Find 5 Star Hotels in Eastern Shore, MD from $230

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Nov 13 - Nov 14
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Nov 14 - Nov 15
This weekend
Nov 13 - Nov 15
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Nov 20 - Nov 22

Our top choices for Eastern Shore 5-star hotels

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

1. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (407 reviews)
"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
United States
Virgilio
$459 nightly
The price is $505
Dec 7 - Dec 8
Total with taxes and fees
Inn at Perry Cabin
A brick pathway leading to a pool area with a fence and potted plants.

2. Cypress River Inn & Spa

Cypress River Inn & Spa
5.0 star property
Snow Hill
8.6 out of 10, Excellent, (8 reviews)
"I fell in love with the charm of this Inn, I can't wait for the restaurant to be up and running so I can come back and stay."
United States
Hans
$205 nightly
The price is $230
Nov 25 - Nov 26
Total with taxes and fees
Cypress River Inn & Spa
Restaurant

3. Inn at 202 Dover

Inn at 202 Dover
5.0 star property
Easton
10.0 out of 10, Exceptional, (14 reviews)
"Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience."
United States
James
Inn at 202 Dover

Top Eastern Shore Hotel Reviews

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels

10/10 Excellent

This is an elegant old hotel with lovely gardens and a great view of the bay. Restaurant was very nice with fantastic views and excellent food. Best crab cakes ever! The main part of the hotel is original with low ceilings and uneven floors, and has several nice sitting rooms, nooks and alcoves. Reminds me of some European hotels I have visited.
United States
Norm
Reviewed July 23, 2014
Inn at Perry Cabin

Find out more about Eastern Shore

You enjoy the finer things in life, both at home and on vacation. Add further luxury on your next trip to Eastern Shore by treating yourself to the best of the best when it comes to accommodation. It's an ideal pairing. There's no reason to delay a getaway to Eastern Shore any longer. You'll join the multitudes of vacationers who have made Eastern Shore so fashionable in the last year. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Eastern Shore and indulge in the finer things in life for a while.

Get a Great Deal on 5-Star Hotels in Eastern Shore

You'll have a fantastic time at one of these 5-star hotels. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. How do you want to relax? A mud wrap treatment that will leave you feeling outstanding? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A deep-tissue massage to help your cares fall away?

Can't wait to get outside? We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Eastern Shore are the perfect place to relax after an exciting day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs.

Your Getaway Starts Today

Numerous visitors make Eastern Shore the place to vacation. Why not join their ranks? If you've been dreaming about a vacation set here, then go ahead and book it. A surge in interest means these great hotel rooms will go quickly. It's time to plan your next great escape. Opt for one of our Eastern Shore 5-star hotels today and decompress in total tranquility tomorrow.

Frequently Asked Questions

How much does it cost to stay in a 5-star hotel in Eastern Shore?

How much you pay for a 5-star hotel in Eastern Shore can vary based on when you want to travel and how long you plan to stay, among several factors. Use our price per night filter and other search tools to score the best rate on a plush stay.

  • Search for the lowest price per night from $230

What makes a hotel 5 stars in Eastern Shore?

From high-end dining venues and all-day fitness centers to pools and superior bedding, the 5-star experience in Eastern Shore is all about luxury and comfort. But it calls for more than just upscale perks to earn a 5-star rating. Hotels must also provide outstanding guest services like in-room massages, laundry and dry cleaning and 24-hour room service.

Are there any 5-star all-inclusive resorts in Eastern Shore?

Use our handy filters to find an upscale getaway in Eastern Shore where most of what you need is included. After your initial search, narrow your results for hotels that have a rating of 5 stars and are categorized as "All inclusive." The most important thing on the itinerary at these stays? Relaxation and indulgence.

Are there any 5-star vacation rentals in Eastern Shore?

Our site doesn't offer any 5-star vacation rentals in Eastern Shore. However, you will still find a range of top-rated properties where the only thing on your itinerary will be to kick back and enjoy yourself. View what's available by searching through our vacation rentals in Eastern Shore.

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