Hotels in Winchester

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Where to stay in Winchester?

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

A hotel room with two beds, a dining table with a plate of food, a glass of water, and a bottle of wine.

A modern hotel lobby with a large TV screen displaying the hotel name, red chairs, wooden shelves, and a clock on the wall.

A hotel lobby with a seating area, red curtains, and a view of the outdoors.

1. Hotel UMass

Amherst

$126

$142 total

includes taxes & fees

Oct 26 - Oct 27

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

A spacious outdoor seating area with a fire feature, white brick walls, and multiple windows with shutters.

A spacious living room with a fireplace, comfortable seating, and elegant chandeliers.

A modern living room with a sofa, armchairs, a coffee table, and a wine rack.

2. Inn on Boltwood

Amherst

$206

$230 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel room with a bed, a sofa, a small table, and a painting on the wall.

A hotel room with a bed, a desk with a phone, a sofa with cushions, a red ottoman, a kitchenette with a microwave, and a painting on the wall.

A spacious lobby with a fireplace, seating area, and large windows.

3. Comfort Inn & Suites Hadley - Amherst

Hadley

$115

$128 total

includes taxes & fees

Nov 15 - Nov 16

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

A windmill, a row of cabins, and a grassy field at night.

A grassy area with picnic tables and a clock tower.

A bedroom with a geometric-patterned headboard, a bed with a textured white duvet, two pillows, a bedside table with a clock, and a potted plant.

4. Windmill Motel Restaurant

Bernardston

$105

$117 total

includes taxes & fees

Nov 2 - Nov 3

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

A pool area with lounge chairs and potted plants.

A brick building with a steeple, arched windows, and flags.

A wooden pergola structure in a garden setting with a paved walkway leading to it.

5. The Colonial Hotel

Gardner

$144

$161 total

includes taxes & fees

Nov 1 - Nov 2

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

A wooden interior with a fireplace, a staircase, and a dining area.

A cozy room with a wooden wall, a red sofa, a small table with a bottle, a book, and a plant.

A rustic wooden cabin with a thatched roof, a stone wall, and a wooden staircase leading to a balcony.

6. Vikings Villages Resort

Guilford

$208

$243 total

includes taxes & fees

Oct 26 - Oct 27

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

A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.

A hotel room with a television, a sofa, a coffee table, a desk, and a chair.

A gaming area with arcade machines, a seating area with tables and chairs, and large windows providing natural light.

7. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

$89

$100 total

includes taxes & fees

Nov 8 - Nov 9

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

A hotel room with a bed, a desk, a chair, a wooden door, and a window.

A modern kitchen with wooden cabinets, a coffee machine, a fruit juice dispenser, and a refrigerator.

An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.

8. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

$130

$141 total

includes taxes & fees

Oct 29 - Oct 30

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

A motel with multiple floors, each with balconies and windows.

A dining table with a vase of flowers, a chair, and a window with a view.

A hotel room with a sofa, a coffee table, a desk with a telephone, a mirror, and a television.

9. Colonial Motel

Brattleboro

$99

$109 total

includes taxes & fees

Nov 1 - Nov 2

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

A wooden gazebo with a peaked roof, surrounded by a gravel area with potted plants.

A room with a built-in bench, a window with curtains, and a wooden railing.

A red building with white trim, surrounded by lush greenery and fruit trees.

10. Centennial House

Northfield

$179

$190 total

includes taxes & fees

Oct 28 - Oct 29

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

A banquet hall with round tables, chairs, and a staircase.

A hotel lobby with a reception desk, seating area, and a large window.

A lobby with a central circular platform, a statue, and a fountain. There are paintings on the walls and a staircase to the left.

11. Latchis Hotel

Brattleboro

$141

$155 total

includes taxes & fees

Nov 9 - Nov 10

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

A lobby with wooden paneling, a fireplace, and two green armchairs.

A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.

12. Hampton Inn Brattleboro

Brattleboro

$110

$121 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel room with two beds, a sofa, a desk, a TV, and a picture on the wall.

A bathroom with a bathtub, toilet, and shower curtain.

A bathroom with a toilet, a shower, and a towel rack.

13. River Valley Inn

West Hatfield

$84

$94 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

A covered outdoor area with a wooden deck, white railings, and string lights.

14. Best Western Plus Keene Hotel

Keene

$142

$154 total

includes taxes & fees

Nov 1 - Nov 2

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

A spacious lobby with a central seating area, a reception desk, and a television screen.

A conference room with two Dell computers, a large autumn-themed painting, and two wall-mounted lamps.

A dining table set with multiple wine glasses, a centerpiece with flowers, and candles.

15. Courtyard by Marriott Hadley Amherst

Hadley

$143

$160 total

includes taxes & fees

Nov 15 - Nov 16

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

A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.

