Chester Hotel Guide - 5 Stars Hotels in Chester, Vermont

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Check availability on Chester 5 Star Hotels

Our top choices for Chester 5-star hotels

Front of property
The Weston

The Weston

The Weston
5.0 star property
Weston
10.0 out of 10, Exceptional, (9)
"Beautiful accommodations! You can't use enough flattering adjectives for this property and it's staff!"
United States
LISA
The price is Rp6.753.780
Rp7.361.620 total
includes taxes & fees
11 Jan - 12 Jan 2026
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
The price is Rp5.657.232 per night from 16 Dec to 17 Dec
Rp5.657.232
Rp6.957.227 total
16 Dec - 17 Dec
includes taxes & fees
9.2/10 Wonderful! (553 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

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.

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aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

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 depends on things like when you plan to go and the length of your trip. A top tip for landing the best deal? Use our pricing filters to check out all of the available hotels for your chosen dates.

  • Search for the lowest price per night from Rp3.414.365

What makes a hotel 5 stars in Chester?
Flawless guest service is integral to every 5-star hotel in Chester. From the minute you step through the door, staff cater to your every need, whether recommending activities and tours or providing in-room massages. What's more, hotels must offer upscale amenities to qualify for a 5-star rating. These can include luxury bathrooms, on-site spa facilities, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chester?
Use our handy filters to find an upscale escape in Chester where most of what you need is included in the price. After your initial search, narrow your results for properties that have 5 stars and are described as "All inclusive." The main thing on the agenda at these stays? Pure enjoyment and indulgence.