Winchester Hotel & Accommodation Deals 2026 from NZ$165 - Fully Refundable Options

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

NZ$297

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

A grassy area with picnic tables and a clock tower.

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

2. Windmill Motel Restaurant

Bernardston

Donna

NZ$255

includes taxes & fees

11 Oct - 12 Oct

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

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

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

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

3. The Inn At Crumpin Fox

Bernardston

Heather

NZ$224

includes taxes & fees

1 Nov - 2 Nov

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

4. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

NZ$272

includes taxes & fees

8 Nov - 9 Nov

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

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

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

5. Latchis Hotel

Brattleboro

Deborah

NZ$278

includes taxes & fees

1 Nov - 2 Nov

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

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

6. Best Western Plus Keene Hotel

Keene

Ruddy

NZ$274

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.

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.

7. Hampton Inn & Suites Keene

Keene

Rebecca

NZ$291

includes taxes & fees

10 Nov - 11 Nov

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

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

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.

8. Hampton Inn Brattleboro

Brattleboro

Francesca

NZ$220

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.

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

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

9. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Angelo

NZ$230

includes taxes & fees

2 Nov - 3 Nov

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

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.

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

10. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

NZ$217

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

11. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Jason

NZ$294

includes taxes & fees

8 Nov - 9 Nov

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

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

A cozy room with a wooden floor, a rocking chair, a blue armchair, a bookshelf, and a globe on a table.

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

12. The Carriage Barn Inn

Keene

Richard

NZ$287

includes taxes & fees

15 Oct - 16 Oct

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

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.

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

13. Vikings Villages Resort

Guilford

Cecil

NZ$389

includes taxes & fees

12 Oct - 13 Oct

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

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.

14. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

NZ$335

includes taxes & fees

25 Oct - 26 Oct

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 Days Inn with a brick facade, a central entrance, and a parking lot.

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

15. Days Inn by Wyndham Keene NH

Keene

CHERYL

NZ$179

includes taxes & fees

25 Oct - 26 Oct

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

A hotel room with two beds, a nightstand, a lamp, and a chair.

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.

16. Econo Lodge Brattleboro South

Brattleboro

David

NZ$195

includes taxes & fees

8 Nov - 9 Nov

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

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

A hallway with a white radiator, a wooden staircase, and a door with decorative glass panels.

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

17. The Burrell House

Keene

Justin

NZ$272

includes taxes & fees

21 Oct - 22 Oct

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

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

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

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

18. The Covered Bridge Inn

Brattleboro

Adolfo

NZ$206

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

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

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

19. Courtyard by Marriott Keene Downtown

Keene

Deborah

NZ$365

includes taxes & fees

25 Oct - 26 Oct

A blue house with a porch, a sign reading "The One Cat", and a garden with various plants and flowers.

A bedroom with a bed, a headboard with a birdcage design, a nightstand with a lamp, and a window with blue curtains.

A cozy living room with a television, books, and a comfortable couch.

A wooden desk with a variety of books and pamphlets, a small tiger figurine, and a mirror reflecting the room.

20. The One Cat B&B

Brattleboro

marjie

NZ$553

includes taxes & fees

18 Oct - 19 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

Recent Reviews in Winchester

Gardner Inn

8/10 Good

"Our room was clean. Some things were outdated but it was a good place to stop for the night. No issues"

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."

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 accommodation in Winchester

The Putney Inn

57 Putney Landing Rd Putney VT

NZ$165

25 Oct - 26 Oct

includes taxes & fees