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

Manor And Mutts #2 - Beach Front, Pet Friendly, Wi-fi, Parking, W/d, King Bed - Chesapeake Bay
8.6 39 reviews
Chesapeake Bay
30/07 – 05/08
₹49503/nighttotal: â‚¹297018 (6 )

Manor And Mutts #2 - Beach Front, Pet Friendly, Wi-fi, Parking, W/d, King Bed

3 6
cottage , Norfolk
This charming beach house is situated in Willoughby Spit, just a short distance from Norfolk Beaches, Sarah Constant Shrine Beach, and Ocean View Beach. The cottage is rated very good by previous guests.
This comfortable holiday home has three bedrooms and can accommodate up to eight guests. The property includes a fully equipped kitchen, a fireplace, a patio, a garden, and free Wi-Fi, as well as a playground and barbecue grills for guests to enjoy.
Charming Lower Level Guest Unit, Fully Equipped Kitchen, Wifi, Free Onsite Park - Chesapeake Bay
9.6 4 reviews
Chesapeake Bay
02/07 – 05/07
₹17520/nighttotal: â‚¹52560 (3 )

Charming Lower Level Guest Unit, Fully Equipped Kitchen, Wifi, Free Onsite Park

1 2
apartment , Glen Burnie
This Pasadena apartment, minutes from Downs Park and the Baltimore & Annapolis Trail, offers easy access to attractions such as the Baltimore Cruise Terminal and Arundel Mills Mall.
The 111-square-metre (1194 sq ft) self-catering flat features one bedroom, one bathroom, sleeps three, and includes a fully equipped kitchen, in-unit laundry, free parking, and a spa.
Coles Point Marina And Campground - Chesapeake Bay
Chesapeake Bay
30/07 – 03/08
₹88355/nighttotal: â‚¹353420 (4 )

Coles Point Marina And Campground

2 10
house , Montross
This detached house is situated in Hague, 48 kilometres from Memorial House and the George Washington Birthplace National Monument, and 112 kilometres from Richmond International Airport.
This property offers a private entrance, air conditioning, complimentary WiFi, free private parking, and a well-equipped kitchen with a fridge, microwave, and dishwasher, providing a comfortable stay for guests visiting Montross.
Cottage On A Private Island In The York River - Chesapeake Bay
10 373 reviews
Chesapeake Bay
29/08 – 05/09
₹21894/nighttotal: â‚¹153258 (7 )

Cottage On A Private Island In The York River

3 2
cottage , Gloucester Point
This charming waterfront cottage is located in Gloucester Point, just 9 kilometres from Machicomoco State Park, Yorktown Beach, and Yorktown Farmers Market, offering easy access to a variety of attractions and activities. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
This 3-bedroom property spans 139 square metres and can accommodate up to 8 guests, making it ideal for families or groups. The cottage features a fully equipped kitchen, a private garden, a swimming pool, a spa, and a terrace, ensuring a relaxing and enjoyable stay.

Best Chesapeake Bay vacation rentals with a pool

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

Rod 'N' Reel Resort - Chesapeake Bay
8.6 1686 reviews
Chesapeake Bay
02/07 – 05/07
₹27225/nighttotal: â‚¹81675 (3 )

Rod 'N' Reel Resort

1 2
resort , Chesapeake Beach
Rod 'N' Reel Resort is situated on the Chesapeake Bay, a short drive from North Beach and Twin Shields Golf Club, making it a convenient base for exploring the area. The resort enjoys excellent ratings for its location, cleanliness, and overall experience.
The resort offers a range of accommodation options, including rooms with balconies and water views. Guests can enjoy a variety of amenities, including a swimming pool, fitness centre, spa, and on-site dining options, as well as activities like fishing charters and casino entertainment.
Bury Oasis: Pool, Hottub, Movie Theatre, Game Room - Chesapeake Bay
9.8 77 reviews
Chesapeake Bay
30/07 – 03/08
₹103166/nighttotal: â‚¹412664 (4 )

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

4 10
apartment , Salisbury
This four-bedroom apartment is situated in a residential area near Salisbury University, approximately 5 kilometres from local restaurants and 40 kilometres from the beach in Ocean City.
The property boasts a large backyard with a swimming pool, hot tub, and a spacious deck, ideal for families and groups of up to 12 guests.
Lovely 1 Bedroom By The Beach, W/ Porch & Pool - Chesapeake Bay
8.0 2 reviews
Chesapeake Bay
02/07 – 05/07
₹69239/nighttotal: â‚¹207717 (3 )

Lovely 1 Bedroom By The Beach, W/ Porch & Pool

1 2
apartment , Virginia Beach
This Virginia Beach holiday home is situated in Northeast Virginia Beach, a short walk (0.8km) from Pacific Avenue and the Virginia Beach Boardwalk, and 4km from Sandbridge Beach, offering easy access to local attractions.
This self-catering property boasts 70 square metres of space, comprising one bedroom, one bathroom, and sleeping up to four guests; features include a swimming pool, tennis court, and free Wi-Fi.
Oceanfront Beach Condo, Pool, Gym, Fishing Surfing - Chesapeake Bay
Chesapeake Bay
29/08 – 05/09
₹44039/nighttotal: â‚¹308273 (7 )

Oceanfront Beach Condo, Pool, Gym, Fishing Surfing

2 2
house , Virginia Beach
This oceanfront apartment offers direct access to Virginia Beach, situated a mere 200 metres from the Virginia Beach Boardwalk.
This two-bedroom, two-bathroom apartment sleeps up to six guests and features a fully equipped kitchen, a balcony with sea views, air conditioning, and access to a communal fitness centre, with WiFi provided and a check-out time of 10:00 AM.

