Photo by Donny Campos

Find hotels in Winchester, NH from NT$2,876

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.4 out of 10, Exceptional, (436)
"Super cute place! Would stay here again"
United States
Danielle
Riverhouse by Weekender (Formerly Jack Daniels Inn)

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1003)
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

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.6 out of 10, (17)
Explore attractions like Dunn State Park from this convenient lodging in Gardner. Free parking, WiFi, and 24-hour front desk make your visit seamless. Worcester Regional Airport is 44 minutes away.

"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is NT$2,806
NT$3,135 total
includes taxes & fees
Jan 4 - 2026/1/5
Gardner Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (124)
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.

"Excellent! Really fun space with beautiful objects all around you. One of a kind, well run, seamless experience. "
United States
Ben
The price is NT$2,126
NT$3,918 total
includes taxes & fees
Jan 5 - 2026/1/6
Blooming Inn

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
Discover Centennial House, a charming colonial B&B adjacent to Northfield Golf Club. Enjoy free full breakfast, WiFi, and parking. Explore nearby hiking trails, cross-country skiing routes, or relax in the garden and terrace after visiting local attractions.

"The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. "
United States
Paul
The price is NT$6,342
NT$6,704 total
includes taxes & fees
Dec 28 - Dec 29
Centennial House

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36)
Set in scenic Ashburnham, this charming B&B offers complimentary daily breakfast and outdoor adventures like rowing, cross-country skiing, and sledding. The peaceful property features a garden, terrace, and snack bar, all near Stevens Memorial Library and Ashburnham State Forest.

"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is NT$8,661
NT$8,661 total
includes taxes & fees
Jan 7 - 2026/1/8
The Maguire House Bed & Breakfast

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1000)
"Nice motel. "
United States
Richard
The Putney Inn

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 NT$5,676
NT$6,159 total
includes taxes & fees
Jan 1 - 2026/1/2
Fairfield Inn & Suites by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1003)
Stylish accommodations in Keene Downtown, close to Colonial Theatre and Central Square. Enjoy a refreshing swim in the indoor pool, grab a bite at the coffee shop, then unwind at the bar. Free WiFi and parking make exploring the area convenient.

"Very comfortable and clean."
United States
Christina
The price is NT$5,669
NT$6,151 total
includes taxes & fees
Dec 24 - Dec 25
Courtyard by Marriott Keene Downtown

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)
Escape to this quiet retreat with an indoor pool and fitness center 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 travelers.

"The room was perfect, and the food was great "
United States
Paul
The price is NT$3,710
NT$4,025 total
includes taxes & fees
Dec 22 - Dec 23
Keene Elm City Hotel, an Ascend Collection Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1000)
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 center or unwind with a drink at the bar after exploring nearby attractions.

"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is NT$4,068
NT$4,414 total
includes taxes & fees
Dec 21 - Dec 22
Best Western Plus Keene Hotel

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (14)
Tucked away in Walpole, this cozy inn offers a tranquil garden escape with free WiFi and parking. Close to Hooper Golf Course and Club, it provides a peaceful base for exploring local attractions.

"Picturesque, family run bed and breakfast."
United States
Jay
The price is NT$4,781
NT$5,187 total
includes taxes & fees
Dec 21 - Dec 22
Inn at Valley Farms

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 NT$2,650
NT$2,876 total
includes taxes & fees
Dec 25 - Dec 26
Days Inn by Wyndham Keene NH

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (879)
Explore Old Greenfield Village from this welcoming hotel with daily buffet breakfast, free WiFi, and parking. Energize in the fitness center, 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 NT$5,914
NT$6,606 total
includes taxes & fees
Dec 24 - Dec 25
Hampton Inn & Suites Greenfield

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (343)
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 NT$3,997
NT$4,464 total
includes taxes & fees
Dec 19 - Dec 20
The Inn At Crumpin Fox

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
Walking distance to Central Square, this inviting guesthouse offers complimentary WiFi and self parking. Enjoy the outdoor picnic area after exploring nearby attractions like CC&H Framing and Pepper Pete's Hot Shop.

"Very helpful, kind staff"
United States
Paitris
The Burrell House

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
This cozy 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 NT$4,014
NT$4,355 total
includes taxes & fees
Dec 29 - Dec 30
The Carriage Barn Inn

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (353)
Free breakfast, parking, and 24-hour fitness center make this Keene hotel a great choice. Swim in the indoor pool or request room service after exploring nearby Cheshire Children's Museum. Travelers praise the helpful staff and morning meal.

