A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.

Hotels in Winchester

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Dates

November 2026

December 2026

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Where to stay in Winchester?

A modern living room with a fireplace, red curtains, and a wooden dining table.

1. Hotel UMass

Amherst

$142 total

includes taxes & fees

Dec 9 - Dec 10

A large, historic building with a prominent tower and a well-lit entrance labeled "Bollywood".

2. Inn on Boltwood

Amherst

$230 total

includes taxes & fees

Nov 12 - Nov 13

A hotel with a covered entrance, a flag, and a clear sky.

3. Comfort Inn & Suites Hadley - Amherst

Hadley

$133 total

includes taxes & fees

Dec 1 - Dec 2

A windmill, a row of cabins, and a forest backdrop.

4. Windmill Motel Restaurant

Bernardston

$117 total

includes taxes & fees

Nov 11 - Nov 12

A grand lobby with a staircase, a piano, comfortable seating, and large windows.

5. The Colonial Hotel

Gardner

$179 total

includes taxes & fees

Nov 11 - Nov 12

A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.

6. Vikings Villages Resort

Guilford

$223 total

includes taxes & fees

Nov 15 - Nov 16

A hotel reception area with a stone wall, leather chairs, a reception desk, and a sign indicating free Wi-Fi.

7. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

$100 total

includes taxes & fees

Dec 6 - Dec 7

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

8. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

$144 total

includes taxes & fees

Nov 11 - Nov 12

A cozy living room with a fireplace, a coffee station, and a view of the outside.

9. Colonial Motel

Brattleboro

$94 total

includes taxes & fees

Nov 11 - Nov 12

A two-story house with a red door, green shutters, and a snow-covered front yard.

10. Centennial House

Northfield

$190 total

includes taxes & fees

Nov 15 - Nov 16

The exterior of Latchis Hotel with a prominent entrance, large windows, and potted plants.

11. Latchis Hotel

Brattleboro

$131 total

includes taxes & fees

Nov 11 - Nov 12

A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.

12. Hampton Inn Brattleboro

Brattleboro

$130 total

includes taxes & fees

Nov 16 - Nov 17

A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

13. River Valley Inn

West Hatfield

$111 total

includes taxes & fees

Nov 22 - Nov 23

A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

14. Best Western Plus Keene Hotel

Keene

$154 total

includes taxes & fees

Nov 12 - Nov 13

An outdoor seating area with wicker furniture, a fire pit, and decorative lamps.

15. Courtyard by Marriott Hadley Amherst

Hadley

$200 total

includes taxes & fees

Nov 15 - Nov 16

A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

16. Comfort Inn & Suites Brattleboro I-91

Brattleboro

$125 total

includes taxes & fees

Nov 22 - Nov 23

A hotel room with two beds, a desk, and a TV.

17. The Putney Inn

Putney

$93 total

includes taxes & fees

Nov 11 - Nov 12

A modern hotel lobby with a stone wall, a fireplace, a bar area, and seating arrangements.

18. Homewood Suites by Hilton Hadley Amherst

Hadley

$164 total

includes taxes & fees

Nov 29 - Nov 30

A room with a bed, a sofa, a coffee table, and a television.

19. Black Walnut Inn

North Amherst

$207 total

includes taxes & fees

Nov 11 - Nov 12

A hotel with a covered entrance, a clear sky, and a tree in the foreground.

20. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

$158 total

includes taxes & fees

Nov 22 - Nov 23

View all properties

Go beyond your typical stay in Winchester

Top landmarks in Winchester

Winchester Speedpark

Wanna race? You could pay a visit to Winchester Speedpark located 2.6 mi (4.2 km) from central Winchester.

See properties

Learn more about Winchester

Winchester is well-known for its attractions such as Winchester Speedpark and New England Sweetwater Farm & Distillery. The city has something for everyone including sights like Birch Point and Pisgah State Park within a scenic setting.

See all hotels in Winchester

Check out reviews of Winchester hotels guests love

Centennial House

Northfield

10/10 Exceptional

My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne

Anonymous traveler

A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

Inn on Putney Road

Brattleboro

10/10 Exceptional

Victoria

A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

The Inn At Crumpin Fox

Bernardston

10/10 Exceptional

I've traveled quite frequently the past several years and I can say in all honesty that this is without doubt one of the nicest places I have stayed. I was there for 2 nights and could not have asked for nicer accomodations. The room was spacious, the bed very comfortable and the bathroom spotless. The manager was very gracious, he even lent me his umbrella when it rained the day I had planned to do genealogy research in a local cemetery.

Anonymous traveler

A dock extending into a lake with a grassy area in the foreground and trees in the background.

Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

10/10 Exceptional

James

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

10/10 Exceptional

Anthony

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

10/10 Exceptional

Kristine

Best Western Plus Keene Hotel

Keene

10/10 Exceptional

Susan

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

The Carriage Barn Inn

Keene

10/10 Exceptional

William

A large, two-story house with a snow-covered driveway and surrounding trees.

Chesterfield Inn

West Chesterfield

10/10 Exceptional

Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.

Beverly

Latchis Hotel

Brattleboro

10/10 Exceptional

Anonymous traveler

Comfort Inn & Suites Brattleboro I-91

Brattleboro

10/10 Exceptional

Julianne

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

Hampton Inn & Suites Keene

Keene

10/10 Exceptional

kristin

Hampton Inn Brattleboro

Brattleboro

10/10 Exceptional

Arrived late and were greeted by 2 friendly associates at the desk. There were coffee, tea, hot cocoa, cookies, cheese and crackers available. A welcoming lobby with fireplace. Room was nice, comfortable and clean. Lots of outlets in room. Indoor pool was nice, clean, and heated. hot tub was very relaxing after days of skiing. Continental breakfast was very good and had a variety of choices. We were pleasantly surprised with our choice.

K.White

A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.

Courtyard by Marriott Keene Downtown

Keene

10/10 Exceptional

Vic

A room with two single beds, a desk, and a radiator.

Colonel Williams Inn

Brattleboro

10/10 Exceptional

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

Frequently Asked Questions

What hotels do travelers like in Winchester?

Guests like Windmill Motel Restaurant .

Can I book refundable hotels in Winchester?

If you need the flexibility to change your travel plans to Winchester, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Winchester be like during my vacation?

July and August are typically the warmest months in Winchester when the average temp is 67°F. January and February are the coldest months when the average temperature is 28°F. October and July are the months with the most rain.

Why should I book my Winchester hotel through Hotels.com?

There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.