Find hotels in Winchester, NH from AED 366

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Compare 442 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Colonial Hotel

3.0 star property
Gardner
8.8 out of 10, Excellent, (1002)
"Great hotel, fantastic restaurant, wonderful place!"
United States
Kate
The Colonial Hotel

The Inn At Crumpin Fox

2.5 star property
Bernardston
9.2 out of 10, Wonderful, (343)
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
United States
Christine
The price is AED 479
AED 535 total
includes taxes & fees
8 Dec - 9 Dec
The Inn At Crumpin Fox

The Covered Bridge Inn

2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is AED 291
AED 320 total
includes taxes & fees
8 Dec - 9 Dec
The Covered Bridge Inn

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
The price is AED 558
AED 614 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very Good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is AED 511
AED 554 total
includes taxes & fees
9 Dec - 10 Dec
Best Western Plus Keene Hotel

Gardner Inn

2.0 star property
Gardner
5.6 out of 10, (17)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is AED 327
AED 366 total
includes taxes & fees
4 Jan - 5 January 2026
Gardner Inn

Travelodge by Wyndham Brattleboro VT

2.5 star property
Brattleboro
6.0 out of 10, (736)
"Reasonable rate for the the accomadations."
United States
David
The price is AED 261
AED 287 total
includes taxes & fees
9 Dec - 10 Dec
Travelodge by Wyndham Brattleboro VT

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
Peterborough
9.4 out of 10, Exceptional, (433)
"Super cute place! Would stay here again"
United States
Danielle
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (628)
"Clean room, beautiful location"
United States
Marcie
The price is AED 559
AED 606 total
includes taxes & fees
6 Jan - 7 January 2026
Riverside Hotel, an Ascend Collection Hotel

Days Inn by Wyndham Keene NH

2.0 star property
Keene
7.0 out of 10, Good, (1001)
"Not exactly spotless by the experience was better than at the Courtyard by Marriott on Railroad St. in Keene NH."
United States
Miroslaw
The price is AED 353
AED 383 total
includes taxes & fees
31 Dec - 1 January 2026
Days Inn by Wyndham Keene NH

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
8.6 out of 10, Excellent, (737)
"Staff was friendly and pool was nice"
United States
Joshua
The price is AED 423
AED 465 total
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn & Suites Brattleboro I-91

Black Mountain Inn

2.0 star property
Brattleboro
7.4 out of 10, Good, (474)
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is AED 375
AED 413 total
includes taxes & fees
8 Dec - 9 Dec
Black Mountain Inn

Latchis Hotel

2.5 star property
Brattleboro
8.4 out of 10, Very Good, (835)
"Great stay"
United States
Jason
The price is AED 465
AED 511 total
includes taxes & fees
8 Dec - 9 Dec
Latchis Hotel

Hampton Inn Brattleboro

2.5 star property
Brattleboro
8.2 out of 10, Very Good, (924)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is AED 526
AED 579 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Brattleboro

Colonial Motel And Spa

3.0 star property
Brattleboro
6.8 out of 10, (1001)
"Nice place to stay for the night."
United States
Robin
The price is AED 441
AED 485 total
includes taxes & fees
8 Dec - 9 Dec
Colonial Motel And Spa

Hampton Inn & Suites Greenfield

2.5 star property
Greenfield
8.6 out of 10, Excellent, (877)
"Friendly staff, great breakfast, comfy beds"
United States
Lori
The price is AED 673
AED 752 total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Greenfield

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
Keene
8.8 out of 10, Excellent, (755)
"Front desk pleasant and helpful Breakfast was good Room was spacious and clean Able to walk to shopping and dining. "
United States
Stephen
The price is AED 661
AED 717 total
includes taxes & fees
13 Dec - 14 Dec
Fairfield Inn & Suites by Marriott Keene Downtown

Hampton Inn & Suites Keene

2.5 star property
Keene
8.8 out of 10, Excellent, (352)
"Clean comfy nice staff "
United States
Katherine
The price is AED 541
AED 587 total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Keene

