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

Chester Hotel Guide - 5 Stars Hotels in Chester, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 Rp7.874.558
Rp8.662.013 total
includes taxes & fees
9 Dec - 10 Dec
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 Rp6.326.676
Rp7.212.479 total
includes taxes & fees
17 Nov - 18 Nov
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 Rp2.357.922 per night from 29 Nov to 30 Nov
Rp2.357.922
Rp2.688.031 total
29 Nov - 30 Nov
includes taxes & fees
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chester?
The amount you pay for a 5-star hotel in Chester can vary based on what time of year you travel and how long you plan to be away, among several factors. Take advantage of our price per night filter and other search tools to land the best deal on a luxurious getaway.

  • Search for the lowest price per night from Rp1.842.738

What makes a hotel 5 stars in Chester?
Outstanding guest service characterises every 5-star hotel in Chester. From the moment you arrive, staff cater to your every whim, whether offering luggage assistance and storage or providing in-room massage treatments. In addition, hotels must feature superior conveniences to meet the standard for a 5-star rating. These can include luxury bathrooms, saunas or spas, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chester?
Use our filter tool to find a luxury escape in Chester where most of what you need is included in the price. From there, refine your results for accommodation that have a 5-star rating and are deemed "All inclusive." The most important thing on the agenda at these stays? Relaxation and enjoyment.