Title: Book The Best Hotels in Winchester, NH for 2026 from CA $153 - Fully Refundable Options - 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)

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

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## Go beyond your typical stay in Winchester

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&amenities=PETS)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&travelerType=family_friendly)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&amenities=POOL)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&amenities=HOT_TUB)

Cabin

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=CABIN)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=APARTMENT)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=COTTAGE)

Chalet

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=CHALET)

## Check prices for these dates

Tonight

[Jan 21 - Jan 22](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-21&endDate=2026-01-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 22 - Jan 23](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-22&endDate=2026-01-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

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

## Our top choices for Winchester hotels

![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/6a4870a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/01fdfd63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/8a97a85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/56f95948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Maguire House Bed & Breakfast

[](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information)

Ashburnham

10/10

Exceptional

(36 reviews)

"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "

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

Ranjit

CA $358

CA $358 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/eaeba6bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/23d6d222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/2e815906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Colonial Hotel

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

Gardner

8.8/10

Excellent

(1,006 reviews)

"Well-kept hotel with a great restaurant."

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

Adam

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

![Lobby](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/bdf98f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d92bd689.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d66e17b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d13ce465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gardner Inn

[](https://www.expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information)

Gardner

5.2/10

(19 reviews)

"Clean room, comfy bed, quiet guests around my room. Staff was cordial when I checked in. "

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

Kathy

CA $137

CA $153 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information)

![BBQ/picnic area](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/94272c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/757a6ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/93d41afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Guesthouse B](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/4298e900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Riverhouse by Weekender (Formerly Jack Daniels Inn)

[](https://www.expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information)

Peterborough

9.4/10

Exceptional

(444 reviews)

"Room was clean, spacious and staff was pleasant. "

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

Susan

[](https://www.expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/b4d09cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Triple Room, Ensuite (Sally Room-205)](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/1a3c79a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/29f5823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/0de4f49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Monadnock Inn

[](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.Hotel-Information)

Jaffrey

7.6/10

Good

(278 reviews)

"The Inn was cozy, the room was clean and comfortable. The owner was engaging and helpful. Would definitely stay there again. "

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

E S

[](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.Hotel-Information)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/df603ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/a625cff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/f54cc2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/d8604c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Carriage Barn Inn

[](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information)

Keene

9.6/10

Exceptional

(167 reviews)

"Very helpful and welcoming host. "

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

Bruce

CA $171

CA $186 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information)

![Pub](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/9384b42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/2a21d8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pub](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/a75a25f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/30a7f959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Keene Downtown

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

Keene

8.8/10

Excellent

(1,004 reviews)

"Really clean hotel, friendly staff and great location."

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

Aaron

CA $249

CA $270 total

includes taxes & fees

Jan 29 - Jan 30

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

![Exterior](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/41372bd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/a258302a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Loft, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/cb9ce75a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/5c506444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Keene Downtown

[](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information)

Keene

8.8/10

Excellent

(759 reviews)

"Everything was clean, comfortable and the staff quite conversational"

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

Diane

CA $242

CA $263 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/a0cdde49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room, 1 Queen Bed](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/5e1ddcf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/d7fa40cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room | Private kitchenette](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/b9a1accb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Burrell House

[](https://www.expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.Hotel-Information)

Keene

9.6/10

Exceptional

(156 reviews)

"The building and room were very nice. The location is great, very walkable to the center of town. "

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

Rochelle

[](https://www.expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2557x3y3-db499e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-baca4e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-dbaacfef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Keene Hotel

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

Keene

8.4/10

Very good

(1,000 reviews)

"Great stay pool was very nice"

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

Patrick

CA $192

CA $209 total

includes taxes & fees

Jan 22 - Jan 23

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

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/f95623cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/facc91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/bbdb2e0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/189b6d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Keene

[](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information)

Keene

8.8/10

Excellent

(364 reviews)

"Room is very clean , breakfast is good and fresh .coffee serve well all time . Will back to stay again . "

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

Raymond

CA $242

CA $262 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/7a5af75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/0940a25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/0c7292b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/95e5b046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Keene

8.4/10

Very good

(978 reviews)

"Staff was very welcoming and the room was very clean. "

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

Rebecca

CA $166

CA $180 total

includes taxes & fees

Jan 26 - Jan 27

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

![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/39253ee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/fa5ce310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/9e4b70fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Days Inn by Wyndham Keene NH

[](https://www.expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information)

Keene

7.0/10

Good

(1,000 reviews)

"Checkin was quick. I like the pre-check in process."

