Hotels in Chester

Chester: Where Mountain Trails Meet Small Town Charm

Nestled in the heart of Vermont, Chester is a charming small town that beckons travelers seeking a peaceful escape. Surrounded by picturesque mountains and lush forests, it offers stunning landscapes perfect for hiking, biking, and leaf-peeping in the fall. Stroll through the quaint village, where you'll find delightful shops, cozy cafés, and the historic Chester Village Green. Don't miss the iconic stone-covered bridge and the vibrant arts scene that showcases local talent. Chester is the perfect off-the-beaten-path destination for those looking to unwind and embrace the beauty of New England’s countryside.

Discover great hotels in Chester

Chester, Vermont offers a variety of hotel accommodations, from charming inns to budget-friendly options. Whether you're seeking a cozy stay or a more upscale experience, you'll find a range of choices that cater to different preferences and budgets, making it easy to enjoy your visit to this picturesque town. These are some of the hotels preferred by our travelers in Chester:

1. Grafton InnOpens in a new window: This 3.5-star hotel offers a vibrant adventure experience in Chester, Vermont, making it perfect for leisure travelers seeking excitement. With a variety of adventure sports available onsite and nearby—including skiing, snow tubing, and mountain biking—this hotel ensures an exhilarating stay. Families can enjoy the arcade game room, while the pet-friendly policies enhance the welcoming atmosphere. Emphasizing comfort and distinctive experiences, guests appreciate the engaging recreational activities and the opportunity to explore the beautiful surroundings.
2. The Hartness HouseOpens in a new window: The Hartness House is a 3.0-star hotel that caters to adventure-seeking travelers eager for outdoor thrills. With activities like rock climbing, skiing, and mountain biking nearby, this property provides an enticing environment for those wanting to immerse themselves in nature. The inviting ambiance encourages guests to embrace the great outdoors while enjoying the charm and character of Chester. This hotel is ideal for those looking to create memorable experiences filled with excitement and exploration.
3. The Inn at WeathersfieldOpens in a new window: The Inn at Weathersfield is a 4.0-star inn that proudly welcomes LGBTQIA travelers, offering a unique and inclusive experience. With an emphasis on personal comfort and distinctive hospitality, this property features elegantly designed accommodations and a warm environment that resonates with all guests. The inn's inviting atmosphere allows for relaxation and connection, making it a popular choice for those seeking a welcoming retreat. Its commitment to inclusivity and exceptional service elevates the stay, ensuring a memorable experience for all.

Top locations to stay in Chester

Some great areas to stay in when visiting Chester, Vermont, are Ludlow, Londonderry, and Cavendish. Ludlow is perfect for ski and snowboarding enthusiasts, while Londonderry offers stunning mountain views and outdoor adventures. Cavendish combines skiing with a quaint village atmosphere. For first-time visitors, Ludlow is best suited due to its vibrant ski culture and amenities.

1. LudlowOpens in a new window: Ludlow is a fantastic destination for those who love winter sports, as it is home to the popular Okemo Mountain Resort. This vibrant area offers excellent skiing and snowboarding opportunities, making it a perfect getaway for thrill-seekers. Beyond winter activities, you can explore charming local shops and enjoy cozy cafes after an exhilarating day on the slopes. In the summer, Ludlow transforms into a hub for hiking and biking enthusiasts, with beautiful trails and stunning views that showcase Vermont's natural beauty.
2. LondonderryOpens in a new window: Londonderry is a serene spot for travelers who appreciate the great outdoors, featuring picturesque mountain landscapes and lush greenery. Known for its hiking trails, including the scenic route leading to the majestic Bromley Mountain, it’s ideal for adventurous souls in search of breathtaking views. The quaint town atmosphere provides a perfect backdrop for relaxing strolls, and you’ll find unique local shops that showcase the charm of small-town Vermont. Whether you’re hitting the slopes or enjoying the fall foliage, Londonderry offers a welcoming retreat.
3. CavendishOpens in a new window: Cavendish is a charming destination that attracts visitors with its rich history and beautiful natural surroundings. It’s a great base for skiing and snowboarding enthusiasts, particularly at nearby ski resorts. The tranquil landscapes are perfect for those looking to unwind, and you can explore local parks and trails that highlight the area's scenic beauty. Cavendish also offers a glimpse into Vermont's past with historical sites that showcase its heritage, making it an appealing place for both adventure and cultural exploration.

