Hotels in Winchester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Feb 12 - Feb 13
Tomorrow
Feb 13 - Feb 14
This weekend
Feb 13 - Feb 15
Next weekend
Feb 20 - Feb 22

Where to stay in Winchester?

Free daily full breakfast
Centennial House
Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173 reviews)
Wake up to a full breakfast at this historic Northfield B&B adjacent to golf facilities. Explore nearby hiking trails or enjoy cross-country skiing, then relax in the garden or terrace. Free WiFi and parking complement your stay near Dickinson Memorial Library.
The price is $199
$211 total
includes taxes & fees
Feb 15 - Feb 16
Centennial House
Exterior
The Inn At Crumpin Fox
The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (352 reviews)
Nestled in Bernardston with nearby hiking trails, kayaking, and mountain biking opportunities, this welcoming inn offers free WiFi and parking. Close to Cushman Library and Powers Institute Museum, guests consistently praise the helpful staff and clean rooms.
The price is $130
$146 total
includes taxes & fees
Feb 25 - Feb 26
The Inn At Crumpin Fox
Seasonal outdoor pool
Econo Lodge Brattleboro South
Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.4 out of 10, (619 reviews)
Escape to this comfortable Brattleboro motel offering a seasonal outdoor pool, free breakfast, and WiFi. Just minutes from Vermont Marketplace and Estey Organ Museum, with winter sports nearby and convenient train station access.
The price is $67
$74 total
includes taxes & fees
Mar 15 - Mar 16
Econo Lodge Brattleboro South
Exterior
Latchis Hotel
Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (848 reviews)
The price is $123
$135 total
includes taxes & fees
Mar 2 - Mar 3
Latchis Hotel
Front of property
The One Cat B&B
The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78 reviews)
Wake up to a complimentary full breakfast at this cozy cat-themed B&B. Just a 5-minute walk from Brattleboro Station with nearby hiking trails, kayaking, and mountain biking. New England Youth Theatre and Brattleboro Museum & Art Center wait to be explored.
The price is $150
$165 total
includes taxes & fees
Feb 17 - Feb 18
The One Cat B&B
Breakfast area
The Covered Bridge Inn
The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,000 reviews)
Tucked into scenic Brattleboro, this inn welcomes outdoor enthusiasts with nearby hiking, snowboarding, and sledding options. Start each day with complimentary continental breakfast before exploring local attractions like the Brattleboro Bowl just minutes away.
The price is $79
$87 total
includes taxes & fees
Feb 15 - Feb 16
The Covered Bridge Inn
Restaurant
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,001 reviews)
Quiet rooms welcome travelers to this restful retreat near the Ashuelot River and Thorne Sagendorph Art Gallery. The restaurant and bar provide delicious meals, while fellow guests rave about the free breakfast and helpful staff.
The price is $139
$151 total
includes taxes & fees
Feb 15 - Feb 16
Best Western Plus Keene Hotel
Lobby
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, (982 reviews)
Escape to this welcoming hotel in Keene, where you'll find an indoor pool and fitness center near local shops and eateries. Despite its commercial location, guests enjoy a quiet atmosphere, free breakfast, and helpful staff to enhance your stay.
The price is $119
$129 total
includes taxes & fees
Feb 15 - Feb 16
Keene Elm City Hotel, an Ascend Collection Hotel
Front of property
Vikings Villages Resort
Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (163 reviews)
Enjoy mountain adventures from this secluded retreat with free WiFi and parking. Kayak, bike, or snowshoe directly from the property. Helpful staff ensure a memorable stay near Shattuck Brook Wildlife Management Area.
The price is $132
$155 total
includes taxes & fees
Feb 22 - Feb 23
Vikings Villages Resort
Indoor pool
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (942 reviews)
Immerse yourself in Brattleboro charm at this welcoming hotel with complimentary breakfast and parking. Unwind in the hot tub, energize at the fitness center, or grab a coffee at the café while exploring nearby attractions like Brattleboro Bowl.
The price is $114
$125 total
includes taxes & fees
Mar 1 - Mar 2
Hampton Inn Brattleboro
Lunch and dinner served, American cuisine
Colonial Motel And Spa
Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1,002 reviews)
Unwind at this Brattleboro motel offering massage treatments, American cuisine at India Masala House, and 2 indoor pools. Rooms include refrigerators and microwaves, with free WiFi and parking. Just minutes from Brattleboro Bowl and local attractions.
The price is $100
$110 total
includes taxes & fees
Feb 16 - Feb 17
Colonial Motel And Spa
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
Keene
7.0 out of 10, Good, (1,000 reviews)
The price is $99
$108 total
includes taxes & fees
Feb 25 - Feb 26
Days Inn by Wyndham Keene NH
Sundeck
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (637 reviews)
The price is $160
$174 total
includes taxes & fees
Mar 15 - Mar 16
Riverside Hotel, an Ascend Collection Hotel
Lobby
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (760 reviews)
Warm Brattleboro accommodations with complimentary breakfast, WiFi, and parking just minutes from United States Navy Seabee Bridge. Energize at the fitness center after exploring nearby attractions. Fellow travelers consistently praise the exceptionally helpful staff.
The price is $123
$135 total
includes taxes & fees
Mar 5 - Mar 6
Comfort Inn & Suites Brattleboro I-91
Front of property
Black Mountain Inn
Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (482 reviews)
This tranquil inn offers a seasonal outdoor pool surrounded by nature's calm. Nearby hiking and mountain biking trails await adventurous guests. Free breakfast, WiFi, and parking enhance your Brattleboro stay, just minutes from local attractions.
The price is $108
$118 total
includes taxes & fees
Feb 16 - Feb 17
Black Mountain Inn
Free daily buffet breakfast
Hampton Inn & Suites Keene
Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (364 reviews)
Located in Keene with easy access to Cheshire Children's Museum, this hotel offers a refreshing indoor pool and 24-hour fitness center. Enjoy complimentary breakfast, free parking, and attentive staff to enhance your stay while exploring nearby attractions.
The price is $169
$184 total
includes taxes & fees
Feb 22 - Feb 23
Hampton Inn & Suites Keene
Reception
Travelodge by Wyndham Brattleboro VT
Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (750 reviews)
This cozy motel in Brattleboro offers free WiFi and parking with convenient room service. Nearby cross-country and downhill skiing adventures await, plus Brattleboro Bowl and the Navy Seabee Bridge are just minutes away. Only a 7-minute drive to the train station.
The price is $71
$78 total
includes taxes & fees
Feb 15 - Feb 16
Travelodge by Wyndham Brattleboro VT
Exterior
Inn on Putney Road
Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
Overlooking the West River, this charming B&B offers lush gardens and a cozy bar/lounge. Just a 15-minute walk from Brattleboro Station and near local attractions. Enjoy free breakfast, WiFi, and parking, plus relaxing deep-tissue massages.
The price is $235
$258 total
includes taxes & fees
Feb 16 - Feb 17
Inn on Putney Road
Lobby
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, (1,003 reviews)
Splash into the indoor pool at this welcoming Brattleboro hotel near United States Navy Seabee Bridge. Free breakfast, WiFi and parking enhance your stay while the 24-hour fitness center keeps routines on track. Guests consistently praise the helpful staff.
The price is $152
$167 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Free daily continental breakfast
The Carriage Barn Inn
The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
Wake up to continental breakfast at this cozy Keene B&B, located near the Thorne-Sagendorph Art Gallery. Enjoy free WiFi and parking while exploring the area, with Manchester-Boston Regional Airport and Brattleboro Station both accessible for day trips.
The price is $153
$166 total
includes taxes & fees
Feb 25 - Feb 26
The Carriage Barn 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.
View all properties

