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Find holiday rentals that suit your style

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Apartments
Apartments
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Aparthotels
Aparthotels

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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.
The price is NZ$645
includes taxes & fees
22 Nov - 23 Nov
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
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, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
The price is NZ$1,252
includes taxes & fees
15 Nov - 16 Nov
Secluded Cozy Cottage in Historic Downtown
14

3. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is NZ$947
includes taxes & fees
15 Dec - 16 Dec
Plum Point Cottage #14
Fire pit (2)

4. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is NZ$997
includes taxes & fees
15 Dec - 16 Dec
Plum Point Cottage #15
A covered patio with a table and chairs, large windows, and an American flag.

5. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
Plum Point Cottage #17
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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Learn more about Shady Side

Love dining, parks and museums? Get away to Shady Side!

See all hotels in Shady Side
A river with boats, a marina, and a town with houses and buildings.

Top reviews in Shady Side

A historic brick building with a red roof, multiple windows, and a central staircase.
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District

10/10 Excellent

The only place to stay when you visit Annapolis! We loved it!
Australia
Katrina
Reviewed July 15, 2026
Historic Inns of Annapolis

Frequently Asked Questions

How much do cottages in Shady Side cost?

Cottages in Shady Side range between NZ$644 and NZ$1,252 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.

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.