Hotels in Chesterfield

Some of the best places to stay in Chesterfield are West Dummerston, Keene and Stratton. West Dummerston, Keene, and Stratton each offer unique attractions for travelers. West Dummerston is known for its scenic beauty and quiet charm, while Keene boasts vibrant culture and dining options. Stratton is perfect for outdoor enthusiasts with its ski resorts and hiking trails. Accommodations range from cozy inns and motels to more upscale hotels, ensuring a variety of choices. For first-time visitors, Keene is the best option, offering a mix of activities and accessibility. Here are some of the most popular hotels with our guests in Chesterfield:

1. West DummerstonOpens in a new window: West Dummerston is an outdoor paradise, perfect for adventure seekers and nature lovers. With attractions like Stratton Mountain Resort and Mount Snow nearby, it’s ideal for skiing and outdoor sports. The area is also home to The Stone Church, a venue for live music. For accommodations, consider Chesterfield InnOpens in a new window, a 4.0-star Bed & Breakfast offering business amenities and pet-friendly options, along with activities like hiking and kayaking. Another great option is Inn on Putney RoadOpens in a new window, also a 4.0-star Bed & Breakfast, featuring a 24-hour business center and adventure sports like snow tubing and rafting.
2. KeeneOpens in a new window: Keene is a vibrant city rich in culture and history, featuring landmarks like Keene State College and the Colonial Theatre. The Historic Main Street offers a charming atmosphere for exploring local shops and eateries. Crotched Mountain ResortOpens in a new window is a 3.0-star hotel perfect for those interested in golf and outdoor activities, while Colby Hill InnOpens in a new window is a luxurious 4.0-star inn offering romantic experiences and spa amenities. Additionally, The Common Man Inn & RestaurantOpens in a new window, a 3.5-star inn, provides business facilities and easy access to skiing and snowboarding activities.
3. StrattonOpens in a new window: Stratton is a top destination for ski enthusiasts, featuring Stratton Mountain Resort and adventure activities for all ages. This area offers picturesque landscapes and thrilling outdoor sports, making it perfect for family trips. For a luxurious experience, The Equinox, a Luxury Collection Golf Resort & Spa, VermontOpens in a new window is a 4.5-star resort with golf and various adventure activities. The Equinox Golf Resort & SpaOpens in a new window, another 4.5-star hotel, provides family-friendly amenities and a range of outdoor activities. Kimpton Taconic Hotel, an IHG HotelOpens in a new window, a 4.0-star hotel, is also family-oriented and offers opportunities for golfing and skiing.

Three days in Chesterfield is ideal for exploring scenic spots, indulging in vineyard tours, and experiencing outdoor adventures. Enjoy leisurely activities like hiking and boating, while uncovering the charm of this vibrant destination that offers a perfect blend of relaxation and excitement for travelers. Here's a quick itinerary to make the most of your trip to Chesterfield:

• Day 1: Start your adventure at the beautiful Spofford Lake, where you can enjoy lakeside activities such as kayaking or picnicking. After soaking in the serene atmosphere, make your way to Stonewall Farm, an educational farm that offers a glimpse into sustainable farming practices. Here, you can meet farm animals and perhaps even participate in a farm tour. Conclude your day with a visit to the Chesterfield Gorge Natural Area, where you can hike along the scenic trails and witness stunning views of the gorge carved by the Connecticut River.
• Day 2: Begin your day exploring the enchanting Madame Sherri Forest, known for its unique rock formations and lush trails. This mystical area is perfect for a morning hike. Next, challenge yourself with a trek up Wantastiquet Mountain, where the panoramic views from the summit will leave you in awe. Afterward, head to the New England Center for Circus Arts, where you can either take a fun circus skills class or watch an exciting performance, adding a touch of whimsy to your day.
• Day 3: Kick off your day at Brattleboro Common, a vibrant gathering spot where you can enjoy a leisurely stroll or grab a coffee from a nearby café. From there, make your way to the intriguing Madame Sherri's Castle Ruins, a historic site that offers a glimpse into the area's past and provides great photo opportunities. Finally, immerse yourself in culture at the Brattleboro Museum & Art Center, where you can explore contemporary art exhibits and engage with local artists. This day perfectly blends nature, history, and art for a well-rounded experience.

1. Book for the cheapest times: For those looking to experience Chesterfield on a budget, the best months to visit are April, July, and November, when hotel prices are more affordable. To truly enjoy the area's main attractions, it's recommended to stay for at least 2-3 days. Chesterfield offers a variety of beautiful spots to explore, including scenic lakes and stunning parks, making it a great value for money destination.
2. Look for last-minute deals on Hotels.com: If you're looking for last-minute deals to Chesterfield, you might find some excellent offers on hotel accommodations. To explore these options on Hotels.com, head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section, where you're more likely to come across discounted hotel rates as your travel date approaches. Consider setting up email alerts or push notifications from Hotels.com to stay informed about flash sales and exclusive last-minute promotions, helping you to potentially snag the best hotel deals in Chesterfield.
3. Be flexible with dates: Hotel prices can fluctuate due to factors like the hotel's location, star rating, and the season. As a result, being flexible with your travel dates may help you save on hotel expenses in Chesterfield.
4. Consider your location: When booking on Hotels.com for your vacation, think about your location. Staying near major attractions or city centers can offer convenience, but it usually tends to be pricier. For more affordable options, consider hotels in less central neighborhoods, balancing your budget with the ease of getting to the places you plan to explore.
5. Upgrade with One Key: Make your next booking in Chesterfield and sign up to Hotels.com's free One Key program, letting you earn and use reward points on your next stay. Progress through the Blue, Silver, Gold and Platinum tiers to unlock various advantages like room upgrades when available, discounted rates, and exclusive offers for members. Don't hesitate, sign up today.

Chesterfield experiences its lowest average temperature in January, at 22.5°F (-5.3°C), while July is the hottest month, with an average temperature of 70.7°F (21.5°C). October tends to be the wettest month. The peak travel months to visit Chesterfield are July to September, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, January, November, and December are ideal if you're looking for a calmer vacation, marked by light rainfall and mostly sunny conditions.