Photo by Donny Campos

Winchester Hotels

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6 Nov - 7 Nov
Tomorrow
7 Nov - 8 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

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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, (1001)
"Excellent customer service, friendly and genuine! The property is beautiful!, luxurious and cost effective. Highly recommend!"
United States
Kathryn
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, (337)
"Stayed twice with you now great staff nice rooms convenient location. They were good to be with. "
United States
Sergio
The price is €127
includes taxes & fees
9 Nov - 10 Nov
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, (1002)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is €98
includes taxes & fees
9 Nov - 10 Nov
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, (1000)
"Hotel was great."
United States
Heidi
The price is €141
includes taxes & fees
9 Nov - 10 Nov
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, (1007)
"Beth at the front desk is the best"
United States
Sean
The price is €136
includes taxes & fees
22 Nov - 23 Nov
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, (730)
"For the money during peep season it was ok. Otherwise it’s a low quality stay"
United States
Thomas
The price is €68
includes taxes & fees
9 Nov - 10 Nov
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 €92
includes taxes & fees
1 Dec - 2 Dec
Black Mountain Inn
Single Room
Gardner Inn
Gardner Inn
2.0 star property
5.4 out of 10, (12)
"Clean room "
United States
Luis
The price is €96
includes taxes & fees
9 Nov - 10 Nov
Gardner Inn
Sun deck
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 €144
includes taxes & fees
7 Dec - 8 Dec
Riverside Hotel, an Ascend Collection Hotel
In-room safe, desk, blackout curtains, 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, (1000)
"Very professional people good service good staff "
United States
George
The price is €95
includes taxes & fees
9 Nov - 10 Nov
Days Inn by Wyndham Keene NH
Hiking
Latchis Hotel
Latchis Hotel
2.5 star property
8.4 out of 10, Very good, (816)
"Well preserved old hotel one block from train station. "
United States
John
The price is €121
includes taxes & fees
11 Nov - 12 Nov
Latchis Hotel
Lobby
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 star property
8.6 out of 10, Excellent, (723)
"Check in was easy and there is coffee available 24 hours a day!"
United States
Michelle
The price is €101
includes taxes & fees
12 Nov - 13 Nov
Comfort Inn & Suites Brattleboro I-91
Exterior
Colonial Motel And Spa
Colonial Motel And Spa
3.0 star property
6.8 out of 10, (1001)
"Excellent staff"
United States
Barry
The price is €134
includes taxes & fees
9 Nov - 10 Nov
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, (432)
"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, (749)
"Lovely spotless well-appointed room. Kind and very helpful staff. Thank you!"
United States
Margaret
The price is €174
includes taxes & fees
23 Nov - 24 Nov
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, (916)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is €87
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn Brattleboro
Room, 2 Queen Beds, Non Smoking
Hampton Inn & Suites Greenfield
Hampton Inn & Suites Greenfield
2.5 star property
8.6 out of 10, Excellent, (871)
"Everything was great except the snacks and food they sold in the lobby and drinks were expensive.."
United States
Angela
The price is €139
includes taxes & fees
13 Nov - 14 Nov
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 €135
includes taxes & fees
16 Nov - 17 Nov
Hampton Inn & Suites Keene
Exterior
The Putney Inn
The Putney Inn
2.5 star property
8.4 out of 10, Very good, (1000)
"Reasonable price for an overnight stay. Ample parking, very quiet and easy access to I 91."
United States
MICHAEL
The Putney Inn
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, (945)
"Room was clean and staff was friendly. "
United States
Britney
The price is €111
includes taxes & fees
27 Nov - 28 Nov
Keene Elm City Hotel, an Ascend Collection 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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Stay near popular Winchester attractions

New England Sweetwater Farm & Distillery

You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside.
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Richmond Wildlife Manangement Area

Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond.
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
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

More cheap stays in Winchester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT
The price is €98 per night from 9 Nov to 10 Nov
€98
9 Nov - 10 Nov
includes taxes & fees
7.6/10 Good! (1,004 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 The Covered Bridge Inn and Travelodge by Wyndham Brattleboro VT. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC: This holiday home rental outside of Winchester is located in the mountains, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. You and your friends and family can relax into your holiday with amenities such as a selection of games. 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 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 Rhododendron State Park, Ashuelot River and Cass Pond. 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.

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