Photo by Donny Campos

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Top hotels and accommodation in Winchester

Our top choices for Winchester hotels

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1001)
"Beautiful hotel with very clean and comfortable rooms. The atmosphere was relaxing, and everything felt well maintained. Perfect stay!"
The Colonial Hotel

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (319)
"It was a peaceful, clean, quiet stay. "
The price is AU$295
includes taxes & fees
17 Sept - 18 Sept
The Inn At Crumpin Fox

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1001)
"Good value for a two night stay for work "
The price is AU$155
includes taxes & fees
25 Sept - 26 Sept
The Covered Bridge Inn

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (464)
"Friendly staff. Room was nice "
The price is AU$227
includes taxes & fees
25 Sept - 26 Sept
Black Mountain Inn

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1001)
"Great for stay"
The price is AU$228
includes taxes & fees
15 Sept - 16 Sept
Best Western Plus Keene Hotel

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 AU$299
includes taxes & fees
21 Sept - 22 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (702)
"I was only there for a few hours sleep "
The price is AU$134
includes taxes & fees
14 Sept - 15 Sept
Travelodge by Wyndham Brattleboro VT

Gardner Inn

2.0 star property
5.0 out of 10, (7)
"The property needs work but hte staff was pleasant and the facility was quiet. "
The price is AU$172
includes taxes & fees
14 Sept - 15 Sept
Gardner Inn

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
9.6 out of 10, Exceptional, (596)
"Great place!"
The price is AU$263
includes taxes & fees
15 Sept - 16 Sept
Riverside Hotel, an Ascend Collection Hotel

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (420)
"Highly recommend PEARL restaurant nearby! Always comfortable accommodations. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (685)
"This was a nice stay, thanks"
The price is AU$218
includes taxes & fees
14 Sept - 15 Sept
Comfort Inn & Suites Brattleboro I-91

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (788)
"Great stay!"
The price is AU$214
includes taxes & fees
14 Sept - 15 Sept
Latchis Hotel

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1001)
"Always a pleasure to stay at the Colonial"
The price is AU$233
includes taxes & fees
25 Sept - 26 Sept
Colonial Motel And Spa

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (879)
"Super easy check in and nice room! "
The price is AU$226
includes taxes & fees
17 Sept - 18 Sept
Hampton Inn Brattleboro

Days Inn by Wyndham Keene NH

2.0 star property
7.0 out of 10, Good, (1000)
"Would stay again"
The price is AU$155
includes taxes & fees
14 Sept - 15 Sept
Days Inn by Wyndham Keene NH

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1001)
"Very enjoyable stay"
The Putney Inn

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is AU$224
includes taxes & fees
22 Sept - 23 Sept
Blooming Inn

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (737)
"We stayed in the loft room and it was great! Right downtown, free parking right out the back and the staff is super nice. I would definitely go back!"
The price is AU$287
includes taxes & fees
17 Sept - 18 Sept
Fairfield Inn & Suites by Marriott Keene Downtown

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
8.4 out of 10, Very good, (896)
"Clean room - friendly staff - convenient location "
The price is AU$205
includes taxes & fees
22 Sept - 23 Sept
Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (847)
"The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. "
The price is AU$272
includes taxes & fees
21 Sept - 22 Sept
Hampton Inn & Suites Greenfield
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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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

More cheap accommodation in Winchester

More cheap accommodation in Winchester

Find out more about 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Hampton Inn Brattleboro and Keene Elm City Hotel, an Ascend Collection Hotel. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

Lovely 2nd Floor Apartment: This holiday home rental outside of Winchester offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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 Keene Elm City Hotel, an Ascend Collection 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 6 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, Ashuelot River and Cass Pond. A couple of additional sights to add to your itinerary are Pisgah State Park and New England Sweetwater Farm & Distillery. 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.