5 Stars Hotels in Chester, Maryland from CA $177

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Check availability on Chester 5 Star Hotels

Our top choices for Chester 5-star hotels

Breakfast, lunch, dinner and brunch served

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (390 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is CA $929
CA $1,022 total
includes taxes & fees
Jul 1 - Jul 2
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, sun loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (15 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is CA $460
CA $525 total
includes taxes & fees
Jun 14 - Jun 15
The Inn at Tacaro Estate
Dinner served

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.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
The price is CA $155 per night from Jun 15 to Jun 16
CA $155
CA $177 total
Jun 15 - Jun 16
includes taxes & fees
8.8/10 Excellent! (1,016 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.

Learn more about Chester

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

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Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It was a wonderful stay. The rooms were clean, the staff helpful and the food marvelous. I intend to visit again!"
Bill 2-night trip
Posted 4 days ago
Inn at Perry Cabin

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 $177

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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