Title: Winchester Chalets from CA $513 | Expedia.ca

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![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Search Chalets in Winchester from CA $513

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## Check prices for these dates

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Winchester Chalets

![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/52e194b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/dfb0d0fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/f2b8d538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Chalet mins from Mt Snow Skiing/hiking

East Dover

9.8/10

Exceptional

(9)

"Easy to find! Clean! Cozy!! Would definitely stay again! "

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

Roy-michael G.

CA $131

CA $567 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/14b70d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/3a874a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/c26da9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/083f8263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow 

West Dover

10/10

Exceptional

(20)

"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."

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

Jeannine A.

CA $216

CA $788 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/6eef057c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/2d0f8d7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/0b026459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/d3aa8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vikings Villages Resort - Double Bed Room

Guilford

CA $384

CA $513 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages-Resort-Double-Bed-Room.h110890615.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=2025-12-19&endDate=2025-12-20&regionId=3000447144&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Top Winchester Hotel Reviews

![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg)

### Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"The customer service at this hotel is consistently exceptional. Every staff member is friendly, professional, and welcoming, creating an atmosphere that feels truly comfortable. The property is impeccably clean, and the breakfast offerings are always enjoyable. I have had an excellent experience during each of my visits, and I highly recommend this hotel to others"

[](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information)

![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60_y.jpg)

### Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent

"Everything was great "

[](https://expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information)

![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg)

### The Putney Inn

10/10 Excellent

"Nice motel. "

[](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information)

![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg)

### Latchis Hotel

10/10 Excellent

"The Victrola and records in the room were awesome!"

[](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information)

![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg)

### The Covered Bridge Inn

10/10 Excellent

"Room very nice, comfortable clean "

[](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information)

![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg)

### The Colonial Hotel

10/10 Excellent

"Have stayed here over past years. Always good stay."

[](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information)

![Courtyard by Marriott Keene Downtown](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/7bc7321f_y.jpg)

### Courtyard by Marriott Keene Downtown

10/10 Excellent

"Clean room"

[](https://expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information)

![Riverside Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg)

### Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent

"All good"

[](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information)

![Hampton Inn & Suites Greenfield](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg)

### Hampton Inn & Suites Greenfield

10/10 Excellent

"Staff was friendly, room was very nice and really appreciate the breakfast."

[](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information)

## Find out more about Winchester

## Winchester Chalets information

| Number of reviews | 29        |
| ----------------- | --------- |
| Accommodation     | 9 Chalets |
| Lowest Price      | CA $513   |
| Highest Price     | CA $788   |

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