Hotels in Winchester

Winchester: Where Serene Lakes Meet Enchanted Forests

Nestled in the serene landscapes of New Hampshire, Winchester is a hidden gem for nature lovers and adventure seekers. With its picturesque lake and lush forests, this charming town invites visitors to explore the great outdoors through hiking, boating, and fishing. Stroll along the quaint streets of downtown Winchester, where local shops and warm eateries welcome you with open arms. Don’t miss the scenic marina, perfect for a peaceful day by the water. Whether you're seeking a romantic getaway or an off-the-beaten-path escape, Winchester's tranquil beauty and inviting community make it an unforgettable destination. For great hotel rates in Winchester, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Discover great hotels in Winchester

Winchester, New Hampshire offers a variety of hotel accommodations ranging from cozy inns to charming bed-and-breakfasts. Whether you’re looking for a peaceful retreat or a comfortable base for exploring the area, you’ll find options that cater to different preferences and budgets, making your stay enjoyable and convenient. Here are some of the best hotels in Winchester that our travelers love:

1. Centennial HouseOpens in a new window: This inviting 3.5-star Bed and Breakfast is perfect for leisure travelers seeking adventure and comfort. The property features a cozy atmosphere with friendly owners who go above and beyond to ensure a delightful stay. Guests can indulge in delicious meals prepared on-site and enjoy various adventure sports nearby, including skiing, ziplining, and hiking. The warm hospitality and home-like feel create a distinctive experience that resonates with travelers looking for a memorable getaway.
2. Chesterfield InnOpens in a new window: A sophisticated 4.0-star Bed and Breakfast, this hotel caters to adventure enthusiasts and pet lovers alike. With excellent meeting facilities and conference space, it ensures a seamless experience for business travelers while also welcoming pets. Guests can partake in thrilling activities such as snowshoeing, kayaking, and skiing, all just a stone’s throw away. This property’s combination of upscale amenities and the ability to accommodate furry companions makes it a standout choice for discerning travelers seeking a unique blend of comfort and adventure.
3. Inn on Putney RoadOpens in a new window: This elegant 4.0-star Bed and Breakfast is tailored for leisure travelers eager for adventure and relaxation. Surrounded by beautiful gardens, the inn provides an idyllic setting to unwind and enjoy quiet moments. The property boasts a 24-hour business center for those who need to stay connected while offering a variety of recreational activities nearby, including mountain biking and snowboarding. Guests rave about the superb breakfasts, beautifully presented and crafted with care, which elevate the overall experience of their stay.

Top locations to stay in Winchester

Some of the best areas to stay in when visiting Winchester, New Hampshire, are Brattleboro, Northfield, and Keene. Brattleboro offers charming riverside parks and vibrant arts. Northfield features scenic trails and waterfalls, perfect for nature lovers. Keene boasts historic sites and lively nightlife. For first-time visitors, Keene is the best option due to its variety of attractions.

1. BrattleboroOpens in a new window: Brattleboro is a vibrant town known for its rich cultural scene and beautiful natural surroundings. With attractions like the scenic Brattleboro Common and the picturesque Lake Raponda, it's perfect for those who enjoy outdoor beauty. The town's cultural offerings include the Latchis Theatre and the Hooker-Dunham Theater & Gallery, showcasing local performances and events. Brattleboro also has a charming shopping scene, featuring the Brattleboro Farmers' Market and unique boutiques like Delectable Mountain Cloth, making it a delightful place to explore local goods and crafts.
2. KeeneOpens in a new window: Keene boasts a lively atmosphere with its Historic Main Street, where you can stroll through quaint shops and cafes. Nature lovers will appreciate nearby Monadnock State Park, perfect for hiking and enjoying stunning vistas. For those interested in cultural experiences, the Colonial Theatre offers an array of performances, while the Mole Hill Theatre provides a cozy venue for film lovers. Keene's shopping options, including the Brattleboro Farmers' Market and the Vermont Country Store, add to its charm, making it a fantastic place to stay for a mix of relaxation and activity.
3. NorthfieldOpens in a new window: Northfield is a charming, smaller town that offers a cozy getaway. The Madame Sherri Forest is a must-visit for nature enthusiasts, featuring beautiful trails and unique rock formations. For a taste of local life, the Brattleboro Common is a great spot to relax and enjoy seasonal events. Northfield is also home to the Berkshire East Ski Resort, attracting adventure seekers in the winter months. With its serene environment and access to beautiful landscapes, Northfield is an excellent option for travelers looking for a quieter experience.

