Best Winchester Hotels in 2026 from HK$718 - 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 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 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.

1. Best Western Plus Keene Hotel

Keene

Ruddy

HK$1,169

HK$1,268 total

includes taxes & fees

24 Sept - 25 Sept

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 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.

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

2. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

David

HK$1,098

HK$1,191 total

includes taxes & fees

24 Sept - 25 Sept

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

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

A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.

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

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Daniel

HK$1,530

HK$1,682 total

includes taxes & fees

27 Sept - 28 Sept

A two-story house with a red door, green shutters, and a snow-covered front yard.

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.

A sign for the Centennial House, indicating it is a bed and breakfast with a historical theme, established in 1811.

4. Centennial House

Northfield

Alan

HK$1,408

HK$1,488 total

includes taxes & fees

27 Sept - 28 Sept

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

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.

A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.

5. Hampton Inn Brattleboro

Brattleboro

Francesca

HK$1,072

HK$1,179 total

includes taxes & fees

29 Sept - 30 Sept

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.

6. Comfort Inn & Suites Brattleboro I-91

Brattleboro

John

HK$1,080

HK$1,188 total

includes taxes & fees

29 Sept - 30 Sept

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

sheri

HK$1,254

HK$1,361 total

includes taxes & fees

30 Sept - 1 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 room with a round table and two leather chairs, a window with curtains, and a view of a parking lot outside.

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

A grassy area with picnic tables and a clock tower.

8. Windmill Motel Restaurant

Bernardston

Dan

HK$1,006

HK$1,124 total

includes taxes & fees

4 Oct - 5 Oct

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

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."

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

9. The Inn At Crumpin Fox

Bernardston

Alan

HK$1,274

HK$1,423 total

includes taxes & fees

24 Sept - 25 Sept

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

Caroline

HK$1,706

HK$1,851 total

includes taxes & fees

30 Sept - 1 Oct

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

11. Vikings Villages Resort

Guilford

Cecil

HK$1,082

HK$1,262 total

includes taxes & fees

20 Oct - 21 Oct

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

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.

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.

12. The Carriage Barn Inn

Keene

Jonathan

HK$1,235

HK$1,340 total

includes taxes & fees

24 Sept - 25 Sept

A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

A two-story white house with a front porch and a garage, surrounded by lush greenery.

A grassy field with a playground and trees in the background.

A motel with a parking lot, a covered walkway, and a staircase leading to the entrance.

13. The Putney Inn

Putney

JANE

HK$854

HK$940 total

includes taxes & fees

24 Sept - 25 Sept

A hotel with a clock tower, a parking lot, and a well-maintained garden.

A cozy reading area with wooden chairs, a table with newspapers, and potted plants.

A building entrance with a white door, number 959, and a small porch area decorated with pumpkins, flowers, and scarecrows.

A swimming pool with lounge chairs and a covered umbrella.

14. Black Mountain Inn

Brattleboro

"Absolutely spotless room, the bedding was amazing, the beds were super comfortable. The people were the nicest people ever and we enjoyed them very much. We had a wonderful stay in Vermont. They advised us on where to dine, at the Marina and it was spot on amazing. We had breakfast at The Porch in the morning and the lovely girl even called to make sure they were open before we drove there. We had amazing food there as well."

Denise

HK$1,191

HK$1,311 total

includes taxes & fees

27 Sept - 28 Sept

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.

15. Days Inn by Wyndham Keene NH

Keene

Alex

HK$727

HK$788 total

includes taxes & fees

28 Sept - 29 Sept

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

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

16. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Jason

HK$1,260

HK$1,368 total

includes taxes & fees

29 Sept - 30 Sept

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

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.

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

17. The One Cat B&B

Brattleboro

marjie

HK$2,353

HK$2,588 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

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

18. The Covered Bridge Inn

Brattleboro

VINCENT JOEL

HK$949

HK$1,044 total

includes taxes & fees

25 Sept - 26 Sept

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.

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

19. Courtyard by Marriott Keene Downtown

Keene

Deborah

HK$1,706

HK$1,851 total

includes taxes & fees

30 Sept - 1 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 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.

20. Inn on Putney Road

Brattleboro

Karla

HK$2,848

HK$3,133 total

includes taxes & fees

24 Sept - 25 Sept

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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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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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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.

