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

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.
Golden Anchor Retreat Lux Living! - Chesapeake Bay
10 3 reviews
Chesapeake Bay
30/07 – 05/08
$693/nighttotal: $4158 (6 )

Golden Anchor Retreat Lux Living!

3 6
house , Mayo
This Mayo house, situated 14.6 kilometres from Annapolis Harbour and within easy reach of Baltimore and Washington D.C., offers convenient access to major attractions.
This 217 square metre property sleeps 11 guests in three bedrooms, boasting two bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, parking, and air conditioning.
The Charming Cozy 4-bedroom Getaway In Glen Burnie - Chesapeake Bay
10 2 reviews
Chesapeake Bay
30/07 – 05/08
$517/nighttotal: $3102 (6 )

The Charming Cozy 4-bedroom Getaway In Glen Burnie

4 6
house , Glen Burnie
This recently renovated Cape Cod property is located in Glen Burnie, Maryland, offering convenient access to local amenities.
This allergy-free, non-smoking holiday home spans 117 square meters and accommodates up to 8 guests across 4 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, free WiFi, complimentary private parking, and a balcony.
Be Persuaded To Experience This Vintage Cottage By The Sassa - Chesapeake Bay
9.2 11 reviews
Chesapeake Bay
30/07 – 05/08
$556/nighttotal: $3336 (6 )

Be Persuaded To Experience This Vintage Cottage By The Sassa

4 6
cottage , Galena
This charming cottage is located on the banks of a river, just 20 kilometres from attractions like Dutch Country Farmers Market, Betterton Beach, and Washington College. It has received excellent reviews from previous guests.
This four-bedroom property comfortably sleeps eight guests and includes two bathrooms. The cottage offers a fully-equipped kitchen, a garden, barbecue facilities, a terrace, free Wi-Fi, and parking.

Best Chesapeake Bay vacation rentals with a pool

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

Loraine's Retreat - Chesapeake Bay
Chesapeake Bay
29/08 – 05/09
$837/nighttotal: $5859 (7 )

Loraine's Retreat

3 2
house , Virginia Beach
Loraine's Retreat is a three-bedroom, two-bathroom house in Virginia Beach, conveniently located 1.9km from the Virginia Beach Convention Center, 4.5km from the Virginia Aquarium & Marine Science Center, and 29km from Norfolk International Airport.
This self-catering property sleeps up to 17 guests and boasts a swimming pool, free Wi-Fi, on-site parking, and a fully equipped kitchen including a fridge and dishwasher; nearby attractions include the King Neptune Statue and Neptune's Park.
Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia - Chesapeake Bay
8.2 3026 reviews
Chesapeake Bay
23/08 – 28/08
$338/nighttotal: $1690 (5 )

Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia

1 2
resort , Virginia Beach
Ocean Sands Resort by VSA Resorts is situated on the oceanfront in Virginia Beach, just half a mile from the amusement park and one mile from the convention centre. The resort consistently receives excellent ratings for its location and cleanliness, as well as very good reviews for its overall experience.
The resort offers a range of self-catering suites with Caribbean-style decor, each with a private balcony or terrace. Guests have access to a variety of on-site amenities, including a swimming pool, hot tub, sauna, fitness centre, tennis court, restaurant, bar, and spa, ensuring a relaxing and enjoyable stay.
Oceanfront Beach Condo, Pool, Gym, Fishing Surfing - Chesapeake Bay
Chesapeake Bay
29/08 – 05/09
$949/nighttotal: $6643 (7 )

Oceanfront Beach Condo, Pool, Gym, Fishing Surfing

3 2
house , Virginia Beach
This oceanfront condominium in Virginia Beach offers direct access to the beach, just a 200-metre stroll away, and is located 27 kilometres from Norfolk International Airport.
This 100 square metre apartment, suitable for up to 8 guests, features 3 bedrooms, 2 bathrooms, air conditioning, a fully equipped kitchen, a private balcony, and on-site access to a swimming pool and fitness centre, with nearby opportunities for fishing and surfing.
One Bedroom Condo With Marina View - Chesapeake Bay
10 1 review
Chesapeake Bay
01/10 – 05/10
$313/nighttotal: $1252 (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 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

Sun Outdoors Cape Charles - Chesapeake Bay
8.4 11 reviews
Chesapeake Bay
29/08 – 05/09
$392/nighttotal: $2744 (7 )

