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Our top choices for Winchester hotels

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
10.0 out of 10, Exceptional, (2 reviews)
"Staff was friendly and accommodating "
Canada
James
The price is NZ$153
includes taxes & fees
15 Apr - 16 Apr
Windmill Motel Restaurant

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (162 reviews)
"We had a wonderful stay at The Burrell House. The room was large, beautifully renovated with a well thought out design. It is a very short walk or drive to Main Street where there were a multitude of restaurants and shops. We truly enjoyed our stay and plan to book again soon. "
United States
Melissa
The price is NZ$213
includes taxes & fees
15 Apr - 16 Apr
The Burrell House

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is NZ$277
includes taxes & fees
14 Apr - 15 Apr
Blooming Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is NZ$239
includes taxes & fees
15 Apr - 16 Apr
Four Columns Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
"Great Stay!"
United States
Nicholas
The price is NZ$141
includes taxes & fees
20 Apr - 21 Apr
The Putney Inn

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (72 reviews)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is NZ$367
includes taxes & fees
14 Apr - 15 Apr
The Inn At Quail Run

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,001 reviews)
"Clean room, quiet, good price "
United States
Derek
The price is NZ$134
includes taxes & fees
20 Apr - 21 Apr
The Covered Bridge Inn

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (957 reviews)
"I wish I could have stayed longer. Very nice hotel "
United States
Rosa
The price is NZ$200
includes taxes & fees
28 Apr - 29 Apr
Hampton Inn Brattleboro

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,009 reviews)
"Great staff, great food, clean, friendly"
United States
Thomas
The price is NZ$253
includes taxes & fees
19 Apr - 20 Apr
The Colonial Hotel

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, (1,004 reviews)
"Clean room, polite staff,kids enjoyed the indoor heated pool they also have a small gym and breakfast in the morning couldn't beat the price definitely a great place for the family dogs are also welcome!!"
United States
Sean
The price is NZ$238
includes taxes & fees
16 Apr - 17 Apr
Keene Elm City Hotel, an Ascend Collection Hotel

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (351 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is NZ$276
includes taxes & fees
26 Apr - 27 Apr
Colonel Williams Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (490 reviews)
"Pet friendly for $15 plus tax. The place noisy with heat turned on in the room "
United States
Angela
The price is NZ$181
includes taxes & fees
14 Apr - 15 Apr
Black Mountain Inn

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (17 reviews)
"Warm hospitality, very nice breakfast"
United States
Christopher
The price is NZ$279
includes taxes & fees
14 Apr - 15 Apr
Inn at Valley Farms

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (171 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is NZ$251
includes taxes & fees
15 Apr - 16 Apr
The Carriage Barn Inn

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,004 reviews)
"Nice rooms"
United States
Kim
The price is NZ$268
includes taxes & fees
14 Apr - 15 Apr
Best Western Plus Keene Hotel

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (181 reviews)
"Great place and very clean!!"
United States
Emil
The price is NZ$406
includes taxes & fees
16 Apr - 17 Apr
Vikings Villages Resort

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.2 out of 10, Wonderful, (457 reviews)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
The price is NZ$251
includes taxes & fees
19 Apr - 20 Apr
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (863 reviews)
"Great location, great staff really cool old building with lots of character"
Canada
David
The price is NZ$236
includes taxes & fees
15 Apr - 16 Apr
Latchis Hotel

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is NZ$448
includes taxes & fees
18 Apr - 19 Apr
The One Cat B&B

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (357 reviews)
"Perfect place for what we needed!"
United States
Cathleen
The price is NZ$352
includes taxes & fees
15 Apr - 16 Apr
The Inn At Crumpin Fox
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.

Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

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

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 traveller data. Two other choices for your trip to the area are Colonial Motel And Spa and Hampton Inn Brattleboro. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Beautiful Custom Built Timber Frame Home, Sleeps 11: This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What are some hotels with pools in Winchester?
The Colonial Hotel: Features a sauna, an indoor pool and free self parking. Colonial Motel And Spa and Hampton Inn Brattleboro are a couple of other choices that offer an on-site pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester will definitely enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 7 hotels and other accommodation options to choose from. Find out more about Winchester.
What are the top places to visit in Winchester?
Natural beauty is on display at Cass Pond, Rhododendron State Park and Royalston State Forest. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Winchester Speedpark. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

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