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 £361
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 £603
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 £443
includes taxes & fees
27 Oct - 28 Oct
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 £409
includes taxes & fees
27 Oct - 28 Oct
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 9 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
£361
Highest Price
£603

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between £361 and £603 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.