Title: 4 Stars Hotels in Chester, Vermont from CA $234 - Find Cheap Chester Hotels With 4 Stars | Expedia.ca

[Chester Travel Guide](https://expedia.ca/Chester.dx89014)[Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d89014.Travel-Guide-Flights)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d89014.Destination-Travel-Guides)

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## Check availability on Chester 4 Star Hotels

Tonight

[Feb 14 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-14&endDate=2026-02-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 15 - Feb 16](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-15&endDate=2026-02-16&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-20&endDate=2026-02-22&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-27&endDate=2026-03-01&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester 4-star hotels

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07b171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/645e5fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/1c6e2228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Woodstock Inn & Resort

[](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information)

Woodstock

9.2/10

Wonderful

(564 reviews)

"Excellent hotel, staff well trained. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christian

CA $421

CA $523 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information)

![Meeting facility](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/21acdcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/a88566dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/e86f622b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/a1990aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kimpton Taconic Hotel by IHG

[](https://www.expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information)

Manchester Village Historic District

9.4/10

Exceptional

(831 reviews)

"Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Heather

CA $233

CA $308 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/c6f78187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/e0c2a7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/f766d453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor wedding area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0ab2343d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Equinox Golf Resort & Spa

[](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information)

Manchester Village Historic District

7.4/10

Good

(595 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patricia

CA $147

CA $234 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/91483dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/b9dbfee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/e0958349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Jackson 

[](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information)

West Woodstock

9.8/10

Exceptional

(266 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Abby

[](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information)

![Hallway](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/6a840315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/cafde7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast and dinner served](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/f34b38d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### On The River Inn

[](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information)

West Woodstock

9.4/10

Exceptional

(1,001 reviews)

"Everything was amazing from the room to the pool to the restaurant and staff. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ilana

CA $201

CA $271 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information)

![American cuisine](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/b36aec9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/d69b46ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/8359157a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/47528d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Reluctant Panther Inn and Restaurant

[](https://www.expedia.ca/Bennington-Hotels-The-Reluctant-Panther-Inn-And-Restaurant.h3908442.Hotel-Information)

Manchester Village Historic District

9.8/10

Exceptional

(347 reviews)

"Great room, nice staff."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gary

CA $230

CA $253 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Bennington-Hotels-The-Reluctant-Panther-Inn-And-Restaurant.h3908442.Hotel-Information)

![Land view from property](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/w1023h453x0y0-571ad601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dinner served, garden views ](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/24332bc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/w1025h684x0y3-22b2c22c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/ea836d50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Four Columns Inn

[](https://www.expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information)

Newfane

9.8/10

Exceptional

(21 reviews)

"Everything was great 👍 I will stay there again and highly recommend to others "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda

[](https://www.expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/32000000/31710000/31708400/31708312/67360152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/32000000/31710000/31708400/31708312/a49a5b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/32000000/31710000/31708400/31708312/c15d5356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Traditional Cabin, 3 Bedrooms](https://images.trvl-media.com/lodging/32000000/31710000/31708400/31708312/9bb7587a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Seesaw's Lodge

[](https://www.expedia.ca/Bennington-Hotels-Seesaws-Lodge.h31708312.Hotel-Information)

Peru

10/10

Exceptional

(26 reviews)

"Great cabin with an even greater staff!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Eyasser

CA $364

CA $396 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Bennington-Hotels-Seesaws-Lodge.h31708312.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/58a46b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/10e9f6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms, Mountainside (Winter Place, plus Loft) | Living room](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/f29c7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/ca09f1cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Winterplace at Okemo, A Vail Resorts Property

[](https://www.expedia.ca/Ludlow-Hotels-Winterplace-At-Okemo.h12522689.Hotel-Information)

Clock Tower Base Area

8.8/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathia

[](https://www.expedia.ca/Ludlow-Hotels-Winterplace-At-Okemo.h12522689.Hotel-Information)

