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

Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac - Chesapeake Bay
10 5 reviews
Chesapeake Bay
30/07 – 05/08
₹24160/nighttotal: ₹144960 (6 )

Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac

2 6
cottage , Piney Point
This Piney Point waterfront holiday home is situated near St Mary's River State Park and the Piney Point Lighthouse, offering tranquil river views.
Sleeping up to six guests, the two-bedroom property boasts a fully equipped kitchen, air conditioning, Wi-Fi, smart TVs, and on-site barbecue facilities, making it ideal for families exploring the local area's attractions including the Patuxent River Naval Air Museum.
Kings Creek Plantation By Tripforth - Chesapeake Bay
9.1 726 reviews
Chesapeake Bay
29/08 – 05/09
₹29729/nighttotal: ₹208103 (7 )

Kings Creek Plantation By Tripforth

3 2
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.
Cozy Modern Apt In The Heart Of Fells Point! - Chesapeake Bay
9.0 22 reviews
Chesapeake Bay
23/08 – 28/08
₹16744/nighttotal: ₹83720 (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.
Charming Federal Hill! One Bedroom With Vibes - Chesapeake Bay
9.7 231 reviews
Chesapeake Bay
23/08 – 28/08
₹15250/nighttotal: ₹76250 (5 )

Charming Federal Hill! One Bedroom With Vibes

1 2
apartment , Baltimore
This smoke-free flat is located in Federal Hill, a short walk from Federal Hill Park and M&T Bank Stadium, offering a mix of historic charm and modern amenities. The property has received excellent ratings for location, cleanliness and overall experience.
The apartment has one bedroom, one bathroom and can accommodate up to three guests. It features a fully equipped kitchen, a washer/dryer, a comfortable sofa bed, a Smart TV with Netflix and games for entertainment.

Best Chesapeake Bay vacation rentals with a pool

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

Exceptional North End Vb Condo - Chesapeake Bay
10 2 reviews
Chesapeake Bay
27/06 – 04/07
₹28406/nighttotal: ₹198842 (7 )

Exceptional North End Vb Condo

1 3
apartment , Virginia Beach
This two-bedroom, two-bathroom apartment in Virginia Beach's tranquil North End offers direct beach access across the street and is within walking or cycling distance of restaurants such as Atlantic on Pacific and attractions including the Virginia Aquarium.
The renovated condo sleeps six, features a fully equipped kitchen with a large island, a private patio with barbecue overlooking a communal pool, two dedicated parking spaces, and keyless entry; nearby activities include Ocean Breeze Waterpark.
Barclay Towers Resort Direct Oceanfront Unit - Chesapeake Bay
9.8 71 reviews
Chesapeake Bay
27/06 – 04/07
₹16242/nighttotal: ₹113694 (7 )

Barclay Towers Resort Direct Oceanfront Unit

1 3
resort , Virginia Beach
This one-bedroom apartment in Virginia Beach is situated directly across the street from the Barclay Towers Resort, offering stunning oceanfront views. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment features a fully equipped kitchen and living room, comfortably accommodating up to four guests. Amenities include a swimming pool, jacuzzi, garden, parking, and access to the resort's laundry facilities, providing a relaxing and convenient experience.
First Floor Studio Apartment In Historic Chestertown - Chesapeake Bay
9.7 290 reviews
Chesapeake Bay
23/08 – 28/08
₹12708/nighttotal: ₹63540 (5 )

First Floor Studio Apartment In Historic Chestertown

1 2
studio , Kingstown
This apartment is located in Chestertown, a short distance from Washington College and Rolphs Wharf Marina, offering easy access to cultural attractions and scenic waterfront views. The apartment has consistently received excellent ratings for location, cleanliness, and overall experience.
This self-catering home can accommodate up to three guests and offers a comfortable living space with a bedroom, a bathroom, and a fully equipped kitchen. The apartment comes with a range of amenities, including a private pool, a fitness centre, a spa, and a terrace, perfect for relaxing and enjoying the surrounding area.
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.

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

Historic Old Towne Southern Charm - Chesapeake Bay
9.6 35 reviews
Chesapeake Bay
01/10 – 05/10
₹18551/nighttotal: ₹74204 (4 )

Historic Old Towne Southern Charm

2 3
apartment , Portsmouth
This charming 2-bedroom flat is located in Old Towne Portsmouth, just a short walk from the city's restaurants, shops, and attractions. The area is known for its historic architecture and lively atmosphere, making it a great base for exploring the city. The apartment has a very good user rating, indicating a positive experience for previous guests.
This spacious home can comfortably accommodate up to 7 guests. It features a well-equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a terrace, and a garden. Guests can also enjoy free Wi-Fi and the convenience of a washing machine and dryer.
A Little Slice Of Heaven On The Choptank River. - Chesapeake Bay
10 29 reviews
Chesapeake Bay
30/07 – 05/08
₹38636/nighttotal: ₹231816 (6 )

A Little Slice Of Heaven On The Choptank River.

