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

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21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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Our top choices for Winchester hotels

1. Centennial House

Centennial House
Northfield
United Kingdom
Alan
AU$255
includes taxes & fees
25 Oct - 26 Oct
Centennial House

2. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Donna
AU$196
includes taxes & fees
11 Nov - 12 Nov
Windmill Motel Restaurant

3. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
Heather
AU$179
includes taxes & fees
4 Nov - 5 Nov
The Inn At Crumpin Fox

4. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Lisa
AU$197
includes taxes & fees
25 Oct - 26 Oct
Keene Elm City Hotel, an Ascend Collection Hotel

5. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Timothy
AU$232
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG

6. Latchis Hotel

Latchis Hotel
Brattleboro
United States
Erik
AU$222
includes taxes & fees
1 Nov - 2 Nov
Latchis Hotel

7. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Faith
AU$173
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn Brattleboro

8. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
AU$176
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Brattleboro I-91

9. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Thomas
AU$235
includes taxes & fees
19 Nov - 20 Nov
Riverside Hotel, an Ascend Collection Hotel

10. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
AU$219
includes taxes & fees
3 Nov - 4 Nov
Best Western Plus Keene Hotel

11. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
CHERYL
AU$143
includes taxes & fees
26 Oct - 27 Oct
Days Inn by Wyndham Keene NH

12. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Neil
AU$251
includes taxes & fees
19 Nov - 20 Nov
Hampton Inn & Suites Keene

13. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Cecil
AU$312
includes taxes & fees
1 Nov - 2 Nov
Vikings Villages Resort

14. Black Mountain Inn

Black Mountain Inn
Brattleboro
United States
Ron
AU$209
includes taxes & fees
28 Oct - 29 Oct
Black Mountain Inn

15. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
Christopher
AU$300
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Keene Downtown

16. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Richard
AU$238
includes taxes & fees
27 Oct - 28 Oct
The Carriage Barn Inn

17. The Burrell House

The Burrell House
Keene
United States
Carol
AU$212
includes taxes & fees
2 Nov - 3 Nov
The Burrell House

18. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
United States
Luis
AU$156
includes taxes & fees
19 Nov - 20 Nov
Econo Lodge Brattleboro South

19. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
Adolfo
AU$165
includes taxes & fees
22 Oct - 23 Oct
The Covered Bridge Inn

20. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
United States
Deborah
AU$293
includes taxes & fees
3 Nov - 4 Nov
Courtyard by Marriott Keene Downtown
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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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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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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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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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Attleboro Mountain

Commune with nature and explore the great outdoors at Attleboro Mountain during your travels in Richmond.
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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 bridge over a river with a red roof, surrounded by trees and buildings.

Top Winchester Hotel Reviews

Recent Reviews in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

8/10 Good
"Clean comfortable room with a comfortable bed. I didn’t like the smell of whatever cleaning product they used, it was a bit bit strong let the kind you used to cover up something. Was this recently a smoking hotel? Also I missed an cycle in the fitness center, although the machines that were there seemed to work well. All in all it’s about what you would expect for a moderately priced hotel in New Hampshire during leaf peeper season."
Judith 1-night trip
Posted 9 hours ago
Days Inn by Wyndham Keene NH
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The hotel was fairly new. Coffee was the only thing I felt needed changed."
Debbie 1-night trip
Posted 10 hours ago
Hampton Inn Brattleboro
Colonial Motel

Colonial Motel

8/10 Good
"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."
Andrea 3-night trip
Posted 1 day ago
Colonial Motel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Excellent place to stay"
Matthew 1-night trip
Posted 1 day ago
Best Western Plus Keene Hotel
The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"This hotel is amazing. A relief to tired travelers. Clean, quiet, and friendly. And a good associated restaurant near by at the golf course. Very happy with our stay."
Sallie 1-night trip
Posted 2 days ago
The Inn At Crumpin Fox
The Putney Inn

The Putney Inn

10/10 Excellent
"Our room was quiet, clean and very comfortable. Breakfast was nice--more than enough for a decent breakfast before heading out-- waffle maker, toast, yogurt, cold cereal, fruit, juice coffee, and tea, etc. The grounds were beautiful and well kept. The staff was very helpful and parking was super easy right next to the room. The only slight downside was a strong musty odor in the entryway of the room (106), but the room itself smelled clean and was just fine."
Donna 1-night trip
Posted 2 days ago
The Putney Inn
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

8/10 Good
"Great location for access to southern VT and southwest NH, clean rooms, great views of river, and easy access from highway. No breakfast, but coffee bar provided. Free parking. Walls are a little thin."
Laura 3-night trip
Posted 2 days ago
Riverside Hotel, an Ascend Collection Hotel
The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"We love this hotel! We stay every year when we go to Wachusett Mountain"
Mollie 1-night trip
Posted 2 days ago
The Colonial Hotel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

8/10 Good
"Was a good room for a one night stay on a road trip."
Thomas 1-night trip
Posted 2 days ago
Comfort Inn & Suites Brattleboro I-91

More cheap accommodation in Winchester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
AU$132
11 Nov - 12 Nov
includes taxes & fees
The Putney Inn
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
AU$143
26 Oct - 27 Oct
includes taxes & fees
7/10 Good! (1,003 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
AU$169
4 Nov - 5 Nov
includes taxes & fees
7.8/10 Good! (81 reviews)
Gardner Inn
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
AU$176
15 Nov - 16 Nov
includes taxes & fees
8.6/10 Excellent! (889 reviews)
Comfort Inn & Suites Brattleboro I-91
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
AU$197
25 Oct - 26 Oct
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
AU$222
1 Nov - 2 Nov
includes taxes & fees
Latchis Hotel

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

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 cancelled 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 can I save on a hotel booking in Winchester with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Winchester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Winchester?
Prices for hotels in Winchester often vary, but you can find a great deal from AU$132 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 our cheapest rates.

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