Find 5 Star Hotels in Preston, MD from $200

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Check availability on Preston 5 Star Hotels

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Dec 23 - Dec 24
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Dec 24 - Dec 25
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Dec 26 - Dec 28
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Jan 2 - Jan 4

Our top choices for Preston 5-star hotels

Breakfast, lunch, dinner served; ocean views
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
$535 nightly
The price is $588
Dec 28 - Dec 29
Total with taxes and fees
Inn at Perry Cabin
Dinner served
Inn at 202 Dover

Inn at 202 Dover

Inn at 202 Dover
5.0 star property
Easton
10.0 out of 10, Exceptional, (14)
"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
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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 Preston.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD
$197 nightly
The price is $224 total per night from Jan 1 to Jan 2
$224 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.6/10 Excellent! (1,002 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 Preston Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. "
Joseph 1-night trip
Posted 2 months ago
Inn at Perry Cabin

Find out more about Preston

Preston Five Star Hotel Information

If you’re searching for the celebrity treatment, the 5 star hotels in Preston are your dreams come true. From sprawling resorts to fancy hot spots, thesePreston 5 star hotels immerse each traveler in the most elite experience money can buy. Want to unwind with a VIP-worthy spa treatment? These hotels have the leisure you're looking for.

Interested in sampling world-class cuisine? The on-site restaurants at the 5 stars hotels in Preston, Maryland, let you do just that. You’ll even be able to book a room (or perhaps a penthouse?) at first-rate hotels near the region’s can’t-miss sights and most bustling shopping centers. Plus, many globe-trotters who visit Preston five star hotels find incredible rates and deep discounts thanks to Expedia, so you can score a deal without sacrificing an ounce of quality.

Everything you could possibly want (and a few things you didn’t know you needed): That’s what you’ll receive when you stay at Preston 5 star hotels.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Preston?
The amount you pay for a 5-star hotel in Preston can vary based on when you prefer to travel and how long you plan to stay, among other factors. Use our price per night filter and other search tools to score the best deal on a high-end stay.

  • Search for the lowest price per night from $200

What makes a hotel 5 stars in Preston?
From fine dining venues and all-day fitness centers to swimming pools and dreamy bedding, the 5-star experience in Preston is all about relaxation and luxury. But it calls for more than just upscale perks to earn a 5-star rating. Accommodations must also provide outstanding guest-focused services like beauty treatments, laundry and dry cleaning and 24/7 room service.
Are there any 5-star all-inclusive resorts in Preston?
Find a luxurious escape that includes your lodging, food, activities and entertainment in Preston with our filter tool. Search for hotels with a 5-star rating and select the "All inclusive" filter. Be sure to check what's included in the upfront price. That way, you're ready to take advantage of all the perks on offer when you get there.

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