Compare Shady Side Cottage Rentals

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Featured Cottages in Shady Side

Firefly Cottage at the Cape, Hot Tub, Community beach enjoy summer USNA visits.

Firefly Cottage at the Cape, Hot Tub, Community beach enjoy summer USNA visits.

Annapolis MD
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Hot Tub
Breakfast included
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

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

Tilghman Island MD
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Annapolis MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills. Helpful staff is there to provide concierge services, as well as offer insight about the area.
Kitchen
Washer
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!

Saint Michaels MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Deale MD
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Hot Tub
Kitchen
Waterfront River Cottage for 2, dog-friendly

Waterfront River Cottage for 2, dog-friendly

Severna Park MD
Guests staying at this cottage enjoy free WiFi in public areas, an arcade/game room, and a garden. Onsite parking is offered for a fee. This beach cottage also has barbecue grills.
Kitchen
Pet friendly
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Royal Oak MD
At this cottage, guests have access to a gym, laundry facilities, and a garden.
Kitchen
Washer
Beachfront Home Minutes to Downtown Annapolis Dogs OK

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Annapolis MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
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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
    $136 nightly
    The price is $155 total per night from Jul 19 to Jul 20
    $155 total
    Jul 19 - Jul 20
    Total with taxes and fees
    9/10 Wonderful! (1,896 reviews)
    DoubleTree by Hilton Hotel Annapolis

    DoubleTree by Hilton Hotel Annapolis

    210 Holiday Court Annapolis MD
    $111 nightly
    The price is $127 total per night from Jul 14 to Jul 15
    $127 total
    Jul 14 - Jul 15
    Total with taxes and fees
    8.6/10 Excellent! (1,033 reviews)
    Crowne Plaza Annapolis by IHG

    Crowne Plaza Annapolis by IHG

    173 Jennifer Rd Annapolis MD
    $119 nightly
    The price is $135 total per night from Jul 16 to Jul 17
    $135 total
    Jul 16 - Jul 17
    Total with taxes and fees
    8.8/10 Excellent! (1,017 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
76 Cottages
Lowest Price
$127
Highest Price
$155
Popular accommodation
Firefly Cottage at the Cape, Hot Tub, Community beach enjoy summer USNA visits., "Point of View" Waterfront cottage with panoramic views on Tilghman Island, The Yellow Cottage on Harness Creek, Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK, Waterfront River Cottage for 2, dog-friendly, Spacious waterfront house in charming Royal Oak with WiFi, AC, dock, Beachfront Home Minutes to Downtown Annapolis Dogs OK

More to Explore