2 6
chalet , Cambridge
This charming chalet is located in East New Market, just across from the Hyatt Resort and a short distance from Cambridge town centre. The chalet is highly rated, receiving excellent reviews from previous guests.
The chalet has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, air conditioning, a terrace, a garden, and private waterfront access, offering a range of activities from swimming and kayaking to enjoying stunning sunsets.
Elegant Reservoir Hill Home With Parking Sleeps 8 - Chesapeake Bay
Chesapeake Bay
30/07 – 05/08
₹31876/nighttotal: ₹191256 (6 )

Elegant Reservoir Hill Home With Parking Sleeps 8

1 6
house , Baltimore
This Reservoir Hill villa offers a convenient base, situated a short walk from Druid Hill Park and 1.92 kilometres from Oriole Park at Camden Yards, with the Penn-North Metro station 0.96 kilometres away.
This detached house accommodates 8 guests and features a fully equipped kitchen, air conditioning, Wi-Fi, and in-unit laundry, with ample outdoor space provided by a garden and balcony.
Charming Victorian Farmhouse On Historic Main St - Chesapeake Bay
8.0 1 review
Chesapeake Bay
30/07 – 05/08
₹29209/nighttotal: ₹175254 (6 )

Charming Victorian Farmhouse On Historic Main St

3 6
house , Trappe
This Victorian farmhouse is located on Trappe's Historic Main Street, approximately 69 kilometres from Salisbury-Ocean City Wicomico Regional Airport.
The 195-square-metre property offers three bedrooms, three bathrooms, and sleeps up to 11 guests, boasting a fully equipped kitchen, laundry facilities, air conditioning, Wi-Fi, and a patio; local shops and restaurants are easily accessible.

Best Chesapeake Bay holiday rentals with parking

Barclay Towers Resort Direct Oceanfront Unit - Chesapeake Bay
9.4 184 reviews
Chesapeake Bay
27/06 – 04/07
₹16242/nighttotal: ₹113694 (7 )

Barclay Towers Resort Direct Oceanfront Unit

1 3
resort , Virginia Beach
This one-bedroom apartment is located in the Barclay Towers Resort, just a short walk from Virginia Beach's bustling boardwalk and the sandy shores of the Atlantic Ocean. It has received excellent user and location ratings and a very good cleanliness rating.
The apartment comfortably sleeps four guests and comes equipped with a full kitchen, allowing you to prepare meals during your stay. You'll also have access to a range of resort amenities, including a swimming pool, jacuzzi, fitness centre, and laundry facilities.
Virginia Retreat W/ Porch & Grill, Near Beaches! - Chesapeake Bay
10 3 reviews
Chesapeake Bay
30/07 – 05/08
₹36869/nighttotal: ₹221214 (6 )

Virginia Retreat W/ Porch & Grill, Near Beaches!

3 6
house , Wachapreague
This Wachapreague holiday home is situated approximately 43 kilometres from the Mid-Atlantic Regional Spaceport and 105 kilometres from Salisbury-Ocean City Wicomico Regional Airport.
This three-bedroom property, boasting 130 square metres of floor space, comfortably sleeps 15 guests and includes a fully equipped kitchen with dishwasher and microwave, air conditioning, free Wi-Fi, and a washing machine.
Bay Front Manor House - Chesapeake Bay
9.0 1 review
Chesapeake Bay
29/08 – 05/09
₹15085/nighttotal: ₹105595 (7 )

Bay Front Manor House

1 2
house , Deale
Bay Front Manor House in Deale offers a waterfront location with bay views, situated 32 kilometres from Annapolis Harbour and 48 kilometres from Washington D.C. attractions such as Nationals Park.
This 1400 square metre dwelling accommodates up to 11 guests, featuring one bedroom, one bathroom, air conditioning, a fully equipped kitchen, free WiFi, and private parking, with check-out between 8 AM and 11 AM.
Entire Private 2 Bedrooms House, Nice Neighborhood - Chesapeake Bay
9.4 84 reviews
Chesapeake Bay
01/10 – 05/10
₹22091/nighttotal: ₹88364 (4 )

Entire Private 2 Bedrooms House, Nice Neighborhood

2 3
apartment , Arnold
This two-bedroom home is situated in Arnold, a peaceful neighbourhood just 10 miles from Annapolis Harbor and 14 miles from Baltimore-Washington International Airport. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious apartment, spanning 111 square metres, comfortably accommodates up to 5 guests. Enjoy a range of amenities including a private hot tub, a peaceful garden, a fully equipped kitchen, air conditioning, free Wi-Fi and private parking.
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