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Find hotels in Winchester, NH from ￥13,575

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Dec 15 - Dec 16
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Dec 16 - Dec 17
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

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Our top choices for Winchester hotels

Breakfast area
The Covered Bridge Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"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 ￥12,340
￥13,575 total
includes taxes & fees
Dec 22 - Dec 23
The Covered Bridge Inn
Lobby
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very Good, (963)
"Staff were very friendly. The pool was the perfect temperature. Would definitely stay again. "
United States
Tiffany
The price is ￥18,354
￥19,915 total
includes taxes & fees
Dec 17 - Dec 18
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1002)
"Nice motel. "
United States
Richard
The Putney Inn
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (740)
"Price, clean and spacious room, comfy bed."
United States
June
The price is ￥17,410
￥19,151 total
includes taxes & fees
Dec 21 - Dec 22
Comfort Inn & Suites Brattleboro I-91
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (124)
"Excellent! Really fun space with beautiful objects all around you. One of a kind, well run, seamless experience. "
United States
Ben
The price is ￥10,201
￥19,030 total
includes taxes & fees
Dec 17 - Dec 18
Blooming Inn
Exterior
The Inn At Crumpin Fox

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (343)
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
United States
Christine
The price is ￥19,772
￥22,084 total
includes taxes & fees
Dec 19 - Dec 20
The Inn At Crumpin Fox
In-room safe, desk, blackout drapes, iron/ironing board
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1000)
"Not exactly spotless by the experience was better than at the Courtyard by Marriott on Railroad St. in Keene NH."
United States
Miroslaw
The price is ￥12,714
￥13,795 total
includes taxes & fees
Dec 18 - Dec 19
Days Inn by Wyndham Keene NH
Interior
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1003)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
The Colonial Hotel
Free daily buffet breakfast
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (353)
"Clean comfy nice staff "
United States
Katherine
The price is ￥22,935
￥24,884 total
includes taxes & fees
Dec 24 - Dec 25
Hampton Inn & Suites Keene
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is ￥19,658
￥21,329 total
includes taxes & fees
Dec 31 - Jan 1, 2026
The Carriage Barn Inn
Restaurant
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1002)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ￥20,099
￥21,808 total
includes taxes & fees
Dec 21 - Dec 22
Best Western Plus Keene Hotel
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
The price is ￥28,046
￥30,430 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fairfield Inn & Suites by Marriott Keene Downtown
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (925)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is ￥22,312
￥24,543 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Brattleboro
Exterior
Latchis Hotel

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (837)
"Great stay"
United States
Jason
The price is ￥19,437
￥21,380 total
includes taxes & fees
Dec 16 - Dec 17
Latchis Hotel
Lobby
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1000)
"Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. "
United States
Belinda
The price is ￥22,437
￥24,681 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Front of property
Black Mountain Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (474)
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is ￥15,926
￥17,518 total
includes taxes & fees
Dec 16 - Dec 17
Black Mountain Inn
Land view from property
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (14)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Reception
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (737)
"Reasonable rate for the the accomadations."
United States
David
The price is ￥10,751
￥11,826 total
includes taxes & fees
Dec 16 - Dec 17
Travelodge by Wyndham Brattleboro VT
Front of property
Colonel Williams Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is ￥23,069
￥25,375 total
includes taxes & fees
Dec 16 - Dec 17
Colonel Williams Inn
Exterior
The Burrell House

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
"Very helpful, kind staff"
United States
Paitris
The Burrell House
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

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

New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskeys while learning about the distillation process in a warm space adorned with reclaimed wood.
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 downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester
Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"Very clean room. Plenty of hot water for shower. Good heat"
Carlene 1-night trip
Posted 3 days ago
The Putney Inn

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is ￥12,714 per night from Dec 18 to Dec 19
￥12,714
￥13,795 total
Dec 18 - Dec 19
includes taxes & fees
7/10 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 Hampton Inn & Suites Greenfield and The Covered Bridge Inn. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals in Winchester?
Lovely 2nd Floor Apartment: Visitors like this Winchester vacation home rental. It 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, 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.
Where can I learn more about changing or cancelling my trip to Winchester?
For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.
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 Comfort Inn & Suites Brattleboro I-91 are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is the best hotel near Hartness State Airport (VSF)?
The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.
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 7 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 Birch Point, Ashuelot River, and Cass Pond. A couple of additional sights to add to your agenda are New England Sweetwater Farm & Distillery and Winchester Speedpark. 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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