Explore top 2026 4 Star Hotels in Chester

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Top Chester 4 Star hotels

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
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
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free ...
Opens in a new windowWoodstock Inn & Resort
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$176 nightly
The price is $194 total per night from Nov 15 to Nov 16
$194 total
Nov 15 - Nov 16
Total with taxes and fees
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, ...
Opens in a new windowThe Jackson
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
3567 Main Street Manchester VT
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $182 total per night from Nov 23 to Nov 24
$182 total
Nov 23 - Nov 24
Total with taxes and fees
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of ...
7.4/10 Good! (682 reviews)
"Very unique property with a feel like home feel Good breakfast ."

Reviewed on Nov 10, 2026

Opens in a new windowThe Equinox Golf Resort And Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$224 nightly
The price is $246 total per night from Nov 23 to Nov 24
$246 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need ...
Opens in a new windowKimpton Taconic Hotel by IHG
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$158 nightly
The price is $174 total per night from Nov 15 to Nov 16
$174 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the ...
9.2/10 Wonderful! (1,007 reviews)
"Clean-safe-great pool sauna and spa. Excellent dinner and breakfast. Comfortable bed, quiet, friendly staff."

Reviewed on Nov 8, 2026

Opens in a new windowOn The River Inn
The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant

4 out of 5
17-39 West Rd Manchester VT
$199 nightly
The price is $219 total per night from Nov 29 to Nov 30
$219 total
Nov 29 - Nov 30
Total with taxes and fees
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking. A ...
Opens in a new windowThe Reluctant Panther Inn and Restaurant
Four Columns Inn

Four Columns Inn

4 out of 5
21 West Street Newfane VT
$144 nightly
The price is $157 total per night from Nov 23 to Nov 24
$157 total
Nov 23 - Nov 24
Total with taxes and fees
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and ...
9.8/10 Exceptional! (63 reviews)
"Nice place, the town was beautiful, felt like you stepped back into the 1800s with-all the large buildings, also has a great country store, just a short walk away, the 1832 Tavern was very nice and I recommend it"

Reviewed on Oct 26, 2026

Opens in a new windowFour Columns Inn
The Hermitage Inn Vermont

The Hermitage Inn Vermont

4 out of 5
25 Handle Road West Dover VT
$371 nightly
The price is $408 total per night from Nov 25 to Nov 26
$408 total
Nov 25 - Nov 26
Total with taxes and fees
This smoke-free inn features 2 hot tubs, a 24-hour gym, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna ...
9/10 Wonderful! (21 reviews)
"Could not have had a more perfect stay. Highly recommend."

Reviewed on Nov 2, 2026

Opens in a new windowThe Hermitage Inn Vermont
The Inn at Weathersfield

The Inn at Weathersfield

4 out of 5
1342 Vt Route 106 Perkinsville VT
$236 nightly
The price is $257 total per night from Nov 29 to Nov 30
$257 total
Nov 29 - Nov 30
Total with taxes and fees
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. ...
9.8/10 Exceptional! (83 reviews)
"Such a nice and kind family of owners. Breakfast was delicious, as well as dinner the previous night in their restaurant. It’s a very rustic Inn, full of history and charm. We would love to return in the near future."

Reviewed on Oct 8, 2026

Opens in a new windowThe Inn at Weathersfield
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
77 Okemo Ridge Rd Ludlow VT
Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the ...
8.8/10 Excellent! (29 reviews)
"Large unit - well laid out for three generation visit. Comfortable beds. Kitchen well appointed."

Reviewed on Oct 20, 2026

Opens in a new windowWinterplace at Okemo, A Vail Resorts Property
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4 Star Hotels Chester

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Chester 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Chester will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Chester, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.

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