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Our top choices for Winchester hotels

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
United States
Megan
$78 nightly
The price is $86
Dec 29 - Dec 30
Total with taxes and fees
The Covered Bridge Inn

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (746)
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
$120 nightly
The price is $132
Dec 31 - Jan 1, 2026
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1001)
"The room was okay for a quick stop to rest. "
United States
Janice
$76 nightly
The price is $84
Dec 28 - Dec 29
Total with taxes and fees
The Putney Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (126)
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
$128 nightly
The price is $137
Dec 28 - Dec 29
Total with taxes and fees
Blooming Inn

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (345)
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
United States
Christine
$141 nightly
The price is $158
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Inn At Crumpin Fox

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very Good, (968)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
$124 nightly
The price is $135
Dec 28 - Dec 29
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (928)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
$147 nightly
The price is $161
Jan 3 - Jan 4, 2026
Total with taxes and fees
Hampton Inn Brattleboro

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (15)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
$129 nightly
The price is $141
Dec 30 - Dec 31
Total with taxes and fees
Four Columns Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
$130 nightly
The price is $142
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Carriage Barn Inn

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (839)
"Great stay"
United States
Jason
$113 nightly
The price is $125
Dec 29 - Dec 30
Total with taxes and fees
Latchis Hotel

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
$180 nightly
The price is $195
Jan 3 - Jan 4, 2026
Total with taxes and fees
Fairfield Inn & Suites by Marriott Keene Downtown

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
$139 nightly
The price is $151
Dec 28 - Dec 29
Total with taxes and fees
Best Western Plus Keene Hotel

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1000)
"Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. "
United States
Belinda
$144 nightly
The price is $158
Dec 31 - Jan 1, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1000)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
$84 nightly
The price is $91
Dec 31 - Jan 1, 2026
Total with taxes and fees
Days Inn by Wyndham Keene NH

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156)
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
$129 nightly
The price is $140
Dec 28 - Dec 29
Total with taxes and fees
The Burrell House

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1000)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
$157 nightly
The price is $176
Jan 25 - Jan 26, 2026
Total with taxes and fees
The Colonial Hotel

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (881)
"Friendly staff, great breakfast, comfy beds"
United States
Lori
$188 nightly
The price is $210
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (359)
"Clean comfy nice staff "
United States
Katherine
$167 nightly
The price is $181
Jan 25 - Jan 26, 2026
Total with taxes and fees
Hampton Inn & Suites Keene

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (630)
"Clean room, beautiful location"
United States
Marcie
$152 nightly
The price is $165
Jan 26 - Jan 27, 2026
Total with taxes and fees
Riverside Hotel, an Ascend Collection Hotel

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (71)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
$225 nightly
The price is $248
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Inn At Quail Run
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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 downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

More cheap stays in Winchester

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Enjoy skiing at local resorts and explore scenic nature reserves, forests, and parks.
  • Family Fun: Visit the exciting dropzone waterpark for a day of thrilling activities with the family.
  • Wine Country: Indulge in delightful wine tastings in nearby wine regions for a refreshing experience.
  • Live Music: Catch live music events to enhance your vacation atmosphere and enjoy local talent.
  • Charming Accommodations: Choose from cozy bed & breakfasts or modern hotels, catering to every traveler's needs.

Find great hotels near Winchester

Discover a variety of accommodation options in Winchester, New Hampshire, perfect for every traveler. Whether you're seeking a cozy bed & breakfast for a charming getaway or a modern hotel equipped with business amenities, Winchester has it all. Enjoy pet-friendly options and adventure-filled experiences, alongside competitive room rates and luxurious stays. Explore the best hotels in the area and find the ideal spot for your vacation.