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

Anthony

CA $142

CA $154 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information)

![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/3e2c5f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/4886f728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sturbridge Queen](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/fb914a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/12886762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Centennial House

[](https://www.expedia.ca/Northfield-Hotels-Centennial-House.h893968.Hotel-Information)

Northfield

9.6/10

Exceptional

(173 reviews)

"great proprietors beautiful vintage home excellent breakfast"

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

JAMES

CA $261

CA $276 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Northfield-Hotels-Centennial-House.h893968.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/114000000/113060000/113050700/113050601/62d3b33d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113060000/113050700/113050601/98aefc9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe House, Mountain View | Living area](https://images.trvl-media.com/lodging/114000000/113060000/113050700/113050601/4858ba1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior King Room, Garden View](https://images.trvl-media.com/lodging/114000000/113060000/113050700/113050601/cd839203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Valley Farms

[](https://www.expedia.ca/Walpole-Hotels-Inn-At-Valley-Farms.h113050601.Hotel-Information)

Walpole

10/10

Exceptional

(14 reviews)

"Picturesque, family run bed and breakfast."

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

Jay

CA $210

CA $228 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Walpole-Hotels-Inn-At-Valley-Farms.h113050601.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/5cfd9172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard view](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/15d3021c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, desk, blackout drapes](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/35f23d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/e940457b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn At Crumpin Fox

[](https://www.expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information)

Bernardston

9.2/10

Wonderful

(350 reviews)

"Staff very accomodating when we needed to check in very early"

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

Bill

CA $176

CA $196 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.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](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/f1ce012c.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)

![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 $425

CA $461 total

includes taxes & fees

Feb 2 - Feb 3

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

![Reception](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/1b1adba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/d0279da0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/3ec00e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/148f2c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Greenfield

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

Greenfield

8.6/10

Excellent

(886 reviews)

"Friendly staff, great breakfast, comfy beds"

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

Lori

CA $260

CA $290 total

includes taxes & fees

Jan 27 - Jan 28

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/3973f8d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/8319d109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/acae342c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Putney Inn

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

Putney

8.4/10

Very good

(1,000 reviews)

"perfect room, very clean and friendly staff"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Marc-André

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Theatre show](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/afa5570f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hiking](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Theatre show](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/2424bc13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Latchis Hotel

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

Brattleboro

8.4/10

Very good

(843 reviews)

"Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!"

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

Jaime

CA $181

CA $199 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.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=2026-02-04&endDate=2026-02-05&regionId=3000447144&adults=2&sort=RECOMMENDED&openPlayBack=true)

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Save an average of 15% on thousands of hotels when you're signed in

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## Learn more about Winchester

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

[See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2026-02-04&endDate=2026-02-05&adults=2&regionId=3000447144)

![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=900&h=591&p=1&q=high)

## More cheap stays in Winchester

![Days Inn by Wyndham Keene NH](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

CA $142

CA $154 total

Jan 27 - Jan 28

includes taxes & fees

7/10 Good! (999 reviews)

[](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information)

![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Latchis Hotel

50 Main Street Brattleboro VT

CA $181

CA $199 total

Jan 22 - Jan 23

includes taxes & fees

8.4/10 Very Good! (843 reviews)

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

![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

CA $184

CA $203 total

Jan 29 - Jan 30

includes taxes & fees

8.4/10 Very Good! (758 reviews)

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

![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

CA $203

CA $223 total

Jan 31 - Feb 1

includes taxes & fees

8.2/10 Very Good! (935 reviews)

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

![Hampton Inn & Suites Greenfield](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn & Suites Greenfield

184 Shelburne Rd Greenfield MA

CA $260

CA $290 total

Jan 27 - Jan 28

includes taxes & fees

8.6/10 Excellent! (886 reviews)

