Title: Browse the Best Chester Resorts from CA $161 | Expedia.ca

 

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# Search Resort Hotels in Chester from CA $161

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## Check prices for these dates

Next weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Chester Resorts

![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/61c9c6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/501f4323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

9.0/10

Wonderful

(776)

"Very welcoming, spacious, clean. Perfect for a family of 4. "

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

Kathleen

CA $130

CA $161 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/4e3f46ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Yoga](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/3d6e59aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor spa tub](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Black Bear Lodge at Stratton Mountain Resort

Stratton

7.6/10

Good

(935)

"Great place for the price "

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

Karen

CA $236

CA $286 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/57303655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/910c669e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/047760f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/fea584b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mount Snow Grand Summit Resort

West Dover

8.8/10

Excellent

(242)

"Great place to stay!"

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

Sonia

CA $216

CA $259 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59840000/59831900/59831898/8145803a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/60000000/59840000/59831900/59831898/a037cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/60000000/59840000/59831900/59831898/0b0b143a.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/60000000/59840000/59831900/59831898/9d01db5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palmer House Resort - Deluxe King Bed 2

Manchester Center,

8.0/10

Very good

(2)

"My wife and I selected Palmer House based on the photos on VRBO. Upon driving the property towards our room we suddenly realized things looked different. Upon entering the room we noticed a distinct smell. The bathroom shown online looks very nice and updated with a beautiful shower, white cabinets and looked very modern. Ours was nothing like that. We had a tan handicap tub, urine stained tiles, a counter and sink that looked very old, and old brown cabinets. Needless to say we were...

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

Mark A.

CA $223

CA $315 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Bennington-Hotels-The-Palmer-House-Resort-Deluxe-King-Bed-2.h59831898.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009362/a78b20a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, hair dryer, towels](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009362/035f9d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009362/55fa52e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009362/c7f88d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deluxe 2xQueen- 2nd floor in Historic Inn

West Dover

10/10

Exceptional

(5)

"Everything was just fantastic! Everyone was friendly and accommodating. Owners were so nice! Property is amazing and a great location to Mount Snow. Can not go wrong with this spot."

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

Brendan M.

CA $208

CA $343 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-Deluxe-2xQueen-2nd-Floor-In-Historic-Inn.h59009362.Hotel-Information)

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

![Interior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07d4fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/cd86c3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/2ed69ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Woodstock Inn & Resort

Woodstock

9.2/10

Wonderful

(552)

"Highly recommend stay here"

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

Margie

CA $461

CA $569 total

includes taxes & fees

Nov 30 - Dec 1

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

![Exterior](https://images.trvl-media.com/lodging/62000000/61580000/61573200/61573106/a014e323.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/62000000/61580000/61573200/61573106/6a316daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathtub, hair dryer, towels](https://images.trvl-media.com/lodging/62000000/61580000/61573200/61573106/445a3520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/62000000/61580000/61573200/61573106/86d47725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deluxe King, kitchenette, fireplace

West Dover

10/10

Exceptional

(4)

"End of season special. Perfect size, fireplace was great on a cold rainy night. Last night restaurant was open for a few weeks."

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

john L.

CA $305

CA $459 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-Deluxe-King.h61573106.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421932/75d1b69b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421932/c0f68089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421932/bab1c826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421932/e32ad19d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Dover

9.4/10

Exceptional

(6)

"This is a beautiful, large suite in a quaint Vermont town. There are two main rooms: a bedroom with a king bed and a bunk bed, and a separate living room with a fireplace. The main inn also has lounge areas open to guests all night, and is a perfect stay for both families and couples. "

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

Olivia

CA $337

CA $500 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-Deluxe-King.h55421932.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421906/9dee853e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421906/81e72463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421906/57fd6588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421906/f2499060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deluxe King Room w/fireplace and separate entrance

West Dover

10/10

Exceptional

(4)

"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."

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

Charles B.

CA $305

CA $466 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-Deluxe-King-Room-Wfireplace-And-Separate-Entrance.h55421906.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59840000/59832400/59832375/be741c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/60000000/59840000/59832400/59832375/53cc8469.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/60000000/59840000/59832400/59832375/bb3bf563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/60000000/59840000/59832400/59832375/5ec74078.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palmer House Resort - Deluxe King Bed 5

Manchester Center, , VT, US

9.4/10

Exceptional

(12)

"Lovely place to stay, kind staff and great accomodations."

