Top 10 Hotels in Winchester, NH from ₩124,061 - Competitive Prices

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 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.

A kitchenette with a refrigerator, a coffee station, and a fruit basket.

1. Centennial House

Northfield

Alan

₩240,548

₩254,259 total

includes taxes & fees

Oct 13 - Oct 14

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

₩171,888

₩191,999 total

includes taxes & fees

Oct 12 - Oct 13

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

₩186,296

₩204,926 total

includes taxes & fees

Nov 8 - Nov 9

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

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

A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

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

4. Best Western Plus Keene Hotel

Keene

Ruddy

₩189,714

₩205,840 total

includes taxes & fees

Nov 1 - Nov 2

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."

5. The Inn At Crumpin Fox

Bernardston

Heather

₩150,779

₩168,417 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

6. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

₩232,401

₩252,155 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

7. Hampton Inn & Suites Keene

Keene

Rebecca

₩197,085

₩213,837 total

includes taxes & fees

Nov 11 - Nov 12

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

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

8. Latchis Hotel

Brattleboro

Erik

₩189,982

₩208,981 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

A hotel room with a bed, a desk, a chair, a wooden door, and a window.

9. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Angelo

₩159,491

₩173,048 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

10. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

₩148,273

₩163,101 total

includes taxes & fees

Nov 8 - Nov 9

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

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.

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

11. Vikings Villages Resort

Guilford

Cecil

₩251,120

₩292,881 total

includes taxes & fees

Oct 12 - Oct 13

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

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.

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

12. Hampton Inn Brattleboro

Brattleboro

Francesca

₩152,656

₩167,921 total

includes taxes & fees

Nov 8 - Nov 9

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".

13. Courtyard by Marriott Keene Downtown

Keene

Deborah

₩253,376

₩274,913 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

14. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Jason

₩203,921

₩221,255 total

includes taxes & fees

Nov 9 - Nov 10

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

15. Days Inn by Wyndham Keene NH

Keene

CHERYL

₩124,175

₩134,730 total

includes taxes & fees

Oct 25 - Oct 26

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

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

16. Inn on Putney Road

Brattleboro

Karla

₩357,742

₩393,514 total

includes taxes & fees

Nov 1 - Nov 2

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

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

17. The Carriage Barn Inn

Keene

Richard

₩226,214

₩245,443 total

includes taxes & fees

Oct 12 - Oct 13

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.

18. Chesterfield Inn

West Chesterfield

Wayne

₩403,606

₩437,917 total

includes taxes & fees

Oct 18 - Oct 19

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

19. Econo Lodge Brattleboro South

Brattleboro

David

₩133,289

₩146,618 total

includes taxes & fees

Nov 9 - Nov 10

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

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

20. The Covered Bridge Inn

Brattleboro

Adolfo

₩140,727

₩154,800 total

includes taxes & fees

Oct 12 - Oct 13

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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 whiskeys 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 license 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 artifacts 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 downtown 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

Best Western Plus Keene Hotel

10/10 Excellent

"Very clean, breakfast was very good. And the restaurant attached to the hotel was amazing"

Latchis Hotel

10/10 Excellent

"For being a historic hotel this place was nice. Sound machines in the rooms to make up for being on a busy street. Fan in the room to help with circulation. Historic charm in great walkable downtown location. Parking lot was small but there is additional parking in a city lot and on the street."

Hampton Inn Brattleboro

8/10 Good

"Nice property. Room was nice and clean and Robert at the front desk was great."

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."

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."

More cheap stays in Winchester

The Putney Inn

57 Putney Landing Rd Putney VT

₩112,783

₩124,061 total

Oct 25 - Oct 26

includes taxes & fees

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

₩124,175

₩134,730 total

Oct 25 - Oct 26

includes taxes & fees

7/10 Good! (1,002 reviews)

Gardner Inn

22 Pearson Blvd Gardner MA

₩132,686

₩148,211 total

Oct 18 - Oct 19

includes taxes & fees

7.8/10 Good! (77 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

₩148,273

₩163,101 total

Nov 8 - Nov 9

includes taxes & fees

8.6/10 Excellent! (881 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

₩159,491

₩173,048 total

Nov 2 - Nov 3

includes taxes & fees

Latchis Hotel

50 Main Street Brattleboro VT

₩189,982

₩208,981 total

Nov 1 - Nov 2

includes taxes & fees

8.6/10 Excellent! (1,010 reviews)

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 traveler data. Other good options for your stay in 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, most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.

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 two additional hotels with an onsite pool. View all hotels with pools in Winchester.

What is the best hotel near Hartness State Airport (VSF)?

The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.

What is staying in Winchester like?

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

What should I do while I'm visiting Winchester?

Natural beauty is on display at Birch Point, Cass Pond, and Royalston State Forest. A couple of additional sights to add to your agenda are Winchester Speedpark and New England Sweetwater Farm & Distillery. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.

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Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, NH from ₩124,061

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. The Inn At Crumpin Fox

6. Fairfield Inn & Suites by Marriott Keene Downtown

7. Hampton Inn & Suites Keene

8. Latchis Hotel

9. Keene Elm City Hotel, an Ascend Collection Hotel

10. Comfort Inn & Suites Brattleboro I-91

11. Vikings Villages Resort

12. Hampton Inn Brattleboro

13. Courtyard by Marriott Keene Downtown

14. Riverside Hotel, an Ascend Collection Hotel

15. Days Inn by Wyndham Keene NH

16. Inn on Putney Road

17. The Carriage Barn Inn

18. Chesterfield Inn

19. Econo Lodge Brattleboro South

20. The Covered Bridge Inn

Stay near popular Winchester attractions

Winchester Speedpark

New England Sweetwater Farm & Distillery

Cass Pond

Richmond Wildlife Manangement Area

Attleboro Mountain

Loring Field

Bennett Gorge

Conant Public Library

Learn more about Winchester

Top Winchester Hotel Reviews

Best Western Plus Keene Hotel

Latchis Hotel

Hampton Inn Brattleboro

Gardner Inn

The Colonial Hotel

Otherland Hotel

Colonial Motel

The Inn At Crumpin Fox

Hampton Inn & Suites Greenfield

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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