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Find 5 Star Hotels in Chester, VT from $182

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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.

1. The Weston

The Weston
5.0 star property
Weston
9.6 out of 10, Exceptional, (15 reviews)
"The Weston is a spectacular small hotel. The restaurant is delicious and the staff go oabove and beyond to make your stay lovely."
United States
astrid
$379 nightly
The price is $413
Nov 22 - Nov 23
Total with taxes and fees
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
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
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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

You enjoy the finer things in life, both at home and on vacation. Indulge your every whim on your upcoming getaway. There's no reason to delay a getaway to Chester any longer. You'll join the multitudes of vacationers who have made Chester so fashionable recently. 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 are you waiting for? Our 5-star hotels in Chester are the perfect places to relax in when you really need to escape.

5-Star Hotels in Chester

Don't be afraid to be pampered during your trip, along with pristine rooms. High-end restaurants, concierges, and in-room spa sessions are all at the ready. You're sure to find exactly the accommodation you need. 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 make reservations at that outstanding restaurant? A deep-tissue massage to help your cares fall away? Plush carpeting, piping hot coffees, and even a hot tub in the bathroom...these hotels have it all.

Ready for experiences outside your hotel room? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Chester are waiting for you to rest up after an exciting day. Ready to learn more? Plenty of visitors recommend this location.

Make Your Escape

The results are in, and Chester 5-star hotels are the place to be when you book your next vacation. These beautiful hotels are highly rated by the guests who stay in them, and you're about to join their ranks. Expedia can help you land a great deal on accommodation. Don't put off your dream vacation any longer. Opt for one of the 5-star hotels in Chester today and decompress in total tranquility 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 depends on things like when you plan to go and the length of your stay. A top tip for landing the best deal? Use our pricing filters to compare all of the available accommodations for your selected dates.

  • Search for the lowest price per night from $182

What makes a hotel 5 stars in Chester?
From high-end restaurants and 24-hour fitness centers to swimming pools and luxury bedding, the 5-star experience in Chester is all about luxury and relaxation. But it takes more than just upscale conveniences to earn a 5-star rating. Accommodations also have to provide superb services like massage treatments, on-site laundry and 24/7 room service.
Are there any 5-star all-inclusive resorts in Chester?
Find an upscale stay that includes your lodging, food, activities and entertainment in Chester with our filters. Search for properties rated 5 stars and select the "All inclusive" filter. Make sure you check what's included in the price. This way, you'll be ready to maximize all the perks on offer when you get there.

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