Find 4 Star Hotels in Chester, VT from $138

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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, (578 reviews)
"Everything was excellent"
United States
Jerry
$359 nightly
The price is $395
May 25 - May 26
Total with taxes and fees
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, (841 reviews)
"We always love this property!!"
United States
Barbara
$201 nightly
The price is $221
May 25 - May 26
Total with taxes and fees
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, (621 reviews)
"No coffee makers in the rooms and no coffee service in the lobby except in the morning. No refrigerators in the rooms. Bed was comfortable and clean. Room was spacious and lovely. Hot tub was wonderful. The stay was nice."
United States
Maria
$182 nightly
The price is $200
May 20 - May 21
Total with taxes and fees
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, (1,009 reviews)
"Clean room, friendly staff, family-friendly. "
United States
Suwei
$211 nightly
The price is $232
Jun 10 - Jun 11
Total with taxes and fees
On The River Inn

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, (362 reviews)
"Spacious room with sitting area and fireplace."
United States
Jean
$199 nightly
The price is $219
May 20 - May 21
Total with taxes and fees
The Reluctant Panther Inn and Restaurant

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (39 reviews)
"The hot tub was so amazing"
United States
Mark
$126 nightly
The price is $138
May 20 - May 21
Total with taxes and fees
Four Columns Inn

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (280 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
$149 nightly
The price is $164
May 25 - May 26
Total with taxes and fees
The Jackson

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (41 reviews)
"The room was wonderful. SO spacious and well-appointed, extremely clean. Loved the excellent bedding, the soaking tub, the perfect water pressure in the shower. We did not expect the flat-screen TV, so it was a treat to have. Don't let the lack of restaurant bother you: There are plenty of great choices around, though you have a bit of a drive. For a leisurely romantic weekend, I can't think of a better place. "
United States
Debbie
$200 nightly
The price is $218
Jun 4 - Jun 5
Total with taxes and fees
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
$312 nightly
The price is $343
May 25 - May 26
Total with taxes and fees
The Hermitage Inn Vermont

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
$196 nightly
The price is $213
May 20 - May 21
Total with taxes and fees
The Inn at Weathersfield

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
$183 nightly
The price is $200
May 20 - May 21
Total with taxes and fees
Seesaw's Lodge

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

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

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

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
"Fabulous home, breakfast, staff, and location. Excellent value! Will definitely be back!"
United States
Mary
$284 nightly
The price is $312
May 20 - May 21
Total with taxes and fees
Inn on Putney Road

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
"Great stay"
United States
Wayne
$301 nightly
The price is $327
May 20 - May 21
Total with taxes and fees
Chesterfield Inn

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!

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!

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
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Explore similar 5-star hotels

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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.

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

Find out more about Chester

The beginning of any much-needed holiday kicks off with selecting a location. Chester has been a popular destination with tourists because it offers so much. Yet, "location, location, location" applies to more than just what city where your plane lands. Now that you have a feeling for the area, it is time you to learn a little more about your new digs.

Properties as Picturesque as Chester

Chester saw its fair share of visitors this past year. Our review section provides reviews that highlight how astounding these rooms are. The hotels found here strive to make your vacation as pleasant as your evenings exploring Chester. These hotels work to make the facilities and grounds hospitable from the minute you step out of your car. You won't need to venture far to keep up with your workout schedule, enjoy a refreshing plunge, or find a nice meal during your stay with everything they provide.

Rooms have been configured to keep your utmost comfort in mind, with amenities like premium bedding, and in-room tea or coffee, and designer bathroom products. So, lay back and decompress. Moreover, if you find yourself in need of anything further, you can trust the staff will try their best to ensure you remain pleased during your time there. These properties are so nice that you'll regret the day you have to leave.

Book a 4-Star Hotel in Chester Today!

A vacation to Chester should be one where you won't have to be concerned about the little things. Of course, your getaway should be all about getting the most out of your destination. And getting the most means giving yourself the very best. Expedia has 4-star hotels that allow you to do just that. Book through Expedia today!

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
With Expedia's handy search filters, bagging a terrific deal on a 4-star hotel in Chester just got simpler. Start by keying in your chosen arrival date and length of your break. Then sort the results by price and pick a hotel that best fits your style and budget.

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What's the difference between 5-star and 4-star hotels in Chester?
Offering an inviting traveler experience and upscale décor, 4-star hotels are a great option for your Chester trip. These kinds of accommodations generally feature lots of handy amenities that make it easy to unpack and unwind — think 24-hour room service, restaurants and pools. Or get a taste of the high life at a 5-star hotel designed to indulge you in exclusive perks and amenities. On-site health clubs, complimentary toiletries and gourmet dining are typically included at these deluxe retreats.
Does Chester have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to find your next dream getaway in Chester where just about everything is taken care of, from your accommodations to your meals, activities and entertainment. We can also help you find standard 4-star stays in and around this destination.

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