Things to do in Chester

Nestled between serene mountains and lush forests, Chester invites travelers to explore its stunning natural beauty. Enjoy invigorating hikes through scenic trails, hit the slopes for some exhilarating skiing, or indulge in a charming shopping spree. With its blend of outdoor thrills and quaint town vibes, it’s a delightful getaway!

• Lake NinevahOpens in a new window – Spend a relaxing day by the serene waters of Lake Ninevah. Enjoy a picnic on the shore, take a refreshing swim, or simply unwind while soaking in the beautiful mountain views that surround this hidden gem.
• Weston PrioryOpens in a new window – Visit Weston Priory, a peaceful monastery where you can experience tranquility and reflection. Explore the picturesque grounds and take part in a prayer service if you’re interested in connecting with the local community.
• Lake RescueOpens in a new window – Head over to Lake Rescue for a day filled with outdoor fun! This lovely lake is perfect for kayaking or canoeing, making it an ideal spot for water enthusiasts looking to enjoy Vermont's natural beauty.
• Buttermilk FallsOpens in a new window – Hike to Buttermilk Falls, where you can witness the cascading waters creating a stunning display. It's a perfect spot for a family outing or a romantic escape into nature.
• Lowell Lake State ParkOpens in a new window – Explore Lowell Lake State Park, a national state park offering picturesque trails and opportunities for birdwatching. Pack your hiking boots and enjoy a scenic walk while observing the diverse wildlife that calls this park home.

5 tips for savvy savings when booking a hotel in Chester

1. Book for the cheapest times: The most affordable time to visit Chester is during April, May, and November, when hotel prices may drop. For a budget-friendly experience, staying at least 2 to 3 days is recommended to fully explore the city’s key historical landmarks, cultural attractions, and scenic spots. This allows you to enjoy hiking trails, discover charming small-town shops, and savor delicious local dining options, all while keeping your trip great value for money.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Chester, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window section on Hotels.com, where you may find discounted rates on hotels as your travel date approaches. You can also enable email alerts or push notifications to stay informed about flash sales and special last-minute promotions, helping you capitalize on opportunities to save. Additionally, use the Smart ShoppingOpens in a new window tool via the app to compare hotel prices and amenities, ensuring you're among the first to know if prices drop or rooms become available for your getaway.
3. Be flexible with dates: Prices can fluctuate depending on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates may help you save on your stay at a Chester hotel. If you're seeking something special, boutique hotels can provide a more personalized experience and often better value. When you book through Hotels.com, we'll inform you if the price for your chosen dates is above or below the average. If the price is on the higher end, we’ll suggest alternative dates that could be more affordable, helping you find a better deal.
4. Consider your location: Staying near major attractions or city centers can be convenient, but it usually tends to come with higher prices. For more budget-friendly options, you might want to look at hotels in less central neighborhoods, finding a balance between cost and accessibility to the places you want to visit. Exploring independent hotels a bit farther out can often provide a more authentic experience while being more likely to be affordable.
5. Become a Member: Join for free and unlock great savings on your next stay in Chester! As a member, you’ll gain access to exclusive prices on over 100,000 hotels worldwide. Enjoy benefits like fast tracking through membership tiers, complimentary room upgrades when available, and discounts on food and beverages at select VIP Access properties. Don’t miss out on these fantastic perks—sign up today and start planning your getaway!

Best time to go to Chester

Chester experiences its lowest average temperature in January, at 20.7°F (-6.3°C), while July is the hottest month, with an average temperature of 69.3°F (20.7°C). October are typically the wettest months. If you’re looking to soak up the lively atmosphere in Chester, July to September are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, with light rainfall. However, if you prefer a more relaxed experience, January to March are perfect for a quieter getaway, marked by light rainfall and mostly cloudy conditions.