Explore top 2026 5 Star Hotels in Eastern Shore

Name: Inn at Perry Cabin
Price range: $540 total
Rating: 9.6

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Top Eastern Shore 5 Star hotels

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

$491 nightly

$540 total

Nov 18 - Nov 19

Total with taxes and fees

This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room ...

9.6/10 Exceptional! (407 reviews)

"Beautiful property but rooms in need of some updates. (Dirty carpets, moldy curtains). Beds very comfortable!For $1200 a night with no amenities, it was a disappointment but was a fun trip!"

Reviewed on Oct 18, 2026

Cypress River Inn & Spa

201 E Market St Snow Hill MD

$196 nightly

$219 total

Oct 26 - Oct 27

Total with taxes and fees

A restaurant, free self parking, and a garden are among this bed & breakfast's amenities. WiFi in public areas is free. A snack bar/deli, a communal living room, ...

8.4/10 Very Good! (7 reviews)

"The bathroom vent had mold. I have photos of the vent"

Reviewed on Sep 25, 2026

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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.

Eastern Shore Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Eastern Shore to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Eastern Shore 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Eastern Shore before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

Recent Eastern Shore hotel reviews by fellow wanderers

Quality Inn Oceanfront

4 out of 5

Posted 3 hours ago

Travelocity Verified Review

"We stayed in a first floor beachfront room during the offseason. Definitely a great beach hotel which I can see myself staying at in the summer, but not somewhere I'd stay again otherwise (if that makes sense?). Like, the door opened right up to the beach entrance which was amazing but only if you're there for the beach. Otherwise, it's dated, kinda dingy, and just "mid." Oh, and be warned, there birds in the atrium. And not birds that found their way in from outside. They are the largest parrots I have ever seen and they are LOUD. Our door was right next to their cages. It was kinda shocking because I didn't notice when I first entered the room. After a few minutes of settling in, we hear "BACAWWWW!!" a couple of times. We opened the door to investigate and, lo and behold, giant Amazonian parrots! lol. Crazy. I don't remember seeing that mentioned in any of the reviews I read. The staff covers their cages for the night and they did not disrupt our sleep. Definitely worth mentioning though! Overall, it was okay. Easy check in and out. Ample parking. Friendly staff. Go in the summer"

A verified traveler stayed at Quality Inn Oceanfront

Grand Hotel Ocean City Oceanfront

4 out of 5

Posted 13 hours ago

Travelocity Verified Review

"We found our room to be surprisingly spacious, very clean, and comfortable; however, the kitchenette/bathroom areas were a bit dated. The property location was excellent and there were restaurants and a pool within the property. The common areas inside the hotel and the outdoor space at the front of the hotel were adequate, but guests were somewhat disrespectful, leaving their trash, not replacing chairs after their use, etc... The staff was pleasant enough when checking-in and helpful when we had a question but were ignoring simple tasks like straightening up the common areas when time allowed. Although this was a little off-putting, we would return if the opportunity presented itself."

A verified traveler stayed at Grand Hotel Ocean City Oceanfront