  • Best Western Plus Keene Hotel: Nestled 11 miles from Winchester, the Best Western Plus Keene Hotel is a welcoming retreat aimed at families and business travelers alike. This 3-star hotel embraces inclusivity, offering services tailored for LGBTQIA guests. Business-friendly amenities include a fully equipped Business Center, multiple meeting rooms, and ample conference space. Families will appreciate the availability of free cribs, ensuring a comfortable stay for guests of all ages. With its modern facilities and warm atmosphere, this hotel is perfect for both relaxation and productivity.
  • Colonial Motel And Spa: Located 12 miles from Winchester, Colonial Motel And Spa presents a charming blend of comfort and leisure. This 3-star motel is not only pet-friendly but also features a full-service spa, making it an ideal choice for those looking to unwind. Guests can indulge in spa treatments or relax in the hot tub after a day of exploration. The outdoor pool, requiring adult supervision, offers a refreshing escape. Business travelers will find the necessary amenities to stay productive. With a welcoming pet policy, this motel ensures both you and your furry friends enjoy an enjoyable stay.
  • Days Inn by Wyndham Keene NH: Situated 11 miles from Winchester, Days Inn by Wyndham Keene NH is a cozy lodging option that caters to business and pet-friendly travelers. This hotel provides essential amenities for business needs, including a 24-hour Business Center. Guests traveling with pets will find a welcoming environment, with specific policies allowing dogs. The hotel’s comfortable rooms and convenient location make it a great base for exploring the area, ensuring a practical yet enjoyable stay.

Where to stay in and around Winchester

Winchester, New Hampshire, is a charming city perfect for outdoor enthusiasts and those seeking a romantic getaway. Explore the scenic landscapes and indulge in leisurely strolls through the area. Venture into nearby wine country for a refreshing experience, or enjoy the friendly atmosphere of family-friendly neighborhoods. Whether you're looking for adventure or a secluded retreat, Winchester offers a delightful blend of relaxation and exploration for every traveler.

  • Brattleboro: Located a mere 10 miles from Winchester, Brattleboro is a vibrant city that draws visitors year-round. Known for its adventurous spirit, Brattleboro is a hotspot for skiing enthusiasts, offering access to excellent ski fields and resorts. The scenic beauty of this area is complemented by its picturesque lake, mountains, and valleys, making it perfect for both outdoor activities and relaxation. The peak tourist season runs from July to September, attracting those looking for adventure sports and breathtaking landscapes.
  • Keene: Just 12 miles away from Winchester, Keene is another charming city that welcomes outdoor lovers and adventure seekers. With a blend of stunning scenery and recreational possibilities, it’s a great place to explore ski fields and enjoy the local college atmosphere. The area is rich in natural beauty, featuring lakes and mountains that invite hiking and exploration. Peak visitor times are typically from July to August and in October, making it a lively destination during these months.
  • Richmond: Nestled within the Winchester area, Richmond is a quaint village that offers a more seasonal travel experience. Peak visitor times occur in February and from June to July, attracting those keen on outdoor adventures and scenic views. Richmond features recreational areas and ski fields, perfect for winter sports enthusiasts. Its proximity to a national state park and beautiful lakes adds to its allure, making it an ideal spot for nature lovers and those seeking a tranquil getaway.

Things to do near Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Enjoy skiing at local resorts and explore the scenic beauty of the area. Don't miss the exciting dropzone waterpark for family fun, indulge in delightful wine tastings, and catch some live music to enhance your vacation experience. With a blend of adventure and relaxation, Winchester offers something for everyone.

Shopping

In Winchester, you can shop at Delectable Mountain Cloth for unique gifts. Vermont Marketplace, located 10 miles away, offers entertainment and a family-friendly atmosphere. If you're up for a drive, visit the Brattleboro Farmers' Market, 12 miles away, for local produce and crafts amidst a vibrant city vibe.

Recreation

Enjoy a round of golf at Crumpin-Fox Golf Club, where you can immerse yourself in luxury amidst beautiful landscapes. For entertainment, catch a live performance at The Stone Church or the Vermont Jazz Center, both offering vibrant atmospheres and delightful music experiences within a short drive from Winchester.

