Compare Shady Side Cottage Rentals

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Featured Shady Side Cottages

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

At this cottage, guests have access to features like laundry facilities.
The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

At this cottage, guests have access to a gym, laundry facilities, and barbecue grills. This beach cottage also has a garden.
Chesapeake Cottage

Chesapeake Cottage

This vacation home is a smoke-free vacation home.
Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Guests staying at this cottage enjoy an outdoor pool, laundry facilities, and local meal delivery service. Additional amenities include a garden and barbecue grills.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
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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
    $145 nightly
    The price is $166 total per night from Nov 2 to Nov 3
    $166 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (1,857 reviews)
    DoubleTree by Hilton Hotel Largo/Washington DC

    DoubleTree by Hilton Hotel Largo/Washington DC

    9100 Basil Court, Upper Marlboro, MD
    $97 nightly
    The price is $109 total per night from Nov 3 to Nov 4
    $109 total
    Nov 3 - Nov 4
    Total with taxes and fees
    7.8/10 Good! (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
    $85 nightly
    The price is $96 total per night from Oct 7 to Oct 8
    $96 total
    Oct 7 - Oct 8
    Total with taxes and fees
    5.8/10 (1,897 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
70 Cottages
Lowest Price
$96
Highest Price
$166
Popular accommodation
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, The Middle Point Cabin in Saint Michaels, Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK, Chesapeake Cottage, Relaxing Waterfront Cottage Near St Michaels, Maryland, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

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