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (14)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn

The Putney Inn

2.5 star property
Putney
8.4 out of 10, Very Good, (1001)
"Nice motel. "
United States
Richard
The Putney Inn
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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 lush forests in Winchester's stunning nature reserves.
  • Charming Atmosphere: Stroll through picturesque streets that offer a warm and friendly vibe throughout the town.
  • Wine Tastings: Visit nearby wine country for delightful tastings and a refreshing getaway.
  • Family-Friendly Activities: Experience fun-filled attractions like the Dropzone Waterpark, perfect for all ages.
  • Cozy Accommodations: Choose from a range of hotels and charming bed and breakfasts for a comfortable stay.

Find great hotels near Winchester

Discover a range of hotel accommodations in Winchester, New Hampshire, perfect for every traveler. From cozy bed and breakfasts to modern hotels, you'll find options that cater to business needs, adventure seekers, and pet-friendly travelers. Explore the best hotels, room rates, and luxury accommodations to ensure a comfortable stay in this charming New England town.

  • Best Western Plus Keene Hotel: Located 17.7km from Winchester, the Best Western Plus Keene Hotel is a welcoming retreat for business travelers and families alike. This 3-star hotel prides itself on being LGBTQIA-friendly and offers a range of child-friendly amenities, including complimentary cribs. With a focus on comfort and convenience, guests can enjoy modern accommodations and easy access to local attractions, making it an ideal choice for both leisure and business trips.
  • Colonial Motel And Spa: Just 19.3km from Winchester, the Colonial Motel And Spa offers a unique spa-themed experience paired with pet-friendly accommodations. This 3-star motel features an onsite full-service spa, indoor pool, and hot tub, perfect for relaxation after a day of exploration. The property warmly welcomes pets and provides amenities such as a dog-only policy and waived fees for service animals. Guests can experience the best of both worlds with business-friendly facilities and a serene atmosphere.
  • Hampton Inn Brattleboro: Situated 19.3km away from Winchester, the Hampton Inn Brattleboro is an ideal choice for travelers looking for a blend of comfort and practicality. This hotel is LGBTQIA-friendly and accommodates pets, with policies that allow dogs and cats. Guests can expect top-notch service and amenities, ensuring a pleasant stay. The Hampton Inn offers easy access to the surrounding area, making it perfect for both business and leisure travelers seeking a welcoming atmosphere.

Where to stay near Winchester

Winchester, New Hampshire, offers a delightful blend of outdoor adventures and scenic relaxation. Stroll through its charming streets and experience the warm, friendly atmosphere that the city and its surrounding areas provide. Discover nearby wine country for a refreshing getaway, or enjoy leisurely walks in the picturesque landscapes. Whether you're seeking family-friendly activities or a romantic escape, Winchester promises an unforgettable experience filled with beauty and tranquility.

  • Brattleboro: Located 16.1km from Winchester, Brattleboro is a vibrant city that offers a unique blend of adventure and outdoor activities. Known for its scenic beauty, this area attracts visitors year-round, with peak seasons from July to September. Travellers flock here for skiing and various outdoor sports, taking advantage of the nearby ski fields and resorts. The local landscape features picturesque lakes and majestic mountains, along with the nearby national state park, making it a perfect destination for nature lovers and adventure seekers alike.
  • Keene: Situated 19.3km from Winchester, Keene is a charming city renowned for its stunning scenery and outdoor experiences. Similar to Brattleboro, it sees high visitor numbers during the warm months of July and August, as well as in October. Outdoor enthusiasts will enjoy the skiing opportunities at local resorts and the beautiful lakes and mountains in the vicinity. Additionally, Keene is home to a modern college university, adding a youthful energy to the area, making it a great spot for both relaxation and exploration.
  • Ashuelot: Just 3.2km from Winchester, Ashuelot is a quaint city ideal for those seeking a romantic getaway amidst nature. With a steady stream of visitors peaking during the summer and fall, this area offers a serene escape with its tranquil lakes, winding rivers, and rolling mountains. It's a perfect destination for couples and outdoor enthusiasts looking to enjoy peaceful hikes or scenic picnics, surrounded by the beauty of the New England landscape.

