Compare and book 5 Star hotels in Shady Side, Maryland

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Check availability on Shady Side 5 Star Hotels

Tonight
5 Jul - 6 Jul
Tomorrow
6 Jul - 7 Jul
Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul

Top Shady Side 5 Star Hotels

Inn at Perry Cabin
Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (352)
"Grounds are beautiful. Staff very friendly and attentive "
The price is 16.139.970 ₫
19.529.496 ₫ total
includes taxes & fees
16 Jul - 17 Jul
Inn at Perry Cabin
The Inn at Tacaro Estate
Horse riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"1940’s estate is maintained to remind you of those times. There was a “Speak-EZ” in the basement they had open Friday and Saturday evenings. My room was spacious and included a balcony. Huge front lawn with a pool and a view to the Bay. "
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.
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St, Annapolis, MD
The price is 4.057.376 ₫ per night from 13 Jul to 14 Jul
4.057.376 ₫
4.625.410 ₫ total
13 Jul - 14 Jul
includes taxes & fees
9.4/10 Exceptional! (1,013 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 4.057.376 ₫

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.