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

Nicolas S.

CA $223

CA $315 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Bennington-Hotels-The-Palmer-House-Resort-Deluxe-King-Bed-5.h59832375.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009357/ce9fb178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009357/6e9205cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, jetted tub, hair dryer, towels](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009357/e27b2a53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, jetted tub, hair dryer, towels](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009357/c1f72e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury King w/balcony, accessible

West Dover

10/10

Exceptional

(2)

"My husband and I had a wonderful time at the Inn . our room was beautiful and we had two delicious meals in the restaurant I would definitely recommend this Inn to anyone traveling in southern Vermont."

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

Kimberley B.

CA $192

CA $321 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-Luxury-King-Wbalcony.h59009357.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59840000/59832100/59832068/186e933f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/60000000/59840000/59832100/59832068/f4c97550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/60000000/59840000/59832100/59832068/4736b3c4.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/60000000/59840000/59832100/59832068/42a8b9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palmer House Resort - Deluxe King Bed 3

Manchester Center,

8.8/10

Excellent

(5)

"Efficient and helpful staff. Great location. "

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

Kevin

CA $223

CA $315 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Bennington-Hotels-The-Palmer-House-Resort-Deluxe-King-Bed-3.h59832068.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009367/54481016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009367/c4e42549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009367/b33e0b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009367/9ebd8c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury King with balcony

West Dover

CA $192

CA $324 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-Luxury-King-With-Balcony.h59009367.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59840000/59831900/59831843/234c7d01.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/60000000/59840000/59831900/59831843/8d8f137e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/60000000/59840000/59831900/59831843/94b00c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/60000000/59840000/59831900/59831843/f80f0d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palmer House Resort - Deluxe King Bed 1

Manchester Center,

8.0/10

Very good

(4)

"It was a beautiful stay. Lovely Accommodations. "

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

Linda P.

CA $223

CA $315 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Bennington-Hotels-The-Palmer-House-Resort-Deluxe-King-Bed.h59831843.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59840000/59832900/59832839/6c4f0f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/60000000/59840000/59832900/59832839/aa687c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/60000000/59840000/59832900/59832839/e2a9b428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/60000000/59840000/59832900/59832839/cdc42663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palmer House Resort - Deluxe Two Double Beds 2

Manchester Center,

8.0/10

Very good

(1)

"I will start with the negatives and close with the positives. I wasn't convinced the towels were clean and there was literally only one each for us, seemed there was no attention to detail with cleaning (lots of hair and dust in corners in bathroom, 1/2 used sugar packet in the selection at the coffeemaker, bed skirt dragging on the floor, etc.), breakfast was lame, but I get it, because it's covid. For the positives, location was AWESOME, the room was super spacious with updated climate...

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

Bridget N.

CA $251

CA $352 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Bennington-Hotels-Palmer-House-Resort-Deluxe-Two-Double-Beds-2.h59832839.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/59000000/58940000/58937700/58937631/f61131e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/59000000/58940000/58937700/58937631/cbfc6327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/59000000/58940000/58937700/58937631/3912061e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/59000000/58940000/58937700/58937631/bf9de5f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths

West Dover

8.0/10

Very good

(1)

"The inn and grounds were wonderful. Great food at the Sawmill. Wonderful area to explore leading to an all around wonderful time."

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

Craig C.

CA $224

CA $364 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-Luxury-King-Suite.h58937631.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009360/1924d691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009360/e3bc4f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009360/108eaf37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009360/dece0f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King with Bunk Bed- 2nd floor in Historic Inn

West Dover

10/10

Exceptional

(2)

"Very well apportioned room. Super clean and comfortable. Restaurant was delicious. Bartender is cool to chat with."

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

Forrest W.

CA $208

CA $343 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-King-With-Bunk-Bed-2nd-Floor-In-Historic-Inn.h59009360.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59840000/59833100/59833001/d4db56b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/60000000/59840000/59833100/59833001/1533c345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/60000000/59840000/59833100/59833001/34d05ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/60000000/59840000/59833100/59833001/3d8a77c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palmer House Resort - Deluxe Two Double Beds 4

Manchester Center,

8.0/10

Very good

(6)

"We enjoyed our stay at the Palmer House in Manchester Center, VT. The staff was friendly and accommodating. Especially enjoyed sitting by the fire pit on a chilly evening."

