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

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Check availability on Shady Side 5 Star Hotels

Tonight
5 Mar - 6 Mar
Tomorrow
6 Mar - 7 Mar
This weekend
6 Mar - 8 Mar
Next weekend
13 Mar - 15 Mar

Our top choices for Shady Side 5-star hotels

Premium bedding, down duvets, in-room safe, desk

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (374 reviews)
"Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. "
United States
Joseph
The price is Rp6.251.076
Rp6.876.184 total
includes taxes & fees
8 Mar - 9 Mar
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
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
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 Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
The price is Rp1.509.807 per night from 8 Mar to 9 Mar
Rp1.509.807
Rp1.721.179 total
8 Mar - 9 Mar
includes taxes & fees
8.6/10 Excellent! (1,011 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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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 Rp1.721.179

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.