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 house with a red door, a small porch, and a view of a river with a bridge in the background.

1. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A building with a black metal gate, a brick pathway, and greenery.

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 AED 1,837
AED 2,965 total
includes taxes & fees
8 Nov - 9 Nov
Secluded Cozy Cottage in Historic Downtown
A covered patio with a table and chairs, large windows, and an American flag.

3. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AED 1,047
AED 1,740 total
includes taxes & fees
5 Nov - 6 Nov
Plum Point Cottage #17
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 AED 1,256
AED 2,056 total
includes taxes & fees
27 Oct - 28 Oct
Plum Point Cottage #14
Fire pit (2)

5. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is AED 1,252
AED 2,165 total
includes taxes & fees
5 Nov - 6 Nov
Plum Point Cottage #15
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
"The one thing that I am so impressed with is how quiet the property is. So many hotels are noisy all night and day. This one, even though it's right next to a busy highway, is pin drop quiet. So much appreciated."
JoAnn 4-night trip
Posted 1 hour ago
Crowne Plaza Annapolis by IHG

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between AED 1,740 and AED 2,965 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.