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

Hampton Inn & Suites Greenfield

10/10 Excellent

"Bed was very comfortable, shower clean and had good water pressure. Didn’t spend much time there. Checked in at 4:00am and they gave us late check out at noon."

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent

"Amazingly spacious room overlooking the river. The room was clean and the decor was wonderful. The bed was exceptionally comfortable. It was a lovely stay."

The Inn At Crumpin Fox

10/10 Excellent

"Amazing would stay again -"

Latchis Hotel

10/10 Excellent

"WE enjoyed the architecture of the whole complex - reception coffee lounge (Hot Drinks day and night as a compliment). Parking was right there. Center of town. The staff helped us when we needed to extend at the special rate. It attracts fun guests. It is a special place - not the run of the mill franchise. The linen is first class, nice thick towels. The room had a microwave and a refrig, plus the record player theme is another theme for folks who appreciate the vinyl era. Remember - Art Deco Era - not modern era."

Best Western Plus Keene Hotel

10/10 Excellent

"Great! Clean, comfortable, friendly staff!"

Windmill Motel Restaurant

10/10 Excellent

"I love the windmill. The gentleman is very polite and helpful. The room reminds me of being in the country farmhouse. So quiet and its close to 90 and 5 and 10."

The Putney Inn

8/10 Good

"The rooms are clean and the staff was helpful. The building and rooms were outdated but for the price it was a good stay. Not much at exit but available 20-30 minutes away."

Hampton Inn Brattleboro

10/10 Excellent

"The breakfast room was great"

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Though it's not a luxury hotel, the staff is exceptionally nice & helpful. the property is clean, there are carts for moving luggage, the breakfast service is fine. It's quiet. the bathroom is spacious w.nice towels & toiletries. Parking is easy."

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

HK$727

HK$788 total

28 Sept - 29 Sept

includes taxes & fees

Latchis Hotel

50 Main Street Brattleboro VT

HK$997

HK$1,097 total

28 Sept - 29 Sept

includes taxes & fees

8.6/10 Excellent! (989 reviews)

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

HK$1,072

HK$1,179 total

29 Sept - 30 Sept

includes taxes & fees

8.2/10 Very good! (1,000 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

HK$1,080

HK$1,188 total

29 Sept - 30 Sept

includes taxes & fees

8.6/10 Excellent! (867 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

HK$1,098

HK$1,191 total

24 Sept - 25 Sept

includes taxes & fees

Hampton Inn & Suites Greenfield

184 Shelburne Rd Greenfield MA

HK$1,488

HK$1,662 total

30 Sept - 1 Oct

includes taxes & fees

8.6/10 Excellent! (963 reviews)

Hotels in Winchester with star-rating

Frequently asked questions

What's the best place to stay in Winchester?

The Colonial Hotel, located 26.3 mi (42.3 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 Colonial Motel 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: Features 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$718

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. Best Western Plus Keene Hotel

2. Keene Elm City Hotel, an Ascend Collection Hotel

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

4. Centennial House

5. Hampton Inn Brattleboro

6. Comfort Inn & Suites Brattleboro I-91

7. Hampton Inn & Suites Keene

8. Windmill Motel Restaurant

9. The Inn At Crumpin Fox

10. Fairfield Inn & Suites by Marriott Keene Downtown

11. Vikings Villages Resort

12. The Carriage Barn Inn

13. The Putney Inn

14. Black Mountain Inn

15. Days Inn by Wyndham Keene NH

16. Riverside Hotel, an Ascend Collection Hotel

17. The One Cat B&B

18. The Covered Bridge Inn

19. Courtyard by Marriott Keene Downtown

20. Inn on Putney Road

Stay near popular Winchester attractions

Winchester Speedpark

New England Sweetwater Farm & Distillery

Cass Pond

Richmond Wildlife Manangement Area

Barden State Wildlife Management Area

Loring Field

Bennett Gorge

Conant Public Library

Learn more about Winchester

Top Winchester Hotel Reviews

Hampton Inn & Suites Greenfield

Riverside Hotel, an Ascend Collection Hotel

The Inn At Crumpin Fox

Latchis Hotel

Best Western Plus Keene Hotel

Windmill Motel Restaurant

The Putney Inn

Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

Latchis Hotel

Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn & Suites Greenfield

Hotels in Winchester with star-rating

Frequently asked questions

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