A river with boats, a marina, and a town with houses and buildings.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Shady Side cottages

A covered patio with a table and chairs, large windows, and an American flag.

1. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AU$661
includes taxes & fees
27 Oct - 28 Oct
Plum Point Cottage #17
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

2. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is AU$1,120
includes taxes & fees
8 Nov - 9 Nov
Secluded Cozy Cottage in Historic Downtown
Fire pit (2)

3. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is AU$823
includes taxes & fees
31 Oct - 1 Nov
Plum Point Cottage #15
14

4. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is AU$774
includes taxes & fees
9 Nov - 10 Nov
Plum Point Cottage #14
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.
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Top Shady Side Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great location, friendly staff."
Joel 3-night trip
Posted 3 hours ago
Hilton Garden Inn Annapolis Downtown

Find out more about Shady Side

Shady Side Cottages information

Number of reviews
31
Accommodation
78 Cottages
Lowest Price
AU$661
Highest Price
AU$1,120

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between AU$661 and AU$1,120 per night. These properties offer a chance to get in tune with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What is there to do in Shady Side near my cottage?
You'll find loads of fantastic things to fill your itinerary with in Shady Side. Head for leading attractions like Thanksgiving Farm Wines, Triton Beach and Bay Ridge Beach. Sparrows Beach, Carrs Beach and Franklin Point State Park also appeal to many visitors.

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