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

Sun Outdoors Cape Charles - Chesapeake Bay
8.4 11 reviews
Chesapeake Bay
29/08 – 05/09
₹26759/nighttotal: â‚¹187313 (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.
13 Mi To Annapolis: Dog-friendly Home W/ Fire Pit! - Chesapeake Bay
10 1 review
Chesapeake Bay
30/07 – 05/08
₹37943/nighttotal: â‚¹227658 (6 )

13 Mi To Annapolis: Dog-friendly Home W/ Fire Pit!

3 6
house , Crofton
This dog-friendly Crofton house, situated approximately 21 kilometres from Annapolis and 35 kilometres from Washington, D.C., offers easy access to Annapolis Harbour and Baltimore-Washington International Airport.
The 174 square metre property boasts three bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, air conditioning, a garden, a spa, parking, and free Wi-Fi.
Cottage On The Bay - Chesapeake Bay
9.8 9 reviews
Chesapeake Bay
30/07 – 03/08
₹38122/nighttotal: â‚¹152488 (4 )

Cottage On The Bay

3 10
apartment , Fishing Creek
This charming cottage is located on Hoopers Island in Fishing Creek, a peaceful rural area on the Chesapeake Bay, within half a mile of a free county boat ramp. The property has received excellent ratings from previous guests.
This three-bedroom, two-bathroom holiday home offers ample space for families or groups. The cottage is fully equipped with a kitchen, fireplace, washer/dryer, and a terrace, and guests can enjoy access to fishing and crabbing charters, kayaks, and boat docking facilities at the nearby Riverside Lodge.
Beach Days & Dtwn Charm! Cape Charles Cottage - Chesapeake Bay
8.0 1 review
Chesapeake Bay
29/08 – 05/09
₹26507/nighttotal: â‚¹185549 (7 )

Beach Days & Dtwn Charm! Cape Charles Cottage

2 2
house , Cheriton
This holiday cottage in Cheriton is situated approximately 51 kilometres from Norfolk International Airport, offering a coastal escape.
This 98 square metre holiday home accommodates up to 13 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, a fully equipped kitchen with a dishwasher and oven, complimentary on-site parking, and free WiFi, along with a private patio and outdoor dining area.

Best Chesapeake Bay holiday rentals with parking

Baltimore Home < 2 Mi To Dtwn Towson - Chesapeake Bay
10 1 review
Chesapeake Bay
02/07 – 05/07
₹21648/nighttotal: â‚¹64944 (3 )

Baltimore Home < 2 Mi To Dtwn Towson

1 2
house , Baltimore
This charming Baltimore house is situated in Towson, less than 3.2 km from downtown Towson, 6.4 km from the Baltimore Museum of Art, and 6.6 km from Clifton Park, offering a peaceful suburban setting close to the city's attractions. The property provides a comfortable and convenient stay, with a fully equipped kitchen, a washing machine, and free Wi-Fi.
The house has one bedroom and one bathroom, with a floor area of 60 square metres, comfortably accommodating two guests. Amenities include a flat-screen TV, towels, bed linen, and parking, ensuring a pleasant and relaxing stay.
Cabin At Holdens Creek On Eastern Shore Of Va - Chesapeake Bay
9.8 187 reviews
Chesapeake Bay
29/08 – 05/09
₹12117/nighttotal: â‚¹84819 (7 )

Cabin At Holdens Creek On Eastern Shore Of Va

1 2
cabin , Sanford
This cabin is located in a peaceful rural setting, just 25 kilometres from Bloxom Winery, Wallops Flight Facility, and the Eastern Shore Railway Museum. It has received excellent user ratings.
The cabin is a one-bedroom, one-bathroom property with a floor area of 74 square metres and a capacity of six guests. It offers a range of amenities including a kitchen with a fridge and microwave oven, air conditioning, a terrace, a garden, parking, and free Wi-Fi.
Hearing Accessible King Studio W/ Free Breakfast - Chesapeake Bay
Chesapeake Bay
02/07 – 05/07
₹14461/nighttotal: â‚¹43383 (3 )

Hearing Accessible King Studio W/ Free Breakfast

1 2
studio , Baltimore
This communications-accessible apartment is located in Baltimore's Inner Harbour, 500 metres from Historic Ships in Baltimore and 600 metres from the National Aquarium.
This studio apartment accommodates two guests and offers a fully equipped kitchen with a full-size fridge, dishwasher, and stovetop, as well as complimentary hot breakfast, evening receptions, and free WiFi.
Restored 1920's Cottage On 1 Acre W/ Fire Pit - Chesapeake Bay
9.5 187 reviews
Chesapeake Bay
29/08 – 05/09
₹22978/nighttotal: â‚¹160846 (7 )

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

2 2
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.
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