![House, 5 Bedrooms (Meadow) | Terrace/patio](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920085/b4207cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920085/8d4d123d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920085/1817a3c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sauna, steam room, body treatments, hydrotherapy, aromatherapy](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920085/3d7b5f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Equinox Resort Residences

[](https://www.expedia.ca/Equinox-Resort-Residences.h99920085.Hotel-Information)

Manchester Village Historic District

8.0/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kurt

[](https://www.expedia.ca/Equinox-Resort-Residences.h99920085.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/f55f386b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/59f5ffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/5baffb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/16188707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn on Putney Road

[](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information)

Brattleboro

9.8/10

Exceptional

(57 reviews)

"Room was super clean and the hosts are excellent. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joe

CA $319

CA $351 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19540000/19532700/19532700/470d5daa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room 3 | Bathroom](https://images.trvl-media.com/lodging/20000000/19540000/19532700/19532700/2886e41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/20000000/19540000/19532700/19532700/773ceea0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/20000000/19540000/19532700/19532700/b20565b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Village Inn of Woodstock

[](https://www.expedia.ca/Woodstock-Hotels-The-Village-Inn-Of-Woodstock.h19532700.Hotel-Information)

Woodstock

9.6/10

Exceptional

(95 reviews)

"Super clean and the ambiance was so perfect for such a neat place. Owners are awesome!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Curtis

[](https://www.expedia.ca/Woodstock-Hotels-The-Village-Inn-Of-Woodstock.h19532700.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/56bf2e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/2a0f95de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/726c249b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/a22d6eb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hermitage Inn Vermont

[](https://www.expedia.ca/West-Dover-Hotels-The-Hermitage-Inn-Vermont.h74248370.Hotel-Information)

West Dover

8.8/10

Excellent

(17 reviews)

"Wonderful stay at the Carriage House! Beautiful property and excellent amenities! Perfect winter getaway! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Caroline

[](https://www.expedia.ca/West-Dover-Hotels-The-Hermitage-Inn-Vermont.h74248370.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/7179648d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![King Whirlpool Fireplace Room with Private Deck | Garden view](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/ef4a9650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/a23bd7ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dinner served, Regional cuisine](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/3339dfd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chesterfield Inn

[](https://www.expedia.ca/Keene-Hotels-Chesterfield-Inn.h1576027.Hotel-Information)

West Chesterfield

9.0/10

Wonderful

(104 reviews)

"Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Wayne

CA $418

CA $454 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Keene-Hotels-Chesterfield-Inn.h1576027.Hotel-Information)

![Room, 1 Queen Bed, Garden View | Mountain view](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/ee964e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/b3c06bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Room, 1 King Bed](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/26455a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/b590c7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Windham Hill Inn

[](https://www.expedia.ca/West-Townshend-Hotels-Windham-Hill-Resort.h94650035.Hotel-Information)

West Townshend

8.4/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

J

CA $242

CA $264 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/West-Townshend-Hotels-Windham-Hill-Resort.h94650035.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/13000000/12530000/12521300/12521237/740d68de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Solitude Village Two Bedroom Suite Mountainside](https://images.trvl-media.com/lodging/13000000/12530000/12521300/12521237/6dfb926b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Solitude Village Two Bedroom Suite Mountainside | Private kitchen](https://images.trvl-media.com/lodging/13000000/12530000/12521300/12521237/676d662f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/13000000/12530000/12521300/12521237/57033131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Solitude Village at Okemo by Vail Resorts

[](https://www.expedia.ca/Ludlow-Hotels-Solitude-Village-At-Okemo.h12521237.Hotel-Information)

Clock Tower Base Area

8.0/10

Very good

(33 reviews)

"Great location!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

DIEN

[](https://www.expedia.ca/Ludlow-Hotels-Solitude-Village-At-Okemo.h12521237.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/bb7b6824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/f382420a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![King Room with Spa Bath](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/8a170d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![King Room with Garden View](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/4f6e289d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Weathersfield

