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

Compare and book 5 Star hotels in Shady Side, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shady Side 5 Star Hotels

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, (390 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is 17.529.786 ₫
19.282.765 ₫ total
includes taxes & fees
1 Jul - 2 Jul
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
9.6 out of 10, Exceptional, (15 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is 8.690.273 ₫
9.906.911 ₫ total
includes taxes & fees
14 Jun - 15 Jun
The Inn at Tacaro Estate
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court Upper Marlboro MD
The price is 3.000.068 ₫ per night from 7 Jul to 8 Jul
3.000.068 ₫
3.390.077 ₫ total
7 Jul - 8 Jul
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
Still don't see what you're looking for?
See all properties in Shady Side.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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

Love dining, parks and museums? Get away to Shady Side!

See all hotels in Shady Side
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?
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 3.337.042 ₫

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.