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5 Stars Hotels in Chester, Vermont from CA $556

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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 white two-story house with a front porch, a covered patio, and a well-maintained garden.
A bathroom with a glass shelf holding toiletries, a vase with sunflowers, and a window with blinds.
A living room with a sofa, a coffee table, and a painting on the wall.
A dining table with plates of food, two glasses of white wine, and a bottle of wine.

1. The Weston

The Weston
Weston
United States
LISA
CA $543
CA $592 total
includes taxes & fees
Oct 20 - Oct 21
The Weston
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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.
Woodstock Inn & Resort

Woodstock Inn & Resort

Fourteen The Green Woodstock VT
CA $1,121
CA $1,295 total
Sep 24 - Sep 25
includes taxes & fees
9.4/10 Exceptional! (609 reviews)
Woodstock Inn & Resort
The Jackson

The Jackson

43 Senior Lane Woodstock VT
CA $505
CA $556 total
Sep 24 - Sep 25
includes taxes & fees
9.6/10 Exceptional! (322 reviews)
The Jackson
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

3835 Main St. Manchester VT
CA $452
CA $556 total
Oct 22 - Oct 23
includes taxes & fees
Kimpton Taconic Hotel by IHG
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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

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

Find out more about Chester

Five Star Hotels in Chester

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chester so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chester and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Chester

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Chester

The results are in, and Chester 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Chester! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chester today and settle down in the lap of luxury tomorrow.

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 according to when you prefer to travel and how long you plan to be away, among a range of factors. Use our price per night filter and other search tools to find the best deal on an indulgent stay.
  • Search for the lowest price per night from CA $556
What makes a hotel 5 stars in Chester?
Outstanding guest service is the hallmark of every 5-star hotel in Chester. From the minute you step through the door, staff cater to your every need, whether offering luggage assistance and storage or providing a turn-down service. In addition, hotels must offer upscale conveniences to meet the standard for a 5-star rating. These can include luxury baths, saunas or spas, pools, fine dining kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chester?
Expedia's filter tool is the quickest way to find exactly what you're looking for. Check the "All inclusive" and "5-star" boxes to see the most luxurious hotels in Chester where your meals, room, entertainment and activities are included in the upfront price. At these escapes, your trip is pure relaxation and indulgence from the moment you check in.

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