𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester from RM378 (2026) - 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 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 red building with white trim, surrounded by lush greenery and fruit trees.

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

1. Centennial House

Northfield

Alan

RM733

RM774 total

includes taxes & fees

18 Oct - 19 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 large, single-story building with a central entrance and a covered walkway.

A grassy area with picnic tables and a clock tower.

2. Windmill Motel Restaurant

Bernardston

Donna

RM523

RM585 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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.

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

RM567

RM624 total

includes taxes & fees

15 Nov - 16 Nov

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 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.

4. Best Western Plus Keene Hotel

Keene

Ruddy

RM578

RM627 total

includes taxes & fees

1 Nov - 2 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 covered bridge with a stone foundation, surrounded by lush greenery and a well-maintained lawn.

5. Latchis Hotel

Brattleboro

Erik

RM579

RM636 total

includes taxes & fees

1 Nov - 2 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 room with a long table, six chairs, a projector screen, and a brick wall.

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

6. The Inn At Crumpin Fox

Bernardston

Heather

RM459

RM513 total

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

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

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

7. Hampton Inn & Suites Keene

Keene

Rebecca

RM631

RM685 total

includes taxes & fees

25 Oct - 26 Oct

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

8. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

RM452

RM497 total

includes taxes & fees

15 Nov - 16 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 fitness center with cardio machines, weightlifting equipment, and a large mirror.

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

9. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Lisa

RM518

RM562 total

includes taxes & fees

25 Oct - 26 Oct

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

10. Hampton Inn Brattleboro

Brattleboro

Faith

RM454

RM500 total

includes taxes & fees

15 Nov - 16 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 living room with a large window, a patterned rug, and multiple seating options including a sofa and armchairs.

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

RM621

RM674 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

12. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Christopher

RM791

RM858 total

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 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

CHERYL

RM378

RM410 total

includes taxes & fees

25 Oct - 26 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.

14. Vikings Villages Resort

Guilford

Cecil

RM765

RM892 total

includes taxes & fees

29 Oct - 30 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 room with a dining table, chairs, a sofa, and a red carpet leading to a door.

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

15. Econo Lodge Brattleboro South

Brattleboro

Tasha

RM406

RM447 total

includes taxes & fees

16 Nov - 17 Nov

A large, two-story house with a snow-covered driveway and surrounding trees.

A bedroom with a large bed, a blue armchair, a wooden desk, and a view through a glass door.

A cozy room with a brick fireplace, floral wallpaper, and comfortable seating.

A cozy living room with a fireplace, leather chairs, a sofa, and a table with wine glasses.

16. Chesterfield Inn

West Chesterfield

Wayne

RM1,229

RM1,334 total

includes taxes & fees

18 Oct - 19 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.

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

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

17. Courtyard by Marriott Keene Downtown

Keene

Deborah

RM772

RM837 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

18. The Carriage Barn Inn

Keene

Richard

RM689

RM747 total

includes taxes & fees

18 Oct - 19 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 garden with a sign reading "The One Cat" and various plants and flowers.

19. The One Cat B&B

Brattleboro

marjie

RM1,224

RM1,347 total

includes taxes & fees

20 Oct - 21 Oct

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

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.

A room with a chessboard, leather chairs, a large vase, and a bookshelf.

20. Inn on Putney Road

Brattleboro

Karla

RM1,089

RM1,198 total

includes taxes & fees

3 Nov - 4 Nov

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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.

See properties

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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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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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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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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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.

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

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

Top Winchester Hotel Reviews

Gardner Inn

10/10 Excellent

"The room was clean. They have made improvements. There are now hair dryers in the room and they have installed a coat rack. We had a very enjoyable stay for my class reunion. The only real amenity is 24 hr coffee in the lobby and the ice machine. Restaurants and laundry are within walking distance . Thus was our 2nd time staying at this hotel and I will definitely stay here again."

