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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Shady Side cottages

Marina

1. 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.
$657 nightly
The price is $749
Sep 9 - Sep 10
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"I only stayed overnight because we were at the Renaissance fair, it was clean, many places to eat within walking distance is a plus."
John 1-night trip
Posted 4 hours ago
Crowne Plaza Annapolis by IHG

Find out more about Shady Side

Shady Side Cottages information

Number of reviews
22
Accommodation
78 Cottages
Lowest Price
$749
Highest Price
$749

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between $749 and $749 per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. These prices were 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.
Why book your cottage in Shady Side with Expedia?
Reserving a cottage in Shady Side is as simple as deciding on your travel dates and choosing your ideal place for a getaway in nature. From upscale retreats to affordable stays and cottages that include perks like a pool, Expedia has something for all styles. As for epic deals? We've got them as well!
How can I find cheap cottages in Shady Side?
Expedia is here to help you locate cheap cottages in Shady Side. To book a fantastic stay in a few quick clicks, use our handy filter tool to refine your search results by amenities, star rating and budget.
What is there to do in Shady Side near my cottage?
If you're ready to discover the best of Shady Side, find your way to Shadyside Park. It's a hit among locals and tourists alike.

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