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

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26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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Our top choices for Winchester hotels

1. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Dan
NZ$227
includes taxes & fees
27 Aug - 28 Aug
Windmill Motel Restaurant

2. Centennial House

Centennial House
Northfield
United States
Amy
NZ$298
includes taxes & fees
27 Aug - 28 Aug
Centennial House

3. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Morgan
NZ$217
includes taxes & fees
6 Sept - 7 Sept
Comfort Inn & Suites Brattleboro I-91

4. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Ingrid
NZ$256
includes taxes & fees
30 Aug - 31 Aug
Keene Elm City Hotel, an Ascend Collection Hotel

5. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Timothy
NZ$206
includes taxes & fees
8 Sept - 9 Sept
Hampton Inn Brattleboro

6. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Julia
NZ$270
includes taxes & fees
27 Aug - 28 Aug
Best Western Plus Keene Hotel

7. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Christopher
NZ$274
includes taxes & fees
3 Sept - 4 Sept
Hampton Inn & Suites Keene

8. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Marnie
NZ$311
includes taxes & fees
13 Sept - 14 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG

9. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Juli
NZ$292
includes taxes & fees
20 Sept - 21 Sept
Vikings Villages Resort

10. Latchis Hotel

Latchis Hotel
Brattleboro
United States
Stark
NZ$199
includes taxes & fees
27 Aug - 28 Aug
Latchis Hotel

11. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
VINCENT JOEL
NZ$128
includes taxes & fees
7 Sept - 8 Sept
The Covered Bridge Inn

12. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
Christopher
NZ$303
includes taxes & fees
27 Aug - 28 Aug
The Inn At Crumpin Fox

13. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
Michael
NZ$176
includes taxes & fees
16 Sept - 17 Sept
Days Inn by Wyndham Keene NH

14. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Pauline
NZ$292
includes taxes & fees
21 Sept - 22 Sept
Riverside Hotel, an Ascend Collection Hotel

15. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
James
NZ$315
includes taxes & fees
6 Sept - 7 Sept
Fairfield Inn & Suites by Marriott Keene Downtown

16. Colonial Motel

Colonial Motel
Brattleboro
United States
James
NZ$151
includes taxes & fees
27 Aug - 28 Aug
Colonial Motel

17. Black Mountain Inn

Black Mountain Inn
Brattleboro
United States
Robert
NZ$219
includes taxes & fees
27 Aug - 28 Aug
Black Mountain Inn

18. The Burrell House

The Burrell House
Keene
United States
Justin
NZ$234
includes taxes & fees
8 Sept - 9 Sept
The Burrell House

19. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Jonathan
NZ$252
includes taxes & fees
27 Aug - 28 Aug
The Carriage Barn Inn

20. The Putney Inn

The Putney Inn
Putney
United States
JANE
NZ$200
includes taxes & fees
1 Sept - 2 Sept
The Putney Inn
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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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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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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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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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Conant Public Library

This historic 1892 library houses Winchester's heritage collection, including one of New England's earliest pipe organs. Browse artefacts or research local history with help from knowledgeable staff.
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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 town with a river running through it, surrounded by mountains and trees.

Top Winchester Hotel Reviews

Recent Reviews in Winchester

Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"Very clean. Good full breakfast."
Barbara 1-night trip
Posted 4 hours ago
Hampton Inn Brattleboro
Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Viking Village was such a unique and enjoyable stay! It was impeccable, every detail (and there were a lot of very fine ones) was perfectly executed. Very comfortable, quiet, and felt much more luxurious than we are used to as budget travelers. Every amenity was quality and in working condition, we especially appreciated the fireplace. Beautiful scenery and wildlife. No notes, everything was perfect!"
Annmarie 2-night trip
Posted 4 hours ago
Vikings Villages Resort
Gardner Inn

Gardner Inn

10/10 Excellent
"My room was clean and comfortable. The staff was excellent and very responsive to any and all requests and to even just chat with. Plenty of parking with a special spot for a Veteran - Because We Served - to park."
Sharon 3-night trip
Posted 5 hours ago
Gardner Inn
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"Clean room breakfast was good"
Lori 1-night trip
Posted 9 hours ago
Best Western Plus Keene Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"It was good!"
Ingrid 4-night trip
Posted 22 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"Loved this place! Coffee and fruit available in the common room super early (4:30am)! Very nice staff! Will stay here again for sure."
Kerry 2-night trip
Posted 1 day ago
The Inn At Crumpin Fox
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

8/10 Good
"Basic room. Felt a little dated. Breakfast was amazing."
Jessica 1-night trip
Posted 2 days ago
Hampton Inn & Suites Greenfield
Windmill Motel Restaurant

