Shady Side Cottages ￥68,372

A river with boats, a marina, and a town with houses and buildings.

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Our top choices for Shady Side cottages

A two-story building with a covered outdoor area, a staircase, and trees with autumn leaves.

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

West Annapolis

Jill R.

￥68,372 total

includes taxes & fees

Nov 5 - Nov 6

A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

2. Secluded Cozy Cottage in Historic Downtown

Historic District

Tim G.

￥128,882 total

includes taxes & fees

Nov 12 - Nov 13

A covered patio with a table and chairs, large windows, and an American flag.

3. Plum Point Cottage #17

Huntingtown

￥72,984 total

includes taxes & fees

Nov 14 - Nov 15

An outdoor dining area with a wooden table and chairs, a bottle of wine, and a vase of flowers.

4. Plum Point Cottage #15

Maryland

￥90,888 total

includes taxes & fees

Nov 14 - Nov 15

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Top Shady Side Hotel Reviews

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Clean room. Great breakfast."

Historic Inns of Annapolis

10/10 Excellent

"We stayed here overnight so that we didn't have to travel from MoCo to Annapolis for an early morning conference. We stayed in the Maryland Inn, it was quaint, very clean, and cute. We really enjoyed the property, its location to the water and the conference. We'd definitely stay here again."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"We stayed at the Wilson’s Cove section next to the marina. Very nice accommodations. Restaurant was at the main hotel two blocks away. The staff was very friendly and the check-in staff at the main hotel helped me to get the room without having to pay extra since there was an Expedia reservation foul up."

St Michaels Inn

10/10 Excellent

"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent

"The hotel is well maintained and looks modern. Our room is clean and spacious. It has all the amenities I need, particularly microwave and refrigerator. It has a complimentary continental breakfast as well, basic and has limited options. What I like most of this hotel is the location! We are so near to a lot of restaurants, grocery store, department stores - I love my Target and Ross, and even movie theater. All in all, a great value hotel! We’ll definitely be staying here again in the future."

Find out more about Shady Side

Shady Side Cottages information

Number of reviews	116
Accommodation	82 Cottages
Lowest Price	￥68,372
Highest Price	￥128,882

Frequently asked questions

How much do cottages in Shady Side cost?

Cottages in Shady Side range between ￥68,372 and ￥128,882 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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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Shady Side cottages

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