Top 10 Hotels in Winchester, NH from ₩123,549 - 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 kitchenette with a refrigerator, a coffee station, and a fruit basket.

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

₩239,567

₩253,222 total

includes taxes & fees

Oct 27 - Oct 28

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 grassy area with picnic tables and a clock tower.

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.

2. Windmill Motel Restaurant

Bernardston

Donna

₩171,188

₩191,216 total

includes taxes & fees

Oct 20 - Oct 21

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

₩197,550

₩217,305 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 gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

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

A conference table set for a meeting with chairs and folded red napkins.

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

5. The Inn At Crumpin Fox

Bernardston

Heather

₩150,165

₩167,731 total

includes taxes & fees

Nov 1 - Nov 2

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 fireplace, seating, and a TV.

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

₩258,684

₩280,672 total

includes taxes & fees

Oct 26 - Oct 27

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.

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

7. Hampton Inn & Suites Keene

Keene

Rebecca

₩207,338

₩224,962 total

includes taxes & fees

Oct 25 - Oct 26

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

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

8. Latchis Hotel

Brattleboro

Erik

₩189,208

₩208,130 total

includes taxes & fees

Nov 11 - Nov 12

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.

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

Mary

₩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.

A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.

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.

10. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

₩148,273

₩163,101 total

includes taxes & fees

Nov 8 - Nov 9

A conference room with a long table, chairs, a projector, and a whiteboard.

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.

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

11. Hampton Inn Brattleboro

Brattleboro

Faith

₩154,934

₩170,429 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

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

12. Vikings Villages Resort

Guilford

Cecil

₩250,096

₩291,688 total

includes taxes & fees

Oct 19 - Oct 20

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 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.

13. Courtyard by Marriott Keene Downtown

Keene

Deborah

₩252,344

₩273,793 total

includes taxes & fees

Oct 26 - Oct 27

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 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

₩203,090

₩220,352 total

includes taxes & fees

Nov 11 - Nov 12

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

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

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

₩123,669

₩134,181 total

includes taxes & fees

Oct 26 - Oct 27

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 cozy living room with a piano, leather sofa, armchair, and a globe on a coffee table.

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

16. Inn on Putney Road

Brattleboro

Karla

₩356,285

₩391,911 total

includes taxes & fees

Nov 1 - Nov 2

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 bench in front of an apple tree with ripe apples.

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

17. The Carriage Barn Inn

Keene

Richard

₩225,292

₩244,442 total

includes taxes & fees

Oct 14 - Oct 15

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

An outdoor dining area with tables and chairs, umbrellas, and a view of a forested landscape.

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

₩401,962

₩436,133 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 sunroom with large windows, a dining area with a table and chairs, and a sofa.

19. Econo Lodge Brattleboro South

Brattleboro

David

₩133,289

₩146,618 total

includes taxes & fees

Nov 11 - Nov 12

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 garden with a sign reading "The One Cat" and various plants and flowers.

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

20. The One Cat B&B

Brattleboro

marjie

₩400,440

₩440,484 total

includes taxes & fees

Oct 18 - Oct 19

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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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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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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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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.

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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

Hampton Inn Brattleboro

8/10 Good

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

Days Inn by Wyndham Keene NH

10/10 Excellent

"I got a quiet room to stay. That was great. Staff was very nice and helpful. Cleaners came every day to clean room"

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"This is a great place to stay in Keene! The location is perfect, the room was immaculate, and the breakfast was great!"

Vikings Villages Resort

10/10 Excellent

"Enjoyed the ambiance and tranquility of the property."

Hampton Inn & Suites Greenfield

10/10 Excellent

"This was the perfect location and having modern amenities and snacks and breakfast was lovely."

Best Western Plus Keene Hotel

8/10 Good

"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."

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"

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."

More cheap stays in Winchester

The Putney Inn

57 Putney Landing Rd Putney VT

₩112,323

₩123,549 total

Oct 26 - Oct 27

includes taxes & fees

8.4/10 Very Good! (1,009 reviews)

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

₩123,669

₩134,181 total

Oct 26 - Oct 27

includes taxes & fees

7/10 Good! (1,004 reviews)

Gardner Inn

22 Pearson Blvd Gardner MA

₩132,145

₩147,606 total

Nov 1 - Nov 2

includes taxes & fees

7.6/10 Good! (78 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

8.6/10 Excellent! (1,006 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

₩189,208

₩208,130 total

Nov 11 - Nov 12

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 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 ₩123,549

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. Hampton Inn Brattleboro

12. Vikings Villages Resort

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 One Cat B&B

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

Hampton Inn Brattleboro

Days Inn by Wyndham Keene NH

Keene Elm City Hotel, an Ascend Collection Hotel

Vikings Villages Resort

Hampton Inn & Suites Greenfield

Best Western Plus Keene Hotel

Gardner Inn

Otherland Hotel

Colonial Motel

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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