Chester 4 Stars Hotels

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Our top choices for Chester 4-star hotels

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (574 reviews)
"Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍"
United States
Daniele
The price is HK$3,048
HK$3,697 total
includes taxes & fees
18 May - 19 May
Woodstock Inn & Resort

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
4.0 star property
Manchester Village Historic District
9.4 out of 10, Exceptional, (840 reviews)
"Best atmosphere and family stay ever. Kids friendly."
United States
Simona
The price is HK$1,261
HK$1,689 total
includes taxes & fees
25 May - 26 May
Kimpton Taconic Hotel by IHG

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (617 reviews)
"We love the Equinox. We usually stay here during ski season. Always looking forward to rest after a long day of ski. Amenities are amazing, the restaurant and bar are great to eat and hangout. "
United States
Patricia
The price is HK$741
HK$1,235 total
includes taxes & fees
18 May - 19 May
The Equinox Golf Resort & Spa

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,003 reviews)
"Clean room, friendly staff, family-friendly. "
United States
Suwei
The price is HK$1,492
HK$1,928 total
includes taxes & fees
27 May - 28 May
On The River Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (36 reviews)
"The hot tub was so amazing"
United States
Mark
The price is HK$1,022
HK$1,114 total
includes taxes & fees
11 May - 12 May
Four Columns Inn

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (279 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
The price is HK$1,169
HK$1,286 total
includes taxes & fees
20 May - 21 May
The Jackson

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
4.0 star property
Manchester Village Historic District
9.8 out of 10, Exceptional, (361 reviews)
"Great stay, the lodge room was spacious and spotless with a huge bathroom and fireplace. Food in the restaurant was excellent. Would stay there again. "
United States
Laurie
The price is HK$1,559
HK$1,715 total
includes taxes & fees
5 May - 6 May
The Reluctant Panther Inn and Restaurant

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (96 reviews)
"Inn was beautiful, the details exactly what you'd want for a weekend getaway. Room was cozy (room 6), bed was comfortable, jetted tub was awesome for us not having a tub at home, bar was a nice place to hang out and breakfast was excellent. Location was perfect, it was an easy walk into the center of town, even in winter. Honestly, nothing bad to say."
United States
Nicholas
The Village Inn of Woodstock

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very good, (40 reviews)
"We had a fantastic room! Staff was very friendly and accommodating. Though we visited during peak foliage season, we’ll be trying to book again in the near future to try out the pool."
United States
J
The price is HK$1,398
HK$1,524 total
includes taxes & fees
18 May - 19 May
Windham Hill Inn

The Hermitage Inn Vermont

The Hermitage Inn Vermont
4.0 star property
West Dover
8.8 out of 10, Excellent, (18 reviews)
"Wonderful stay! Loved the amenities!"
United States
Keely
The price is HK$2,470
HK$2,717 total
includes taxes & fees
4 Jun - 5 Jun
The Hermitage Inn Vermont

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
"Great stay"
United States
Wayne
The price is HK$2,359
HK$2,560 total
includes taxes & fees
5 May - 6 May
Chesterfield Inn

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (79 reviews)
"Great location, service and restaurant "
United States
LUDJANE
The price is HK$1,222
HK$1,620 total
includes taxes & fees
26 May - 27 May
The Inn at Weathersfield

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is HK$2,225
HK$2,448 total
includes taxes & fees
5 May - 6 May
Inn on Putney Road

Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts
4.0 star property
Clock Tower Base Area
7.8 out of 10, Good, (35 reviews)
"Great location!"
United States
DIEN
Solitude Village at Okemo by Vail Resorts

Seesaw's Lodge

Seesaw's Lodge
4.0 star property
Peru
10.0 out of 10, Exceptional, (26 reviews)
"Great cabin with an even greater staff!!"
United States
Eyasser
The price is HK$1,372
HK$1,496 total
includes taxes & fees
5 May - 6 May
Seesaw's Lodge

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property
4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (26 reviews)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo, A Vail Resorts Property

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The Woodstocker B&B

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
4.0 star property
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful four night stay at this great condo! Perfect if you are skiing out of Okemo! The condo was beautiful, clean and the host Bill was so communicative and responded to texts immediately. The gym and spa was also an added bonus! Great time! "
United States
Nipa
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

Bromley Mountain Escape w/ 2 Balconies: Hike & Ski

Bromley Mountain Escape w/ 2 Balconies: Hike & Ski
4.0 star property
Bromley Mountain
6.0 out of 10, (1 review)
"The property is low cost in a nice area of Peru seconds from Bromley Mtn. BUT the property needs some serious updating -No AC. The host was more than accomodating. "
United States
Chris
Bromley Mountain Escape w/ 2 Balconies: Hike & Ski

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
4.0 star property
West Dover
Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester.
The Weston

The Weston

630 Main St Weston VT
The price is HK$2,154 per night from 7 May to 8 May
HK$2,154
HK$2,348 total
7 May - 8 May
includes taxes & fees
10/10 Exceptional! (9 reviews)
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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.

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 4-star hotel in Chester?
To book a 4-star hotel in Chester that matches your budget, make use of Expedia's sort and search filters. Check out what's available during your getaway dates and use our pricing filter to set your maximum rate. You can also sort your results by the most economical property first.

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What's the difference between 5-star and 4-star hotels in Chester?
Give yourself the luxury treatment during your Chester getaway by choosing a 4-star hotel. As well as featuring upscale accommodation, these properties are usually packed with amenities like bathrobes, large beds and more. A 5-star hotel will go the extra mile to make your trip an even more lavish and memorable one. Concierge assistance, luxurious spas and gourmet dining are a few of the first-rate conveniences and services you'll likely have access to.
Does Chester have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to search for your next escape in Chester where just about everything is taken care of, from your accommodation to your food, activities and entertainment. We can also help you find standard 4-star stays in and around this sought-after destination.

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