Things to do in Winchester

Winchester beckons with its stunning lakes, lush forests, and inviting marina. Travelers can enjoy sun-soaked days boating, kayaking, or swimming in tranquil waters, while scenic trails offer perfect spots for hiking and exploring nature. It’s an idyllic getaway for outdoor enthusiasts looking to connect with the great outdoors.

• Historical Old NMH Campus Building #3Opens in a new window – Discover the charm of this historic building, where you can appreciate its unique architecture while surrounded by lush landscapes. The campus offers a glimpse into the past, making it a delightful stop for those interested in history.
• Spofford LakeOpens in a new window – Spend a day by the water at Spofford Lake, a picturesque spot perfect for swimming, fishing, or simply relaxing on the shore. The surrounding forests provide a serene backdrop, inviting you to enjoy nature and take in the fresh air.
• Northern IllusionOpens in a new window – Venture to Northern Illusion, an attraction that promises an exciting experience. Whether you’re looking to explore the natural beauty of the area or engage in recreational activities, this spot will not disappoint.
• Brattleboro CommonOpens in a new window – Take a leisurely stroll around Brattleboro Common, an urban park that serves as a community hub. Here, you can enjoy open spaces, local events, and the vibrant atmosphere as you connect with the heart of the town.
• Asbury United Methodist ChurchOpens in a new window – Visit Asbury United Methodist Church, a welcoming place that invites travelers to reflect and appreciate its beautiful architecture. This church offers a peaceful environment, perfect for a quiet moment of contemplation.

5 tips for savvy savings when booking a hotel in Winchester

1. Book for the cheapest times: The most budget-friendly time to visit Winchester is in January, March, and December when hotel prices are typically lower. For those looking to explore the city’s rich history and culture, an ideal stay would be at least 2 to 3 days. This duration allows visitors to fully appreciate the key landmarks, including picturesque lakes, lush forests, and the charming marina, all of which offer great value for money. If you plan ahead, you might find that prices could drop even further during these months, making your trip even more affordable.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Winchester, explore the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted rates on nearby hotels as your travel date approaches. You could also enable email alerts or push notifications to stay informed about flash sales and special promotions. Additionally, the Smart ShoppingOpens in a new window tool available in the app helps you compare hotel prices and amenities, ensuring you’re more likely to see the best options. With these features, you'll be among the first to know about any price drops or available rooms for your last-minute getaway.
3. Be flexible with dates: Prices can fluctuate based on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates might help you save on your stay at a hotel in Winchester. If you're interested in unique accommodations, boutique hotels often provide a more personalized experience and may offer better value. When you book through Hotels.com, we'll inform you if the price for your chosen dates is above or below average. If the price is higher, we’ll suggest alternative dates that could be more affordable, helping you find the best deal possible.
4. Consider your location: Staying near major attractions or city centers can be convenient, but it usually tends to come with higher prices. If you're looking for more affordable options, consider hotels in less central areas or neighborhoods that strike a balance between cost and accessibility to the sights you want to see. You might also look into independent hotels located a bit farther out, as they can offer a more authentic and budget-friendly experience.
5. Join One Key™: Become a One Key MemberOpens in a new window for free and book your next stay in Winchester. Save on over 100,000 hotels worldwide with exclusive member prices. As a member, you can quickly progress through the tiers and enjoy perks, like free room upgrades when available and food and beverage discounts at select VIP Access properties.

Best time to go to Winchester

Winchester experiences its lowest average temperature in January, at 23.2°F (-4.9°C), while July is the hottest month, with an average temperature of 71.2°F (21.8°C). October is typically the wettest month. If you’re looking to soak up the lively atmosphere in Winchester, June, July, and September are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, accompanied by light rainfall. However, if you prefer a more relaxed experience, February, November, and December are perfect for a quieter getaway, marked by light rainfall and mostly sunny conditions.