A coastal town with a marina, a bridge, and a highway.

5 Stars Hotels in Chester, Maryland from CA $144

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Check availability on Chester 5 Star Hotels

Our top choices for Chester 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
The price is CA $615
CA $676 total
includes taxes & fees
Dec 9 - Dec 10
Inn at Perry Cabin
A hot tub in a grassy area with a building in the background.

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (20 reviews)
"The owners are very friendly and accommodating. Relaxing getaway"
United States
kristine
The price is CA $420
CA $479 total
includes taxes & fees
Nov 12 - Nov 13
The Inn at Tacaro Estate
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
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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 Chester.
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St Annapolis MD
The price is CA $184 per night from Nov 29 to Nov 30
CA $184
CA $210 total
Nov 29 - Nov 30
includes taxes & fees
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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.

Learn more about Chester

Chester awaits: its island views, sunny weather, golf, and more!

See all hotels in Chester
A coastal town with a marina, a bridge, and a highway.

Top Chester Hotel Reviews

Find out more about Chester

Luxury is the name of the game at the best 5 Stars hotels in Chester. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Chester 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them.

Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Chester hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Chester without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Chester.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chester?
How much you pay for a 5-star hotel in Chester depends on things such as when you plan to travel and the length of your break. An insider tip for bagging an awesome deal? Use our pricing filters to compare the available options for your chosen dates.

  • Search for the lowest price per night from CA $144

What makes a hotel 5 stars in Chester?
In Chester, a hotel must provide a specific amount of high-end amenities to be designated 5 stars. These may include gourmet restaurants, on-site gyms, saunas and spas, premium bedding, luxury bathroom products and more. What also sets 5-star hotels apart is their guest-focused service. You'll enjoy things like nightly turn-down services, concierge services and in-room massages. Some may also offer special touches like a welcome gift.
Are there any 5-star all-inclusive resorts in Chester?
Our filters are the easiest way to search for exactly what you're looking for. Check the "All inclusive" and "5-star" boxes to show the most luxurious hotels in Chester where your lodging, meals, activities and entertainment are included in the price. At these getaways, your vacation is pure extravagance from the moment you check in.

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