Windmill Motel Restaurant

10/10 Excellent
"Beautifully restored. Modern electronics, including security."
Steven 1-night trip
Posted 2 days ago
Windmill Motel Restaurant
Colonial Motel

Colonial Motel

8/10 Good
"X"
Steven 1-night trip
Posted 3 days ago
Colonial Motel

More cheap accommodation in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
NZ$176
16 Sept - 17 Sept
includes taxes & fees
7/10 Good! (1,006 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
NZ$185
27 Aug - 28 Aug
includes taxes & fees
7.8/10 Good! (56 reviews)
Gardner Inn
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
NZ$199
27 Aug - 28 Aug
includes taxes & fees
Latchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
NZ$206
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
NZ$217
6 Sept - 7 Sept
includes taxes & fees
8.6/10 Excellent! (849 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
NZ$256
30 Aug - 31 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Enjoy skiing at local resorts and explore scenic hiking trails in the stunning landscapes of Winchester.
  • Beautiful Nature Reserves: Immerse yourself in the region’s natural beauty with a visit to local forests and parks, ideal for nature enthusiasts.
  • Historic Winchester Cathedral: Discover the impressive architecture and history of Winchester Cathedral, a must-visit landmark.
  • Charming City Centre: Stroll through the friendly city centre, featuring unique shops and a welcoming atmosphere.
  • Diverse Accommodation: Choose from a variety of lodging options, from cosy bed & breakfasts to modern hotels, catering to all travellers.

Find great hotels near Winchester

Discover a range of accommodation options in Winchester, New Hampshire, perfect for every kind of traveller. From charming bed & breakfasts to modern hotels, you'll find facilities tailored for business trips, adventure seekers, and pet-friendly stays. Experience the best of Winchester with affordable options and notable choices like the voco Winchester Hotel, ensuring a delightful getaway in this picturesque town.

  • Best Western Plus Keene Hotel: Nestled 17.7km from Winchester, Best Western Plus Keene Hotel offers a welcoming environment perfect for families, business travellers, and pet owners. This 3-star hotel provides a range of business amenities, including accessible meeting rooms and a well-equipped business centre. Families will appreciate the free cribs available for young children, while furry companions are also welcome, with specific policies in place for dogs. The hotel combines comfort with convenience, ensuring a pleasant stay for all guests.
  • Colonial Motel And Spa: Located 19.3km from Winchester, Colonial Motel And Spa is an ideal retreat for those seeking adventure and relaxation. This 3-star motel features a full-service spa, complete with a hot tub and pool that require adult supervision, making it a perfect spot to unwind after a day of exploration. Adventure enthusiasts can indulge in nearby activities such as skiing, snowboarding, and mountain biking. The business facilities cater to corporate travellers, ensuring a well-rounded experience that balances work and leisure.
  • Days Inn by Wyndham Keene NH: Situated 17.7km from Winchester, Days Inn by Wyndham Keene NH offers a convenient stay for pet owners and business travellers alike. This lodging features a 24-hour business centre, catering to the needs of those on the go. Pets are welcome, with specific restrictions in place for dogs. The hotel combines practicality with comfort, making it a suitable choice for visitors looking to explore the surrounding area while enjoying a relaxing stay.

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 or a relaxing retreat. Explore the charming Winchester city centre with its friendly atmosphere and shopping areas, or venture into nearby regions for family-friendly activities and secluded spots. Whether you're after leisurely strolls or exciting adventures, Winchester provides a memorable experience for every traveller looking to unwind and connect with nature.

  • Brattleboro: Nestled around 16.1km from Winchester, Brattleboro is a vibrant city that attracts visitors year-round, especially during the peak months of July to September. Known for its fantastic skiing experiences, adventure sports, and an outdoor lifestyle, Brattleboro boasts numerous ski fields and resorts. The surrounding natural beauty, including lakes, mountains, and valleys, makes it a haven for outdoor enthusiasts. Visitors can immerse themselves in the local culture, enjoy artsy cafés, and explore charming shops, all while soaking in the stunning scenery.
  • Keene: Located approximately 19.3km from Winchester, Keene is another charming city known for its beautiful landscapes and outdoor activities. With visitor numbers peaking in the summer months of July and August, Keene offers a diverse array of experiences, from skiing to scenic hikes. The presence of a modern college university adds a youthful energy to the city, where travellers can enjoy parks, local festivals, and vibrant art scenes. The nearby lakes and mountains enhance the area’s allure, making Keene ideal for nature lovers and adventure seekers alike.
  • Richmond: Just a stone's throw from Winchester, Richmond is a quaint village that shines in the seasons, particularly in February and during the summer months of June to July. Known for its outdoor activities and scenic views, Richmond provides access to recreational areas, ski fields, and stunning national state parks. The nearby lakes and mountains create a picturesque backdrop for relaxation and adventure. Whether you’re hiking through the woods or enjoying a peaceful day by the lake, Richmond is perfect for those looking to connect with nature.

