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4 Stars Hotels in Chester, Vermont from CA $287

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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, (589 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
The price is CA $834
CA $979 total
includes taxes & fees
Aug 11 - Aug 12
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, (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
The price is CA $325
CA $417 total
includes taxes & fees
Aug 11 - Aug 12
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, (1,007 reviews)
"convenient location with very comfortable accommodations"
United States
Tonine
The price is CA $367
CA $434 total
includes taxes & fees
Aug 4 - Aug 5
On The River Inn
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, (646 reviews)
"The hotel was beautiful!"
United States
Lorajean
The price is CA $223
CA $324 total
includes taxes & fees
Aug 12 - Aug 13
The Equinox Golf Resort & Spa
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (294 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is CA $438
CA $482 total
includes taxes & fees
Jul 18 - Jul 19
The Jackson
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (46 reviews)
"The hot tub was so amazing"
United States
Mark
The price is CA $300
CA $327 total
includes taxes & fees
Jul 27 - Jul 28
Four Columns Inn
Restaurant

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, (373 reviews)
"Great location! The staff was polite and kind and the best part of the trip was the restaurant at the Reluctant Panther. Food was mouthwatering"
United States
Shama
The price is CA $381
CA $419 total
includes taxes & fees
Jul 13 - Jul 14
The Reluctant Panther Inn and Restaurant
Exterior

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
The price is CA $417
CA $459 total
includes taxes & fees
Jul 13 - Jul 14
Inn on Putney Road
Interior

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
The price is CA $243
CA $317 total
includes taxes & fees
Jul 20 - Jul 21
The Inn at Weathersfield
Terrace/patio

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (98 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
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! Loved the amenities!"
United States
Keely
The price is CA $455
CA $501 total
includes taxes & fees
Jul 13 - Jul 14
The Hermitage Inn Vermont
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
Exterior

Seesaw's Lodge

Seesaw's Lodge
4.0 star property
Peru
10.0 out of 10, Exceptional, (27 reviews)
"Great cabin with an even greater staff!!"
United States
Eyasser
The price is CA $316
CA $344 total
includes taxes & fees
Jul 19 - Jul 20
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)
"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
Front of property - evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (106 reviews)
"Great stay"
United States
Wayne
The price is CA $426
CA $462 total
includes taxes & fees
Jul 13 - Jul 14
Chesterfield Inn
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
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (43 reviews)
"The view of mountains id stunning, as is the aroma of fresh air and the enchanting songbirds. We had a great time in the small but adequate swimming pool. It is easy to miss the turn onto Laurence Lane, so it would be good if a sign were to be installed there."
United States
Nadine
The price is CA $263
CA $287 total
includes taxes & fees
Jul 23 - Jul 24
Windham Hill Inn
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

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
Apartment (3 Bedrooms) | Interior

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

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester.
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

3567 Main Street Manchester VT
Get rates
7.8/10 Good! (10 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
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Staff was friendly and helpful. Room was clean and amenities appreciated. Breakfast was very good, a great way to start the day."
Marcella 3-night trip
Posted 2 days ago
On The River Inn

Find out more about Chester

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chester are calling your name. Known for providing first-rate service in amazing locations, each of the Chester 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Chester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chester, Vermont, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chester hotels with 4 Stars provide everything you need to unwind in style.

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 fits your budget, take advantage of Expedia's filter tool. Check out the availability during your chosen dates and use our pricing filter to set your maximum rate. You can also list your results by the most budget-friendly retreat first.

  • Search for the lowest price from CA $625

What's the difference between 5-star and 4-star hotels in Chester?
Offering a welcoming guest experience and upmarket décor, 4-star hotels are an excellent option for your Chester trip. These types of accommodations generally come with lots of handy amenities that make it easy to kick back and relax — think complimentary bathrobes, gyms and restaurants. Or enjoy even more lavishness at a 5-star hotel designed to indulge you in high-end perks and amenities. 24-hour front desk, complimentary toiletries and gourmet dining are typically featured at these swanky retreats.
Does Chester have any 4-star all-inclusive resorts?
Finding your dream vacation in Chester is as easy as typing in your travel details and selecting our "All inclusive" filter. Stay and play where everything is already taken care of like your accommodations, meals and activities, or opt for a standard 4-star resort in or around this popular destination.

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