"Clean rooms, comfortable beds, smooth remote check-in with door code,
showerhead was great and the barn door into the bathroom was a unique use of space. We enjoyed our stay."
"Clean rooms, comfortable beds, smooth remote check-in with door code,
showerhead was great and the barn door into the bathroom was a unique use of space. We enjoyed our stay."
"I asked him on the front desk if I get a coffee machine but hi said no wen i order online they said breakfast is available but is not the guy in front desk was rude"
"I asked him on the front desk if I get a coffee machine but hi said no wen i order online they said breakfast is available but is not the guy in front desk was rude"
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.
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.
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.
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.
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 license to fully enjoy this tranquil natural retreat.
This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskeys while learning about the distillation process in a warm space adorned with reclaimed wood.
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.
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.
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.
My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne
My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne
I've traveled quite frequently the past several years and I can say in all honesty that this is without doubt one of the nicest places I have stayed. I was there for 2 nights and could not have asked for nicer accomodations. The room was spacious, the bed very comfortable and the bathroom spotless. The manager was very gracious, he even lent me his umbrella when it rained the day I had planned to do genealogy research in a local cemetery.
I've traveled quite frequently the past several years and I can say in all honesty that this is without doubt one of the nicest places I have stayed. I was there for 2 nights and could not have asked for nicer accomodations. The room was spacious, the bed very comfortable and the bathroom spotless. The manager was very gracious, he even lent me his umbrella when it rained the day I had planned to do genealogy research in a local cemetery.
Anonymous traveler
Reviewed September 26, 2014Reviewed September 26, 2014
Wonderful updated king room with a heating element in the bathroom that was cozy and perfect on a cold night.
The king bed was comfortable to sleep on. There was a refrigerator with a small freezer and Kureig coffee machine. They also provided some snacks which were appreciated.
I highly recommend staying at the Windmill Hotel.
Wonderful updated king room with a heating element in the bathroom that was cozy and perfect on a cold night.
The king bed was comfortable to sleep on. There was a refrigerator with a small freezer and Kureig coffee machine. They also provided some snacks which were appreciated.
I highly recommend staying at the Windmill Hotel.
Marjorie
Reviewed October 29, 2026Reviewed October 29, 2026
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.
Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.
Great Location! Parking is little tight, accommodations are made and you are informed on where else you can leave your car safely. Plenty of things to do within walking distance. Our room was large and well appointed, with a wonderful view. Would stay there again, in a heartbeat
Great Location! Parking is little tight, accommodations are made and you are informed on where else you can leave your car safely. Plenty of things to do within walking distance. Our room was large and well appointed, with a wonderful view. Would stay there again, in a heartbeat
Anonymous traveler
Reviewed September 28, 2015Reviewed September 28, 2015
Arrived late and were greeted by 2 friendly associates at the desk. There were coffee, tea, hot cocoa, cookies, cheese and crackers available. A welcoming lobby with fireplace. Room was nice, comfortable and clean. Lots of outlets in room. Indoor pool was nice, clean, and heated. hot tub was very relaxing after days of skiing. Continental breakfast was very good and had a variety of choices. We were pleasantly surprised with our choice.
Arrived late and were greeted by 2 friendly associates at the desk. There were coffee, tea, hot cocoa, cookies, cheese and crackers available. A welcoming lobby with fireplace. Room was nice, comfortable and clean. Lots of outlets in room. Indoor pool was nice, clean, and heated. hot tub was very relaxing after days of skiing. Continental breakfast was very good and had a variety of choices. We were pleasantly surprised with our choice.
K.White
Reviewed February 22, 2016Reviewed February 22, 2016
Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...
Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...
Outdoor Adventures: Enjoy skiing, hiking, and exploring stunning nature reserves and parks, perfect for outdoor enthusiasts.
Scenic Beauty: Experience picturesque views and charming streets that invite relaxation and exploration.
Live Music and Events: Immerse yourself in the local culture with vibrant live music and exciting events.
Wine Tasting: Discover nearby wine country and indulge in delightful wine tastings for a refreshing experience.
Cozy Accommodations: Choose from a variety of charming hotels and bed & breakfasts for a memorable stay.
