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

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13 Oct - 14 Oct
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Our top choices for Winchester hotels

A two-story house with a red door, green shutters, and a snow-covered front yard.
A kitchenette with a refrigerator, a coffee station, and a fruit basket.
A red building with white trim, surrounded by lush greenery and fruit trees.
A golf course with a brick pathway, wooden boxes, and a tee box.

1. Centennial House

Centennial House
Northfield
United Kingdom
Alan
SAR 607
SAR 641 total
includes taxes & fees
25 Oct - 26 Oct
Centennial House
A bedroom with a geometric-patterned headboard, a bed with a textured white duvet, two pillows, a bedside table with a clock, and a potted plant.
A flat-screen TV mounted on a wall displaying a streaming service interface.
A grassy area with picnic tables and a clock tower.
A room with a round table and two leather chairs, a window with curtains, and a view of a parking lot outside.

2. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Donna
SAR 482
SAR 538 total
includes taxes & fees
18 Oct - 19 Oct
Windmill Motel Restaurant
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.
A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.
A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.
A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Timothy
SAR 556
SAR 611 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

4. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
SAR 532
SAR 577 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Plus Keene Hotel
The exterior of Latchis Hotel with a prominent entrance, large windows, and potted plants.
A lobby with a central circular platform, a statue, and a fountain. There are paintings on the walls and a staircase to the left.
A hotel lobby with a reception desk, seating area, and a large window.
A banquet hall with round tables, chairs, and a staircase.

5. Latchis Hotel

Latchis Hotel
Brattleboro
United States
Erik
SAR 532
SAR 586 total
includes taxes & fees
1 Nov - 2 Nov
Latchis Hotel
A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.
A conference table set for a meeting with chairs and folded red napkins.
A conference room with a long table, six chairs, a projector screen, and a brick wall.
A brick building with a red awning and a sign that reads "The Inn."

6. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
Heather
SAR 456
SAR 510 total
includes taxes & fees
26 Oct - 27 Oct
The Inn At Crumpin Fox
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.
A modern kitchen with wooden cabinets, a coffee machine, a fruit juice dispenser, and a refrigerator.

7. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Mary
SAR 447
SAR 485 total
includes taxes & fees
2 Nov - 3 Nov
Keene Elm City Hotel, an Ascend Collection Hotel
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.
A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.
A hotel suite shop with shelves stocked with snacks and sundries, a refrigerated display case, and a sign indicating 24-hour availability.

8. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Rebecca
SAR 581
SAR 630 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn & Suites Keene
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.
A lobby with wooden paneling, a fireplace, and two green armchairs.
A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.
A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

9. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Faith
SAR 434
SAR 478 total
includes taxes & fees
8 Nov - 9 Nov
Hampton Inn Brattleboro
A bathroom with a freestanding bathtub, a toilet, and a shower area.
A dock extending into a lake with a grassy area in the foreground and trees in the background.
A building with a large balcony overlooking a body of water, a bridge in the foreground, and trees with autumn foliage.
A spacious living room with a large window, a patterned rug, and multiple seating options including a sofa and armchairs.

10. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Jason
SAR 571
SAR 620 total
includes taxes & fees
11 Nov - 12 Nov
Riverside Hotel, an Ascend Collection Hotel
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.

11. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
SAR 416
SAR 457 total
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Brattleboro I-91
A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.
A cozy room with a wooden wall, a red sofa, a small table with a bottle, a book, and a plant.
A wooden log cabin with a snow-covered entrance and a wooden fence in a snowy forest.
A rustic wooden cabin with a thatched roof, a stone wall, and a wooden staircase leading to a balcony.

12. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Cecil
SAR 704
SAR 821 total
includes taxes & fees
19 Oct - 20 Oct
Vikings Villages Resort
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.
A room with a chessboard, leather chairs, a large vase, and a bookshelf.
A dining area with a round wooden table, white chairs, and a green wall.
A living room with a fireplace, a pool table, and comfortable seating.

13. Inn on Putney Road

Inn on Putney Road
Brattleboro
United States
Karla
SAR 1,002
SAR 1,103 total
includes taxes & fees
10 Nov - 11 Nov
Inn on Putney Road
A large, two-story house with a snow-covered driveway and surrounding trees.
A cozy room with a brick fireplace, floral wallpaper, and comfortable seating.
A cozy living room with a fireplace, leather chairs, a sofa, and a table with wine glasses.
A bedroom with a large bed, a blue armchair, a wooden desk, and a view through a glass door.

14. Chesterfield Inn

Chesterfield Inn
West Chesterfield
United States
Wayne
SAR 1,131
SAR 1,227 total
includes taxes & fees
18 Oct - 19 Oct
Chesterfield Inn
Exterior
A bar area with a dark wooden bar, multiple bar stools, and a large screen displaying the hotel name.
A living room with a brick wall, two armchairs, a sofa, a coffee table, and a patterned rug.
A hotel room with a brick wall, a large bed with white bedding, a flat-screen TV, and a desk with a lamp.

15. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
Caroline
SAR 728
SAR 790 total
includes taxes & fees
3 Nov - 4 Nov
Fairfield Inn & Suites by Marriott Keene Downtown
A hotel room with two beds, a TV, a desk, and a window with curtains.
A reception area with a black marble counter, wooden cabinets, and a 'Staff Only' door.
A conference room with a black table, wooden chairs, a mounted TV, and a decorative mirror.
A hotel gym with treadmills, an elliptical, dumbbells, and a stationary bike.

16. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
CHERYL
SAR 348
SAR 378 total
includes taxes & fees
25 Oct - 26 Oct
Days Inn by Wyndham Keene NH
A blue house with a porch, a sign reading "The One Cat", and a garden with various plants and flowers.
A bedroom with a bed, a headboard with a birdcage design, a nightstand with a lamp, and a window with blue curtains.
A cozy living room with a television, books, and a comfortable couch.
A wooden desk with a variety of books and pamphlets, a small tiger figurine, and a mirror reflecting the room.

17. The One Cat B&B

The One Cat B&B
Brattleboro
United States
marjie
SAR 991
SAR 1,091 total
includes taxes & fees
20 Oct - 21 Oct
The One Cat B&B
A wooden table set with plates, cutlery, and a folded napkin.
A cozy room with a wooden floor, a rocking chair, a blue armchair, a bookshelf, and a globe on a table.
A bench in front of an apple tree with ripe apples.
A corner room with wooden flooring, a wooden table, and four chairs. Large windows with curtains are visible, offering a view of a green landscape and a red deck outside.

18. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Richard
SAR 578
SAR 627 total
includes taxes & fees
26 Oct - 27 Oct
The Carriage Barn Inn
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
A hotel room with two beds, a nightstand, a lamp, and a chair.
A room with a dining table, chairs, a sofa, and a red carpet leading to a door.
A sunroom with large windows, a dining area with a table and chairs, and a sofa.

19. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
United States
David
SAR 374
SAR 411 total
includes taxes & fees
11 Nov - 12 Nov
Econo Lodge Brattleboro South
A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.
A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.
An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.
A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".

20. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
United States
Deborah
SAR 710
SAR 770 total
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.
See properties

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 license to fully enjoy this tranquil natural retreat.
See properties

New England Sweetwater Farm & Distillery

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.
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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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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 downtown 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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"Clean room. Breakfast good for quick bite and coffee was good"
JAMES 1-night trip
Posted 10 hours ago
Hampton Inn Brattleboro
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

10/10 Excellent
"I got a quiet room to stay. That was great. Staff was very nice and helpful. Cleaners came every day to clean room"
Vandana 3-night trip
Posted 13 hours ago
Days Inn by Wyndham Keene NH
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"This is a great place to stay in Keene! The location is perfect, the room was immaculate, and the breakfast was great!"
Mary 1-night trip
Posted 14 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Enjoyed the ambiance and tranquility of the property."
Stan Lee 2-night trip
Posted 15 hours ago
Vikings Villages Resort
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"This was the perfect location and having modern amenities and snacks and breakfast was lovely."
Margaret 2-night trip
Posted 1 day ago
Hampton Inn & Suites Greenfield
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."
Teresa D 1-night trip
Posted 1 day ago
Best Western Plus Keene Hotel
Gardner Inn

Gardner Inn

8/10 Good
"Our room was clean. Some things were outdated but it was a good place to stop for the night. No issues"
Sara 1-night trip
Posted 3 days ago
Gardner Inn
Otherland Hotel

Otherland Hotel

8/10 Good
"Beautiful hotel clean quiet"
Nelson 1-night trip
Posted 4 days ago
Otherland Hotel
Colonial Motel

Colonial Motel

8/10 Good
"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."
Leonard 3-night trip
Posted 4 days ago
Colonial Motel

More cheap stays in Winchester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
SAR 316
SAR 348 total
25 Oct - 26 Oct
includes taxes & fees
The Putney Inn
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
SAR 348
SAR 378 total
25 Oct - 26 Oct
includes taxes & fees
7/10 Good! (1,004 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
SAR 372
SAR 415 total
1 Nov - 2 Nov
includes taxes & fees
7.6/10 Good! (78 reviews)
Gardner Inn
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
SAR 416
SAR 457 total
8 Nov - 9 Nov
includes taxes & fees
8.6/10 Excellent! (881 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
SAR 447
SAR 485 total
2 Nov - 3 Nov
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
SAR 532
SAR 586 total
1 Nov - 2 Nov
includes taxes & fees
Latchis Hotel

Find out more about Winchester

Top reasons to visit Winchester

  • 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.

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

When visiting Winchester, New Hampshire, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is 96.6km away, with nearby hotels like DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and Simsbury 1820 House, 11.3km away. Manchester, NH (MHT-Manchester-Boston Regional) is 78.9km away, featuring hotels such as The Grand at Bedford Village Inn, 6.4km from the airport, and DoubleTree by Hilton Manchester Downtown, also 6.4km away. Lastly, Worcester, MA (ORH-Worcester Regional) is 46.4km from Winchester, with options like Beechwood Hotel, located 8.0km from the airport, and AC Hotel by Marriott Worcester, just 6.4km away.

Frequently asked questions

What's the best place to stay in Winchester?
Colonial Motel, located 11.5 mi (18.5 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good options for your stay in the area are The Colonial Hotel and Latchis Hotel. See all available top hotels, or vacation rentals in 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?
For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.
What are some hotels with pools in Winchester?
The Colonial Hotel: Offers a sauna, an indoor pool, and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel and Best Western Plus Keene Hotel are two additional hotels with an onsite pool. View all hotels with pools in 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.
What should I do while I'm visiting Winchester?
Natural beauty is on display at Birch Point, Cass Pond, and Royalston State Forest. A couple of additional sights to add to your agenda are Winchester Speedpark and New England Sweetwater Farm & Distillery. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in 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.