Sun Outdoors Cape Charles

2 2
house , Cape Charles
This beachfront property is located in Cape Charles, Virginia, just 60 kilometres from Norfolk International Airport and a short distance from the town centre.
The house has two bedrooms and one bathroom, offering comfortable accommodation for up to six guests, across a floor area of 399 square metres. Enjoy a range of amenities, including a saltwater pool, a private beach area, a fully equipped kitchenette, and a terrace.
Club Wyndham Governors Green - Chesapeake Bay
9.4 1692 reviews
Chesapeake Bay
23/08 – 28/08
$308/nighttotal: $1540 (5 )

Club Wyndham Governors Green

1 2
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.
Northern Neck Nature Retreat W/ Boat Ramp & Dock! - Chesapeake Bay
Chesapeake Bay
30/07 – 05/08
$380/nighttotal: $2280 (6 )

Northern Neck Nature Retreat W/ Boat Ramp & Dock!

3 6
house , Heathsville
This detached house in Heathsville is situated 106 kilometres from Newport News/Williamsburg International Airport.
This 107 square metre dwelling accommodates up to 13 guests with three bedrooms, two bathrooms, air conditioning, free WiFi, a fully equipped kitchen, and a balcony, offering ample space and convenience for your stay.
1br 1bth - Family Of 4 - Resort Stay 5 Min From Bush Gardens & Water Country Usa - Chesapeake Bay
Chesapeake Bay
20/07 – 27/07
$271/nighttotal: $1897 (7 )

1br 1bth - Family Of 4 - Resort Stay 5 Min From Bush Gardens & Water Country Usa

1 4
resort , Williamsburg
This resort is located in Williamsburg, just 5 kilometres from Water Country USA, a popular water park, and close to other attractions. It's a great base for exploring the area, with its rich history and plenty of things to see and do.
The "1br 1bth - Family Of 4 - Resort Stay 5 Min From Bush Gardens & Water Country Usa" offer provides a comfortable and spacious apartment for up to 6 guests. It includes a range of amenities, including an indoor and outdoor pool, a fitness centre, a sauna, and a concierge service.

Best Chesapeake Bay vacation rentals with parking

Retreat At Fenwick - Chesapeake Bay
9.7 28 reviews
Chesapeake Bay
20/07 – 27/07
$225/nighttotal: $1575 (7 )

Retreat At Fenwick

1 4
apartment , Leonardtown
The Retreat at Fenwick apartment is situated in Leonardtown, Maryland, just 18 km from the Calvert Marine Museum and 19 km from Cape Saint Marys Marina, offering easy access to local attractions. The apartment has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
This one-bedroom apartment spans 56 square metres and comfortably accommodates up to 7 guests. The apartment offers a fully equipped kitchen with a dishwasher, a fireplace for a cosy atmosphere, free Wi-Fi, on-site parking, and towels and bed linen for a hassle-free stay.
Deal Island Bay Cottage - Chesapeake Bay
9.4 319 reviews
Chesapeake Bay
29/08 – 05/09
$226/nighttotal: $1582 (7 )

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.
Restored 1920's Cottage On 1 Acre W/ Fire Pit - Chesapeake Bay
9.5 187 reviews
Chesapeake Bay
20/07 – 27/07
$390/nighttotal: $2730 (7 )

Restored 1920's Cottage On 1 Acre W/ Fire Pit

2 4
house , Gloucester Point
This charming cottage is located in Hayes, Virginia, just a short drive from popular attractions like Busch Gardens, Colonial Williamsburg, and Historic Jamestowne. The property has received excellent ratings for its cleanliness, location, and overall experience.
The 84 square metre cottage comfortably sleeps up to 6 guests and features a fully equipped kitchen, a garden, a spa, and a fire pit for relaxing evenings. Enjoy the scenic river views, the spacious acreage, and the restored 1920s character of this unique property.
Historic Cottage On Ware River Estate - Chesapeake Bay
10 511 reviews
Chesapeake Bay
29/08 – 05/09
$269/nighttotal: $1883 (7 )

Historic Cottage On Ware River Estate

1 2
cottage , Gloucester Courthouse
This charming cottage is situated on a picturesque river, just 8.7 kilometres from Riverside Walter Reed Hospital and 19.3 kilometres from Machicomoco State Park, offering a peaceful retreat for those seeking tranquility. The property consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The self-catering property has one bedroom and one bathroom, comfortably accommodating up to four guests. The cottage provides a range of amenities, including a fully equipped kitchen, a private patio, a hot tub, and a garden, offering everything you need for a relaxing and enjoyable getaway.
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