A snow-covered town with a river running through it, surrounded by mountains and trees.

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22 Aug - 23 Aug
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23 Aug - 24 Aug
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Our top choices for Winchester hotels

1. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Robert
£99
includes taxes & fees
23 Aug - 24 Aug
Windmill Motel Restaurant

2. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
James
£91
includes taxes & fees
3 Sept - 4 Sept
Keene Elm City Hotel, an Ascend Collection Hotel

3. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Timothy
£93
includes taxes & fees
8 Sept - 9 Sept
Hampton Inn Brattleboro

4. Latchis Hotel

Latchis Hotel
Brattleboro
United States
Stark
£87
includes taxes & fees
26 Aug - 27 Aug
Latchis Hotel

5. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
VINCENT JOEL
£57
includes taxes & fees
27 Aug - 28 Aug
The Covered Bridge Inn

6. The Burrell House

The Burrell House
Keene
United States
Justin
£103
includes taxes & fees
10 Sept - 11 Sept
The Burrell House

7. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
Michael
£77
includes taxes & fees
22 Sept - 23 Sept
Days Inn by Wyndham Keene NH

8. Colonial Motel

Colonial Motel
Brattleboro
United States
James
£66
includes taxes & fees
21 Sept - 22 Sept
Colonial Motel

9. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Karen
£118
includes taxes & fees
20 Sept - 21 Sept
Best Western Plus Keene Hotel

10. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Morgan
£104
includes taxes & fees
31 Aug - 1 Sept
Comfort Inn & Suites Brattleboro I-91

11. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Christopher
£119
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Keene

12. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
Christopher
£133
includes taxes & fees
25 Aug - 26 Aug
The Inn At Crumpin Fox

13. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
Brattleboro
United States
Jessica
£50
includes taxes & fees
23 Aug - 24 Aug
Travelodge by Wyndham Brattleboro VT

14. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Pauline
£114
includes taxes & fees
20 Sept - 21 Sept
Riverside Hotel, an Ascend Collection Hotel

15. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Juli
£146
includes taxes & fees
1 Sept - 2 Sept
Vikings Villages Resort

16. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
United States
Edgardo
£72
includes taxes & fees
30 Aug - 31 Aug
Econo Lodge Brattleboro South

17. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Jonathan
£110
includes taxes & fees
23 Aug - 24 Aug
The Carriage Barn Inn

18. The Putney Inn

The Putney Inn
Putney
United States
JANE
£88
includes taxes & fees
21 Sept - 22 Sept
The Putney Inn

19. Black Mountain Inn

Black Mountain Inn
Brattleboro
United States
Robert
£109
includes taxes & fees
25 Aug - 26 Aug
Black Mountain Inn

20. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Marnie
£135
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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Stay near popular Winchester attractions

Winchester Speedpark

Winchester Speedpark thrills with professionally designed motocross tracks featuring challenging jumps and turns. Experience heart-pounding night races or watch competitors tackle the New England racing circuit.
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Cass Pond

This serene 54-acre pond in Richmond offers peaceful fishing for bass, pickerel, and perch. Bring your own gear and a valid New Hampshire fishing licence to fully enjoy this tranquil natural retreat.
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New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskies while learning about the distillation process in a warm space adorned with reclaimed wood.
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Richmond Wildlife Manangement Area

This protected wilderness features diverse New Hampshire ecosystems across forests, wetlands, and meadows. Explore marked trails for wildlife viewing, especially during spring migration or autumn's foliage display.
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Barden State Wildlife Management Area

This serene wildlife reserve in New Hampshire offers undisturbed natural landscapes for wildlife observation. Bring binoculars for spotting native species while exploring the peaceful trails during spring through fall.
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Conant Public Library

This historic 1892 library houses Winchester's heritage collection, including one of New England's earliest pipe organs. Browse artefacts or research local history with help from knowledgeable staff.
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Loring Field

Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside.
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Bennett Gorge

This secluded woodland trail winds alongside a brook to the remnants of an historic mill. Explore Richmond's industrial past while enjoying the tranquil sounds of flowing water and forest solitude.
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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.

