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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, (445 reviews)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
Riverhouse by Weekender (Formerly Jack Daniels Inn)

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,005 reviews)
"Well-kept hotel with a great restaurant."
United States
Adam
The Colonial Hotel

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.0 out of 10, (20 reviews)
"Clean room, comfy bed, quiet guests around my room. Staff was cordial when I checked in. "
United States
Kathy
Gardner Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (131 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is £114
includes taxes & fees
24 Feb - 25 Feb
Blooming Inn

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is £196
includes taxes & fees
4 Mar - 5 Mar
The Maguire House Bed & Breakfast

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, (985 reviews)
"Staff were great place was clean and nice. "
United States
Alex
The price is £84
includes taxes & fees
23 Feb - 24 Feb
Keene Elm City Hotel, an Ascend Collection Hotel

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, (763 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is £144
includes taxes & fees
28 Feb - 1 Mar
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, (1,004 reviews)
"Really clean hotel, friendly staff and great location."
United States
Aaron
The price is £145
includes taxes & fees
1 Mar - 2 Mar
Courtyard by Marriott Keene Downtown

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,000 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
The Putney Inn

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)
"Great stay pool was very nice"
United States
Patrick
The price is £90
includes taxes & fees
23 Feb - 24 Feb
Best Western Plus Keene Hotel

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)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
The price is £65
includes taxes & fees
24 Feb - 25 Feb
Days Inn by Wyndham Keene NH

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (14 reviews)
"Picturesque, family run bed and breakfast."
United States
Jay
The price is £119
includes taxes & fees
23 Feb - 24 Feb
Inn at Valley Farms

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (158 reviews)
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
The Burrell House

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (366 reviews)
"Clean, comfortable. "
United States
Jacklyn
The price is £133
includes taxes & fees
22 Mar - 23 Mar
Hampton Inn & Suites Keene

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (887 reviews)
"Very clean, including a nice clean bathroom. Friendly staff."
United States
Jennifer
The price is £128
includes taxes & fees
1 Mar - 2 Mar
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, (353 reviews)
"Staff very accomodating when we needed to check in very early"
United States
Bill
The price is £105
includes taxes & fees
27 Feb - 28 Feb
The Inn At Crumpin Fox

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (168 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is £122
includes taxes & fees
23 Feb - 24 Feb
The Carriage Barn Inn

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (168 reviews)
"Great place and very clean!!"
United States
Emil
The price is £165
includes taxes & fees
23 Mar - 24 Mar
Vikings Villages Resort

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)
"Very clean room and super friendly staff!"
United States
Joanne
The price is £127
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is £191
includes taxes & fees
4 Mar - 5 Mar
Inn on Putney Road
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 city centre 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

Find out more about Winchester

Top reasons to visit Winchester

  • Stunning Natural Landscapes: Experience breathtaking scenery with lush forests, serene lakes, and picturesque surroundings perfect for outdoor activities.
  • Historic Attractions: Explore cultural sites such as the notable Winchester Cathedral, adding a rich historical dimension to your visit.
  • Outdoor Adventures: Enjoy activities like skiing and hiking, ideal for adventure seekers and nature lovers alike.
  • Charming Accommodation: Stay in delightful bed and breakfasts or comfortable hotels, ensuring a memorable experience.
  • Romantic Getaway: The tranquil environment makes Winchester perfect for couples seeking a romantic retreat.

Find great hotels near Winchester

Winchester, New Hampshire, offers a delightful selection of accommodations, ranging from charming bed and breakfasts to comfortable hotels. Whether you seek a pet-friendly retreat, a business-oriented stay, or an adventurous getaway, you'll find options tailored to your needs. Explore the best hotels in Winchester, including the renowned Winchester Royal Hotel, and enjoy a memorable stay in this picturesque locale.

