Best Winchester Hotels in 2026 from HK$717 - Fully Refundable Options

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

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Our top choices for Winchester hotels

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

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

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

A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.

1. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Marnie

HK$1,325

HK$1,457 total

includes taxes & fees

13 Sept - 14 Sept

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

A golf course with a brick pathway, wooden boxes, and a tee box.

2. Centennial House

Northfield

Amy

HK$1,407

HK$1,487 total

includes taxes & fees

6 Sept - 7 Sept

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

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

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.

3. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

David

HK$1,105

HK$1,199 total

includes taxes & fees

6 Sept - 7 Sept

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

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

A spacious lobby with a stone wall, a reception desk, and a large window.

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

4. Hampton Inn Brattleboro

Brattleboro

Timothy

HK$939

HK$1,033 total

includes taxes & fees

10 Sept - 11 Sept

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

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

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

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

5. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Ellen

HK$926

HK$1,019 total

includes taxes & fees

13 Sept - 14 Sept

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

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.

A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

6. Best Western Plus Keene Hotel

Keene

Julia

HK$1,168

HK$1,267 total

includes taxes & fees

9 Sept - 10 Sept

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 grassy area with picnic tables and a clock tower.

A room with a round table and two leather chairs, a window with curtains, and a view of a parking lot outside.

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

7. Windmill Motel Restaurant

Bernardston

Dan

HK$953

HK$1,064 total

includes taxes & fees

6 Sept - 7 Sept

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

A hotel suite shop with shelves stocked with snacks and sundries, a refrigerated display case, and a sign indicating 24-hour availability.

A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.

8. Hampton Inn & Suites Keene

Keene

sheri

HK$1,151

HK$1,249 total

includes taxes & fees

10 Sept - 11 Sept

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

A gazebo with a red roof and white walls, surrounded by trees and a brick building.

A conference table set for a meeting with chairs and folded red napkins.

A brick building with a red awning and a sign that reads "The Inn."

9. The Inn At Crumpin Fox

Bernardston

Alan

HK$1,273

HK$1,422 total

includes taxes & fees

6 Sept - 7 Sept

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 wooden log cabin with a snow-covered entrance and a wooden fence in a snowy forest.

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

10. Vikings Villages Resort

Guilford

Cecil

HK$1,081

HK$1,261 total

includes taxes & fees

30 Sept - 1 Oct

A bar area with a dark wooden bar, multiple bar stools, and a large screen displaying the hotel name.

A hotel room with a brick wall, a large bed with white bedding, a flat-screen TV, and a desk with a lamp.

A living room with a brick wall, two armchairs, a sofa, a coffee table, and a patterned rug.

11. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

James

HK$1,520

HK$1,649 total

includes taxes & fees

10 Sept - 11 Sept

A hotel with a clock tower, a parking lot, and a well-maintained garden.

A hotel room with a bed, two bedside lamps, a nightstand, a chair, and a small table.

A cozy reading area with wooden chairs, a table with newspapers, and potted plants.

A building entrance with a white door, number 959, and a small porch area decorated with pumpkins, flowers, and scarecrows.

12. Black Mountain Inn

Brattleboro

Robert

HK$882

HK$970 total

includes taxes & fees

8 Sept - 9 Sept

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

A reception area with a black marble counter, wooden cabinets, and a 'Staff Only' door.

A hotel gym with treadmills, an elliptical, dumbbells, and a stationary bike.

A conference room with a black table, wooden chairs, a mounted TV, and a decorative mirror.

13. Days Inn by Wyndham Keene NH

Keene

Alex

HK$746

HK$810 total

includes taxes & fees

8 Sept - 9 Sept

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.

14. The Putney Inn

Putney

JANE

HK$854

HK$939 total

includes taxes & fees

7 Sept - 8 Sept

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

A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.

An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.

A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".

15. Courtyard by Marriott Keene Downtown

Keene

Deborah

HK$1,482

HK$1,609 total

includes taxes & fees

10 Sept - 11 Sept

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

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

A hotel room with two beds, a desk, a chair, a television, a dresser, and a door leading to a bathroom.

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

16. Colonial Motel

Brattleboro

James

HK$652

HK$717 total

includes taxes & fees

6 Sept - 7 Sept

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.

17. Latchis Hotel

Brattleboro

Stark

HK$924

HK$1,017 total

includes taxes & fees

7 Sept - 8 Sept

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

A cozy living room with a piano, leather sofa, armchair, and a globe on a coffee table.

A dining area with a round wooden table, white chairs, and a green wall.

A living room with a fireplace, a pool table, and comfortable seating.

18. Inn on Putney Road

Brattleboro

Karla

HK$2,311

HK$2,542 total

includes taxes & fees

8 Sept - 9 Sept

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

A building with a large balcony overlooking a body of water, a bridge in the foreground, and trees with autumn foliage.

A spacious living room with a large window, a patterned rug, and multiple seating options including a sofa and armchairs.

A spacious bedroom with a large bed, a desk, and a television.

19. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Jason

HK$1,259

HK$1,367 total

includes taxes & fees

29 Sept - 30 Sept

A dining area with a table and four chairs, a painting of a covered bridge, and a painting of a red building.

A sign for The Covered Bridge Inn with a welcome message.

A multi-story motel with a parking lot, several vehicles parked, and a tree in the foreground.

A reception area with a stone counter, wooden reception desk, and a red carpet.

20. The Covered Bridge Inn

Brattleboro

VINCENT JOEL

HK$948

HK$1,043 total

includes taxes & fees

6 Sept - 7 Sept

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Stay near popular Winchester attractions

Winchester Speedpark

Winchester Speedpark thrills with professionally designed motocross tracks featuring challenging jumps and turns. Experience heart-pounding night races or watch competitors tackle the New England racing circuit.