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

Mark S.

CA $251

CA $352 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Bennington-Hotels-Palmer-House-Resort-Deluxe-Two-Double-Beds-4.h59833001.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009323/d8f122ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, hair dryer, towels, shampoo](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009323/2bf53fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009323/cf89eb69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/60000000/59010000/59009400/59009323/d3f7765a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deluxe King- 2nd floor in Historic Inn

West Dover

CA $192

CA $324 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-Deluxe-King-2nd-Floor-In-Historic-Inn.h59009323.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/59000000/58940000/58937700/58937633/33ab641b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/59000000/58940000/58937700/58937633/9f86bdde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/59000000/58940000/58937700/58937633/003ddc1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, jetted tub, hair dryer, towels](https://images.trvl-media.com/lodging/59000000/58940000/58937700/58937633/879b060e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury King Suite, Living Room w/sofa bed and jacuzzi tub

West Dover

10/10

Exceptional

(2)

"Such a quaint, beautiful Spot. It’s uniqueness, historic feel and common area was very warming. Personnel was very friendly and attentive"

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

Jessica

CA $224

CA $363 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/West-Dover-Hotels-Luxury-King-Suite.h58937633.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-12&endDate=2025-12-13&regionId=89014&adults=2&lodging=HOTEL_RESORT&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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## Top Chester Hotel Reviews

![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg)

### Aspen At Manchester

10/10 Excellent

"Great location Everything updated Pleasant greeting in lobby"

[](https://expedia.ca/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information)

![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg)

### Best Western Plus Keene Hotel

10/10 Excellent

"Staff was accommodating. Got a Free upgrade to my room"

[](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information)

![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg)

### Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"good"

[](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information)

![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg)

### Hampton Inn and Suites Manchester

10/10 Excellent

"It was great. The room was wonderful and the staff great."

[](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information)

![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg)

### The Shire Woodstock

10/10 Excellent

"Clean good service and location "

[](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information)

![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg)

### The Equinox Golf Resort & Spa

10/10 Excellent

"Courteous staff Clean room"

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

![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg)

### Hampton Inn Brattleboro

10/10 Excellent

"Everything was very nice. I was checked in at the desk by "Jolene" who was cordial, friendly, and welcoming. The room was very clean and it was very quiet. The breakfast in the morning was excellent as was the coffee station. I do miss the little snack bag at the front desk where we could grab 'n go off for the day. All was very nice. Thank you!"

[](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information)

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

### On The River Inn

10/10 Excellent

"Hands down one of the best places I have ever stayed. Beautiful view, great room and very cozy no matter where you were in the inn."

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

![Mountaineer Inn](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/7d61f01d_y.jpg)

### Mountaineer Inn

10/10 Excellent

"Small but clean room. Hotel is under construction but staff was accommodating and pleasant to work with durning our travel. If traveling for work we’d stay again "

[](https://expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.Hotel-Information)

## Find out more about Chester

## Chester Resorts information

| Number of reviews | 2,522 |
| --- | --- |
| Accommodation | 41 Resorts |
| Lowest Price | CA $161 |
| Highest Price | CA $569 |

## Frequently asked questions

### What can I expect from a resort vacation in Chester?

> You deserve to get away, and a resort is the perfect place to treat yourself to the amenities and services you need for a relaxing trip to Chester. One of the comfortable resort hotels in the surrounding area might be just what you're looking for, whether you want a luxurious suite, shopping possibilities, or fun activities to try.

