Photo by Donny Campos

Winchester Hotels

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Top 10 trending Winchester hotels

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1000)
"Great for stay"
The price is €147
includes taxes & fees
15 Sept - 16 Sept
Best Western Plus Keene Hotel

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (845)
"The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. "
The price is €158
includes taxes & fees
14 Sept - 15 Sept
Hampton Inn & Suites Greenfield

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (876)
"Super easy check in and nice room! "
The price is €119
includes taxes & fees
14 Sept - 15 Sept
Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (683)
"Really good staff! "
The price is €147
includes taxes & fees
4 Sept - 5 Sept
Comfort Inn & Suites Brattleboro I-91

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (461)
"Friendly staff. Room was nice "
The price is €119
includes taxes & fees
5 Sept - 6 Sept
Black Mountain Inn

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1001)
"Very enjoyable stay"
The Putney Inn

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (318)
"We stayed one night. We were able to get checked early, enjoyed breakfast, quiet and charming atmosphere. Owners are very friendly. "
The price is €148
includes taxes & fees
4 Sept - 5 Sept
Colonel Williams Inn

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
8.4 out of 10, Very good, (891)
"Clean room - friendly staff - convenient location "
The price is €116
includes taxes & fees
14 Sept - 15 Sept
Keene Elm City Hotel, an Ascend Collection Hotel

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is €132
includes taxes & fees
8 Sept - 9 Sept
Blooming Inn

Vikings Villages Resort

2.0 star property
10.0 out of 10, Exceptional, (125)
"Such a unique stay on our road trip up North. The owner was so lovely and approachable. We will definitely stay again. "
The price is €184
includes taxes & fees
9 Sept - 10 Sept
Vikings Villages Resort

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1000)
"Lovely night. Room and bath was clean. "
The price is €88
includes taxes & fees
7 Sept - 8 Sept
The Covered Bridge Inn

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1008)
"Would stay again"
The price is €107
includes taxes & fees
7 Sept - 8 Sept
Days Inn by Wyndham Keene NH

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (700)
"I was only there for a few hours sleep "
The price is €67
includes taxes & fees
14 Sept - 15 Sept
Travelodge by Wyndham Brattleboro VT

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (154)
"Excellent phenomenal cleanliness and so polite"
The price is €164
includes taxes & fees
4 Sept - 5 Sept
The Carriage Barn Inn

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (269)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
Monadnock Inn

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (330)
"Great hotel with friendly staff"
The price is €171
includes taxes & fees
14 Sept - 15 Sept
Hampton Inn & Suites Keene

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (420)
"Highly recommend PEARL restaurant nearby! Always comfortable accommodations. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (141)
"Beautiful room, beautiful house, fun area!"
The Burrell House

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1000)
"Good room, great breakfast options "
The price is €159
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (783)
"Great stay!"
The price is €110
includes taxes & fees
4 Sept - 5 Sept
Latchis Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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 city centre district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

More cheap stays in Winchester

More cheap stays in Winchester

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Keene Elm City Hotel, Ascend Hotel Collection and Colonial Motel And Spa. See all available top hotels, or vacation rentals in Winchester.

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

Lovely 2nd Floor Apartment: This holiday home rental outside of Winchester offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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, Ascend Hotel Collection 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 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 Richmond Wildlife Manangement Area, Rhododendron State Park and Ashuelot River. A couple of additional sights to add to your itinerary are Pisgah State Park 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.