Chester 4 Stars Hotels

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Our top choices for Chester 4-star hotels

Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (560 reviews)
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is NT$10,093
NT$12,494 total
includes taxes & fees
Jan 19 - Jan 20
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, (825 reviews)
"Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! "
United States
Heather
The price is NT$5,817
NT$7,616 total
includes taxes & fees
Feb 12 - Feb 13
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, (586 reviews)
"The resort really needs updating...."
United States
Elizabeth
The price is NT$5,912
NT$8,294 total
includes taxes & fees
Jan 26 - Jan 27
The Equinox Golf Resort & Spa
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (261 reviews)
"Beautiful, quiet inn. We stayed Saturday through Tuesday after the holidyas, so it was especially quiet, just what we wanted. Staff was incredibly attentive and engaging, rooms were unique and comfortable. I highly recommend The Jackson. We will be returning in the spring to see the grounds!"
United States
John
The Jackson
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,011 reviews)
"Our stay was absolutely wonderful. The room was clean & comfortable with a nice view from balcony. The breakfast was good & the bar was very nice on a cold evening. Look forward to staying here again."
United States
Chris
The price is NT$7,498
NT$9,408 total
includes taxes & fees
Feb 12 - Feb 13
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, (340 reviews)
"Room was well appointed and spacious, clean and comfortable"
United States
ANTHONY
The price is NT$5,662
NT$6,228 total
includes taxes & fees
Jan 21 - Jan 22
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, (19 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 NT$8,448
NT$9,208 total
includes taxes & fees
Jan 27 - Jan 28
Seesaw's Lodge
Property grounds

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)
"The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty"
United States
gilza
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)
"3 room townhouse was great . Check in time is 4 . Wasn’t ready till 430 Also I think carpets in house need to be washed Other than that everything was 10 . "
United States
Yasir
Equinox Resort Residences
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56 reviews)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is NT$7,416
NT$8,158 total
includes taxes & fees
Jan 20 - Jan 21
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)
"The owners (Heather and Jared) work extremely hard to make sure everyone enjoys their stay. Breakfast was excellent! Heather prepares a made to order breakfast for each guest every morning. We also decided to have dinner at The Vic Tavern. It's an extremely popular place so make reservations early. Once again, the food was exceptional. Allow at least 90 minutes for dinner because it's not a fast food or chain restaurant. It's supposed to be a relaxing, enjoyable meal. The Inn itself is...
United States
Diane
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, (16 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 NT$9,719
NT$10,545 total
includes taxes & fees
Jan 18 - Jan 19
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, (38 reviews)
"Did not use"
United States
Douglas
The price is NT$5,975
NT$6,513 total
includes taxes & fees
Jan 19 - Jan 20
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, (32 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
9.8 out of 10, Exceptional, (70 reviews)
"First time at an Inn and I really enjoyed my stay. Very clean. "
United States
Munasiba
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 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 NT$12,803 per night from Jan 29 to Jan 30
NT$12,803
NT$13,956 total
Jan 29 - Jan 30
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
"Beautiful, quiet inn. We stayed Saturday through Tuesday after the holidyas, so it was especially quiet, just what we wanted. Staff was incredibly attentive and engaging, rooms were unique and comfortable. I highly recommend The Jackson. We will be returning in the spring to see the grounds!"
John 3-night trip
Posted 8 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.

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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 accommodations, 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 accommodations 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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