  • Best Western Plus Keene Hotel: A welcoming 3-star hotel situated 6.8km from Winchester, this property is perfect for family and pet-friendly vacations. Renowned for its LGBTQIA-friendly atmosphere, Best Western Plus Keene Hotel offers a variety of child-friendly amenities, including complimentary cribs. Pets are also welcome, with a designated dog exercise area. The hotel's inclusive environment and commitment to service make it an ideal choice for travellers seeking a comfortable and supportive stay.
  • Colonial Motel And Spa: Located 7.5km from Winchester, Colonial Motel And Spa is a charming 3-star motel focused on family adventures and relaxation. With an array of nearby outdoor activities such as ice skating, snowshoeing, and mountain biking, this accommodation caters to thrill-seekers. The full-service spa and pool facilities, including a sauna and hot tub, make it a perfect retreat for unwinding after a day of exploration. Child-friendly features like sledding and safety measures ensure a worry-free experience for families.
  • Days Inn by Wyndham Keene NH: This conveniently located hotel, 6.8km from Winchester, is an excellent choice for business travellers and pet owners alike. With a 24-hour business centre and essential amenities, Days Inn by Wyndham Keene NH ensures productivity during your stay. The hotel also accommodates pets, offering a welcoming policy for furry companions. Its combination of business facilities and a friendly atmosphere makes it a versatile option for both work and leisure.

Where to stay in and around Winchester

Winchester, New Hampshire, offers a charming escape for those seeking outdoor adventures and romantic scenery. With its friendly atmosphere, this beautiful city is perfect for family-friendly outings or secluded getaways. Enjoy the warmest months exploring the picturesque surroundings and vibrant neighbourhoods just a short walk from the heart of Winchester. Whether you're after relaxation or adventure, this delightful destination promises unforgettable experiences amidst stunning landscapes.

  • Brattleboro: Situated approximately 6.2km from Winchester, Brattleboro is a vibrant city that attracts visitors year-round, particularly between July and September. Known for its thrilling outdoor activities, it offers a fantastic ski experience in the winter months, as well as opportunities for adventure sports throughout the year. Visitors can explore the stunning local landscapes, including lakes, mountains, and valleys. Don't miss the chance to visit the ski resorts that offer both adrenaline-pumping slopes and a cosy atmosphere after a day of skiing.
  • Keene: Located about 7.5km from Winchester, Keene is another charming city that sees consistent tourism, especially in the peak months of July, August, and October. Renowned for its breathtaking scenery and outdoor adventures, Keene is a gateway to a variety of outdoor pursuits, including skiing and hiking. The presence of a modern college university adds a youthful vibe to the city, making it a lively spot to enjoy local cafes and cultural events. The nearby lakes and mountains provide a picturesque backdrop for any outdoor enthusiast.
  • Richmond: Nestled within the Winchester area, Richmond is a quaint village that experiences moderate seasonal tourism, peaking in February and during the summer months of June and July. This idyllic location is perfect for those seeking a serene outdoor experience, offering beautiful recreational areas and ski fields for winter sports lovers. Visitors can explore the stunning national state park nearby, along with picturesque lakes and mountains that make Richmond a scenic retreat. It’s an ideal spot for those looking to immerse themselves in nature while enjoying adventure activities.

Things to do near Winchester

Winchester, New Hampshire, offers a delightful escape for outdoor enthusiasts and couples seeking a romantic getaway. Popular activities include skiing at local resorts and exploring scenic landscapes. Ideal for a day trip or a city break, this charming destination provides a perfect blend of adventure and relaxation amidst its beautiful surroundings.

Shopping

The nearest shopping destination is Delectable Mountain Cloth, offering unique gifts and souvenirs just 6.2km away. If you're up for a drive, visit Vermont Marketplace, which features a vibrant mix of businesses and entertainment, located 6.2km from Winchester, and Brattleboro Farmers' Market, 7.5km away, showcasing local produce and crafts.

Recreation

At Crumpin-Fox Golf Club, indulge in a luxurious golfing experience amidst picturesque landscapes, just 6.2km from Winchester. Northfield Golf Club, located 3.7km away, offers invigorating outdoor sports in a serene setting, perfect for a refreshing day out. Enjoy live performances at The Stone Church, 6.8km away, for an entertaining evening.

