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Our top choices for Winchester hotels

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (989 reviews)
"The staff was very friendly."
United States
Steven
The price is AU$189
includes taxes & fees
21 June - 22 June
Hampton Inn Brattleboro

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, (1,000 reviews)
"Really friendly, helpful and accommodating staff. Clean and well maintained. Would definitely stay here again!"
United States
Sarah
The price is AU$162
includes taxes & fees
8 June - 9 June
Keene Elm City Hotel, an Ascend Collection Hotel

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.2 out of 10, Wonderful, (12 reviews)
"Clean room, good prices, friendly staff"
United States
Amy
The price is AU$193
includes taxes & fees
9 June - 10 June
Windmill Motel Restaurant

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (170 reviews)
"Self check-in and checkout. Room was very clean but a bit too much potpourri for my allergies. Will stay here again when in Keene. "
United States
Charles
The price is AU$220
includes taxes & fees
14 June - 15 June
The Burrell House

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)
"We love staying here. It’s very clean, staff is always friendly,and the breakfast choices are great!!"
United States
Jennifer
The price is AU$184
includes taxes & fees
10 June - 11 June
Best Western Plus Keene Hotel

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (40 reviews)
"The hot tub was so amazing"
United States
Mark
The price is AU$194
includes taxes & fees
8 June - 9 June
Four Columns Inn

Deerfield Inn

Deerfield Inn
3.0 star property
Deerfield
The price is AU$415
includes taxes & fees
8 June - 9 June
Deerfield Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is AU$263
includes taxes & fees
15 June - 16 June
The Carriage Barn Inn

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (812 reviews)
"Great location for a stay on the way to Maine. Comfortable everything!"
United States
Linda
The price is AU$200
includes taxes & fees
2 July - 3 July
Comfort Inn & Suites Brattleboro I-91

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
The price is AU$234
includes taxes & fees
11 June - 12 June
Colonel Williams Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (137 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is AU$218
includes taxes & fees
8 June - 9 June
Blooming Inn

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (894 reviews)
"Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!"
United States
Sharon
The price is AU$205
includes taxes & fees
8 June - 9 June
Latchis Hotel

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,002 reviews)
"Great breakfast, friendly staff and good place to stay."
United States
Michael
The price is AU$143
includes taxes & fees
10 June - 11 June
Days Inn by Wyndham Keene NH

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,003 reviews)
"Good place to stay "
United States
Glenn
The price is AU$233
includes taxes & fees
15 June - 16 June
The Colonial Hotel

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.2 out of 10, Wonderful, (73 reviews)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is AU$304
includes taxes & fees
8 June - 9 June
The Inn At Quail Run

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (915 reviews)
"Good breakfast buffet"
United States
Jennifer
The price is AU$272
includes taxes & fees
30 June - 1 July
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, (366 reviews)
"Fantastic breakfast!"
United States
allisha
The price is AU$257
includes taxes & fees
8 June - 9 June
The Inn At Crumpin Fox

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.6 out of 10, Excellent, (1,000 reviews)
"Perfect for an overnight!"
United States
Lori
The price is AU$170
includes taxes & fees
9 June - 10 June
The Putney Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,003 reviews)
"Clean room, useful fridge and microwave, safe parking."
United States
Elizabeth
The price is AU$202
includes taxes & fees
9 June - 10 June
The Covered Bridge Inn

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (196 reviews)
"Such a cozy space in the chalet. Wish we had stayed more than an overnight to enjoy accommodations. "
United States
Jan
The price is AU$248
includes taxes & fees
5 July - 6 July
Vikings Villages Resort
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 accommodation in Winchester

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Enjoy activities like skiing, cycling trails, and exploring stunning forests and lakes.
  • Cultural Attractions: Visit historic sites such as Winchester College and the Winchester Cathedral for a taste of history.
  • Relaxing Getaways: Indulge in rejuvenating spa breaks and unwind in tranquil gardens.
  • Unique Shopping Experience: Explore the local shopping centre for a distinctive retail experience.
  • Welcoming Atmosphere: Experience the warmth of friendly locals and a charming city centre perfect for exploration.

