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Check availability on Chester 4 Star Hotels

Our top choices for Chester 4-star hotels

Exterior

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (562 reviews)
"Excellent hotel, staff well trained. "
United States
Christian
The price is 8.007.735 ₫
9.948.769 ₫ total
includes taxes & fees
8 Mar - 9 Mar
Woodstock Inn & Resort
Meeting facility

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
4.0 star property
Manchester Village Historic District
9.4 out of 10, Exceptional, (831 reviews)
"Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! "
United States
Heather
The price is 4.431.465 ₫
5.872.339 ₫ total
includes taxes & fees
10 Mar - 11 Mar
Kimpton Taconic Hotel by IHG
Lobby

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (594 reviews)
"We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. "
United States
Patricia
The price is 3.236.141 ₫
4.958.900 ₫ total
includes taxes & fees
23 Feb - 24 Feb
The Equinox Golf Resort & Spa
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (265 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,006 reviews)
"Everything was amazing from the room to the pool to the restaurant and staff. "
United States
Ilana
The price is 6.141.855 ₫
7.706.344 ₫ total
includes taxes & fees
16 Feb - 17 Feb
On The River Inn
American cuisine

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, (346 reviews)
"Exactly the kind of Inn you want in VT. The room was amazing, staff could not be more accommodating, and the food was excellent!"
United States
Robert
The price is 3.941.672 ₫
4.335.839 ₫ total
includes taxes & fees
1 Mar - 2 Mar
The Reluctant Panther Inn and Restaurant
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.6 out of 10, Exceptional, (20 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Exterior

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 8.649.131 ₫
9.427.553 ₫ total
includes taxes & fees
23 Feb - 24 Feb
Seesaw's Lodge
Exterior

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
House, 5 Bedrooms (Meadow) | Terrace/patio

Equinox Resort Residences

Equinox Resort Residences
4.5 star property
Manchester Village Historic District
8.0 out of 10, Very good, (2 reviews)
"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, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is 6.079.659 ₫
6.687.625 ₫ total
includes taxes & fees
18 Feb - 19 Feb
Inn on Putney Road
Terrace/patio

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (95 reviews)
"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
8.8 out of 10, Excellent, (17 reviews)
"Wonderful stay at the Carriage House! Beautiful property and excellent amenities! Perfect winter getaway! "
United States
Caroline
The Hermitage Inn Vermont
Front of property – evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is 7.967.308 ₫
8.644.467 ₫ total
includes taxes & fees
23 Feb - 24 Feb
Chesterfield Inn
Room, 1 Queen Bed, Garden View | Mountain view

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 4.897.935 ₫
5.338.750 ₫ total
includes taxes & fees
17 Feb - 18 Feb
Windham Hill Inn
Exterior

Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts
4.0 star property
Clock Tower Base Area
8.0 out of 10, Very good, (33 reviews)
"Great location!"
United States
DIEN
Solitude Village at Okemo by Vail Resorts
Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (72 reviews)
"Wonderful experience, Wonderful staff. Thank you!"
United States
Patrick
The Inn at Weathersfield
Property entrance

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
Hiking

The Brattleboro

The Brattleboro
4.0 star property
Brattleboro
10.0 out of 10, Exceptional, (5 reviews)
"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return. "
United States
Roger
The Brattleboro
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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 10.495.575 ₫ per night from 11 Feb to 12 Feb
10.495.575 ₫
11.440.176 ₫ total
11 Feb - 12 Feb
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.

See all hotels in Chester
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.