See all hotels in Winchester
A snow-covered town with a river running through it, surrounded by mountains and trees.

Top Winchester Hotel Reviews

Latchis Hotel

Latchis Hotel

8/10 Good
"The art deco building is gorgeous. I applaud the non-profit organization that saved, renovated and maintains this exceptional building. I very much appreciated the original bathroom fixtures. The hotel really gives you a taste of what it might have been like to travel back in the 1930-40s. On the downside, my experience was not the best: When I arrived, the front desk lady said something like: "I'll be right with you". Two minutes later, she came to the front desk joking about having problems with her Emails. Not acceptable! You should pause your Email activity when someone is waiting in the lobby. My wife and I were looking forward to a drink at the hotel bar. The website indicated that the bar was open, and a note on the door confirmed. There was nobody there. Money and a lady's purse were spread out on the bar. We were told at the front desk that the people running the bar for them decided not to open that evening. Not acceptable. The next morning I took a lukewarm shower, as it took about ten minutes for the water to become warm enough, By then I was done and my feet were in about 5" of dirty water because the drain was clogged. We were also told that if we did not turn in our brass key, they would charge us $75 to replace it. When walked down to the lobby, there was a sign stating that front desk duty started at 9:00."
Denis 1-night trip
Posted 6 hours ago
Latchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Staff were extremely friendly. The whole place was clean. Hit tub was really a whirlpool..movement but no bubbles. So nice and warm though. Great stay!!"
Deborah 2-night trip
Posted 10 hours ago
Hampton Inn Brattleboro
The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"Large room in great condition. Property is dated but not in a bad way in any sense - everything is in great shape for the price point. Would stay again"
Christopher 1-night trip
Posted 14 hours ago
The Inn At Crumpin Fox
The Putney Inn

The Putney Inn

10/10 Excellent
"I had a really good experience. It was clean, comfortable and quiet for the most part. The staff were great."
Robert 2-night trip
Posted 2 days ago
The Putney Inn
Windmill Motel Restaurant

Windmill Motel Restaurant

10/10 Excellent
"Clean room very helpful staff. I’ve stayed here a few times already."
Josiah 1-night trip
Posted 2 days ago
Windmill Motel Restaurant
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Staff was great. Room was fine. Besides the small bathroom set up and basic continental breakfast, stay was great."
Krystal 1-night trip
Posted 3 days ago
Keene Elm City Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

8/10 Good
"Over all, pleasant stay. The balcony and balcony chairs need regular cleaning. Room and bathroom were fine. No coffee downstairs. Cheese and crackers, chips or candy available for sale at the desk or a vending machine would be nice."
Celestine 4-night trip
Posted 3 days ago
Riverside Hotel, an Ascend Collection Hotel
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

8/10 Good
"It was a very pleasant stay"
Joseph 1-night trip
Posted 5 days ago
Days Inn by Wyndham Keene NH
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

8/10 Good
"Clean room, very nice front desk staff. Breakfast was good - nice variety and the coffee machine delivered great fresh coffee. It was worth paying the extra cost for this hotel vs the others in the area that seemed a bit sketchy."
David 1-night trip
Posted 5 days ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
£77
22 Sept - 23 Sept
includes taxes & fees
7/10 Good! (1,003 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
£81
21 Sept - 22 Sept
includes taxes & fees
Gardner Inn
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
£87
26 Aug - 27 Aug
includes taxes & fees
8.6/10 Excellent! (963 reviews)
Latchis Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
£91
3 Sept - 4 Sept
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
£93
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very good! (1,015 reviews)
Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
£104
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (849 reviews)
Comfort Inn & Suites Brattleboro I-91

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 much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from £57 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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