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Check availability on Chester 4 Star Hotels

Our top choices for Chester 4-star hotels

Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (572 reviews)
"Amazing restaurant and attentive staff"
United States
Noelle
The price is 8.136.279 ₫
10.108.471 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Woodstock Inn & Resort
House (Meadow) | View from room

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (609 reviews)
"Accommodations were tires Breakfast staff was surly "
United States
Andreas
The price is 2.746.542 ₫
4.447.800 ₫ total
includes taxes & fees
5 May - 6 May
The Equinox Golf Resort & Spa
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, (836 reviews)
"Best atmosphere and family stay ever. Kids friendly."
United States
Simona
The price is 4.239.291 ₫
5.676.964 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Kimpton Taconic Hotel by IHG
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,004 reviews)
"Had a lovely stay while visiting, enjoyed the breakfast and the staff were all very friendly and accommodating. Would def stay here again"
United States
dylan
The price is 3.879.083 ₫
5.232.497 ₫ total
includes taxes & fees
14 Apr - 15 Apr
On The River Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (277 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
The price is 5.034.487 ₫
5.537.936 ₫ total
includes taxes & fees
5 May - 6 May
The Jackson
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, (357 reviews)
"We have stayed multiple times at the Reluctant Panther and will continue to do so. "
United States
Lisa
The price is 5.239.869 ₫
5.763.856 ₫ total
includes taxes & fees
26 Apr - 27 Apr
The Reluctant Panther Inn and Restaurant
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is 3.436.195 ₫
3.745.452 ₫ total
includes taxes & fees
12 Apr - 13 Apr
Four Columns Inn
Interior

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 4.666.117 ₫
6.055.048 ₫ total
includes taxes & fees
5 May - 6 May
The Inn at Weathersfield
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 4.976.559 ₫
5.424.449 ₫ total
includes taxes & fees
23 Apr - 24 Apr
Windham Hill 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 5.061.872 ₫
5.517.440 ₫ total
includes taxes & fees
13 Apr - 14 Apr
Seesaw's Lodge
Restaurant

The Hermitage Inn Vermont

The Hermitage Inn Vermont
4.0 star property
West Dover
8.8 out of 10, Excellent, (18 reviews)
"Wonderful stay at the Carriage House! Beautiful property and excellent amenities! Perfect winter getaway! "
United States
Caroline
The price is 8.471.999 ₫
9.319.331 ₫ total
includes taxes & fees
4 May - 5 May
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, (105 reviews)
"Great stay"
United States
Wayne
The price is 7.929.317 ₫
8.603.391 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Chesterfield Inn
Exterior

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
Terrace/patio

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
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
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 6.570.901 ₫
7.228.123 ₫ total
includes taxes & fees
12 Apr - 13 Apr
Inn on Putney Road
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)
"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
Apartment (3 Bedrooms) | Interior

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!
Apartment (2 Bedrooms) | Interior

Updated Vintage Apartment < 1/2 Mi to Main St

Updated Vintage Apartment < 1/2 Mi to Main St
4.0 star property
Keene
Updated Vintage Apartment < 1/2 Mi to Main St
Apartment (2 Bedrooms) | Interior

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 8.557.575 ₫ per night from 12 Apr to 13 Apr
8.557.575 ₫
9.327.757 ₫ total
12 Apr - 13 Apr
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

On The River Inn

On The River Inn

8/10 Good
"Everything was cool except the rude woman bartending at the 506 bistro"
ADRIAN 3-night trip
Posted 6 days ago
On The River Inn

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 9.327.757 ₫

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.