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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Shady Side cottages

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)
"We love this place!"
United States
Joan K.
$236 nightly
The price is $250
Dec 11 - Dec 12
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Microwave, oven, stovetop, dishwasher
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)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
$261 nightly
The price is $277
Dec 25 - Dec 26
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

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

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$802 nightly
The price is $885
Dec 13 - Dec 14
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Historic District
9.6 out of 10, Exceptional, (16)
"We had a very lovely stay . This is an excellent location . "
United States
Kimberly B.
$480 nightly
The price is $547
Dec 11 - Dec 12
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
"Great"
stephen 3-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Shady Side

Shady Side Cottages information

Number of reviews
66
Accommodation
70 Cottages
Lowest Price
$250
Highest Price
$885

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between $250 and $885 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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