"Clean comfy nice staff "
United States
Katherine
The price is NT$5,193
NT$5,635 total
includes taxes & fees
Jan 4 - 2026/1/5
Hampton Inn & Suites Keene

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (277)
Set beside Shattuck Golf Course, this charming B&B provides the perfect base for hiking and mountain biking adventures. Enjoy complimentary WiFi and parking while exploring nearby Jaffrey Civic Center.

"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
Monadnock Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (14)
Wake up to free breakfast at this cozy 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
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winchester attractions

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.

Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

More cheap stays in Winchester

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Winchester offers thrilling activities like skiing and waterpark fun, perfect for outdoor enthusiasts.
  • Scenic Nature Reserves: Explore lush forests and beautiful parks, ideal for relaxation and eco-friendly adventures.
  • Charming Romantic Getaways: Enjoy leisurely strolls and wine country exploration, perfect for couples.
  • Vibrant Live Music Events: Experience the local music scene and delightful wine tastings for a fun night out.
  • Diverse Accommodation Options: Choose from cozy bed & breakfasts to luxury hotels, catering to every traveler's needs.

Find great hotels near Winchester

Discover a variety of lodging options in Winchester, New Hampshire, perfect for every traveler. Whether you're seeking a cozy bed & breakfast or a comfortable hotel equipped for business travel and adventure, you'll find it here. Enjoy pet-friendly facilities and explore the best hotels with competitive room rates, including luxury accommodations. Winchester’s welcoming atmosphere and diverse options will ensure a memorable stay for all visitors.

  • Best Western Plus Keene Hotel: Emphasizing a blend of comfort and inclusivity, the Best Western Plus Keene Hotel is a 3-star establishment that caters to both business travelers and leisure seekers. Located 17.7km from Winchester, this hotel is a welcoming space for LGBTQIA individuals and their allies, as well as pet owners, with a dog exercise area for furry friends. Amenities include complimentary Wi-Fi, a fitness center, and a business center, ensuring all guests have everything they need for a productive and enjoyable stay.
  • Colonial Motel And Spa: For those looking for a spa-themed getaway, the Colonial Motel And Spa is an ideal choice located 19.3km from Winchester. This 3-star motel offers an array of adventure sports and recreational activities nearby, making it perfect for families and thrill-seekers alike. Guests can unwind with full spa services, a sauna, and an onsite pool. Families will appreciate the kid-friendly amenities, including window guards and first aid kits, ensuring a safe and fun experience for children.
  • Hampton Inn Brattleboro: Located 19.3km from Winchester, the Hampton Inn Brattleboro is a modern hotel that emphasizes comfort and convenience for all guests. With a focus on being pet-friendly and LGBTQIA welcoming, this accommodation provides a warm atmosphere for travelers. Guests can enjoy complimentary breakfast, a fitness center, and a business center, making it a practical choice for both leisure and business trips. The hotel also maintains a pet policy, allowing guests to bring their furry companions along for the adventure.

Where to stay in and around Winchester

Winchester, New Hampshire, is a charming city perfect for outdoor enthusiasts and those seeking a romantic getaway. Stroll leisurely through its scenic landscapes, explore nearby wine country, or enjoy a refreshing day in nature. The area's friendly atmosphere and family-friendly vibe make it an ideal destination for relaxation or adventure. Don't miss the opportunity to connect with the serene surroundings and create unforgettable memories in this delightful region.

  • Brattleboro: Located a mere 16.1km from Winchester, Brattleboro is a vibrant city that offers a mix of outdoor adventure and cultural experiences. Known for its year-round appeal, the city welcomes visitors primarily from July to September. Travelers flock here for skiing, sports, and thrilling adventure activities. Highlights include access to ski fields and resorts, as well as picturesque locales like lakes, mountains, and national parks, making it a perfect destination for nature lovers and thrill-seekers alike.
  • Keene: Just 19.3km away from Winchester, Keene is a charming city that captivates visitors with its scenic beauty and outdoor adventures. With peak tourist activity in July, August, and October, it's an excellent spot for those looking to enjoy nature’s splendor. Keene is renowned for its ski fields and resorts, while also offering attractions like lakes, mountains, and the vibrant atmosphere of a modern college town. Whether you're seeking adventure or simply want to soak in the beautiful surroundings, Keene has something for everyone.
  • Richmond: Nestled in the vicinity of Winchester, the village of Richmond attracts visitors throughout the year, particularly peaking in February and during the summer months. Known for its outdoor adventures, Richmond is popular among travelers seeking skiing and recreational activities. Local attractions like the town hall, scenic lakes, and urban parks provide a charming backdrop for relaxation and exploration. This small village offers a cozy feel while still delivering access to exhilarating outdoor experiences.

