𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester (2026)

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

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Go beyond your typical stay in Winchester

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Our top choices for Winchester hotels

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

A group of women in formal attire standing in a garden with a house in the background.

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

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

1. Centennial House

Northfield

Alan

S$219

includes taxes & fees

26 Oct - 27 Oct

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

2. Windmill Motel Restaurant

Bernardston

Donna

S$183

includes taxes & fees

11 Oct - 12 Oct

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

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

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.

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

S$196

includes taxes & fees

8 Nov - 9 Nov

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 conference room with a long table, six chairs, a projector screen, and a brick wall.

4. The Inn At Crumpin Fox

Bernardston

Heather

S$161

includes taxes & fees

1 Nov - 2 Nov

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.

5. Hampton Inn Brattleboro

Brattleboro

Francesca

S$158

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

6. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

S$156

includes taxes & fees

8 Nov - 9 Nov

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.

A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.

7. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Angelo

S$165

includes taxes & fees

2 Nov - 3 Nov

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

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

8. Best Western Plus Keene Hotel

Keene

Ruddy

S$197

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.

9. Hampton Inn & Suites Keene

Keene

Rebecca

S$209

includes taxes & fees

10 Nov - 11 Nov

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

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

10. Latchis Hotel

Brattleboro

Deborah

S$200

includes taxes & fees

1 Nov - 2 Nov

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

A living room with a sofa, armchair, and round table, a bedroom with a bed and nightstands, and large windows with curtains.

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

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

11. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Jason

S$211

includes taxes & fees

8 Nov - 9 Nov

A wooden table set with plates, cutlery, and a folded napkin.

A bench in front of an apple tree with ripe apples.

A corner room with wooden flooring, a wooden table, and four chairs. Large windows with curtains are visible, offering a view of a green landscape and a red deck outside.

A two-story building with a porch, a sign indicating guest rooms, and an American flag.

12. The Carriage Barn Inn

Keene

Richard

S$220

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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

13. Days Inn by Wyndham Keene NH

Keene

CHERYL

S$129

includes taxes & fees

25 Oct - 26 Oct

A bar area with a fireplace, seating, and a TV.

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.

14. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

S$241

includes taxes & fees

25 Oct - 26 Oct

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

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

15. Vikings Villages Resort

Guilford

Cecil

S$280

includes taxes & fees

12 Oct - 13 Oct

A historic brick building with a porch and a sign reading "Burrell House."

A kitchen with a microwave, coffee maker, and a KUPPST refrigerator. There are two stools and a small shelf with a vase.

A covered outdoor seating area with tables and chairs, overlooking a residential street with houses and a road.

A bedroom with a large bed, a wooden desk, and three chairs. There are three windows with shutters.

16. The Burrell House

Keene

Justin

S$195

includes taxes & fees

21 Oct - 22 Oct

A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.

A hotel lobby with a red carpet, a reception desk, a sofa, and chairs.

A sunroom with large windows, a dining area with a table and chairs, and a sofa.

A room with a dining table, chairs, a sofa, and a red carpet leading to a door.

17. Econo Lodge Brattleboro South

Brattleboro

David

S$140

includes taxes & fees

8 Nov - 9 Nov

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

A hotel room with two beds, a nightstand, a lamp, a painting of a cabin, and a door.

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

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

18. The Covered Bridge Inn

Brattleboro

Adolfo

S$148

includes taxes & fees

15 Oct - 16 Oct

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

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

A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.

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

19. Courtyard by Marriott Keene Downtown

Keene

Deborah

S$263

includes taxes & fees

25 Oct - 26 Oct

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 grassy field with a playground and trees in the background.

20. The Putney Inn

Putney

Anita

S$119

includes taxes & fees

28 Oct - 29 Oct

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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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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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Attleboro Mountain

Commune with nature and explore the great outdoors at Attleboro Mountain during your travels in Richmond.

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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.

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

See all hotels in Winchester

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

Top Winchester Hotel Reviews

The Colonial Hotel

10/10 Excellent

"Absolutely loved our stay here with our two golden doodles! We were in town for our daughter’s hockey game. We stay in chain hotels most weekends snd leave our dogs home . We made a little trip out of this 2 game series and The Colonial Hotel was the perfect little getaway."

Gardner Inn

8/10 Good

"Was a one night traveling stay over. Easy check in. Room was very nice updated. Plenty of secure parking. Morning coffee."

Latchis Hotel

8/10 Good

"Love the old-fashioned, art, deco, charm, and having the turntables and old records in the room… And having the movie theater attached…. I think this is a work in progress. The carpeting is really old in the rooms and there were laundry bags left out for the laundry to pick up all day… And because they don’t staff from 10 PM to 9 AM on a Saturday I had to literally fill the water jug for the Keurig coffee from my tub… Could you not. But the staff was great and it’s a cool looking old hotel… The windows need to be clean so I could actually see the mountains out of my room… And be able to close the outside windows. If you want old World charm give it a try… But I’m hoping or not for private he has taken this over. I’ll put some more cash into it because it’s worth it."

Otherland Hotel

8/10 Good

"Beautiful hotel clean quiet"

Colonial Motel

8/10 Good

"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."

The Inn At Crumpin Fox

8/10 Good

"Lovely setting."

Hampton Inn & Suites Greenfield

10/10 Excellent

"Staff was helpful and super friendly. Rooms were clean and looked recently renovated. Thank you for a great stay, highly recommended and will return."

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"We had a one night stay recently. We were on the newly-renovated 4th floor, which was very nice. The room was very clean. We were there early, so we went to the 99 Restaurants bar that was right in front of the Comfort Inn. Check-in was easy and the staff were very pleasant. Room was very nice. We did have an issue with the television, but staff responded quickly and solved the issue. The free breakfast in the morning was very nice. Pancakes, waffles (with fruit toppings & syrup), bacon, breads, bagels and muffins, fresh fruit, cereals, yogurts. Many beverage options. A very nice selection! Staff was right there to replenish anything that was running low. Parking was plentiful, and right in front of the entrance. Check-out was fast and easy. I would highly recommend Comfort Inn & Suites!"

The Covered Bridge Inn

8/10 Good

"Poor included breakfast. Not much available. Bagels were very hard"

More cheap stays in Winchester

The Putney Inn

57 Putney Landing Rd Putney VT

S$119

28 Oct - 29 Oct

includes taxes & fees