Vacation Rentals in Chesapeake Bay

9615 available vacation rental offers

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Chesapeake Bay vacation rentals
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9615 Vacation rentals and Airbnb in Chesapeake Bay

Best family friendly Chesapeake Bay vacation rentals

Among the 9615 accommodations in Chesapeake Bay, here are the 4 best family friendly rentals

Waterfront~peaceful~weemsva~nnk~kayaks~views - Chesapeake Bay
10 59 reviews

Waterfront~peaceful~weemsva~nnk~kayaks~views

apartment, Irvington
This peaceful house on Carters Cove in Irvington offers direct kayak access and serene water views, with proximity to nearby towns (distances unspecified).
The three-bedroom, two-bathroom property sleeps six, boasting an open-plan living/dining/kitchen area, a furnished deck, and a fully equipped kitchen including a dishwasher; kayaking is available directly from the private backyard dock.
Kingsmill Resort!  Williamsburg, Va!  3bed 3bath - Chesapeake Bay
9.8 146 reviews

Kingsmill Resort! Williamsburg, Va! 3bed 3bath

house, Williamsburg
This 3-bedroom house is located in the Kingsmill Resort community, just 5km from Busch Gardens and a short drive from other attractions like Water Country USA, Colonial Williamsburg, Jamestown, and Yorktown. The property enjoys excellent ratings for location, cleanliness, and user experience.
The house spans 149 square metres and comfortably sleeps 8 guests. It offers a fully equipped kitchen, a washer and dryer, a swimming pool, a terrace, parking, and access to tennis courts, playgrounds, and walking paths in the community.
Entire Houseby Fells Point, Hopkins & Harbor - Chesapeake Bay
9.6 440 reviews

Entire Houseby Fells Point, Hopkins & Harbor

house, Baltimore
This charming Baltimore townhouse is located in Upper Fells Point, just a short walk from Patterson Park and the lively Fells Point district, offering easy access to Johns Hopkins University, the Inner Harbor, and the stadium. It has consistently received excellent user ratings for its location, cleanliness, and overall experience.
This three-bedroom property comfortably accommodates up to eight guests, providing ample space for families or groups. Guests can enjoy a fully equipped kitchen, a private patio, a washer and dryer, and free street parking, along with the convenience of being in a walkable neighbourhood with plenty of restaurants, bars, and attractions nearby.
Waterfront Cabin! Crabfish~bigporch~paddle~karaoke - Chesapeake Bay
9.9 63 reviews

Waterfront Cabin! Crabfish~bigporch~paddle~karaoke

apartment, Heathsville
This three-bedroom waterfront lodge is situated on a 0.8-hectare plot in the Northern Neck of Virginia, near Vir-Mar Beach and a grocery store, with popular sandy beaches within a 32 km radius.
The property boasts an 87ft private dock, a games room with a mini-pool table, foosball, and arcade games, plus an outdoor movie screen and space for eight guests, offering kayaking, paddleboarding, fishing, and crabbing opportunities directly from the property.

Best Chesapeake Bay vacation rentals with a pool

Among the 9615 accommodations in Chesapeake Bay, here are the 4 best rentals with a pool

One Bedroom Condo With Marina View - Chesapeake Bay
10 1 review

One Bedroom Condo With Marina View

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.
The Colonies At Williamsburg - Chesapeake Bay
8.8 2548 reviews

The Colonies At Williamsburg

resort, Williamsburg
The Colonies At Williamsburg is located in the Williamsburg area, just a short drive from Jamestown and Busch Gardens Williamsburg. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
The resort offers a range of self-catering apartments, each with a kitchen, spa tub, and patio. Guests can enjoy a swimming pool with a slide, a game room, a tennis court, a fitness centre, and a spa, as well as free Wi-Fi throughout the resort.
Vanishing Run Retreat With Pool - Chesapeake Bay
10 5 reviews

Vanishing Run Retreat With Pool

house, Galesville
This Galesville property, a spacious house situated in Harwood, Maryland, is 24 kilometres from Annapolis Harbour and between 45 and 50 kilometres from Washington, D.C. attractions such as Nationals Park and the US Capitol.
The 930 square metre dwelling boasts one bedroom, three bathrooms, and sleeps sixteen guests, offering a private pool, free parking, a fully equipped kitchen, Wi-Fi, laundry facilities, and air conditioning.
Mill Point - Chesapeake Bay
No reviews

Mill Point

house, Tilghman Island
This five-bedroom, five-bathroom house in Neavitt, Maryland, is situated approximately 30 kilometres from the Academy of the Arts and 113 kilometres from Baltimore-Washington International Thurgood Marshall Airport, offering easy access to Tilghman Island.
The 317-square-metre property boasts a private pool, free Wi-Fi, parking, and sleeps up to 19 guests, with a fully equipped kitchen and proximity to Chesapeake Bay activities.