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

![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Putney Inn

57 Putney Landing Rd Putney VT

[Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F02%2F2026&endDate=05%2F02%2F2026&selected=1810866&PinnedHotelID=1810866&HadPinnedHotel=true&regionId=3000447144)

8.4/10 Very Good! (1,004 reviews)

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

## Hotels in Winchester with star-rating

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

4 properties

[](https://expedia.ca/4Star-Winchester-Hotels.s40-0-d3000447144.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

64 properties

[](https://expedia.ca/3Star-Winchester-Hotels.s30-0-d3000447144.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

72 properties

[](https://expedia.ca/2Star-Winchester-Hotels.s20-0-d3000447144.Travel-Guide-Filter-Hotels)

## Recent reviews of Winchester hotels

![Colonel Williams Inn](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/0d3a6bb4_y.jpg)

### Colonel Williams Inn

5/5 Excellent

"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."

A verified traveller stayed at Colonel Williams Inn

Posted 2 days ago

[](https://expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information)

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

### The Putney Inn

5/5 Excellent

"Clean, roomy, and has a mini fridge and microwave. Great for college kids going skiing! "

A verified traveller stayed at The Putney Inn

Posted 3 days ago

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

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

### The Colonial Hotel

5/5 Excellent

"Amazing hotel and outstanding staff. Would absolutely stay here again."

A verified traveller from North Hatfield stayed at The Colonial Hotel

Posted 4 days ago

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

5/5 Excellent

"There was a college sports team staying there and were slamming doors until 1am. Send someone to walk the halls occasionally."

A verified traveller stayed at Best Western Plus Keene Hotel

Posted 10 days ago

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

![The Inn At Crumpin Fox](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a_y.jpg)

### The Inn At Crumpin Fox

5/5 Excellent

"Staff very accomodating when we needed to check in very early"

A verified traveller stayed at The Inn At Crumpin Fox

Posted 10 days ago

[](https://expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information)

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

### Hampton Inn Brattleboro

5/5 Excellent

"Fantastic experience! Great staff! Very comfortable room. Thanks . "

A verified traveller from stamford stayed at Hampton Inn Brattleboro

Posted 12 days ago

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

5/5 Excellent

"The hotel was very clean. Staff was extremely friendly and helpful."

A verified traveller stayed at Holiday Inn Express Hotel & Suites Brattleboro by IHG

Posted 12 days ago

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

![Four Columns Inn](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/be42824d_y.jpg)

### Four Columns Inn

5/5 Excellent

"Beautiful room and property. "

A verified traveller stayed at Four Columns Inn

Posted 2 weeks ago

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

5/5 Excellent

"Great staff"

A verified traveller stayed at Comfort Inn & Suites Brattleboro I-91

Posted 2 weeks ago

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

## Frequently asked questions

### When is the best time to go to Winchester?

> Winchester is particularly vibrant from June to August, during the peak season when tourists flock to experience the lively atmosphere. This is a fantastic period for outdoor activities and sightseeing, as the city's gardens and parks burst into life, inviting visitors to enjoy picnics or simply relax in the sun. The bustling city also hosts various events and festivals that celebrate local culture, providing an excellent opportunity to engage with the community.
> 
>   
> For those who appreciate a more tranquil experience, consider visiting in September. This month still offers pleasant weather, with temperatures hovering around 17°C, but with fewer crowds. You'll find that popular attractions are more accessible, allowing for a more immersive experience without the hustle and bustle of peak tourist season.

### Where can I find the best nightlife in Winchester?

> While nightlife in Winchester isn't as bustling as in bigger cities, you can still find a few local gems. The town has a handful of pubs and bars where you can enjoy a relaxed atmosphere and perhaps catch some live music on weekends. The Village Pizza is a popular spot for a casual dining experience that often transforms into a lively gathering place in the evenings.
> 
>   
> For those willing to venture a bit further, nearby Keene has more vibrant nightlife options, including cocktail lounges, bars, and eateries that stay open later.

### Can I cancel my hotel reservation on Expedia?

### How can I save on a Winchester hotel booking with Expedia?

### How much is the nightly rate at a Winchester hotel?

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- [Flights to Keene ](https://www.expedia.ca/Cheap-Flights-To-Keene.d6057413.Travel-Guide-Flights)
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