Find 5 Star Hotels in Shady Side, MD from SAR 468

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Check availability on Shady Side 5 Star Hotels

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 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, (387 reviews)
"Wonderful location with great views and amenities such as a fire pit"
United States
Craig
The price is SAR 2,263
SAR 2,489 total
includes taxes & fees
21 Jun - 22 Jun
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, sun 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 SAR 1,068
SAR 1,218 total
includes taxes & fees
26 May - 27 May
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 SAR 411 per night from May 31 to Jun 1
SAR 411
SAR 468 total
31 May - 1 Jun
includes taxes & fees
8.6/10 Excellent! (1,008 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.

Learn more about Shady Side

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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

Top Shady Side Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Shady Side?
The amount you pay for a 5-star hotel in Shady Side can vary based on when you want to travel and how long you plan to be away, among several factors. Take advantage of our price per night filter and other search tools to land the best deal on a high-end getaway.

  • Search for the lowest price per night from SAR 468

What makes a hotel 5 stars in Shady Side?
From fine dining venues and all-day fitness centers to swimming pools and superior bedding, the 5-star experience in Shady Side is all about comfort and indulgence. But it calls for more than just top-notch amenities to get a 5-star rating. Accommodations must also offer remarkable guest services like in-room beauty treatments, on-site laundry and dry cleaning and room service any time day or night.
Are there any 5-star all-inclusive resorts in Shady Side?
Our filter tool is the best way to narrow down what you're looking for. Select "All inclusive" and "5-star" to see the most upscale properties in Shady Side where your room, meals, entertainment and activities are included in the price. At these escapes, your trip is pure relaxation and indulgence from the moment you put down your suitcase.

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