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.

Popular destinations

Best Chesapeake Bay holiday rentals with a balcony

The Tides Inn - Chesapeake Bay
9.0 382 reviews

The Tides Inn

resort, Irvington
The Tides Inn is located in West Irvington, a short distance from the charming downtown area and within easy reach of the scenic Chesapeake Bay. The resort has received very good user ratings, with excellent reviews for its location and cleanliness.
The hotel offers a range of amenities and activities, including a swimming pool, fitness centre, tennis court, restaurant, and bar. Guests can also enjoy the peaceful garden setting or explore the area on complimentary bikes.
Waterfront Family Home W/ Dock In Poquoson! - Chesapeake Bay
No reviews

Waterfront Family Home W/ Dock In Poquoson!

house, Poquoson
This waterfront family house in Poquoson, offering river views, is located 8.9 kilometres from Newport News/Williamsburg International Airport and 13.9 kilometres from the Virginia Living Museum.
This spacious three-bedroom, two-bathroom ground-floor property boasts direct waterfront access with a private dock, a swimming pool, a terrace, and accommodates up to nine guests with a fully equipped kitchen and air conditioning.
Dock Access! Family Retreat On The Little Wicomico - Chesapeake Bay
No reviews

Dock Access! Family Retreat On The Little Wicomico

house, Heathsville
This holiday home in Heathsville is located 111 kilometres from Newport News/Williamsburg International Airport.
This property offers 204 square metres of living space, accommodating up to 15 guests with 3 bedrooms and 3 bathrooms, and features air conditioning, WiFi, a fully equipped kitchen, and a garden with an outdoor dining area.
Newly Updated 3 Bedroom Cottage With Solo Stove Fire Pit - Chesapeake Bay
9.8 23 reviews

Newly Updated 3 Bedroom Cottage With Solo Stove Fire Pit

apartment, Kilmarnock
This Kilmarnock riverfront property is situated near Reedville, approximately 3km from both the Reedville Fishermen's Museum and the Reedville Historic District, offering scenic views and proximity to Smith Point Marina and Fleeton Beach (within 10km).
Sleeping six guests, this three-bedroom house boasts a fully equipped kitchen, private balcony, free Wi-Fi, and parking, making it ideal for families or groups exploring the area.

Best Chesapeake Bay holiday rentals with parking

Cozy 1-bedroom Bungalow In Quaint Darlington With Ac - Chesapeake Bay
10 10 reviews

Cozy 1-bedroom Bungalow In Quaint Darlington With Ac

apartment, Darlington
This one-bedroom flat in Darlington is ideally situated, just a 3-minute drive from Conowingo Dam and a 4-minute drive from Susquehanna State Park, offering convenient access to local attractions.
This self-catering accommodation for two guests includes a fully equipped kitchen with a microwave, air conditioning, on-site parking, and in-unit laundry facilities, with Wi-Fi and a television for entertainment.
Newly Constructed 2nd-story Studio Apartment - Chesapeake Bay
10 179 reviews

Newly Constructed 2nd-story Studio Apartment

apartment, Accomac
This Accomac holiday home is conveniently located within a 2.4km walk of the Accomac Historic District and 1.9km from Sawmill Park.
The single-bedroom property sleeps six guests and boasts a fully equipped kitchen, in-unit laundry, a private patio, and free Wi-Fi, perfect for exploring Accomac's attractions.
Summer Breeze Waterfront New Home-private Beach - Chesapeake Bay
9.9 81 reviews

Summer Breeze Waterfront New Home-private Beach

apartment, Kilmarnock
Summer Breeze, a three-bedroom waterfront house in Reedville, offers private beach access and is situated 30.6km from Kilmarnock, close to the Reedville Fisherman's Museum.
This self-catering property sleeps six, boasts a private pier, canoe, screened porch, and access to a neighbourhood boat ramp, plus a dishwasher, fridge, freezer, microwave, air conditioning, Wi-Fi, and parking.
Downtown 2br Apartment Near Convention Center - Chesapeake Bay
8.9 237 reviews

Downtown 2br Apartment Near Convention Center

apartment, Baltimore
This apartment is ideally located in downtown Baltimore, just a short walk from the Sports Legends Museum at Camden Yards and the Baltimore Convention Center, making it perfect for exploring the city's attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment is well-equipped with a fully equipped kitchen, a comfortable living space, and a terrace for enjoying the fresh air. Guests can enjoy a range of amenities, including a fitness centre, swimming pool, and parking, as well as access to a restaurant and bar on-site.