Shady Side Hotel Guide - 5 Stars Hotels in Shady Side, Maryland

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Check availability on Shady Side 5 Star Hotels

Next weekend
12 Jun - 14 Jun
In two weeks
19 Jun - 21 Jun

Our top choices for Shady Side 5-star hotels

Breakfast, lunch, dinner and brunch served

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (388 reviews)
"Wonderful location with great views and amenities such as a fire pit"
United States
Craig
The price is Rp12.661.272
Rp13.927.399 total
includes taxes & fees
6 Jul - 7 Jul
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (15 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is Rp5.954.766
Rp6.788.390 total
includes taxes & fees
16 Jun - 17 Jun
The Inn at Tacaro Estate
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Shady Side.
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court Upper Marlboro MD
The price is Rp2.203.638 per night from 30 Jun to 1 Jul
Rp2.203.638
Rp2.490.110 total
30 Jun - 1 Jul
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
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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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Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Shady Side?
There are a range of pricing options for a 5-star hotel in Shady Side on Expedia. The amount you pay will depend on your travel dates, trip length and other factors. Compare all of the available properties for your desired dates and use our pricing and other filters to lock in the ideal upscale stay.

  • Search for the lowest price per night from Rp1.957.411

What makes a hotel 5 stars in Shady Side?
From high-end dining venues and fitness centres to pools and dreamy bedding, the 5-star experience in Shady Side is all about luxury and comfort. But it calls for more than just top-notch perks to earn a 5-star rating. Hotels also have to deliver superb guest services like in-room massage treatments, on-site dry cleaning and laundry and room service any time night or day.
Are there any 5-star all-inclusive resorts in Shady Side?
Use Expedia's filters to find a luxury escape in Shady Side where everything you need is included in the price. After your initial search, narrow down your results for hotels that have a 5-star rating and are deemed "All inclusive." The first thing on the schedule at these stays? Pure indulgence and relaxation.