Lodging Image

Chester 5 Stars Hotels

  • 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

Tonight
Oct 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 white house with a porch, wooden chairs, and umbrellas.
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
NT$12,809
NT$13,961 total
includes taxes & fees
Nov 1 - Nov 2
The Weston
Save an average of 15% on thousands of hotels when you're signed in

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
NT$11,966
NT$14,589 total
Nov 16 - Nov 17
includes taxes & fees
Woodstock Inn & Resort
The Jackson

The Jackson

43 Senior Lane Woodstock VT
NT$3,995
NT$4,395 total
Nov 16 - Nov 17
includes taxes & fees
9.6/10 Exceptional! (332 reviews)
The Jackson
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

3567 Main Street Manchester VT
NT$3,600
NT$5,688 total
Nov 22 - Nov 23
includes taxes & fees
7.4/10 Good! (674 reviews)
The Equinox Golf Resort And Spa
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.
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

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chester?
There are several pricing options for a 5-star hotel in Chester on Expedia. The amount you pay will depend on when you travel, length of stay and other factors. Compare available properties for your chosen dates and make use of our pricing and other filters to score the perfect luxury stay.
  • Search for the lowest price per night from NT$4,395
What makes a hotel 5 stars in Chester?
From high-end restaurants and 24/7 fitness centers to pools and luxury bedding, the 5-star experience in Chester is all about luxury and comfort. But it takes more than just upscale conveniences to get a 5-star rating. Stays also have to offer remarkable guest services like in-room massage treatments, on-site laundry and a nightly turn-down service.
Are there any 5-star all-inclusive resorts in Chester?
Our filters are the quickest way to find exactly what you're looking for. Check the "All inclusive" and "5-star" boxes to see the most luxurious resorts in Chester where your room, meals, 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.

Explore a world of travel with Expedia