Photo by Donny Campos

Winchester Hotels

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Nov 2 - Nov 3
Tomorrow
Nov 3 - Nov 4
Next weekend
Nov 7 - Nov 9
In two weeks
Nov 14 - Nov 16

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Top 10 trending Winchester hotels

Interior
The Colonial Hotel
The Colonial Hotel
3.0 star property
8.8 out of 10, Excellent, (1013)
"The staff at front desk were very hospitable "
United States
James
The Colonial Hotel
Front of property
The Inn At Crumpin Fox
The Inn At Crumpin Fox
2.5 star property
9.2 out of 10, Wonderful, (335)
"Stayed twice with you now great staff nice rooms convenient location. They were good to be with. "
United States
Sergio
The price is P7,666
P8,564 total
includes taxes & fees
Nov 3 - Nov 4
The Inn At Crumpin Fox
Exterior detail
The Covered Bridge Inn
The Covered Bridge Inn
2.5 star property
7.6 out of 10, Good, (1003)
"Good value for a two night stay for work "
United States
jim
The price is P5,640
P6,204 total
includes taxes & fees
Nov 15 - Nov 16
The Covered Bridge Inn
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3.0 star property
8.4 out of 10, Very Good, (1004)
"Hotel was great."
United States
Heidi
The price is P8,753
P9,498 total
includes taxes & fees
Nov 3 - Nov 4
Best Western Plus Keene Hotel
Free daily on-the-go breakfast
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
8.8 out of 10, Excellent, (1006)
"The nicest Holiday Inn Express I have ever stayed at. Lovely place and super clean."
United States
WOODROW
The price is P8,342
P9,176 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Reception
Travelodge by Wyndham Brattleboro VT
Travelodge by Wyndham Brattleboro VT
2.5 star property
6.0 out of 10, (729)
"For the money during peep season it was ok. Otherwise it’s a low quality stay"
United States
Thomas
The price is P4,177
P4,595 total
includes taxes & fees
Nov 4 - Nov 5
Travelodge by Wyndham Brattleboro VT
Front of property
Black Mountain Inn
Black Mountain Inn
2.0 star property
7.4 out of 10, Good, (474)
"Very friendly and helpful staff, clean and quiet room. No restaurant but staff gave an excellent recommendation just down the road."
United States
Paul
The price is P6,609
P7,270 total
includes taxes & fees
Nov 4 - Nov 5
Black Mountain Inn
Free WiFi
Gardner Inn
Gardner Inn
2.0 star property
5.4 out of 10, (12)
"Clean room "
United States
Luis
The price is P5,816
P6,496 total
includes taxes & fees
Nov 3 - Nov 4
Gardner Inn
Sundeck
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel
2.5 star property
9.6 out of 10, Exceptional, (621)
"Loved my stay"
United States
Christine
The price is P8,938
P9,698 total
includes taxes & fees
Nov 4 - Nov 5
Riverside Hotel, an Ascend Collection Hotel
In-room safe, desk, blackout drapes, iron/ironing board
Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NH
2.0 star property
7.0 out of 10, Good, (1003)
"Great stay"
United States
Michael
The price is P5,942
P6,447 total
includes taxes & fees
Nov 4 - Nov 5
Days Inn by Wyndham Keene NH
Lobby
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 star property
8.6 out of 10, Excellent, (721)
"Check in was easy and there is coffee available 24 hours a day!"
United States
Michelle
The price is P6,292
P6,921 total
includes taxes & fees
Nov 4 - Nov 5
Comfort Inn & Suites Brattleboro I-91
Hiking
Latchis Hotel
Latchis Hotel
2.5 star property
8.4 out of 10, Very Good, (813)
"Is a great historic building with great charm. Hope to stay there again soon."
United States
Roger
The price is P6,873
P7,561 total
includes taxes & fees
Nov 3 - Nov 4
Latchis Hotel
Exterior
Colonial Motel And Spa
Colonial Motel And Spa
3.0 star property
6.8 out of 10, (1003)
"Location and parking are perfect for us. Also the price for the size of the room that we get is definitely fair. We stay here every time I come visit my family."
United States
Kimberly
The price is P8,225
P9,047 total
includes taxes & fees
Nov 3 - Nov 4
Colonial Motel And Spa
Breakfast area
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
9.4 out of 10, Exceptional, (431)
"Great price, close to town and really nice staff"
United States
Nancy
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown
Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
8.8 out of 10, Excellent, (747)
"Perfect downtown location, most comfortable bed and nice to have complimentary breakfast and coffee!"
United States
Kristin
The price is P10,809
P11,728 total
includes taxes & fees
Nov 30 - Dec 1
Fairfield Inn & Suites by Marriott Keene Downtown
Free breakfast
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 star property
8.2 out of 10, Very Good, (912)
"Breakfast area was the best I've seen in a while!"
United States
Michael
The price is P5,923
P6,516 total
includes taxes & fees
Nov 12 - Nov 13
Hampton Inn Brattleboro
Down comforters, desk, blackout drapes, soundproofing
Hampton Inn & Suites Greenfield
Hampton Inn & Suites Greenfield
2.5 star property
8.6 out of 10, Excellent, (871)
"Great place with a walkable eating option"
United States
James
The price is P7,659
P8,556 total
includes taxes & fees
Nov 12 - Nov 13
Hampton Inn & Suites Greenfield
Reception
Hampton Inn & Suites Keene
Hampton Inn & Suites Keene
2.5 star property
8.8 out of 10, Excellent, (343)
"Great hotel with friendly staff"
United States
Robert
The price is P9,729
P10,555 total
includes taxes & fees
Nov 16 - Nov 17
Hampton Inn & Suites Keene
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
8.4 out of 10, Very Good, (940)
"Clean room, good breakfast…..best price relative to other hotels "
United States
Susan
The price is P7,349
P7,974 total
includes taxes & fees
Nov 9 - Nov 10
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior
The Putney Inn
The Putney Inn
2.5 star property
8.4 out of 10, Very Good, (1001)
"Reasonable price for an overnight stay. Ample parking, very quiet and easy access to I 91."
United States
MICHAEL
The Putney Inn
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 downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester
The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.
Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Best value in New England! Staff is supportive and site is super clean. Decor is nice. Comfy beds. Subpar breakfast but who cares?! Free coffee, and the food is a bonus... and again, you can't beat the value!"
Travis 1-night trip
Posted 5 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

More cheap stays in Winchester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT
The price is P5,640 per night from Nov 15 to Nov 16
P5,640
P6,204 total
Nov 15 - Nov 16
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 traveler data. Other good options for your stay in the area are Econo Lodge Brattleboro and Keene Elm City Hotel, an Ascend Collection 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.
What are some hotels with pools in Winchester?
The Colonial Hotel: Features a sauna, an indoor pool, and free self parking. Econo Lodge Brattleboro and Keene Elm City Hotel, an Ascend Collection Hotel are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
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 Rhododendron State Park, Ashuelot River, and Cass Pond. A couple of additional sights to add to your agenda are Pisgah State Park 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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