Shady Side Vacation Homes

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Featured Vacation Homes in Shady Side

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Shady Side

    Historic Inns of Annapolis

    Historic Inns of Annapolis

    58 State Circle Annapolis MD
    $130 nightly
    The price is $148 total per night from Jul 7 to Jul 8
    $148 total
    Jul 7 - Jul 8
    Total with taxes and fees
    9/10 Wonderful! (1,877 reviews)
    DoubleTree by Hilton Hotel Annapolis

    DoubleTree by Hilton Hotel Annapolis

    210 Holiday Court Annapolis MD
    $95 nightly
    The price is $109 total per night from Jul 5 to Jul 6
    $109 total
    Jul 5 - Jul 6
    Total with taxes and fees
    8.6/10 Excellent! (1,022 reviews)
    La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

    La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

    55 Hampton Park Blvd Capitol Heights MD
    $95 nightly
    The price is $107 total per night from Jul 5 to Jul 6
    $107 total
    Jul 5 - Jul 6
    Total with taxes and fees
    6/10 (2,026 reviews)

Shady Side Vacation Homes

Book vacation homes in Shady Side
Next time you take a group getaway top Shady Side, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Shady Side vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Shady Side vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Shady Side; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Shady Side rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Shady Side is sure to be a winner.

Shady Side Vacation Homes essential information

Accommodation
599 Vacation Homes
Lowest Price
$107
Highest Price
$871
Popular accommodation
Grace Cottage, St Michaels Walk to everything!, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Charming Annapolis WaterVIEW Home, Private Pool & Stunning Bay Views on Kent Island, Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, Waterfront Home with Private Dock, Community Beach, Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly, 3-bedroom house in Deale located on Bay many amenities and great views, Circa 1700 Chesapeake Colonial home on the National Register.