Compare Shady Side Cottage Rentals

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Featured Shady Side Cottages

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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

    The Cottage

    The Cottage

    Shady Side
    10/10 Exceptional! (4 reviews)
    Historic Inns of Annapolis

    Historic Inns of Annapolis

    58 State Circle, Annapolis, MD
    The price is $199 per night from May 25 to May 26
    $199
    includes taxes & fees
    $145 per night
    May 25 - May 26
    8.8/10 Excellent! (1,758 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
    The price is $105 per night from May 11 to May 12
    $105
    includes taxes & fees
    $93 per night
    May 11 - May 12
    6/10 (1,590 reviews)

Cottages

Book a cottage in Shady Side
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Shady Side. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Shady Side better.

Cottage apartments in Shady Side range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Shady Side
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Shady Side and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Shady Side cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Shady Side. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Shady Side Cottages essential information

Accommodation
71 Cottages
Lowest Price
$105
Highest Price
$199
Popular accommodation
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Eastern Shore Waterside Cottage Near St. Michaels, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Waterfront dog-friendly home with beach just mins to Downtown Annapolis, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak, Amazing views, short walks to great dining!, Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,