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Our top choices for Winchester hotels

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (786 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is NT$4,524
NT$4,977 total
includes taxes & fees
Mar 29 - Mar 30
Comfort Inn & Suites Brattleboro I-91

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,008 reviews)
"Great staff, great food, clean, friendly"
United States
Thomas
The Colonial Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,000 reviews)
"Great stay pool was very nice"
United States
Patrick
The price is NT$4,765
NT$5,171 total
includes taxes & fees
Mar 29 - Mar 30
Best Western Plus Keene Hotel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,000 reviews)
"Great Stay!"
United States
Nicholas
The Putney Inn

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (999 reviews)
"Clean room, polite staff,kids enjoyed the indoor heated pool they also have a small gym and breakfast in the morning couldn't beat the price definitely a great place for the family dogs are also welcome!!"
United States
Sean
The price is NT$4,030
NT$4,372 total
includes taxes & fees
Apr 14 - Apr 15
Keene Elm City Hotel, an Ascend Collection Hotel

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, (1,001 reviews)
"Room spotless, welcoming & friendly staff especially in the breakfast area"
United States
Dominick
The price is NT$4,062
NT$4,468 total
includes taxes & fees
Mar 29 - Mar 30
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (898 reviews)
"Good stay; great staff and nice clean rooms!"
United States
Peter
The price is NT$4,977
NT$5,560 total
includes taxes & fees
Apr 5 - Apr 6
Hampton Inn & Suites Greenfield

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (766 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is NT$5,597
NT$6,073 total
includes taxes & fees
Apr 1 - Apr 2
Fairfield Inn & Suites by Marriott Keene Downtown

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (179 reviews)
"Great place and very clean!!"
United States
Emil
The price is NT$6,521
NT$7,605 total
includes taxes & fees
Apr 7 - Apr 8
Vikings Villages Resort

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,001 reviews)
"Really clean hotel, friendly staff and great location."
United States
Aaron
The price is NT$5,757
NT$6,246 total
includes taxes & fees
Apr 3 - Apr 4
Courtyard by Marriott Keene Downtown

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (170 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is NT$4,443
NT$4,820 total
includes taxes & fees
Apr 1 - Apr 2
The Carriage Barn Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (488 reviews)
"This is a pet friendly hotel when we told the front desk there were loud dogs they immediately spoke to owners and moved our room Clean rooms and excellent. Firm mattress would def go back"
United States
Rita
The price is NT$2,879
NT$3,166 total
includes taxes & fees
Mar 26 - Mar 27
Black Mountain Inn

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1,000 reviews)
"It was good to have pool option after a ski day"
United States
Aysa
The price is NT$3,038
NT$3,342 total
includes taxes & fees
Apr 8 - Apr 9
Colonial Motel And Spa

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,005 reviews)
"Clean room, quiet, good price "
United States
Derek
The price is NT$2,289
NT$2,518 total
includes taxes & fees
Mar 26 - Mar 27
The Covered Bridge Inn

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
10.0 out of 10, Exceptional, (1 review)
"Staff was friendly and accommodating "
Canada
James
The price is NT$3,798
NT$4,278 total
includes taxes & fees
Apr 4 - Apr 5
Windmill Motel Restaurant

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (762 reviews)
"I will not be back. What’s roach motel must be like for roaches. Loud, gross and just no thanks. Glad it’s iver"
United States
Joseph
The price is NT$2,274
NT$2,501 total
includes taxes & fees
Apr 1 - Apr 2
Travelodge by Wyndham Brattleboro VT

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (954 reviews)
"I wish I could have stayed longer. Very nice hotel "
United States
Rosa
The price is NT$4,170
NT$4,587 total
includes taxes & fees
Apr 8 - Apr 9
Hampton Inn Brattleboro

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (372 reviews)
"Nice room, pool, and breakfast! "
United States
Jennifer
The price is NT$5,437
NT$5,899 total
includes taxes & fees
Apr 19 - Apr 20
Hampton Inn & Suites Keene

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (856 reviews)
"Great location, great staff really cool old building with lots of character"
Canada
David
The price is NT$3,989
NT$4,388 total
includes taxes & fees
Mar 26 - Mar 27
Latchis Hotel

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (349 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is NT$5,037
NT$5,541 total
includes taxes & fees
Apr 1 - Apr 2
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

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 Colonial Motel And Spa and Hampton Inn Brattleboro. 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. Colonial Motel And Spa and Hampton Inn Brattleboro 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 8 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 Cass Pond, Rhododendron State Park, and Royalston State Forest. A couple of additional sights to add to your agenda are New England Sweetwater Farm & Distillery and Pisgah State Park. 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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