### What's a top resort in Chester?

> Here are our top-rated resorts around Chester: [Woodstock Inn & Resort](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) - Luxury resort. 25.2 mi (40.5 km) from Chester. Features 4 restaurants, 2 bars, and a golf course. [Mount Snow Grand Summit Resort](https://www.expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) - Ski resort, 5-minute walk from Mount Snow. 25.5 mi (41 km) from Chester. Has ski-in/ski-out access, a full-service spa, and a fitness center. [Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://www.expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) - 15.4 mi (24.7 km) from Chester. Enjoy the seasonal outdoor pool, bar, and an indoor pool. [The Black Bear Lodge at Stratton Mountain Resort](https://www.expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) - Ski resort, 5-minute walk from Stratton Mountain Resort. 18.7 mi (30.1 km) from Chester. Amenities include 10 restaurants, 2 bars, and a sauna. [Equinox Resort Residences](https://www.expedia.ca/Equinox-Resort-Residences.h99920085.Hotel-Information) - Luxury resort. 25 mi (40.3 km) from Chester. Access to 4 restaurants, 2 bars, and a golf course.

### What can I do in Chester?

> Travelers enjoy the skiing and other winter sports in Chester, and have good things to say about activities such as shopping. Vermont Country Store offers fun for the whole family, while Stratton Mountain Resort is one of the most popular places to visit nearby. A few other attractions you may want to see are DaVallia Art & Accents and Bonnie's Bundles Dolls.

### What's the weather like in Chester?

> The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.

### What's the best way to get to and around Chester?

> Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) away from the city center. You can also search for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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-   [Weston Hotels](https://www.expedia.ca/Weston-Hotels.d177460.Travel-Guide-Hotels)
-   [Hotels & Resorts for Couples in Windham](https://www.expedia.ca/Windham-Hotels-Couples-Resorts-Hotels.0-0-d6150553-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
-   [Windham Hotels](https://www.expedia.ca/Windham-Hotels.d6150553.Travel-Guide-Hotels)
-   [Resorts in Windham](https://www.expedia.ca/Windham-Resort-Hotels.d6150553-aaResortHotels.Travel-Guide-Accommodation)

-   [Flights to Weston](https://www.expedia.ca/Cheap-Flights-To-Weston.d177460.Travel-Guide-Flights)
-   [Flights from Springfield](https://www.expedia.ca/lp/flights/10292/flights-from-springfield)
-   [Flights from Weston](https://www.expedia.ca/lp/flights/177460/flights-from-weston)
-   [Flights from Grafton](https://www.expedia.ca/lp/flights/184049/flights-from-grafton)
-   [Flights from Columbia (CAE) to Springfield (VSF)](https://www.expedia.ca/lp/flights/cae/vsf/columbia-to-springfield)
-   [Flights from Charlotte (CLT) to Springfield (VSF)](https://www.expedia.ca/lp/flights/clt/vsf/charlotte-to-springfield)
-   [Flights from Wilmington (ILM) to Springfield (VSF)](https://www.expedia.ca/lp/flights/ilm/vsf/wilmington-to-springfield)
-   [Flights from Minneapolis (MSP) to Springfield (VSF)](https://www.expedia.ca/lp/flights/msp/vsf/minneapolis-to-springfield)
-   [Flights from Ottawa (YOW) to Springfield (VSF)](https://www.expedia.ca/lp/flights/yow/vsf/ottawa-to-springfield)

-   [Andover Vacations](https://www.expedia.ca/Andover.d6023580.Destination-Travel-Guides)
-   [Visit Andover](https://www.expedia.ca/Andover.dx6023580)
-   [Cavendish Vacations](https://www.expedia.ca/Cavendish.d6023399.Destination-Travel-Guides)
-   [Fletcher Farm School for the Arts and Crafts](https://www.expedia.ca/Fletcher-Farm-School-For-The-Arts-And-Crafts-Ludlow.d553248621532666921.Vacation-Attraction)
-   [Visit Perkinsville](https://www.expedia.ca/Perkinsville.dx184065)
-   [Vermont Country Store](https://www.expedia.ca/Vermont-Country-Store-Bellows-Falls.d553248621532666908.Vacation-Attraction)
-   [Visit Weston](https://www.expedia.ca/Weston.dx177460)

-   [Car rental Grafton](https://www.expedia.ca/Car-Rentals-In-Grafton.d184049.Car-Rental-Guide)
-   [Car rental Windham](https://www.expedia.ca/Car-Rentals-In-Windham.d6150553.Car-Rental-Guide)

-   [Book Resorts in Chester on Expedia.com](https://www.expedia.com/Chester-Resorts.d89014-aaResorts.Travel-Guide-Accommodation)