Winchester Hotels

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23 Dec - 24 Dec
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24 Dec - 25 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Winchester hotels

Exterior detail
The Covered Bridge Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1002)
Set in Brattleboro, this charming inn sits near hiking trails and winter sports activities. Enjoy free continental breakfast each morning, complimentary WiFi, and parking. The United States Navy Seabee Bridge and Brattleboro Bowl are just minutes away.
"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
United States
Megan
The price is €83
includes taxes & fees
25 Dec - 26 Dec
The Covered Bridge Inn
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1001)
"The room was okay for a quick stop to rest. "
United States
Janice
The Putney Inn
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (125)
Explore Glacial Potholes from this welcoming guesthouse offering snowshoeing, sledding, and snowmobiling on site. Enjoy daily housekeeping and easy access to local attractions like the Shelburne Falls Bowling Alley, with Greenfield Station just a 16-minute drive away.
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
The price is €105
includes taxes & fees
7 Jan - 8 Jan 2026
Blooming 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, (742)
Located minutes from Brattleboro Station, this welcoming hotel offers free breakfast, WiFi, and parking. Work out in the fitness centre before dining at the on-site restaurant. United States Navy Seabee Bridge and Brattleboro Bowl are nearby.
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
The price is €110
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Brattleboro I-91
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)
This cosy Carriage Barn Inn provides complimentary continental breakfast, WiFi, and parking. Located near Thorne-Sagendorph Art Gallery, the bed and breakfast creates a perfect base for exploring Keene's cultural attractions.
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is €117
includes taxes & fees
5 Jan - 6 Jan 2026
The Carriage Barn Inn
Front of property
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, (345)
Set in picturesque surroundings, this charming inn offers easy access to nearby hiking and mountain biking trails. Free WiFi and parking enhance your stay while the helpful staff ensures comfort. Just minutes from Cushman Library and Powers Institute Museum.
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
United States
Christine
The price is €120
includes taxes & fees
26 Dec - 27 Dec
The Inn At Crumpin Fox
Indoor pool
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, (967)
Escape to this quiet retreat with an indoor pool and fitness centre near Ashuelot River. Just minutes from local shops and eateries, this hotel offers free breakfast, WiFi, and parking. The helpful staff ensures a comfortable stay for business or leisure travellers.
"The room was perfect, and the food was great "
United States
Paul
The price is €109
includes taxes & fees
28 Dec - 29 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Premium bedding, individually decorated, individually furnished, desk
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, (1001)
This hotel offers quiet rooms and a peaceful environment near the Ashuelot River. Enjoy complimentary breakfast, WiFi, and parking. Guests love the helpful staff and convenient location. Visit the 24-hour fitness centre or unwind with a drink at the bar after exploring nearby attractions.
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is €128
includes taxes & fees
25 Dec - 26 Dec
Best Western Plus Keene Hotel
Free breakfast
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (928)
Located minutes from Brattleboro Station, this welcoming hotel offers a relaxing hot tub and fitness centre for unwinding after exploring. Enjoy the complimentary breakfast before visiting nearby United States Navy Seabee Bridge or grabbing coffee at the café.
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is €137
includes taxes & fees
30 Dec - 31 Dec
Hampton Inn Brattleboro
In-room safe, desk, blackout curtains, 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 €78
includes taxes & fees
31 Dec - 1 Jan 2026
Days Inn by Wyndham Keene NH
Free daily on-the-go breakfast
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)
Experience Vermont comfort at this hotel offering a refreshing indoor pool and 24-hour fitness centre. Located near Brattleboro Bowl with easy access to the train station. Guests love the complimentary breakfast, helpful staff, free WiFi, and convenient parking.
"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 €134
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Interior
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1002)
Set in picturesque Gardner with stunning countryside views, this hotel offers Swedish massages and facials. Guests enjoy the quiet atmosphere, convenient highway access, and thoughtful amenities like an on-site restaurant and bar.
"Easy checkin, pleasant staff and clean room. "
United States
Susan
The Colonial Hotel
Hiking
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 €126
includes taxes & fees
25 Dec - 26 Dec
Latchis Hotel
Garden
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (15)
Wake up to free breakfast at this cosy Vermont inn before exploring nearby Rock River Preserve. The on-site Tavern restaurant serves dinner with beautiful garden views, while the welcoming bar and free WiFi create a relaxing countryside retreat.
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
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 €166
includes taxes & fees
5 Jan - 6 Jan 2026
Fairfield Inn & Suites by Marriott Keene Downtown
Seasonal outdoor pool
The Inn At Quail Run

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (71)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is €164
includes taxes & fees
25 Dec - 26 Dec
The Inn At Quail Run
Sun deck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (629)
This classic New Hampshire hotel offers a 24-hour fitness centre and free WiFi. Located near United States Navy Seabee Bridge, guests can enjoy cross-country skiing and snowboarding. Clean rooms, helpful staff, and complimentary parking enhance your countryside retreat.
"Clean room, beautiful location"
United States
Marcie
The price is €140
includes taxes & fees
22 Jan - 23 Jan 2026
Riverside Hotel, an Ascend Collection Hotel
Reception
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (358)
Free breakfast, parking, and 24-hour fitness centre make this Keene hotel a great choice. Swim in the indoor pool or request room service after exploring nearby Cheshire Children's Museum. Travellers praise the helpful staff and morning meal.
"Clean comfy nice staff "
United States
Katherine
The price is €156
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn & Suites Keene
Room, 2 Queen Beds, Non Smoking
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (881)
Explore Old Greenfield Village from this welcoming hotel with daily buffet breakfast, free WiFi, and parking. Energise in the fitness centre, appreciate the attentive staff, and enjoy easy access to the Museum of Our Industrial Heritage.
"Friendly staff, great breakfast, comfy beds"
United States
Lori
The price is €178
includes taxes & fees
7 Jan - 8 Jan 2026
Hampton Inn & Suites Greenfield
Front of property
Colonel Williams Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
Enjoy a cosy stay at this Brattleboro inn with complimentary local cuisine breakfast and WiFi. Outdoor enthusiasts can explore nearby cross-country and downhill skiing options. A garden, terrace, and helpful staff enhance the peaceful Vermont experience.
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is €147
includes taxes & fees
30 Dec - 31 Dec
Colonel Williams 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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Stay near popular Winchester attractions

New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskies while learning about the distillation process in a warm space adorned with reclaimed wood.
See properties

Bennett Gorge

This secluded woodland trail winds alongside a brook to the remnants of an historic mill. Explore Richmond's industrial past while enjoying the tranquil sounds of flowing water and forest solitude.
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
Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

The Covered Bridge Inn

The Covered Bridge Inn

10/10 Excellent
"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
Megan 2-night trip
Posted 3 days ago
The Covered Bridge 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 €78 per night from 31 Dec to 1 Jan
€78
31 Dec - 1 Jan 2026
includes taxes & fees
7/10 Good! (999 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 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 holiday rentals that Winchester has to offer?
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Winchester is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. 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. Comfort Inn & Suites Brattleboro I-91 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 7 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 Birch Point, Ashuelot River and Cass Pond. A couple of additional sights to add to your itinerary are Winchester Speedpark and Bennett Gorge. 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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