Things to do near Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Enjoy thrilling activities like skiing at the local ski resort or relaxing at the dropzone waterpark. The area also offers vibrant live music events and delightful wine tastings, making it an ideal destination for those looking to immerse themselves in scenic beauty and recreational fun.

Shopping

In Winchester, visit Delectable Mountain Cloth for unique gifts. If you're up for a drive, explore Vermont Marketplace, located 16.1km away, offering a vibrant shopping experience with entertainment and dining options. Additionally, check out the Brattleboro Farmers' Market, 19.3km away, for local produce and crafts.

Recreation

Experience luxury at Crumpin-Fox Golf Club with serene golf courses surrounded by nature. Enjoy vibrant live music at The Stone Church for an entertaining evening. Unwind at Brattleboro Country Club, where you can embrace the upscale atmosphere while playing a round of golf in a picturesque setting.

Adventure

Explore the Metacomet-Monadnock Trail, a scenic hiking trail 9.7km from Winchester, offering beautiful landscapes and outdoor adventure. For winter sports enthusiasts, Harris Hill Ski Jump, located 17.7km away, provides thrilling ski experiences, while Granite Gorge, 19.7km from Winchester, offers more skiing excitement.

Nightlife

Experience the vibrant nightlife in Winchester by visiting the Latchis Theatre, Hooker-Dunham Theater & Gallery, and New England Youth Theatre, all located 16.1km away. Each venue offers a unique atmosphere filled with romance, entertainment, and culture, perfect for a memorable evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, New Hampshire, consider visiting during the cheaper months of March and December to January, avoiding the pricier May and September to October. Book your stay on a Tuesday for the best rates, as Saturdays are typically the most expensive. Use Expedia to compare hotel prices, and consider bundling your hotel with flights and activities for additional savings. Look for free activities and utilize public transport options to keep costs down while enjoying your vacation.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are March and December to January, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Tuesday. The most expensive day to stay in Winchester is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your choices based on your budget, desired location, and preferred hotel type. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and those seeking a romantic getaway. With its stunning nature reserves, lush forests, and beautiful parks, visitors can enjoy a range of eco-friendly and adventurous activities. The local attractions invite travelers to immerse themselves in the area's natural beauty while providing memorable experiences amidst the great outdoors.

  • Moody Center: Located 8.0km from Winchester, the Moody Center is an inspiring institute that offers unique programs and events. Engage in enriching experiences that promote personal growth and community engagement.
  • Thomas Aquinas College: This modern college, also situated 8.0km away, boasts a vibrant campus atmosphere. Explore its beautiful grounds and enjoy the lively interactions among students, all while soaking in the educational spirit of this esteemed institution.
  • Birch Point: Just 6.4km from Winchester, Birch Point is a picturesque jetty that invites relaxation. Enjoy serene views and the calming sounds of nature, making it the perfect spot for a peaceful getaway.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly SunnyAverageSlightly Low
February25.2°F (-3.8°C)Light RainMostly SunnySlightly LowAverage
March32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
April45.0°F (7.2°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageSlightly High
June64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
July71.2°F (21.8°C)Light RainMostly SunnySlightly HighAverage
August69.3°F (20.7°C)Light RainMostly SunnyAverageAverage
September61.9°F (16.6°C)Light RainMostly SunnySlightly HighSlightly High
October50.5°F (10.3°C)Light RainMostly SunnyAverageSlightly High
November38.7°F (3.7°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Winchester

Winchester, New Hampshire, is conveniently accessible via three major airports. Hartford, CT (BDL-Bradley Intl.), located 96.6km away, offers hotel options like the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. Manchester, NH (MHT-Manchester-Boston Regional), 78.9km from Winchester, features the 5-star Grand at Bedford Village Inn, 6.4km away, and the 4-star DoubleTree by Hilton Manchester Downtown, also 6.4km from the airport. Lastly, Worcester, MA (ORH-Worcester Regional), located 46.4km away, has the 4-star Beechwood Hotel, 8.0km from the airport. Each airport provides convenient transportation options to nearby hotels.

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.
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.

Explore a world of travel with Expedia