Find great hotels near Winchester

Discover a range of accommodation options in Winchester, New Hampshire, perfect for your holiday getaway. From charming bed and breakfasts to modern hotels, you'll find choices that cater to various preferences, including pet-friendly and business-focused facilities. Experience the best of Winchester with comfortable lodging that suits your travel needs, whether you're seeking adventure or a peaceful retreat.

  • Colonial Motel And Spa: Nestled 19.3km from Winchester, the Colonial Motel And Spa is a charming 3-star accommodation perfect for families and pet lovers seeking adventure. This motel features a variety of onsite and nearby recreational activities, including snowshoeing, hiking, and mountain biking, ensuring an action-packed stay. Families will appreciate the thoughtful amenities for children, such as sledding opportunities and first aid kits. With a pet-friendly policy that welcomes dogs, this property is an excellent choice for those travelling with furry companions while enjoying the great outdoors.
  • Days Inn by Wyndham Keene NH: Located 17.7km from Winchester, the Days Inn by Wyndham Keene NH offers a business-focused experience combined with pet-friendly accommodations. This hotel provides essential facilities for business travellers, including a 24-hour business centre, making it a convenient choice for those on work trips. The property has specific policies for pets, allowing dogs and service animals, ensuring your furry friends are well-catered for during your stay. With its focus on comfort and convenience, this hotel is ideal for professionals looking to blend work and leisure.
  • The Covered Bridge Inn: Situated 19.3km from Winchester, The Covered Bridge Inn is a fantastic choice for adventure seekers and business travellers alike. This hotel features accessible business amenities, making it suitable for corporate stays while also providing opportunities for thrilling outdoor activities like rafting and snow tubing nearby. Guests can enjoy the balance of work and play, with comfortable accommodations that cater to both leisure and business needs. With its commitment to providing a unique experience, this inn is sure to impress.

Where to stay in and around Winchester

Winchester, New Hampshire, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a romantic getaway. Explore the charming city centre and unwind in the tranquil gardens of Hampshire. Experience the warmth of friendly locals and the adventure of secluded spots nearby. Whether you're strolling through historic sites or enjoying the family-friendly atmosphere, Winchester is a wonderful destination for relaxation and exploration.

  • Brattleboro: Located 16.1km from Winchester, Brattleboro is a charming city known for its vibrant arts scene and outdoor adventures. With a steady flow of visitors throughout the year, this spot peaks between July and September, drawing those eager for skiing, sports, and thrilling experiences. Highlights include access to ski fields and resorts, perfect for winter sports enthusiasts. Nature lovers will appreciate the nearby lakes, mountains, and valleys that offer breathtaking views and recreational opportunities, making it an excellent base for exploration.
  • Keene: Just 19.3km away from Winchester, Keene is a delightful city that captivates visitors with its outdoor activities and stunning scenery. The travel experience here is relatively consistent, with peaks occurring in July, August, and October. Known for its beautiful ski resorts and fields, Keene is perfect for adventurers. Additionally, the presence of lakes and a modern college university adds to the vibrant atmosphere. Outdoor enthusiasts will find plenty of hiking and recreational options that showcase the area's natural beauty.
  • Richmond: Nestled within the vicinity of Winchester, Richmond is a picturesque village that attracts visitors with its scenic landscapes and outdoor adventures. While visitation is moderately seasonal, with peaks in February and June to July, the charm of Richmond lies in its recreational areas and skiing options. With easy access to lakes, the national state park, and mountains, it's an ideal destination for those looking to immerse themselves in nature and enjoy a range of outdoor activities.

Things to do near Winchester

Winchester, New Hampshire, offers a charming getaway perfect for outdoor enthusiasts and couples alike. Enjoy thrilling activities like skiing at local resorts or exploring picturesque cycling trails. For relaxation, indulge in rejuvenating spa breaks, and don’t miss the chance to visit the shopping centre for a unique retail experience. Additionally, consider a campus tour or some adventurous karting in nearby Southampton for a well-rounded holiday.

Shopping

If you're up for a drive, check out Vermont Marketplace, a vibrant shopping centre 16.1km away, offering a mix of business and entertainment. For a local experience, visit Delectable Mountain Cloth, also 16.1km from Winchester, for unique gifts. Brattleboro Farmers' Market is a great stop 19.3km away for local produce and crafts.

