Best Winchester Hotels in 2026 from HK$726 - 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 golf course with a brick pathway, wooden boxes, and a tee box.

A dining area with round tables, chairs, and a kitchen counter with a refrigerator.

1. Centennial House

Northfield

Alan

HK$1,409

HK$1,489 total

includes taxes & fees

27 Oct - 28 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 spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

2. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

HK$1,162

HK$1,278 total

includes taxes & fees

8 Nov - 9 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 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.

3. Best Western Plus Keene Hotel

Keene

Ruddy

HK$1,111

HK$1,205 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 reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.

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

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

4. Hampton Inn & Suites Keene

Keene

Neil

HK$1,271

HK$1,379 total

includes taxes & fees

19 Nov - 20 Nov

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

A grassy area with picnic tables and a clock tower.

5. Windmill Motel Restaurant

Bernardston

Donna

HK$1,006

HK$1,124 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Lisa

HK$997

HK$1,081 total

includes taxes & fees

25 Oct - 26 Oct

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.

7. Latchis Hotel

Brattleboro

Erik

HK$1,112

HK$1,224 total

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

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

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

8. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

HK$878

HK$966 total

includes taxes & fees

15 Nov - 16 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.

9. The Inn At Crumpin Fox

Bernardston

Heather

HK$883

HK$986 total

includes taxes & fees

1 Nov - 2 Nov

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

10. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Christopher

HK$1,521

HK$1,650 total

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

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

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

11. Hampton Inn Brattleboro

Brattleboro

Faith

HK$867

HK$954 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 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 living room with a sofa, armchair, and round table, a bedroom with a bed and nightstands, and large windows with curtains.

12. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Thomas

HK$1,194

HK$1,296 total

includes taxes & fees

19 Nov - 20 Nov

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

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.

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

13. Days Inn by Wyndham Keene NH

Keene

CHERYL

HK$727

HK$789 total

includes taxes & fees

25 Oct - 26 Oct

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.

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.

14. Courtyard by Marriott Keene Downtown

Keene

Deborah

HK$1,484

HK$1,610 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

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

15. Chesterfield Inn

West Chesterfield

Wayne

HK$2,363

HK$2,564 total

includes taxes & fees

22 Oct - 23 Oct

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

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 bench in front of an apple tree with ripe apples.

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

16. The Carriage Barn Inn

Keene

Richard

HK$1,261

HK$1,369 total

includes taxes & fees

19 Nov - 20 Nov

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

17. Vikings Villages Resort

Guilford

Cecil

HK$1,470

HK$1,715 total

includes taxes & fees

22 Oct - 23 Oct

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

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

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

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

18. Inn on Putney Road

Brattleboro

Karla

HK$2,095

HK$2,304 total

includes taxes & fees

3 Nov - 4 Nov

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

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

19. Econo Lodge Brattleboro South

Brattleboro

Luis

HK$781

HK$859 total

includes taxes & fees

19 Nov - 20 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 multi-story motel with a parking lot, several vehicles parked, and a tree in the foreground.

20. The Covered Bridge Inn

Brattleboro

Adolfo

HK$824

HK$906 total

includes taxes & fees

22 Oct - 23 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.

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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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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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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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

Days Inn by Wyndham Keene NH

8/10 Good

"Clean comfortable room with a comfortable bed. I didn’t like the smell of whatever cleaning product they used, it was a bit bit strong let the kind you used to cover up something. Was this recently a smoking hotel? Also I missed an cycle in the fitness center, although the machines that were there seemed to work well. All in all it’s about what you would expect for a moderately priced hotel in New Hampshire during leaf peeper season."

Hampton Inn Brattleboro

10/10 Excellent

"The hotel was fairly new. Coffee was the only thing I felt needed changed."

Colonial Motel

8/10 Good

"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."

Best Western Plus Keene Hotel

10/10 Excellent

"Excellent place to stay"

The Inn At Crumpin Fox

10/10 Excellent

"This hotel is amazing. A relief to tired travelers. Clean, quiet, and friendly. And a good associated restaurant near by at the golf course. Very happy with our stay."

The Putney Inn

10/10 Excellent

"Our room was quiet, clean and very comfortable. Breakfast was nice--more than enough for a decent breakfast before heading out-- waffle maker, toast, yogurt, cold cereal, fruit, juice coffee, and tea, etc. The grounds were beautiful and well kept. The staff was very helpful and parking was super easy right next to the room. The only slight downside was a strong musty odor in the entryway of the room (106), but the room itself smelled clean and was just fine."

Riverside Hotel, an Ascend Collection Hotel

8/10 Good

"Great location for access to southern VT and southwest NH, clean rooms, great views of river, and easy access from highway. No breakfast, but coffee bar provided. Free parking. Walls are a little thin."

The Colonial Hotel

10/10 Excellent

"We love this hotel! We stay every year when we go to Wachusett Mountain"

Comfort Inn & Suites Brattleboro I-91

8/10 Good

"Was a good room for a one night stay on a road trip."

More cheap stays in Winchester

The Putney Inn

57 Putney Landing Rd Putney VT

HK$660

HK$726 total

25 Oct - 26 Oct

includes taxes & fees

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

HK$727

HK$789 total

25 Oct - 26 Oct

includes taxes & fees

7/10 Good! (1,003 reviews)

Gardner Inn

22 Pearson Blvd Gardner MA

HK$833

HK$931 total

1 Nov - 2 Nov

includes taxes & fees

7.8/10 Good! (81 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

HK$878

HK$966 total

15 Nov - 16 Nov

includes taxes & fees

8.6/10 Excellent! (889 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

HK$997

HK$1,081 total

25 Oct - 26 Oct

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

HK$1,112

HK$1,224 total

2 Nov - 3 Nov

includes taxes & fees

Hotels in Winchester with star-rating

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.

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

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Winchester is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. 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: 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 HK$726

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. Holiday Inn Express Hotel & Suites Brattleboro by IHG

3. Best Western Plus Keene Hotel

4. Hampton Inn & Suites Keene

5. Windmill Motel Restaurant

6. Keene Elm City Hotel, an Ascend Collection Hotel

7. Latchis Hotel

8. Comfort Inn & Suites Brattleboro I-91

9. The Inn At Crumpin Fox

10. Fairfield Inn & Suites by Marriott Keene Downtown

11. Hampton Inn Brattleboro

12. Riverside Hotel, an Ascend Collection Hotel

13. Days Inn by Wyndham Keene NH

14. Courtyard by Marriott Keene Downtown

15. Chesterfield Inn

16. The Carriage Barn Inn

17. Vikings Villages Resort

18. Inn on Putney Road

19. Econo Lodge Brattleboro South

20. The Covered Bridge Inn

Stay near popular Winchester attractions

Winchester Speedpark

Cass Pond

Richmond Wildlife Manangement Area

New England Sweetwater Farm & Distillery

Barden State Wildlife Management Area

Attleboro Mountain

Loring Field

Bennett Gorge

Learn more about Winchester

Top Winchester Hotel Reviews

Days Inn by Wyndham Keene NH

Hampton Inn Brattleboro

Colonial Motel

Best Western Plus Keene Hotel

The Inn At Crumpin Fox

The Putney Inn

Riverside Hotel, an Ascend Collection Hotel

The Colonial Hotel

Comfort Inn & Suites Brattleboro I-91

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

Hotels in Winchester with star-rating

Frequently asked questions

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