Adventure

Explore the Metacomet-Monadnock Trail for invigorating hikes amidst stunning scenery, located 3.7km from Winchester. At Harris Hill Ski Jump, 6.8km away, experience thrilling ski sports. For a more serene adventure, the Wetmore Trailhead, 13.7km from Winchester, offers beautiful trails and outdoor exploration.

Nightlife

Enjoy a night at the Latchis Theatre, just 6.2km from Winchester, where you can immerse yourself in captivating performances. Alternatively, visit the Actors Theatre Playhouse, 6.8km away, for a delightful evening of drama and romance, or explore the Hooker-Dunham Theater & Gallery for a unique cultural experience.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, consider visiting during the cheaper months of March or December to January, avoiding the pricier May and September to October. Booking your stay on a Tuesday will also help you cut costs, while Saturdays tend to be more expensive. Use Expedia to search for budget-friendly hotels, and take advantage of their package deals that combine flights, hotels, and activities for additional savings. Look out for eco-certified hotels for sustainable options that may offer better rates.

  • 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: Expedia's search tool enables you to specify your budget, preferred location, and additional criteria. You can organise your search results to display prices from lowest to highest, allowing you to find the most affordable hotels first. Furthermore, you can refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities by booking an Expedia package.

Find the best attractions near Winchester

Winchester, New Hampshire, is perfect for a romantic outdoor getaway, offering stunning scenery and eco-friendly adventures. Visitors can explore lush forests, serene nature reserves, and tranquil lakes. Notable attractions include historic sites and Winchester Cathedral, which add a cultural touch to your trip. Whether you seek outdoor activities or a peaceful retreat, Winchester has something for everyone.

  • Thomas Aquinas College: This modern college offers a vibrant atmosphere, perfect for those interested in contemporary educational settings. With its beautiful campus and engaging community, visitors can enjoy a sense of scholarly pursuit and city vibes.
  • Moody Center: This institute is a hub for various activities and events, providing a dynamic space for learning and interaction. Its proximity to Winchester makes it an accessible destination for those seeking enriching experiences.
  • Historical Old NMH Campus Building #3: Steeped in history, this building provides a glimpse into the past with its cultural significance. The architecture and stories it holds offer a unique opportunity to appreciate local heritage and culture.

Best time to go to Winchester

The best time to visit Winchester is dependant 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 SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnySlightly HighSlightly High
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

For your visit to Winchester, New Hampshire, you can conveniently fly into three major airports. Bradley International Airport (BDL) in Hartford, CT, is situated 37.3km away, with excellent hotel options like the DoubleTree by Hilton Hartford - Bradley Airport, just 621m from the airport. Manchester-Boston Regional Airport (MHT) in Manchester, NH, is 30.4km distant, offering nearby stays such as The Grand at Bedford Village Inn, 2.5km from the airport. Lastly, Worcester Regional Airport (ORH) in Worcester, MA, is located 42.5km away, with hotels like Beechwood Hotel, 3.1km from the airport, providing easy access for your travel needs.

Frequently asked questions

When is the best time to go to Winchester?
The best time to visit Winchester, New Hampshire, is during the autumn months, particularly from late September to late October, for the spectacular fall foliage.

This period offers clear, crisp weather and the vibrant colours of the changing leaves, making it ideal for outdoor activities like hiking, scenic drives, and exploring the local countryside. The area surrounding Winchester is known for its natural beauty, with various trails and viewpoints to experience the seasonal display.

Couples looking for a romantic getaway will find this time particularly appealing. The picturesque landscapes provide a beautiful backdrop for leisurely drives through the New Hampshire countryside or cosy evenings by a fireplace. Many local inns and B&Bs offer special packages during the fall.

Families will also enjoy visiting in autumn. The cooler temperatures are superb for outdoor adventures without the summer heat, and there are often local harvest festivals or apple-picking opportunities in the wider region.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How can I save on a Winchester hotel booking with Expedia?
Members always get our best prices. Find our best Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from £65 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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