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 modern building with a grid-like facade, multiple balconies, and a spacious courtyard with geometric sculptures.

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

A registration desk with a sign above it, a receptionist, and several people standing in line.

1. Hotel UMass

Amherst

$95

$108 total

includes taxes & fees

Sep 20 - Sep 21

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

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

A long dining table set with white tableware, flanked by windows and a skylight.

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

2. Inn on Boltwood

Amherst

$195

$217 total

includes taxes & fees

Sep 13 - Sep 14

A hotel with a covered entrance, a flag, and a sign.

A hotel room with a sofa, a small table, a red stool, a kitchenette, and a bed.

A spacious living area with a fireplace, sofas, and a coffee table.

A hotel room with a bed, a sofa, a round coffee table, and a nightstand.

3. Comfort Inn & Suites Hadley - Amherst

Hadley

$145

$162 total

includes taxes & fees

Sep 16 - Sep 17

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.

A large, single-story building with a central entrance and a covered walkway.

A grassy area with picnic tables and a clock tower.

A flat-screen TV mounted on a wall displaying a streaming service interface.

4. Windmill Motel Restaurant

Bernardston

$135

$151 total

includes taxes & fees

Sep 14 - Sep 15

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

A pool area with lounge chairs and potted plants.

A formal dining room with round tables, dark wooden chairs, and white tablecloths.

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

5. The Colonial Hotel

Gardner

$170

$190 total

includes taxes & fees

Sep 13 - Sep 14

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

$189

$221 total

includes taxes & fees

Sep 27 - Sep 28

A hotel room with two beds, a TV, a desk with a chair, a lamp, a microwave, and a painting on the wall.

A laundry area with a wall-mounted soap and bleach softener dispenser, four stacked washing machines, and a white countertop.

A Red Roof Plus hotel with a modern facade, a parking lot, and a landscaped entrance area.

A hallway with two leather chairs, a small table, a bench, a mirror, and a framed picture on the wall.

7. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

$94

$105 total

includes taxes & fees

Sep 17 - Sep 18

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.

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

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

8. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

$141

$153 total

includes taxes & fees

Sep 14 - Sep 15

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

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

9. Colonial Motel

Brattleboro

$84

$93 total

includes taxes & fees

Sep 13 - Sep 14

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

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

A dining area with a round table set for four, surrounded by wooden chairs. A fireplace is visible in the background, and the room has wooden paneling.

A window with a view of a grassy field and a bench.

10. Centennial House

Northfield

$199

$211 total

includes taxes & fees

Sep 13 - Sep 14

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

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

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

A covered bridge with a stone foundation, surrounded by lush greenery and a well-maintained lawn.

11. Latchis Hotel

Brattleboro

$113

$125 total

includes taxes & fees

Sep 13 - Sep 14

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

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

12. Hampton Inn Brattleboro

Brattleboro

$122

$134 total

includes taxes & fees

Sep 20 - Sep 21

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

A row of single-story motel buildings with a parking lot in front.

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

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

13. River Valley Inn

West Hatfield

$93

$103 total

includes taxes & fees

Sep 20 - Sep 21

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

A spacious lobby with a fireplace, comfortable seating, and large windows offering 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 hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

14. Best Western Plus Keene Hotel

Keene

$149

$162 total

includes taxes & fees

Sep 13 - Sep 14

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

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

15. Courtyard by Marriott Hadley Amherst

Hadley

$161

$180 total

includes taxes & fees

Sep 14 - Sep 15

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.

An indoor swimming pool with a tiled deck, safety signs, and a few chairs.

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

16. Comfort Inn & Suites Brattleboro I-91

Brattleboro

$118

$130 total

includes taxes & fees

Sep 20 - Sep 21

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

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

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

A motel with a parking lot, a covered walkway, and a staircase leading to the entrance.

17. The Putney Inn

Putney

$121

$133 total

includes taxes & fees

Sep 13 - Sep 14

A modern hotel lobby with a seating area, a fireplace, and a television mounted on a stone wall.

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

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

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

18. Homewood Suites by Hilton Hadley Amherst

Hadley

$171

$191 total

includes taxes & fees

Sep 16 - Sep 17

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 large brick building with a prominent entrance and a covered porch area.

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

19. Black Walnut Inn

North Amherst

$165

$185 total

includes taxes & fees

Sep 14 - Sep 15

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

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

A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.

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

20. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

$169

$186 total

includes taxes & fees

Sep 13 - Sep 14

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Go beyond your typical stay in Winchester

Pet friendly

Pool

Cottage

Family friendly

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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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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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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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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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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Conant Public Library

Conant Public Library is worth a visit when in central Winchester.

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Learn more about Winchester

Winchester is well-known for its attractions such as Winchester Speedpark and Birch Point. The city has something for everyone including sights like Pisgah State Park and Barden State Wildlife Management Area within a scenic setting.

See all hotels in Winchester

A snow-covered town with a river running through it, surrounded by mountains and trees.

Check out reviews of Winchester hotels guests love

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent

"Todo muy bien me encanta este cadena de hoteles, nunca he tenido problemas con ellos"

Vikings Villages Resort

10/10 Excellent

"How fun! The cabin was immaculate and well decorated. It was very sturdy and also cozy."

Windmill Motel Restaurant

10/10 Excellent

"Easy to find, clean and friendly staff. New renovations are fabulous!"

Gardner Inn

8/10 Good

"This place was nicer than I expected. My room looked recently remodeled."

Hampton Inn & Suites Greenfield

10/10 Excellent

"this is a convenient and good place to stay, great staff and services, best place around in many miles, highly recommended"

The Putney Inn

8/10 Good

"Room was very clean some things were a little dated but well worth it for the price would stay there again if I was ever in the area the town of Putney isn't much not a lot of shopping not a lot of things to do"

Hampton Inn Brattleboro

10/10 Excellent

"The room was very clean, the tv was very nice (my husband is now looking for one like it), it was quiet, which surprised me because it's near a busy highway. Breakfast was really good & a great variety! Only thing that could be improved is the mattress on the bed - it was a bit flat, but was comfortable enough."

Travelodge by Wyndham Brattleboro VT

10/10 Excellent

"As a single tired woman traveling, I was a little leery of Brattleboro, the gent who checked me in was very pleasant, the room was fine for a one nighter! My only “bummer” was that the coffee wasn’t working. But there was enough food all around the area to accommodate that !"

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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