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Oct 24 - Oct 26
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Nov 7 - Nov 9
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Jan 2 - Jan 4

Cottages in Shady Side

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Terrace/patio

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
$825 nightly
The price is $910
Nov 1 - Nov 2
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.6 out of 10, Exceptional, (15)
"We had a very lovely stay . This is an excellent location . "
$600 nightly
The price is $684
Nov 3 - Nov 4
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"The staff were uniformly attentive and friendly."
Charles 2-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Shady Side

Find out more about Shady Side

Shady Side Cottages information

Number of reviews
15
Accommodation
73 Cottages
Lowest Price
$684
Highest Price
$910

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between $684 and $910 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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Explore a world of travel with Expedia