Chesapeake Bay Vacation Rentals: Tranquility at your Fingertips

Chesapeake Bay is known throughout North America for the natural beauty and rich biodiversity that form the largest estuary on the continent. Numerous outdoor and marine activities alongside historic trails and exciting family attractions await visitors to this neck of the woods, making it ideal for families, couples and independent travelers. For those folks lucky enough to be planning a trip to the region, there is a huge range of Chesapeake Bay vacation rentals available with something to meet every need, want and desire.

Chesapeake Bay Vacation Rentals For Any Mood


Use one of the many Chesapeake Bay rentals as your launching pad to the picturesque land and seascape at your disposal. Take a cruise out on the bay and shake off all your cares in the fresh sea breeze, or go sailing by romantic moonlight and fall in love all over again. Tacklers will be thrilled with the abundant fishing opportunities present in the bay, and those that prefer having their seafood served up to them on a plate will delight in the fresh oysters, crab and fish available in the many fine restaurants found near most Chesapeake Bay vacation rentals.

History Near Chesapeake Bay Vacation Home Rentals


For history buffs the Chesapeake Bay area holds a treasure trove of historical places of interest. From many Chesapeake Bay vacation home rentals you can explore Olde Town, just a few miles away, which is packed with historic 17th and 18th century houses. Or you can sail on an old-fashioned skipjack, take a tour of the old lighthouses, visit one of the region’s many museums or make a trip to one of the old plantation homes of the area.

Activities Abound Around Chesapeake Bay Rentals


Energetic souls staying at Chesapeake Bay vacation rentals will wake each day with one thing on their mind: deciding which recreational activity to try out. You can rent kayaks to explore the bay’s many tributaries, rent bicycles, spy on some of the area’s numerous bird species or take a guided walk along the historic trails in the area’s national parks. Plus, many Chesapeake Bay rentals have their own kayaks, bicycles, and other active equipment you can use. Thrill seekers will enjoy the chance to go waterskiing, jet skiing or go-karting – and maybe even try sky diving!

Chesapeake Bay vacation home rentals make the perfect trip effortless: all you have to do is let the charm of Chesapeake Bay work its magic on you. With Chesapeake Bay rentals you have all the amenities you require and space to spread out and make yourself at home. Once you try Chesapeake Bay vacation home rentals, you will be back again and again to enjoy the stunning sunsets, wonderful scenery, and huge range of recreational pursuits.

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Vacation Rentals Chesapeake Bay, Maryland(143)

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2 Bedrooms,
  • 2 Half Baths
  • , Sleeps 4

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    5 Bedrooms,
  • 5 Half Baths
  • , Sleeps 10

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    3 Bedrooms,
  • 1 Bathroom
  • , Sleeps 6

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    6 Bedrooms,
  • 6 Half Baths
  • , Sleeps 23

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    5 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 10

    No rental rates available - please contact the owner
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    3 Bedrooms,
  • 2 Half Baths
  • , Sleeps 6

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    9 Bedrooms,
  • 7 Bathrooms
  • , 2 Half Baths
  • , Sleeps 20

    $6,950 - $10,000 week
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    4 Bedrooms,
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  • , Sleeps 8

    $400 - $650 night
    $1,800 - $3,000 week
    Accepts Online Payments
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    4 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 10

    $225 - $275 night
    $1,400 week
    Accepts Online Payments
    • Viewed
    4 Bedrooms,
  • 3 Half Baths
  • , Sleeps 12

    $2,500 week
    Accepts Online Payments
    • Viewed
    3 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 6

    $200 - $250 night
    $1,300 week
    $2,700 month
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    4 Bedrooms,
  • 4 Bathrooms
  • , Sleeps 8

    No rental rates available - please contact the owner
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    4 Bedrooms,
  • 2 Bathrooms
  • , 1 Half Bath
  • , Sleeps 12

    $250 - $450 night
    $1,400 - $2,000 week
    Accepts Online Payments
    • Viewed
    4 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 10

    $250 - $500 night
    $1,600 - $2,500 week
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    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 8

    $350 - $850 night
    $2,000 - $2,800 week
    Accepts Online Payments
    • Viewed
    4 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 10

    $225 night
    $1,250 - $1,450 week
    Accepts Online Payments
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    2 Bedrooms,
  • 1 Bathroom
  • , Sleeps 6

    $150 - $200 night
    $600 - $800 week
    Accepts Online Payments
    • Viewed
    4 Bedrooms,
  • 2 Bathrooms
  • , 1 Half Bath
  • , Sleeps 8

    $1,600 week
    Accepts Online Payments
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 8

    $350 night
    $1,825 week
    • Viewed
    5 Bedrooms,
  • 5 Bathrooms
  • , Sleeps 12

    $2,700 week
    Accepts Online Payments
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 8

    $100 - $150 night
    $695 - $895 week
    • Viewed
    3 Bedrooms,
  • 1 Bathroom
  • , Sleeps 6

    $900 - $1,300 week
    Accepts Online Payments
    • Viewed
    2 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 6

    $1,110 week
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 10

    $2,000 week
    Accepts Online Payments
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 8

    $1,790 - $2,370 week
    • Viewed
    3 Bedrooms,
  • 1 Bathroom
  • , 1 Half Bath
  • , Sleeps 6

    $120 - $220 night
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 6

    $100 - $200 night
    $600 - $1,200 week
    • Viewed
    3 Bedrooms,
  • 3 Bathrooms
  • , 1 Half Bath
  • , Sleeps 8

    $200 - $225 night
    $1,100 - $1,400 week
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 7

    $275 night
    $1,300 week
    Accepts Online Payments
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    2 Bedrooms,
  • 1 Bathroom
  • , Sleeps 5

    $1,050 - $1,400 week
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