Photo by Donny Campos

Winchester Hotels

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Top 10 trending Winchester hotels

Our top choices for Winchester hotels

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 €147
includes taxes & fees
23 Sept - 24 Sept
Colonel Williams Inn

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (164)
"The property was wonderful and the hosts exceptional❤️"
The price is €181
includes taxes & fees
30 Sept - 1 Oct
Centennial House

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (54)
"Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries."
The price is €340
includes taxes & fees
23 Sept - 24 Sept
Inn on Putney Road

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
The price is €277
includes taxes & fees
16 Oct - 17 Oct
The Maguire House Bed & Breakfast

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (144)
"Beautiful room, beautiful house, fun area!"
The Burrell House

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (156)
"Very quiet and peaceful but at the same time it's right down the street from Main Street. Joe the owner was so nice! "
The price is €164
includes taxes & fees
23 Sept - 24 Sept
The Carriage Barn Inn

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is €127
includes taxes & fees
29 Sept - 30 Sept
Blooming Inn

The Engel House

3.0 star property
9.4 out of 10, Exceptional, (13)
"The perfect Vermont Bed and Breakfast. "
The Engel House

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
9.6 out of 10, Exceptional, (600)
"Great place!"
The price is €148
includes taxes & fees
25 Sept - 26 Sept
Riverside Hotel, an Ascend Collection Hotel

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (423)
"Great price, close to town and really nice staff"
Riverhouse by Weekender (Formerly Jack Daniels Inn)

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1010)
"Very convenient and clean hotel with well appointed rooms, easy and plentiful parking. "
The Colonial Hotel

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1003)
" see above truly the nicest hotel in keene!"
The price is €175
includes taxes & fees
28 Sept - 29 Sept
Courtyard by Marriott Keene Downtown

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (333)
"Great hotel with friendly staff"
The price is €137
includes taxes & fees
19 Oct - 20 Oct
Hampton Inn & Suites Keene

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1010)
"It was nice place at price point for a quick stay"
The price is €128
includes taxes & fees
23 Sept - 24 Sept
Best Western Plus Keene Hotel

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (739)
"We stayed in the loft room and it was great! Right downtown, free parking right out the back and the staff is super nice. I would definitely go back!"
The price is €148
includes taxes & fees
19 Oct - 20 Oct
Fairfield Inn & Suites by Marriott Keene Downtown

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
8.4 out of 10, Very good, (900)
"the breakfast was good… rooms clean "
The price is €107
includes taxes & fees
28 Sept - 29 Sept
Keene Elm City Hotel, an Ascend Collection Hotel

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (691)
"This was a nice stay, thanks"
The price is €137
includes taxes & fees
29 Sept - 30 Sept
Comfort Inn & Suites Brattleboro I-91

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1008)
"Very enjoyable stay"
The Putney Inn

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1003)
"Good room, great breakfast options "
The price is €158
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (323)
"It was a peaceful, clean, quiet stay. "
The price is €166
includes taxes & fees
23 Sept - 24 Sept
The Inn At Crumpin Fox
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

Get away to relaxing Winchester! Enjoy the lake views, forests and more.

Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

More cheap stays in Winchester

More cheap stays in Winchester

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 Keene Elm City Hotel, an Ascend Collection Hotel. 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. Hampton Inn Brattleboro and Keene Elm City Hotel, an Ascend Collection 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 Rhododendron State Park, Ashuelot River and Cass Pond. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery 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.

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