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Our top choices for Winchester hotels

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is SAR 959
SAR 959 total
includes taxes & fees
11 Feb - 12 Feb
The Maguire House Bed & Breakfast

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,004 reviews)
"Well-kept hotel with a great restaurant."
United States
Adam
The Colonial Hotel

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.2 out of 10, (19 reviews)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is SAR 371
SAR 415 total
includes taxes & fees
21 Jan - 22 Jan
Gardner Inn

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.4 out of 10, Exceptional, (444 reviews)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (278 reviews)
"The Inn was cozy, the room was clean and comfortable. The owner was engaging and helpful. Would definitely stay there again. "
United States
E S
Monadnock Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is SAR 469
SAR 509 total
includes taxes & fees
2 Feb - 3 Feb
The Carriage Barn Inn

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,003 reviews)
"Very comfortable and clean."
United States
Christina
The price is SAR 675
SAR 732 total
includes taxes & fees
29 Jan - 30 Jan
Courtyard by Marriott Keene Downtown

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, (759 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is SAR 656
SAR 712 total
includes taxes & fees
27 Jan - 28 Jan
Fairfield Inn & Suites by Marriott Keene Downtown

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156 reviews)
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
The Burrell House

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,000 reviews)
"Great stay pool was very nice"
United States
Patrick
The price is SAR 521
SAR 566 total
includes taxes & fees
21 Jan - 22 Jan
Best Western Plus Keene Hotel

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (364 reviews)
"Room is very clean , breakfast is good and fresh .coffee serve well all time . Will back to stay again . "
United States
Raymond
The price is SAR 658
SAR 713 total
includes taxes & fees
19 Feb - 20 Feb
Hampton Inn & Suites Keene

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, (978 reviews)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is SAR 450
SAR 488 total
includes taxes & fees
25 Jan - 26 Jan
Keene Elm City Hotel, an Ascend Collection Hotel

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,001 reviews)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
The price is SAR 386
SAR 418 total
includes taxes & fees
25 Jan - 26 Jan
Days Inn by Wyndham Keene NH

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173 reviews)
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
The price is SAR 692
SAR 731 total
includes taxes & fees
1 Feb - 2 Feb
Centennial House

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (14 reviews)
"Picturesque, family run bed and breakfast."
United States
Jay
The price is SAR 589
SAR 639 total
includes taxes & fees
22 Jan - 23 Jan
Inn at Valley Farms

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (350 reviews)
"Staff very accomodating when we needed to check in very early"
United States
Bill
The price is SAR 500
SAR 558 total
includes taxes & fees
3 Feb - 4 Feb
The Inn At Crumpin Fox

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is SAR 1,153
SAR 1,251 total
includes taxes & fees
21 Jan - 22 Jan
Chesterfield Inn

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (886 reviews)
"Friendly staff, great breakfast, comfy beds"
United States
Lori
The price is SAR 704
SAR 787 total
includes taxes & fees
27 Jan - 28 Jan
Hampton Inn & Suites Greenfield

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,005 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
The Putney Inn

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (843 reviews)
"Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!"
United States
Jaime
The price is SAR 470
SAR 517 total
includes taxes & fees
22 Jan - 23 Jan
Latchis Hotel
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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, 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?
The Colonial Hotel, located 26.3 mi (42.3 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 Comfort Inn & Suites Brattleboro I-91 and The Covered Bridge Inn. 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: Features a sauna, an indoor pool, and free self parking. Comfort Inn & Suites Brattleboro I-91 and Hampton Inn Brattleboro 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 8 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 Cass Pond, Barden State Wildlife Management Area, and Ashuelot River. A couple of additional sights to add to your agenda are New England Sweetwater Farm & Distillery and Bennett Gorge. 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.

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