Adventure

Explore the Metacomet-Monadnock Trail for a thrilling hiking experience amidst beautiful scenery, located 6 miles from Winchester. For skiing enthusiasts, the Harris Hill Ski Jump offers an exhilarating adventure 11 miles away, while Granite Gorge, 16 miles from town, provides fantastic ski opportunities for all skill levels.

Nightlife

Experience the vibrant nightlife in nearby theaters like the Hooker-Dunham Theater & Gallery and Latchis Theatre, both offering culture and entertainment. For a bit more distance, check out the Actors Theatre Playhouse, where you can enjoy family-friendly performances in an inviting atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, visit during the cheaper months of March and December to January, and consider staying on a Tuesday for the best rates. Use Expedia to find affordable hotel options by sorting results from lowest to highest price, and take advantage of package deals that combine flights and activities. Joining Expedia's One Key membership can provide exclusive discounts and allow you to earn OneKeyCash for future stays. Don't miss out on free local activities and explore sustainable lodging options for an eco-friendly stay.

  • 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 customize your travel preferences, including your budget and preferred destination. You can easily sort the results to display hotels from the lowest to highest price, ensuring you find the most affordable options first. Additionally, you have the ability to refine your search by hotel type; for instance, if you select the Eco-certified filter, you'll be shown sustainable and eco-friendly hotels available for booking.
  • 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.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and romantic getaways, offering stunning scenery and eco-friendly experiences. Visitors can explore nearby nature reserves, forests, and parks, making it an ideal destination for adventure seekers. Whether you're hiking through lush landscapes or enjoying a peaceful picnic, Winchester caters to those looking for a refreshing outdoor escape.

  • Moody Center: Located 5 miles from Winchester, Moody Center offers a serene and contemplative environment perfect for reflection and inspiration. The institute is known for its community-oriented approach, providing visitors with opportunities for personal growth and spiritual enrichment.
  • Thomas Aquinas College: Also 5 miles away, Thomas Aquinas College boasts a vibrant atmosphere that combines modern education with a classical curriculum. The campus is lively, filled with students engaged in intellectual discussions, making it a great place to experience city vibes and academic excellence.
  • Historical Old NMH Campus Building #3: Situated 5 miles from Winchester, this historic building immerses visitors in rich cultural heritage. Its architecture and surroundings evoke a sense of nostalgia, inviting exploration of the area's educational history and cultural 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

For your trip to Winchester, New Hampshire, consider flying into one of the nearby airports. Hartford, CT (BDL-Bradley Intl.) is 60 miles away, with accommodations like the DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport. Manchester, NH (MHT-Manchester-Boston Regional) is 49 miles away, offering hotels such as The Grand at Bedford Village Inn, located 4 miles from the airport. Lastly, Worcester, MA (ORH-Worcester Regional) is 44 miles away, with options like Beechwood Hotel, situated 5 miles from the airport. Each hotel provides convenient access to their respective airports for an easy travel experience.

Frequently asked questions

When is the best time to go to Winchester?
The best time to visit Winchester is during the pleasant month of September. At this time, the weather is typically mild, with temperatures ranging from the mid-60s to low 70s Fahrenheit, providing a comfortable backdrop for exploring the city's historic sites and charming streets.

As summer wanes, Winchester experiences a decrease in tourist activity compared to the bustling peak season from June through August. This means that while you can still enjoy the beautiful gardens and outdoor attractions, you'll find the atmosphere less crowded, allowing for a more relaxed experience. Consider wandering through the stunning Winchester Cathedral or taking a leisurely walk along the River Itchen, where the autumn foliage adds a picturesque touch to your adventures.

September is also an excellent month for couples and families alike, as various events often take place, showcasing the local culture and heritage. You can savor delightful meals at outdoor cafes, where the mild weather makes dining al fresco a pleasure.

If you're looking for a more budget-friendly option, October can also be a good choice. While temperatures may drop slightly, you can still appreciate the city's charm, with cozy indoor attractions like museums and historic sites, all while enjoying lower accommodation rates.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Winchester hotel for you.
How can I save on a Winchester hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Winchester hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from $84 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 the cheapest rate.

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