Find 5 Star Hotels in Shady Side, MD from $124

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Compare Shady Side 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Inn at Perry Cabin
Breakfast, lunch, dinner served; ocean views
Inn at Perry Cabin
5.0 star property
9.6 out of 10, Exceptional, 298 reviews
"Had the best time! Staff went out of their way to celebrate our 30th! We enjoyed paddle boards, kayaks, tennis, swimming, Bocce, croquet, golf and sailing! So beautiful and everything provided right there!"
The price is $747
$904 total
includes taxes & fees
Jun 25 - Jun 26
Inn at Perry Cabin

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 Annapolis

Graduate Annapolis

126 West St, Annapolis, MD
The price is $153 per night from Jul 1 to Jul 2
$153
$175 total
includes taxes & fees
Jul 1 - Jul 2
9.2/10 Wonderful! (1,033 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.

Why not request total luxury on your trip to Shady Side? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Shady Side so popular in the last year. There's no reason to delay a getaway to Shady Side any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Reserve one of our 5-star hotels in Shady Side and indulge in the finer things in life for a while. What are you waiting for?

5-Star Hotels in Shady Side

You'll have a fantastic time at one of these 5-star hotels. Spa treatments, delicious meals, and attentive guest service are all at your fingertips. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready to kick back and indulge. What kind of amenities will make your stay a wonderful one? A mud wrap treatment that will leave you feeling refreshed and alive? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A Swedish massage to help your cares fall away? Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

But you aren't going to spend your entire vacation in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Shady Side are waiting for you to relax after an exciting day.

Your Getaway Starts Today

The results are in, and Shady Side 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to plan your next great escape. Opt for one of Expedia's Shady Side 5-star hotels 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?
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 $124

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.
Are there any 5-star vacation rentals in Shady Side?
Our site doesn’t have any 5-star vacation rentals in Shady Side. However, you will still find some top-rated stays where the only item on your agenda will be to kick back and enjoy yourself. View what’s available by searching through our vacation rentals in Shady Side.