Find great hotels near Winchester
Discover charming accommodations in Winchester, New Hampshire, where you can choose from a variety of lodging options, including hotels and cozy bed & breakfasts. Whether you're here for business, adventure, or a pet-friendly getaway, you'll find the perfect place to stay. Explore the best hotels, luxury options, and competitive room rates to make your visit enjoyable and memorable.
Best Western Plus Keene Hotel: Nestled 17.7km from Winchester, this 3-star hotel is ideal for family vacations and business travelers alike. The Best Western Plus Keene Hotel offers a welcoming atmosphere for guests traveling with pets, featuring amenities such as a designated dog exercise area and pet-friendly policies. Families will appreciate the complimentary cribs available for younger guests, ensuring a comfortable stay for all. With a focus on convenience and comfort, this hotel provides a perfect base for exploring the surrounding area.
Colonial Motel And Spa: Located 19.3km from Winchester, the Colonial Motel And Spa is a charming 3-star motel that combines relaxation and leisure. This pet-friendly property is perfect for travelers seeking a spa-themed getaway, offering a full-service spa with services such as massages and a hot tub. With adult supervision required for the pool, guests can unwind while enjoying the serene environment. The welcoming atmosphere and spa amenities make this motel a great choice for those looking to rejuvenate during their stay.
Hampton Inn Brattleboro: Situated 19.3km from Winchester, the Hampton Inn Brattleboro is a contemporary hotel that embraces inclusivity, welcoming LGBTQIA travelers with open arms. This pet-friendly establishment offers a comfortable environment for business and leisure travelers alike. With policies that accommodate both dogs and cats, guests can enjoy their stay without leaving their furry friends behind. The hotel's commitment to quality service and guest satisfaction makes it a top choice for those looking to experience the charm of the Brattleboro area.
Where to stay near Winchester
Winchester, New Hampshire, offers a delightful escape for outdoor enthusiasts and those seeking a romantic getaway. Stroll through its charming streets, soak in the scenic beauty, and explore nearby wine country for a refreshing experience. This family-friendly destination invites you to unwind and enjoy the camaraderie of friendly locals while discovering secluded spots perfect for adventure. Whether you’re here for leisure or exploration, Winchester promises a memorable vacation filled with scenic views and tranquil moments.
Brattleboro: Located 16.1km from Winchester, Brattleboro is a vibrant city known for its outdoor adventures and cultural experiences. Visitors flock to this destination year-round, with peak travel occurring from July to September. The area offers excellent skiing opportunities and numerous adventure sports. You can explore scenic lakes, majestic mountains, and the beautiful national state park nearby. Whether you’re hitting the slopes or enjoying the local arts scene, Brattleboro provides a rich travel experience.
Keene: Situated 19.3km from Winchester, Keene is a charming city that captivates travelers with its stunning scenery and outdoor activities. With a seasonal peak in visitor arrivals during July, August, and October, this city is perfect for those who appreciate nature. It features ski fields and resorts, making it a prime location for winter sports enthusiasts. Additionally, the presence of a modern college university adds to the city's vibrant atmosphere. Keene promises a delightful blend of outdoor adventure and academic charm.
Ashuelot: Just 3.2km from Winchester, Ashuelot is a picturesque city that offers a romantic and scenic retreat. Known for its tranquil lakes, flowing rivers, and surrounding mountains, this small town attracts visitors year-round, with peaks in July, August, and October. It’s an ideal spot for couples and nature lovers looking to escape the hustle and bustle. The breathtaking landscapes and serene environment make Ashuelot a hidden gem for those seeking a peaceful getaway.
Things to do near Winchester
Winchester, New Hampshire, offers a delightful blend of outdoor activities and scenic beauty, making it perfect for romantic getaways. Visitors can enjoy skiing at the local ski resort, while the town also features live music events, the exciting Dropzone Waterpark, and delightful wine tastings. Whether you’re looking to hit the slopes or relax with a glass of wine, Winchester has something for everyone.
Shopping
If you're up for a drive, visit Vermont Marketplace, a vibrant shopping mall 16.1km from Winchester, offering a mix of business and entertainment. For a local touch, check out the Brattleboro Farmers' Market, 19.3km away, or Delectable Mountain Cloth, a cozy store also 16.1km from town.