Things to do near Winchester

Winchester offers a perfect blend of outdoor and scenic experiences ideal for a romantic getaway. Visitors can enjoy skiing at local ski fields and resorts, while also exploring good trails for hiking. Additionally, nearby beaches provide a lovely spot for relaxation and leisure activities, making Winchester a delightful destination for tourists keen on adventure and nature.

Shopping

If you're up for a drive, head to Vermont Marketplace, a vibrant shopping mall 16.1km away, offering a mix of entertainment and family-friendly options. For a local experience, visit Delectable Mountain Cloth, also 16.1km away, for unique gifts. Don't miss the Brattleboro Farmers' Market, 19.3km away, for fresh produce and local crafts.

Recreation

Experience luxury at Crumpin-Fox Golf Club, where you can enjoy pristine greens and upscale amenities only 16.1km from Winchester. For a more casual vibe, Northfield Golf Club offers a fun outdoor golfing experience just 9.7km away. Don’t miss The Stone Church for live music entertainment 17.7km away.

Adventure

Explore the Metacomet-Monadnock Trail for a scenic hiking adventure, 9.7km from Winchester, where nature awaits. Experience thrilling sports at the Harris Hill Ski Jump, located 17.7km away, or enjoy outdoor fun at the Wetmore Trailhead, 19.7km from town, for unforgettable moments.

Nightlife

In Winchester, you can enjoy the Hooker-Dunham Theater & Gallery and Latchis Theatre, both offering a rich blend of culture and entertainment just 16.1km away. For a slightly further experience, the Actors Theatre Playhouse, located 17.7km away, promises a delightful evening filled with family-friendly vibes.

*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 trip to Winchester, New Hampshire, consider visiting during March or December to January for lower accommodation prices. Tuesdays are the cheapest days to stay, while Saturdays tend to be pricier. Use Expedia to find budget-friendly options by sorting results from lowest to highest price and refining your search to eco-certified hotels. Additionally, save money by booking your hotel, flights, and activities together through an Expedia package. Keep an eye out for exclusive offers and last-minute deals to maximise your savings during your visit.

  • 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 to June and 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 specify your budget, desired location, and additional preferences. You can arrange your results to display prices from lowest to highest, making it easy to find the most affordable accommodation first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that you can book.
  • Consider bundling your trip: You can save some dollars by combining your Winchester hotel booking with flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester, New Hampshire, is perfect for outdoor and romantic getaways, offering stunning scenery and eco-friendly adventures. Visitors can explore local nature reserves, forests, and parks, making it ideal for nature enthusiasts. A must-visit is the impressive Winchester Cathedral, which adds a touch of history to your trip. Whether you're seeking relaxation or adventure, Winchester has something to delight every traveller.

  • Moody Center: Immerse yourself in the vibrant atmosphere of Moody Center, an institute renowned for its commitment to education and community engagement. Located 8.0km from Winchester, it offers a unique opportunity to explore various educational programmes and events that foster learning and personal growth.
  • Thomas Aquinas College: Experience the lively city vibes at Thomas Aquinas College, situated 8.0km away. This modern institution combines contemporary architecture with a dynamic academic environment, making it an ideal spot for those interested in higher education and intellectual discourse.
  • Historical Old NMH Campus Building #3: Step back in time at Historical Old NMH Campus Building #3, a captivating historic building located 8.0km from Winchester. With its rich cultural heritage and stunning architecture, it offers visitors a glimpse into the past and the opportunity to appreciate its historical significance.

Best time to go to Winchester

The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, 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 HighSlightly High
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 HighAverage
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

To reach Winchester, New Hampshire, you have several airport options nearby. Hartford, CT (BDL-Bradley Intl.) is situated 96.6km away, with hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. Manchester, NH (MHT-Manchester-Boston Regional), located 78.9km away, features the luxury Grand at Bedford Village Inn, a mere 6.4km from the airport. Additionally, Worcester, MA (ORH-Worcester Regional) is 46.4km away, offering accommodations such as the Beechwood Hotel, 8.0km from the airport. Each hotel provides convenient access to their respective airports, ensuring a smooth travel experience.

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, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 NZ$114 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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