Chester 4 Stars Hotels

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Check availability on Chester 4 Star Hotels

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Chester 4 Stars Hotels

Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (553)
"Highly recommend stay here"
United States
Margie
The price is HK$2,639
HK$3,245 total
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort
Exterior
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4.0 star property
Manchester
9.4 out of 10, Exceptional, (816)
"Very nice, beautiful inn"
United States
Susan
The price is HK$1,175
HK$1,593 total
includes taxes & fees
5 Jan - 6 Jan 2026
Kimpton Taconic Hotel by IHG
Exterior
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (574)
"Beautiful hotel! "
United States
sarah
The price is HK$1,276
HK$1,837 total
includes taxes & fees
11 Dec - 12 Dec
The Equinox Golf Resort & Spa
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (256)
"Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. "
United States
Jaunita
The Jackson
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1000)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is HK$2,530
HK$3,068 total
includes taxes & fees
24 Dec - 25 Dec
On The River Inn
Frette Italian sheets, premium bedding, iron/ironing board
The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant

4.0 star property
Manchester
9.8 out of 10, Exceptional, (331)
"Wonderful stay! The room was spacious and the bed was heaven. The breakfast was amazing and they were even able to offer gluten free options!"
United States
Abbie
The price is HK$1,394
HK$1,534 total
includes taxes & fees
8 Dec - 9 Dec
The Reluctant Panther Inn and Restaurant
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (13)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Exterior
Seesaw's Lodge

Seesaw's Lodge

4.0 star property
Peru
10.0 out of 10, Exceptional, (25)
"Super cute place to stay!! Easy check in/out, comfy bed, spacious bathroom. Restaurant right on site, attention to small details, "
United States
Jill
The price is HK$2,592
HK$2,826 total
includes taxes & fees
22 Dec - 23 Dec
Seesaw's Lodge
Property grounds
Winterplace at Okemo

Winterplace at Okemo

4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (26)
"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
Lobby sitting area
Equinox Resort Residences

Equinox Resort Residences

4.5 star property
Manchester
8.0 out of 10, Very good, (2)
"The setting is beautiful. The staff were amazing - kind and attentive. Our room was very dated and in need of updating including the bathrooms. The furniture in the room was an odd collection of pieces that could have come from a yard sale. It was not up to the standard we expected given the cost of the room and the overall resort vibe. "
United States
Kurt
Equinox Resort Residences
Exterior
Inn on Putney Road

Inn on Putney Road

4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is HK$1,826
HK$2,009 total
includes taxes & fees
1 Jan - 2 Jan 2026
Inn on Putney Road
Garden
The Village Inn of Woodstock

The Village Inn of Woodstock

4.0 star property
Woodstock
9.6 out of 10, Exceptional, (95)
"Super clean and the ambiance was so perfect for such a neat place. Owners are awesome!"
United States
Curtis
The Village Inn of Woodstock
Restaurant
The Hermitage Inn Vermont

The Hermitage Inn Vermont

4.0 star property
West Dover
9.2 out of 10, Wonderful, (15)
"Great stay,beautiful property!"
United States
Vibhavasu
The Hermitage Inn Vermont
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is HK$2,344
HK$2,544 total
includes taxes & fees
10 Dec - 11 Dec
Chesterfield Inn
Mountain view
Windham Hill Inn

Windham Hill Inn

4.0 star property
West Townshend
8.6 out of 10, Excellent, (37)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
United States
Brandon
The price is HK$1,442
HK$1,572 total
includes taxes & fees
15 Dec - 16 Dec
Windham Hill Inn
Private kitchen
Solitude Village at Okemo

Solitude Village at Okemo

4.0 star property
Clock Tower Base Area
8.0 out of 10, Very good, (32)
"Great location!"
United States
DIEN
Solitude Village at Okemo
Interior
The Inn at Weathersfield

The Inn at Weathersfield

4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
"The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. "
United States
Joshua
The Inn at Weathersfield
Exterior
The Woodstocker B&B

The Woodstocker B&B

4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51)
"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
Interior
Stratton Mountain Resort ~ Long Trail House with direct mountain views

Stratton Mountain Resort ~ Long Trail House with direct mountain views

4.0 star property
Stratton
10.0 out of 10, Exceptional, (3)
"Exactly what was advertised. Great communication with owner. Beautiful views. "
United States
anthony c.
Stratton Mountain Resort ~ Long Trail House with direct mountain views
Exterior
4+BR pet-friendly w/ hot tub & Stratton parking pass!

4+BR pet-friendly w/ hot tub & Stratton parking pass!

4.0 star property
Winhall
4+BR pet-friendly w/ hot tub & Stratton parking pass!
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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$3,028 per night from 7 Jan to 8 Jan
HK$3,028
HK$3,300 total
7 Jan - 8 Jan 2026
includes taxes & fees
10/10 Exceptional! (9 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.

See all hotels in Chester
aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

The Jackson

The Jackson

10/10 Excellent
"Friend of mine and I stayed overnight just to check out Vermont (I had always wanted to go there). We both LOVED this place. Very charming, lovely decor, and great food--especially at dinner. The staff were very friendly and accomodating. Would definitely recommend this place and return again in the future. "
Susan 1-night trip
Posted 7 days ago
The Jackson

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.

  • Search for the lowest price from HK$3,300

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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