Find 4 Star Hotels in Chester, VT from $141

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Our top choices for Chester 4-star hotels

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (566 reviews)
"Excellent hotel, staff well trained. "
United States
Christian
$349 nightly
The price is $384
Mar 15 - Mar 16
Total with taxes and fees
Woodstock Inn & Resort

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (600 reviews)
"We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. "
United States
Patricia
$164 nightly
The price is $181
Apr 5 - Apr 6
Total with taxes and fees
The Equinox Golf Resort & Spa

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
4.0 star property
Manchester Village Historic District
9.4 out of 10, Exceptional, (834 reviews)
"Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! "
United States
Heather
$190 nightly
The price is $209
Apr 5 - Apr 6
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, (1,003 reviews)
"Everything was amazing from the room to the pool to the restaurant and staff. "
United States
Ilana
$195 nightly
The price is $214
Mar 9 - Mar 10
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, (354 reviews)
"Great room, nice staff."
United States
Gary
$169 nightly
The price is $186
Mar 8 - Mar 9
Total with taxes and fees
The Reluctant Panther Inn and Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (272 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
$169 nightly
The price is $186
Mar 9 - Mar 10
Total with taxes and fees
The Jackson

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (24 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
$129 nightly
The price is $141
Mar 10 - Mar 11
Total with taxes and fees
Four Columns Inn

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (75 reviews)
"Everything was really lovely, clean and nice. Loved the downstairs lounge and bar areas, so warm and relaxing. The host was extremely gracious. Looking forward to going back soon! "
United States
James
$199 nightly
The price is $217
Mar 15 - Mar 16
Total with taxes and fees
The Inn at Weathersfield

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
$189 nightly
The price is $206
Apr 6 - Apr 7
Total with taxes and fees
Windham Hill Inn

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (96 reviews)
"Super nice people. Would definitely stay there again. "
United States
Rich
The Village Inn of Woodstock

Equinox Resort Residences

Equinox Resort Residences
4.5 star property
Manchester Village Historic District
8.0 out of 10, Very Good, (2 reviews)
"The setting is beautiful. The staff were amazing - kind and attentive. Our room was very dated and in need of updating including the bathrooms. The furniture in the room was an odd collection of pieces that could have come from a yard sale. It was not up to the standard we expected given the cost of the room and the overall resort vibe. "
United States
Kurt
Equinox Resort Residences

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

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
$186 nightly
The price is $203
Apr 5 - Apr 6
Total with taxes and fees
Seesaw's Lodge

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
$307 nightly
The price is $334
Mar 9 - Mar 10
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
$274 nightly
The price is $301
Apr 3 - Apr 4
Total with taxes and fees
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 travelled to Vermont to experience the total eclipse of the sun with my so, daughter and her partner. It was an incredible experience, made all that more comfortable by being able to stay in this beautiful apartment. Next time we ate in that area we will not hesitate to book again. Thanks"
United States
alistair
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

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

Renovated Ski-in/ski-out Peru Condo at Bromley Mtn

Renovated Ski-in/ski-out Peru Condo at Bromley Mtn
4.0 star property
Bromley Mountain
6.0 out of 10, (2 reviews)
"Location right next to Bromley Ski Area- easy access to the mountain and short drive to Manchester. Comfortable for our family of 6. Communication with the owner was very easy. "
United States
Jaclyn
Renovated Ski-in/ski-out Peru Condo at Bromley Mtn

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!

West Dover Townhome: Hot Tub, 2 Mi to Mount Snow!

West Dover Townhome: Hot Tub, 2 Mi to Mount Snow!
4.0 star property
West Dover
West Dover Townhome: Hot Tub, 2 Mi to Mount 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
$428 nightly
The price is $467 total per night from Mar 15 to Mar 16
$467 total
Mar 15 - Mar 16
Total with taxes and fees
10/10 Exceptional! (9 reviews)
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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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