A hotel lobby with a reception desk, seating area, and a wall with framed pictures.

A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.

16. Comfort Inn & Suites Brattleboro I-91

Brattleboro

$110

$121 total

includes taxes & fees

Nov 1 - Nov 2

A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

A two-story white house with a front porch and a garage, surrounded by lush greenery.

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

A grassy field with a playground and trees in the background.

17. The Putney Inn

Putney

$84

$93 total

includes taxes & fees

Oct 26 - Oct 27

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

A modern kitchen with stainless steel appliances, a microwave, and a dishwasher. There is a dining area with a table and chairs.

A modern lounge area with a stone wall, a fireplace, a sofa, and two blue armchairs.

A modern hotel with a brick facade, multiple windows, and a well-lit entrance.

18. Homewood Suites by Hilton Hadley Amherst

Hadley

$147

$164 total

includes taxes & fees

Nov 3 - Nov 4

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

A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television mounted on the wall.

A living room with a round coffee table, a sofa, and a wall art piece.

A dining area with a wooden table set for four, surrounded by chairs.

19. Black Walnut Inn

North Amherst

$183

$205 total

includes taxes & fees

Oct 26 - Oct 27

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

A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

A spacious lobby with modern furniture, a large digital map display, and a high ceiling with geometric lighting.

A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

20. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

$144

$158 total

includes taxes & fees

Nov 1 - Nov 2

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Go beyond your typical stay in Winchester

Pet friendly

Pool

Hot tub

Family friendly

Cottage

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.

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Richmond Wildlife Manangement Area

Richmond Wildlife Manangement Area is 1.6 mi (2.6 km) from central Richmond, why not stop by during your stay. Want to stretch your legs some more? Head to Barden State Wildlife Management Area, just a short walk away.

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Cass Pond

Cass Pond is 0.7 mi (1.2 km) from central Richmond, why not stop by during your stay.

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New England Sweetwater Farm & Distillery

New England Sweetwater Farm & Distillery is in the heart of Winchester, so why not stop by during your stay.

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Barden State Wildlife Management Area

Barden State Wildlife Management Area is 1.5 mi (2.4 km) from central Richmond, why not stop by during your stay. Want to stretch your legs some more? Head to Richmond Wildlife Manangement Area, just a short walk away.

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Attleboro Mountain

If you want to stretch your legs and breathe in some fresh mountain air, head out to Attleboro Mountain for a bird's-eye view of Richmond.

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Loring Field

Loring Field is 1 mi (1.6 km) from central Winchester, why not stop by during your stay. Want to stretch your legs some more? Head to Kiwanis Park, located nearby.

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Bennett Gorge

Bennett Gorge is 2.7 mi (4.4 km) from central Richmond, why not stop by during your stay.

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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

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

Check out reviews of Winchester hotels guests love

The Putney Inn

10/10 Excellent

"Great location and wonderful staff! I love staying here every year!"

The Inn At Crumpin Fox

10/10 Excellent

"The room was clean and the area was quiet"

Travelodge by Wyndham Brattleboro VT

8/10 Good

"Great value! Older facility, smaller room and beds but perfect for our stay which basically only involved using the room to sleep."

The Colonial Hotel

8/10 Good

"This is a dated, solid 3-star hotel. The interior finishes all need a serious refresh. I was on the ground floor in a nice room, but the Wi-Fi was terrible and they stuck me down by the mechanical plant and housekeeping offices. Normally not a bid deal but they left the doors open to the mechanical room the entire time I was in my room. They also need to update the quality and number of WAPs. They were confused when I asked if they had a "business center" because they don't. Given the quality of the Wi-Fi in my room, it would've been nice if they had one.😊 The Colonial Grille is awesome; it is a shining star for this somewhat tired hotel. The restuarant/bar staff are awesome, and the food is good American fare. The bar is a lot of fun, and it's big. This is a local destination for weddings. I was there from Friday to Sunday in late October and I think there were not less than 3 weddings."

Best Western Plus Keene Hotel

8/10 Good

"Breakfast Convenient location"

Latchis Hotel

8/10 Good

"It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay."

Days Inn by Wyndham Keene NH

8/10 Good

"Clean comfortable room with a comfortable bed. I didn’t like the smell of whatever cleaning product they used, it was a bit bit strong let the kind you used to cover up something. Was this recently a smoking hotel? Also I missed an cycle in the fitness center, although the machines that were there seemed to work well. All in all it’s about what you would expect for a moderately priced hotel in New Hampshire during leaf peeper season."

Hampton Inn Brattleboro

10/10 Excellent

"The hotel was fairly new. Coffee was the only thing I felt needed changed."

Comfort Inn & Suites Brattleboro I-91

8/10 Good

"Was a good room for a one night stay on a road trip."

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.

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