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Barden State Wildlife Management Area

This serene wildlife reserve in New Hampshire offers undisturbed natural landscapes for wildlife observation. Bring binoculars for spotting native species while exploring the peaceful trails during spring through fall.

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New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskies while learning about the distillation process in a warm space adorned with reclaimed wood.

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Cass Pond

This serene 54-acre pond in Richmond offers peaceful fishing for bass, pickerel, and perch. Bring your own gear and a valid New Hampshire fishing licence to fully enjoy this tranquil natural retreat.

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Richmond Wildlife Manangement Area

This protected wilderness features diverse New Hampshire ecosystems across forests, wetlands, and meadows. Explore marked trails for wildlife viewing, especially during spring migration or autumn's foliage display.

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Loring Field

Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside.

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Bennett Gorge

This secluded woodland trail winds alongside a brook to the remnants of an historic mill. Explore Richmond's industrial past while enjoying the tranquil sounds of flowing water and forest solitude.

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Conant Public Library

This historic 1892 library houses Winchester's heritage collection, including one of New England's earliest pipe organs. Browse artefacts or research local history with help from knowledgeable staff.

See properties

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 city centre district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester

Top Winchester Hotel Reviews

The Colonial Hotel

10/10 Excellent

"My favorite place in Gardener."

The Inn At Crumpin Fox

10/10 Excellent

"Easy to get to and quiet surrounding and helpful people on staff."

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Conveniently located right off Rt. 91, with a restaurant located in the same parking lot and gas stations nearby."

Latchis Hotel

10/10 Excellent

"Great place. Staff are very nice and helpful."

Colonial Motel

10/10 Excellent

"Staff was very helpful. A little seating area under some trees was a beautiful place to relax while the sun was setting."

The Putney Inn

10/10 Excellent

"It’s a motel. It’s clean and the staff is friendly. It’s definitely not fancy, but it gets the job done."

Gardner Inn

8/10 Good

"Pleasant staff, clean room, easy parking So-so coffee…bring a hair dryer."

Vikings Villages Resort

10/10 Excellent

"Great place to stay."

Days Inn by Wyndham Keene NH

8/10 Good

"The staff was helpful. Parking was easy. It was an ok stay. I would stay there again for the price."

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

HK$746

HK$810 total

8 Sept - 9 Sept

includes taxes & fees

7/10 Good! (1,004 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

HK$924

HK$1,017 total

7 Sept - 8 Sept

includes taxes & fees

8.6/10 Excellent! (974 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

HK$926

HK$1,019 total

13 Sept - 14 Sept

includes taxes & fees

8.6/10 Excellent! (853 reviews)

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

HK$939

HK$1,033 total

10 Sept - 11 Sept

includes taxes & fees

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

HK$1,105

HK$1,199 total

6 Sept - 7 Sept

includes taxes & fees

Hampton Inn & Suites Greenfield

184 Shelburne Rd Greenfield MA

HK$1,511

HK$1,687 total

14 Sept - 15 Sept

includes taxes & fees

Hotels in Winchester with star-rating

Frequently asked questions

What's the best place to stay in Winchester?

2 private mountain RV pads for rent. Full hook ups, located 2.1 mi (3.5 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are The Colonial Hotel and Keene Elm City Hotel, an Ascend Collection Hotel. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

Family Friendly Hilltop House In Putney Vermont: This holiday home rental outside of Winchester is located on a lake, and has a balcony, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. See all vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What are some hotels with pools in Winchester?

The Colonial Hotel: Provides a sauna, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel and Hampton Inn Brattleboro are a couple of other choices that offer an on-site pool. View all hotels with pools in Winchester.

What is staying in Winchester like?

Visitors to Winchester will definitely enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 6 hotels and other accommodation options to choose from. Find out more about Winchester.

What are the top places to visit in Winchester?

Natural beauty is on display at Birch Point, Cass Pond and Royalston State Forest. A couple of additional sights to add to your itinerary are Winchester Speedpark and Pisgah State Park. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

Winchester hotels from HK$717

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Holiday Inn Express Hotel & Suites Brattleboro by IHG

2. Centennial House

3. Keene Elm City Hotel, an Ascend Collection Hotel

4. Hampton Inn Brattleboro

5. Comfort Inn & Suites Brattleboro I-91

6. Best Western Plus Keene Hotel

7. Windmill Motel Restaurant

8. Hampton Inn & Suites Keene

9. The Inn At Crumpin Fox

10. Vikings Villages Resort

11. Fairfield Inn & Suites by Marriott Keene Downtown

12. Black Mountain Inn

13. Days Inn by Wyndham Keene NH

14. The Putney Inn

15. Courtyard by Marriott Keene Downtown

16. Colonial Motel

17. Latchis Hotel

18. Inn on Putney Road

19. Riverside Hotel, an Ascend Collection Hotel

20. The Covered Bridge Inn

Stay near popular Winchester attractions

Winchester Speedpark

Barden State Wildlife Management Area

New England Sweetwater Farm & Distillery

Cass Pond

Richmond Wildlife Manangement Area

Loring Field

Bennett Gorge

Conant Public Library

Learn more about Winchester

Top Winchester Hotel Reviews

The Colonial Hotel

The Inn At Crumpin Fox

Comfort Inn & Suites Brattleboro I-91

Latchis Hotel

Colonial Motel

The Putney Inn

Gardner Inn

Vikings Villages Resort

Days Inn by Wyndham Keene NH

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

Latchis Hotel

Comfort Inn & Suites Brattleboro I-91

Hampton Inn Brattleboro

Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn & Suites Greenfield

Hotels in Winchester with star-rating

Frequently asked questions

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