Recreation
Experience luxury at Crumpin-Fox Golf Club, where you can enjoy a round of golf in a serene setting just 16.1km from Winchester. For entertainment, The Stone Church offers live music and vibrant energy 17.7km away, while Brattleboro Country Club provides another luxurious golfing experience 19.3km from your location.
Adventure
Explore the Metacomet-Monadnock Trail for a thrilling hiking experience with stunning scenery and outdoor vibes, located 9.7km from Winchester. For winter sports, head to Harris Hill Ski Jump, 17.7km away, or Granite Gorge, 19.7km away, both offering exciting skiing adventures.
Nightlife
Experience the vibrant nightlife atmosphere in Winchester by visiting the Latchis Theatre for a romantic cultural evening. Alternatively, explore the Hooker-Dunham Theater & Gallery or catch a performance at the New England Youth Theatre, both offering engaging entertainment and a lively ambiance just 16.1km away.
*Distances are measured in a straight line; actual driving distances may vary depending on the route.
Booking tips and Expedia advantages for Winchester
When planning your visit to Winchester, New Hampshire, consider traveling during the cheaper months of March and December to January for lower accommodation rates. Tuesdays are the most affordable days to stay, while Saturdays tend to be pricier. Use Expedia to find great hotel deals by filtering prices from lowest to highest, and consider package deals that combine hotels with flights and activities for additional savings. Take advantage of free activities in the area to enhance your experience while keeping costs down.
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 customize your preferences, such as your budget, desired location, and preferred hotel type. To find the best prices and offers, arrange 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 deal.
Find the best attractions near Winchester
Winchester, New Hampshire, is perfect for outdoor lovers and those seeking a romantic getaway. The area boasts stunning nature reserves, forests, and parks that invite exploration and adventure. Whether you're looking for eco-friendly activities or simply want to enjoy the beautiful scenery, Winchester offers a variety of attractions for every traveler. Experience the charm of this picturesque town while immersing yourself in its natural beauty.
Moody Center: Located 8.0km from Winchester, the Moody Center is a tranquil institute that offers a peaceful environment for reflection and learning. Surrounded by nature, it’s perfect for those seeking a serene escape.
Thomas Aquinas College: Also 8.0km away, this modern college boasts a vibrant atmosphere intertwined with city vibes. Explore its contemporary architecture and engage with students and faculty who are passionate about education.
Historical Old NMH Campus Building #3: Just 8.0km from Winchester, this historic building exudes cultural significance. Its architecture and rich history provide a glimpse into the past, making it a must-see for history enthusiasts.
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.
Calendar Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
23.2°F (-4.9°C)
Light Rain
Mostly Sunny
Average
Slightly Low
February
25.2°F (-3.8°C)
Light Rain
Mostly Sunny
Slightly Low
Average
March
32.9°F (0.5°C)
Light Rain
Mostly Sunny
Average
Slightly Low
April
45.0°F (7.2°C)
Light Rain
Mostly Sunny
Average
Average
May
57.0°F (13.9°C)
Light Rain
Mostly Sunny
Average
Slightly High
June
64.9°F (18.3°C)
Light Rain
Mostly Sunny
Slightly High
Average
July
71.2°F (21.8°C)
Light Rain
Mostly Sunny
Slightly High
Average
August
69.3°F (20.7°C)
Light Rain
Mostly Sunny
Average
Average
September
61.9°F (16.6°C)
Light Rain
Mostly Sunny
Slightly High
Slightly High
October
50.5°F (10.3°C)
Light Rain
Mostly Sunny
Average
Slightly High
November
38.7°F (3.7°C)
Light Rain
Mostly Sunny
Slightly Low
Average
December
29.7°F (-1.3°C)
Light Rain
Mostly Sunny
Slightly Low
Slightly Low
The nearest major airports for your trip to Winchester
What are some of the best vacation rentals in Winchester?
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: Visitors like this Winchester vacation home rental. It is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. See all 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?
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 6 hotels and other accommodations to choose from. Find out more about 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.