Things to do near Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy activities such as skiing at local resorts, exploring scenic landscapes, and attending live music events. Don't miss the chance to experience wine tastings and the fun at Dropzone Waterpark, making it an ideal destination for an exciting and relaxing vacation.

Shopping

In Winchester, you can shop at Delectable Mountain Cloth for unique items. If you're up for a drive, check out the Vermont Marketplace for a vibrant shopping experience or the Brattleboro Farmers' Market for local goods and fresh produce.

Recreation

At Crumpin-Fox Golf Club, enjoy a round of golf surrounded by lush landscapes and luxury amenities, just 16.1km from Winchester. Experience vibrant live music at The Stone Church, located 17.7km away, offering an entertaining atmosphere. Brattleboro Country Club, 19.3km from Winchester, combines elegance with recreational golfing.

Adventure

The Metacomet-Monadnock Trail, located 9.7km from Winchester, offers stunning scenic views and adventurous hiking opportunities. For thrill-seekers, the Harris Hill Ski Jump, 17.7km away, provides an exciting skiing experience, while Granite Gorge, 19.7km away, is perfect for skiing enthusiasts looking for an exhilarating day on the slopes.

Nightlife

In Winchester, the nightlife scene is vibrant with options like Latchis Theatre, Hooker-Dunham Theater & Gallery, and New England Youth Theatre, all within 16.1km. Each venue offers a mix of romance, entertainment, and cultural experiences, perfect for an enjoyable night out.

*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 or December to January, and aim for a Tuesday stay, the least expensive day. Use Expedia’s search tool to filter hotels by price and type, including eco-certified options. Consider booking a package that combines your hotel, flights, and activities for additional savings. Lastly, explore free activities in the area and utilize public transportation where possible to keep costs down while experiencing the local culture.

  • 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: Expedia’s search tool enables you to specify your budget, preferred location, and additional preferences. You can arrange your search results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to filter your choices by hotel type; for instance, selecting the “Eco-certified” filter will showcase sustainable and environmentally-friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your Winchester hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester, New Hampshire, offers a perfect getaway for those seeking outdoor adventures and scenic beauty. With its stunning nature reserves, lush forests, and serene parks, visitors can enjoy a romantic vacation filled with eco-friendly experiences. Whether you're hiking through the woods or relaxing in a park, Winchester provides a delightful escape into nature for travelers looking to connect with the great outdoors.

  • Moody Center: This institute, located 8.0km from Winchester, offers a serene environment ideal for reflection and personal growth. The center hosts various programs that encourage learning and community engagement, making it a perfect spot for those seeking a peaceful retreat.
  • Thomas Aquinas College: Situated 8.0km from Winchester, this modern college exudes vibrant city vibes. Visitors can explore its contemporary campus and appreciate its commitment to a classical education, enjoying a lively atmosphere filled with students and academic discussions.
  • Historical Old NMH Campus Building #3: Just 8.0km away, this historic building showcases rich culture and heritage. As you walk through its halls, you can sense the history and stories that have shaped the local community, making it a fascinating stop 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

For your trip to Winchester, New Hampshire, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is located 96.6km away, with nearby hotels like DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and the 4-star Simsbury 1820 House, 11.3km away. Manchester, NH (MHT-Manchester-Boston Regional) is 78.9km away, offering options 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 away, featuring hotels like Beechwood Hotel, 8.0km from the airport.

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 Hampton Inn & Suites Greenfield and Hampton Inn Brattleboro. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals in Winchester?
Beautiful Custom Built Timber Frame Home, Sleeps 11: You might want to consider this vacation home rental near Winchester, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 garden, a selection of games, and a hot tub 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. Hampton Inn Brattleboro and Comfort Inn & Suites Brattleboro I-91 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, Ashuelot River, and Cass Pond. A couple of additional sights to add to your agenda are Pisgah State Park 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.

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