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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Shady Side cottages

Exterior detail

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
North Beach
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is AU$440
includes taxes & fees
18 Jan - 19 Jan
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Property grounds

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (48 reviews)
"We love this place!"
United States
Joan K.
The price is AU$478
includes taxes & fees
29 Jan - 30 Jan
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Marina

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (16 reviews)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
The price is AU$799
includes taxes & fees
17 Jan - 18 Jan
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Clean room, staff was very friendly and kept in touch throughout stay, to see if I needed anything. Highly recommended staying here"
raymond 2-night trip
Posted 4 days ago
Historic Inns of Annapolis

Find out more about Shady Side

Shady Side Cottages information

Number of reviews
67
Accommodation
76 Cottages
Lowest Price
AU$440
Highest Price
AU$799

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between AU$440 and AU$799 per night. These properties offer a chance to get in tune with nature — at a price you can afford. This price was 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?
You'll find loads of fantastic things to fill your itinerary with in Shady Side. Head for leading attractions like Thanksgiving Farm Wines, Triton Beach and Bay Ridge Beach. Sparrows Beach, Carrs Beach and Franklin Point State Park also appeal to many visitors.

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