𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester (2026)

Our top choices for Winchester hotels

Deerfield Inn

Deerfield

includes taxes & fees

28 May - 29 May

Hampton Inn Brattleboro

Brattleboro

Savanna

includes taxes & fees

21 Jun - 22 Jun

The Burrell House

Keene

Charles

includes taxes & fees

2 Jun - 3 Jun

The Carriage Barn Inn

Keene

Valerie

includes taxes & fees

7 Jun - 8 Jun

Vikings Villages Resort

Guilford

Jan

includes taxes & fees

1 Jun - 2 Jun

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Windmill Motel Restaurant

Bernardston

Amy

includes taxes & fees

9 Jun - 10 Jun

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Sarah

includes taxes & fees

2 Jun - 3 Jun

The Putney Inn

Putney

Lori

includes taxes & fees

31 May - 1 Jun

Colonel Williams Inn

Brattleboro

Billie

includes taxes & fees

1 Jun - 2 Jun

The Colonial Hotel

Gardner

Adnan

includes taxes & fees

1 Jun - 2 Jun

The Inn At Crumpin Fox

Bernardston

Kevin

includes taxes & fees

31 May - 1 Jun

Four Columns Inn

Newfane

Mark

includes taxes & fees

31 May - 1 Jun

Comfort Inn & Suites Brattleboro I-91

Brattleboro

Desiree

includes taxes & fees

7 Jun - 8 Jun

Blooming Inn

Shelburne Falls

Sarah

includes taxes & fees

10 Jun - 11 Jun

In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Keene NH

Keene

Michael

includes taxes & fees

10 Jun - 11 Jun

Latchis Hotel

Brattleboro

Sharon

includes taxes & fees

2 Jun - 3 Jun

Best Western Plus Keene Hotel

Keene

Jennifer

includes taxes & fees

9 Jun - 10 Jun

Hampton Inn & Suites Greenfield

Greenfield

Jennifer

includes taxes & fees

14 Jun - 15 Jun

The Inn At Quail Run

Wilmington

Tami

includes taxes & fees

29 May - 30 May

Hampton Inn & Suites Keene

Keene

Kerry

includes taxes & fees

11 Jun - 12 Jun

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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

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

Top Winchester Hotel Reviews

Days Inn by Wyndham Keene NH

2/10 Terrible

"Worst hotel I’ve ever stayed at never staying there again dirty smelly and gross"

Hampton Inn Brattleboro

8/10 Good

"This is the best option in the area and we are big fans of the Hilton family of hotels (we stay there exclusively when this is an option). Everything was as expected for a Hampton Inn, including the workout room, layout of the room, and amenities. Five stars for pillows, hot water, and lack of noise. It was really hard getting an early check in, much harder than one would expect given the occupancy. We did end up getting it in plenty of time, which we appreciated. (It seemed like there were challenges with staffing.) We enjoyed our stay and would stay there again."

Hampton Inn & Suites Keene

2/10 Terrible

"I am disgusted by the behavior of the general manager who hung up the phone on me. I paid for my room in FULL for 2 nights but when I arrived the next day (flight was delayed) I was told I couldn’t check in because they had cancelled my room (kept my money) and sold my room to another guest So that means they got to benefit TWICE from one room Cancelled my room and left me stranded with nowhere to stay And when asked for my money back on the phone with manager, she hung up the phone on me I will never book this hotel again"

The Covered Bridge Inn

4/10 Poor

"I don’t know where to begin. The place smelled like cigarette smoke. When I tried to check in I had to ring a bell and was to come back as the front desk staff seemed to all go out to lunch. After finally checking in, the tv didn’t work, the iron is broken and spilled water everywhere when I tried to iron my clothes. The bathroom showers had mold everywhere and I was genuinely afraid to step on the carpet, barefooted or touch anything in the room. I had to put my own bedsheets and pillowcases on the bed and pillows in order to sleep the other night. At night, there’s a door right outside my window that bangs every 45 minutes due to people going in and out to smoke. I was up all night. There were questionable people outside at all times, outside of the place was super dirty and trashy. Had i known this place was like that I wouldn’t have stayed. Needless to say I will not be returning turning and in fact if I could ask for my money back, I would."

Best Western Plus Keene Hotel

2/10 Terrible

"This place is a dump Pretty much a motel Looks and smells dirty The curtains in bathroom are filthy The tub is disgusting and black No pride in the upkeep of this property Dirty walls and carpets Exposed outlets Didn’t even clean our room I only stayed here because Hampton inn was sold out NEVERRR AGAIN I even left a day early because I refused to raid a shower there"

More cheap stays in Winchester

The Covered Bridge Inn

1043 Putney Road Brattleboro VT

S$119

10 Jun - 11 Jun

includes taxes & fees

7.6/10 Good! (1,000 reviews)

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 Hampton Inn Brattleboro 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: Features a sauna, an indoor pool and free self parking. Hampton Inn Brattleboro and Colonial Motel And Spa 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 7 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 Rhododendron State Park, Cass Pond and Royalston State Forest. A couple of additional sights to add to your itinerary are Winchester Speedpark and Pisgah State Park. 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 S$119

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Our top choices for Winchester hotels

Deerfield Inn

Hampton Inn Brattleboro

The Burrell House

The Carriage Barn Inn

Vikings Villages Resort

Windmill Motel Restaurant

Keene Elm City Hotel, an Ascend Collection Hotel

The Putney Inn

Colonel Williams Inn

The Colonial Hotel

The Inn At Crumpin Fox

Four Columns Inn

Comfort Inn & Suites Brattleboro I-91

Blooming Inn

Days Inn by Wyndham Keene NH

Latchis Hotel

Best Western Plus Keene Hotel

Hampton Inn & Suites Greenfield

The Inn At Quail Run

Hampton Inn & Suites Keene

Stay near popular Winchester attractions

Winchester Speedpark

Learn more about Winchester

Top Winchester Hotel Reviews

Days Inn by Wyndham Keene NH

More cheap stays in Winchester

The Covered Bridge Inn

Frequently asked questions

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