Top landmarks in Winchester

New England Sweetwater Farm & Distillery

Sample award-winning spirits crafted with local ingredients at this rustic New England distillery. Watch the production process through vintage windows while enjoying tastings of unique vodkas and whiskeys.
See properties

Barden State Wildlife Management Area

Wander through untouched wilderness where deer and wild turkeys roam freely in this secluded New Hampshire reserve. Pack binoculars and sturdy boots to explore the network of trails that wind through diverse habitats.
See properties

Learn more about Winchester

Winchester is well-known for its attractions such as New England Sweetwater Farm & Distillery and Bennett Gorge. The city has something for everyone including sights like Pisgah State Park and Barden State Wildlife Management Area within a scenic setting.

See all hotels in Winchester
Winchester, New Hampshire in winter

Check out reviews of Winchester hotels guests love

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The room was very clean, and the showers hot water was amazing! The staff was friendly and would let us know when breakfast was available so we wouldn’t miss it ! Robert and Destiny always had a smile on their face and greeted us when we arrived and when we left the hotel. I would definitely stay there again when we visit Brattleboro VT!! "
Gina Marie 2-night trip
Posted 3 days ago
Hampton Inn Brattleboro

Frequently asked questions

Can I book refundable hotels in Winchester?
If you need the flexibility to change your travel plans to Winchester, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Winchester be like during my vacation?
July and August are typically the warmest months in Winchester when the average temp is 67°F. January and February are the coldest months when the average temperature is 28°F. October and July are the months with the most rain.
Why should I book my Winchester hotel through Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.