Recreation

Crumpin-Fox Golf Club offers a luxurious retreat with stunning fairways, perfect for golf enthusiasts seeking relaxation. The Stone Church provides vibrant entertainment vibes with live music, while Northfield Golf Club invites you to enjoy outdoor sports in a picturesque setting, perfect for unwinding in nature.

Adventure

Embark on the Metacomet-Monadnock Trail, a 9.7km hiking adventure with breathtaking scenery and outdoor vibes. For thrill-seekers, the Harris Hill Ski Jump, located 17.7km away, offers an exhilarating ski experience. Don't miss the Wetmore Trailhead, 25.7km from Winchester, perfect for outdoor explorations.

Nightlife

Experience the charm of Winchester's nightlife by catching a show at the Latchis Theatre or the Actors Theatre Playhouse, both offering a mix of culture and entertainment. For a unique twist, visit the Hooker-Dunham Theater & Gallery, where art meets performance in a captivating setting.

Booking tips and Expedia advantages for Winchester

For an affordable trip to Winchester, New Hampshire, consider visiting in March or between December and January, as these months offer lower accommodation prices. Booking your stay on a Tuesday can also save you money compared to a Saturday. Use Expedia’s search tool to filter for budget-friendly options and Eco-certified hotels. Combining your hotel, flights, and activities can yield great package deals. Look for accommodations around AU$64 per night to maximise savings while enjoying the charm of Hampshire.

  • 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 set your budget, choose your ideal location, and more. You can organise your results to display prices from lowest to highest, making it easy to find the most affordable accommodation first. Additionally, you can refine your choices by hotel type—if you select the Eco-certified filter, you'll find a selection of sustainable and environmentally friendly hotels ready for booking.
  • Consider bundling your trip: You can save some dollars by combining your Winchester hotel stay with your flights and activities through an Expedia package deal.

Find the best attractions near Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and romantic getaways, offering stunning forests, nature reserves, and lakes. Explore top attractions like Winchester College, the historic Winchester Cathedral, and the Winchester Science Centre for a blend of adventure and eco-friendly experiences. Whether you seek scenic views or cultural insights, Winchester has something for every traveller looking to immerse themselves in nature and history.

  • Thomas Aquinas College: Experience the vibrant atmosphere of this modern university, where academic excellence meets a dynamic community. Located 8.0km from Winchester, the college offers stunning architecture and lively campus life, perfect for a leisurely stroll.
  • Moody Center: This institute, also situated 8.0km from Winchester, provides a serene environment for reflection and learning. Visitors can appreciate the tranquil surroundings and engage in various programs designed to enrich the mind and spirit.
  • Historical Old NMH Campus Building #3: Immerse yourself in the rich cultural history of this historic building, located 8.0km away. Its architectural charm and storied past make it a fascinating stop for history enthusiasts.

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 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

If you're flying to Winchester, New Hampshire, there are three major airports to consider. Hartford, CT (BDL-Bradley Intl.) is situated 96.6km away, with nearby accommodation options like the 4-star Simsbury 1820 House, 11.3km from the airport, and the 3.5-star Sheraton Hartford Hotel, which is right at the airport. Manchester, NH (MHT-Manchester-Boston Regional) is 78.9km away, offering the 5-star Grand at Bedford Village Inn just 6.4km from the airport and the 3.5-star Even Hotels Manchester Airport by IHG, only 3.2km away. Lastly, Worcester, MA (ORH-Worcester Regional) is 46.4km from Winchester, featuring the 4-star Beechwood Hotel, 8.0km away, and the 3.5-star AC Hotel by Marriott, 6.4km away.

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 traveller data. Two other choices for your trip to the area are Latchis Hotel and Hampton Inn Brattleboro. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!: This holiday home rental outside of Winchester is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What are some hotels with pools in Winchester?
The Colonial Hotel: Features a sauna, an indoor pool and free self parking. Hampton Inn Brattleboro and Best Western Plus Keene Hotel are a couple of other choices that offer an on-site pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester will definitely enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 7 hotels and other accommodation options to choose from. Find out more about Winchester.
What are the top places to visit in Winchester?
Natural beauty is on display at Rhododendron State Park, Cass Pond and Royalston State Forest. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Winchester Speedpark. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

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