5 Stars Hotels in Shady Side, Maryland from CA $179

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Check availability on Shady Side 5 Star Hotels

Tonight
Apr 1 - Apr 2
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Apr 2 - Apr 3
This weekend
Apr 3 - Apr 5
Next weekend
Apr 10 - Apr 12

Our top choices for Shady Side 5-star hotels

Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (376 reviews)
"everything was perfect!"
United States
John
The price is CA $770
CA $847 total
includes taxes & fees
Apr 5 - Apr 6
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
9.4 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 price is CA $359
CA $409 total
includes taxes & fees
Apr 5 - Apr 6
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 CA $278 per night from Apr 19 to Apr 20
CA $278
CA $317 total
Apr 19 - Apr 20
includes taxes & fees
9.4/10 Exceptional! (1,005 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.

Top Shady Side Hotel Reviews

Find out more about Shady Side

Five Star Hotels in Shady Side

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Shady Side so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Shady Side and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Shady Side

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Shady Side

The results are in, and Shady Side 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Shady Side! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Shady Side today and settle down in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Shady Side?
You can find many different pricing options for 5-star hotels in Shady Side on Expedia. How much you'll pay will depend on when you want to travel, trip length and other factors. Compare all of the available properties for your desired dates and use our pricing and other filters to find the perfect luxury stay.

  • Search for the lowest price per night from CA $179

What makes a hotel 5 stars in Shady Side?
From gourmet dining venues and fitness centres to pools and luxury bedding, the 5-star experience in Shady Side is all about luxury and relaxation. But it takes more than just upscale amenities to earn a 5-star rating. Accommodations must also deliver extraordinary guest-centric services like in-room massages, laundry and dry cleaning and 24-hour room service.
Are there any 5-star all-inclusive resorts in Shady Side?
Use our filter tool to find an upscale getaway in Shady Side where most of what you need is included. From there, narrow down your results for hotels that have 5 stars and are deemed "All inclusive." The main thing on the agenda at these stays? Pure relaxation and indulgence.

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