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

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Our top choices for Winchester hotels

Shelburne Springs

Shelburne Springs
2.0 star property
Shelburne
The price is NZ$807
includes taxes & fees
13 July - 14 July
Shelburne Springs

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,013 reviews)
"Staff was very professional and friendly"
United States
Ramica
The price is NZ$224
includes taxes & fees
13 July - 14 July
Keene Elm City Hotel, an Ascend Collection Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,015 reviews)
"Great staff. Clean and comfortable. Fantastic breakfast. Loved the Andes mints."
United States
Gordon
The price is NZ$224
includes taxes & fees
2 Aug - 3 Aug
Best Western Plus Keene Hotel

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.0 out of 10, Wonderful, (25 reviews)
"Clean room, good prices, friendly staff"
United States
Amy
The price is NZ$235
includes taxes & fees
15 July - 16 July
Windmill Motel Restaurant

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is NZ$306
includes taxes & fees
26 July - 27 July
The Carriage Barn Inn

Deerfield Inn

Deerfield Inn
3.0 star property
Deerfield
10.0 out of 10, Exceptional, (3 reviews)
"We thoroughly enjoyed all aspects of our stay. The Inn was incredibly charming and comfortable. We will definitely be back."
United States
Dan
The price is NZ$541
includes taxes & fees
13 July - 14 July
Deerfield Inn

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (926 reviews)
"This hotel was the perfect landing place from a lot of traveling. It was clean, had unique historic ambience, and walkable to the whole town. Highly recommend!"
United States
Laurel
The price is NZ$247
includes taxes & fees
19 July - 20 July
Latchis Hotel

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (1,007 reviews)
"A little overpriced but a good stay"
United States
David
The price is NZ$241
includes taxes & fees
28 July - 29 July
Hampton Inn Brattleboro

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (357 reviews)
"Great breakfast!"
United States
Billie
The price is NZ$298
includes taxes & fees
14 July - 15 July
Colonel Williams Inn

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (173 reviews)
"Self check-in and checkout. Room was very clean but a bit too much potpourri for my allergies. Will stay here again when in Keene. "
United States
Charles
The price is NZ$262
includes taxes & fees
20 July - 21 July
The Burrell House

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,011 reviews)
"Food at restaurant was phenomenal"
United States
Zachary
The price is NZ$296
includes taxes & fees
19 July - 20 July
The Colonial Hotel

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (207 reviews)
"It was very unique and great"
United States
Christopher
The price is NZ$349
includes taxes & fees
15 July - 16 July
Vikings Villages Resort

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (376 reviews)
The price is NZ$315
includes taxes & fees
16 July - 17 July
The Inn At Crumpin Fox

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,002 reviews)
"The staff was able to recommend places to go and eat, which was really nice."
United States
Alyssa
The price is NZ$248
includes taxes & fees
26 July - 27 July
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (833 reviews)
"Staff wasfriendly and my room is very clean"
United States
Michael
The price is NZ$254
includes taxes & fees
26 July - 27 July
Comfort Inn & Suites Brattleboro I-91

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (141 reviews)
"Appealing common spaces, lovely selections at the coffee/tea station, library and games. Everything for a cozy respite in a great location. Walk to the local village and attractions, central to exploring the Mohawk Trail."
United States
Annette
The price is NZ$294
includes taxes & fees
13 July - 14 July
Blooming Inn

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,009 reviews)
"Great breakfast, friendly staff and good place to stay."
United States
Michael
The price is NZ$166
includes taxes & fees
26 July - 27 July
Days Inn by Wyndham Keene NH

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (926 reviews)
"Check in was very good. Customer service was exceptional. The room however smelled of cigarette smoke. Overall a good experience."
United States
Joseph
The price is NZ$300
includes taxes & fees
26 July - 27 July
Hampton Inn & Suites Greenfield

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (497 reviews)
"Bed was comfy. Room was clean. "
United States
Katherine
The price is NZ$258
includes taxes & fees
15 July - 16 July
Black Mountain Inn

Gardner Inn

Gardner Inn
2.0 star property
Gardner
7.6 out of 10, Good, (34 reviews)
"Great for a quick stay while passing through!"
United States
Cristen
The price is NZ$192
includes taxes & fees
19 July - 20 July
Gardner Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Winchester attractions

Learn more about Winchester

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic city centre district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

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

Top Winchester Hotel Reviews

Recent Reviews in Winchester

More cheap accommodation in Winchester

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 programme – gives you instant access to perks and 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$166 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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