Best Western Plus Keene Hotel

10/10 Excellent

"nice pool"

Days Inn by Wyndham Keene NH

8/10 Good

"I arrived late and exhausted. Young man at front counter was friendly and efficient. Carpet in hallway slightly warn. Room and bath very clean, no complaints. Bed was large and soft. I slept well. Parking lot safe and quiet. Free breakfast was… nothing special. Other businesses close by. Would definitely stay there again. Thank you."

Colonial Motel

10/10 Excellent

"Value for money. Clean and conveniently located. Friendly staff."

The Colonial Hotel

10/10 Excellent

"."

Travelodge by Wyndham Brattleboro VT

10/10 Excellent

"Old, but clean, friendly, everything worked. Good size TV, microwave and fridge."

Deerfield Inn

10/10 Excellent

"This is a beautiful historic hotel"

Vikings Villages Resort

10/10 Excellent

"Love our stay in Vikings. Staff was amazing and very attentive and helpful. The cabins were beautiful, clean and had everything we needed. Very recommended. Hope to go back in the future."

Hampton Inn Brattleboro

8/10 Good

"Clean room. Breakfast good for quick bite and coffee was good"

More cheap stays in Winchester

The Putney Inn

57 Putney Landing Rd Putney VT

RM343

RM378 total

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (1,003 reviews)

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

RM378

RM410 total

25 Oct - 26 Oct

includes taxes & fees

7/10 Good! (1,002 reviews)

Gardner Inn

22 Pearson Blvd Gardner MA

RM404

RM451 total

19 Oct - 20 Oct

includes taxes & fees

7.8/10 Good! (81 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

RM452

RM497 total

15 Nov - 16 Nov

includes taxes & fees

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

RM518

RM562 total

25 Oct - 26 Oct

includes taxes & fees

Latchis Hotel

50 Main Street Brattleboro VT

RM579

RM636 total

1 Nov - 2 Nov

includes taxes & fees

Frequently asked questions

What's the best place to stay in Winchester?

Colonial Motel, located 11.5 mi (18.5 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 Latchis Hotel. See all available top hotels, or 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: Offers a sauna, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel and Best Western Plus Keene Hotel 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 New England Sweetwater Farm & Distillery. 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 RM378

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. Centennial House

2. Windmill Motel Restaurant

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

4. Best Western Plus Keene Hotel

5. Latchis Hotel

6. The Inn At Crumpin Fox

7. Hampton Inn & Suites Keene

8. Comfort Inn & Suites Brattleboro I-91

9. Keene Elm City Hotel, an Ascend Collection Hotel

10. Hampton Inn Brattleboro

11. Riverside Hotel, an Ascend Collection Hotel

12. Fairfield Inn & Suites by Marriott Keene Downtown

13. Days Inn by Wyndham Keene NH

14. Vikings Villages Resort

15. Econo Lodge Brattleboro South

16. Chesterfield Inn

17. Courtyard by Marriott Keene Downtown

18. The Carriage Barn Inn

19. The One Cat B&B

20. Inn on Putney Road

Stay near popular Winchester attractions

Winchester Speedpark

Cass Pond

New England Sweetwater Farm & Distillery

Richmond Wildlife Manangement Area

Barden State Wildlife Management Area

Attleboro Mountain

Loring Field

Bennett Gorge

Learn more about Winchester

Top Winchester Hotel Reviews

Gardner Inn

Best Western Plus Keene Hotel

Days Inn by Wyndham Keene NH

Colonial Motel

The Colonial Hotel

Travelodge by Wyndham Brattleboro VT

Deerfield Inn

Vikings Villages Resort

Hampton Inn Brattleboro

More cheap stays in Winchester

The Putney Inn

Days Inn by Wyndham Keene NH

Gardner Inn

Comfort Inn & Suites Brattleboro I-91

Keene Elm City Hotel, an Ascend Collection Hotel

Latchis Hotel

Frequently asked questions

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