A boat docked at a pier during twilight with a city skyline in the background.

5 Stars Hotels in Chester, Maryland from CA $133

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Check availability on Chester 5 Star Hotels

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Chester 5-star hotels

A room with a view of a wooden deck and a gazebo by the water.
A hotel room with a large bed, a chair, a desk, and a television.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
A golf course with a water hazard and surrounding trees.

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
CA $848
CA $933 total
includes taxes & fees
Oct 13 - Oct 14
Inn at Perry Cabin
A hot tub in a grassy area with a building in the background.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
A pool with two Adirondack chairs and a basket of items on the grass.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
James
CA $529
CA $603 total
includes taxes & fees
Sep 24 - Sep 25
The Inn at Tacaro Estate

3. Inn at 202 Dover

Inn at 202 Dover
Easton
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.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
CA $117
CA $133 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,195 reviews)
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St Annapolis MD
CA $219
CA $249 total
Sep 27 - Sep 28
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
Graduate by Hilton Annapolis
The Westin Annapolis

The Westin Annapolis

100 Westgate Cir Annapolis MD
CA $252
CA $287 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
The Westin Annapolis
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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 boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr

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 $133
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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