Search Cottages in Shady Side

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct

Cottages in Shady Side

Our top choices for Shady Side cottages

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

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

10.0 out of 10, Exceptional, (47)
"We had a great stay! Thanks."
The price is SAR 652
SAR 1,236 total
includes taxes & fees
24 Aug - 25 Aug
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is SAR 1,689
SAR 2,785 total
includes taxes & fees
24 Aug - 25 Aug
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shady Side Hotel Reviews

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

10/10 Excellent
"It's poorly maintained. Baseboard in room coming off corner into the bathroom. Paint peeling off the bathroom door. Bathroom faucet was loose. The toilet seat was loose. Toilet runs on and off all the time. It was a very dark room, low wattage light bulbs and one of the lamps didn't work. There's a leak somewhere from the tub even when the shower curtain is closed and leaves a puddle. The Staff was very friendly though the lobby was old and dirty. We were supposed to stay there 6 days but left after the first night."
KENNETH 6-night trip
Posted 22 hours ago
Hampton Inn & Suites Annapolis

Frequently asked questions

How much do cottages in Shady Side cost?
Cottages in Shady Side range between SAR 1,689 and SAR 1,689 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.