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Find 4 Star Hotels in Chester, VT from $134

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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, (589 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
$479 nightly
The price is $527
Jun 30 - Jul 1
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, (854 reviews)
"A little overboard on the pride flags and and pushing the pride stuff on everybody but otherwise a nice place to stay"
Canada
Trevor
$266 nightly
The price is $293
Jul 28 - Jul 29
Total with taxes and fees
Kimpton Taconic Hotel by IHG

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,004 reviews)
"Beautiful place to stay"
United States
Jeff
$226 nightly
The price is $249
Jun 30 - Jul 1
Total with taxes and fees
On The River Inn

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (641 reviews)
"The hotel was beautiful!"
United States
Lorajean
$213 nightly
The price is $234
Jul 28 - Jul 29
Total with taxes and fees
The Equinox Golf Resort & Spa

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (291 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
$175 nightly
The price is $193
Jul 2 - Jul 3
Total with taxes and fees
The Jackson

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, (370 reviews)
"Spacious room with sitting area and fireplace."
United States
Jean
$269 nightly
The price is $296
Jun 30 - Jul 1
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, (44 reviews)
"The hot tub was so amazing"
United States
Mark
$123 nightly
The price is $134
Jun 30 - Jul 1
Total with taxes and fees
Four Columns Inn

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
$295 nightly
The price is $324
Jun 30 - Jul 1
Total with taxes and fees
Inn on Putney Road

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (80 reviews)
"Great location, service and restaurant "
United States
LUDJANE
$198 nightly
The price is $215
Jul 1 - Jul 2
Total with taxes and fees
The Inn at Weathersfield

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (97 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

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
$358 nightly
The price is $393
Jul 2 - Jul 3
Total with taxes and fees
The Hermitage Inn Vermont

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
$195 nightly
The price is $212
Jul 1 - Jul 2
Total with taxes and fees
Seesaw's Lodge

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

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

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (41 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
$186 nightly
The price is $203
Jul 15 - Jul 16
Total with taxes and fees
Windham Hill 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

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
Jul 1 - Jul 2
Total with taxes and fees
Chesterfield Inn

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!

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

All-season Ludlow Apartment: 3 Mi to Okemo Resort!

All-season Ludlow Apartment: 3 Mi to Okemo Resort!
4.0 star property
Ludlow
All-season Ludlow Apartment: 3 Mi to Okemo Resort!
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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.

A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

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.

  • Search for the lowest price from $446

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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