[](https://www.expedia.ca/Perkinsville-Hotels-The-Inn-At-Weathersfield.h1154949.Hotel-Information)

Perkinsville

10/10

Exceptional

(73 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

James

[](https://www.expedia.ca/Perkinsville-Hotels-The-Inn-At-Weathersfield.h1154949.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/6f38eb9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/99b8436e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, soundproofing](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/ff272214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/c2bef1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Woodstocker B&B

[](https://www.expedia.ca/Woodstock-Hotels-The-Woodstocker-BB.h25079404.Hotel-Information)

Woodstock

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kavina

[](https://www.expedia.ca/Woodstock-Hotels-The-Woodstocker-BB.h25079404.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/35000000/34140000/34138500/34138473/af9416cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34140000/34138500/34138473/6cac2f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34140000/34138500/34138473/d8574766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34140000/34138500/34138473/b663e33c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stratton Mountain Long Trail House mountain view for families NOT adults only

[](https://www.expedia.ca/Stratton-Hotels-Stratton-Mountain-Resort-Long-Trail-House-With-Direct-Mountain-Views.h34138473.Hotel-Information)

Stratton

10/10

Exceptional

(7 reviews)

"Exactly what was advertised. Great communication with owner. Beautiful views. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

anthony c.

[](https://www.expedia.ca/Stratton-Hotels-Stratton-Mountain-Resort-Long-Trail-House-With-Direct-Mountain-Views.h34138473.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71820000/71814900/71814822/2ed25ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71820000/71814900/71814822/33b62d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/72000000/71820000/71814900/71814822/a8d08d34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/72000000/71820000/71814900/71814822/fce8197a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4+BR pet-friendly w/ hot tub & Stratton parking pass!

[](https://www.expedia.ca/Bondville-Hotels-4BR-Pet-Friendly-W-Hot-Tub-Stratton-Parking.h71814822.Hotel-Information)

Winhall

[](https://www.expedia.ca/Bondville-Hotels-4BR-Pet-Friendly-W-Hot-Tub-Stratton-Parking.h71814822.Hotel-Information)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

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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](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/5fa05705_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Weston

630 Main St Weston VT

CA $576

CA $628 total

Feb 18 - Feb 19

includes taxes & fees

10/10 Exceptional! (9 reviews)

[](https://expedia.ca/Weston-Hotels-The-Weston.h100702715.Hotel-Information)

Still don't see what you're looking for?

[See all properties in Chester.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&regionId=89014&star=40)

You can also use these popular filters to refine your search.

[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&regionId=89014&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&regionId=89014&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&regionId=89014&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&regionId=89014&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&regionId=89014&star=40&star=40&amenities=WATER_PARK)

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](https://www.expedia.ca/Hotel-Search?startDate=2026-02-28&endDate=2026-03-01&adults=2&regionId=89014)

![aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=900&h=530&p=1&q=high)

## Top Chester Hotel Reviews

![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg)

### On The River Inn

10/10 Excellent

"Room was excellent! Very clean and very comfortable. Bed and comforter were fantastic. Beautiful view in the back . The whole hotel is so nicely dec with antics all around. Have stayed few before will continue to come back. Sent my daughter here as well As a little gift. "

[](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information)

![Kimpton Taconic Hotel by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg)

### Kimpton Taconic Hotel by IHG

10/10 Excellent

"Best atmosphere and family stay ever. Kids friendly."

[](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information)

![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg)

### The Jackson 

10/10 Excellent

"Easy check-in, we were texted a door code in advance. Very quaint and pretty Inn. Staff were very nice and accommodating, specifically Stacey. The on-premise restaurant is amazing, we ended up having dinner and breakfast there. Bartender, Rita was great."

[](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information)

## 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?

> - Search for the lowest price from CA $628

### What's the difference between 5-star and 4-star hotels in Chester?

### Does Chester have any 4-star all-inclusive resorts?

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