Photo by Donny Campos

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Top 10 Winchester hotels and places to stay

Our top choices for Winchester hotels

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1001)
"We have stayed at this property a few times and it is always a pleasant experience. "
The Colonial Hotel

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (315)
"Spacious rooms, tends to be very quiet, stayed several times"
The price is £145
includes taxes & fees
4 Sept - 5 Sept
The Inn At Crumpin Fox

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1001)
"Was great for the price "
The price is £136
includes taxes & fees
19 Sept - 20 Sept
The Covered Bridge Inn

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1000)
"It was a great stay"
The price is £120
includes taxes & fees
24 Aug - 25 Aug
Best Western Plus Keene Hotel

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (459)
"The bed was super comfortable and the sheets were very soft and also comfortable. "
The price is £102
includes taxes & fees
26 Aug - 27 Aug
Black Mountain Inn

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1000)
"Good room, great breakfast options "
The price is £139
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (418)
"Highly recommend PEARL restaurant nearby! Always comfortable accommodations. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (697)
"I was only there for a few hours sleep "
The price is £58
includes taxes & fees
24 Aug - 25 Aug
Travelodge by Wyndham Brattleboro VT

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (589)
"Lovely, and very peaceful stay nestled beside the Connecticut River"
The price is £123
includes taxes & fees
4 Sept - 5 Sept
Riverside Hotel, Ascend Hotel Collection

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1002)
"Always a pleasure to stay at the Colonial"
The price is £114
includes taxes & fees
28 Aug - 29 Aug
Colonial Motel And Spa

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1000)
"Would stay again"
The price is £90
includes taxes & fees
1 Sept - 2 Sept
Days Inn by Wyndham Keene NH

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (677)
"Really good staff! "
The price is £107
includes taxes & fees
2 Sept - 3 Sept
Comfort Inn & Suites Brattleboro I-91

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (775)
"Great stay!"
The price is £111
includes taxes & fees
7 Sept - 8 Sept
Latchis Hotel

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (110)
"Lovely Inn and very responsive and approachable staff. "
The price is £117
includes taxes & fees
28 Aug - 29 Aug
Blooming Inn

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (881)
"Had a great time at this location"
The price is £101
includes taxes & fees
28 Aug - 29 Aug
Keene Elm City Hotel, Ascend Hotel Collection

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (868)
"Great beach and nice rooms Breakfast can improve and pool is small "
The price is £100
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn Brattleboro

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (732)
"Loved our stay from the seamless staff checkin to the large, quiet room, to the ease of the parking lot to a great breakfast. Who could ask for more. Keene is a sweet area to window shop & find great dining & cocktail experiences. "
The price is £141
includes taxes & fees
1 Sept - 2 Sept
Fairfield Inn & Suites by Marriott Keene Downtown

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1003)
"Very enjoyable stay"
The Putney Inn

Vikings Villages Resort

2.0 star property
10.0 out of 10, Exceptional, (122)
"My family and I loved staying here! The cabin was very clean, nicely decorated, comfy beds. Hope to be back during the winter b/c I’m sure it's absolutely magical with snow on the ground"
The price is £171
includes taxes & fees
31 Aug - 1 Sept
Vikings Villages Resort

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (837)
"Great place with a walkable eating option"
The price is £135
includes taxes & fees
21 Sept - 22 Sept
Hampton Inn & Suites Greenfield
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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.

Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

Find out more about 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 most popular time to visit Winchester is during the summer months, particularly July. At this time, the city enjoys warm weather with average temperatures around 20°C, great for exploring its rich history and beautiful surroundings. The longer days allow for leisurely walks through the enchanting streets, visiting iconic sites such as the Winchester Cathedral and the Great Hall.

Winchester is particularly vibrant from June to August, during the peak season when tourists flock to experience the lively atmosphere. This is a fantastic period for outdoor activities and sightseeing, as the city's gardens and parks burst into life, inviting visitors to enjoy picnics or simply relax in the sun. The bustling city also hosts various events and festivals that celebrate local culture, providing an excellent opportunity to engage with the community.

For those who appreciate a more tranquil experience, consider visiting in September. This month still offers pleasant weather, with temperatures hovering around 17°C, but with fewer crowds. You'll find that popular attractions are more accessible, allowing for a more immersive experience without the hustle and bustle of peak tourist season.
Where can I find the best nightlife in Winchester?
Winchester may be a charming small town, but it offers some delightful spots for a pleasant evening out.

While nightlife in Winchester isn't as bustling as in bigger cities, you can still find a few local gems. The town has a handful of pubs and bars where you can enjoy a relaxed atmosphere and perhaps catch some live music on weekends. The Village Pizza is a popular spot for a casual dining experience that often transforms into a lively gathering place in the evenings.

For those willing to venture a bit further, nearby Keene has more vibrant nightlife options, including cocktail lounges, bars, and eateries that stay open later.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Winchester hotel for you.
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 £86 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.