Hotels in Chester

Chester: A Timeless Journey Through History and Nature's Embrace

Nestled in the heart of the Hudson Valley, Chester, New York, is a charming escape that blends natural beauty with quaint small-town allure. Surrounded by rolling hills and lush forests, this idyllic destination invites outdoor enthusiasts to hike, fish, and explore its scenic landscapes. Discover the vibrant local arts scene, unique boutiques, and farm-to-table dining that celebrate the region's rich culture. With its friendly atmosphere and stunning views, Chester is perfect for a romantic getaway or a peaceful retreat, making it a hidden gem for travelers seeking a taste of authentic New York charm. For our best hotel rates in Chester and to enhance your stay, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Discover great hotels in Chester

Chester, New York, offers a variety of hotel accommodations, ranging from cozy inns and motels to charming bed and breakfasts. Visitors can find comfortable stays with convenient amenities, whether for a weekend getaway or an extended vacation. Enjoy the scenic surroundings while exploring local options that cater to different preferences and budgets. Here are some of the most popular hotels with our travelers in Chester:

1. Inn at Stony CreekOpens in a new window: This charming 3.0-star inn offers a delightful escape with beautiful outdoor scenery and a warm, welcoming atmosphere. Guests can savor a complimentary breakfast while enjoying the picturesque views of nearby ducks and geese. The character of this historic property adds to its allure, making it an appealing choice for leisure travelers seeking a quaint and unique experience during their stay in Chester.
2. Stagecoach InnOpens in a new window: This inviting 3.5-star bed and breakfast is perfect for travelers looking for a cozy yet upscale retreat. With amenities such as a coffee shop, complimentary continental breakfast, and a relaxed bar and lounge, it creates an environment that fosters relaxation and enjoyment. The warm and friendly service enhances the overall experience, making it an ideal choice for those seeking a home-like ambiance with a touch of luxury.
3. The Dominion House Bed & BreakfastOpens in a new window: This exquisite 3.5-star bed and breakfast offers a serene escape for travelers seeking tranquility and comfort. With only three rooms, guests can enjoy an intimate atmosphere complemented by a refreshing swimming pool and stunning natural surroundings. The thoughtfully curated amenities, such as locally sourced breakfasts and a cozy library, create a distinctive experience that emphasizes relaxation and rejuvenation in a peaceful setting.

Top locations to stay in Chester

When visiting Chester, New York, consider staying in Goshen, Middletown, or Warwick. Goshen offers rich architecture and cultural sites like Storm King Art Center. Middletown features beautiful churches and the serene Neversink River. Warwick boasts stunning countryside and outdoor adventures. For first-time visitors, Goshen is best suited due to its diverse attractions and vibrant atmosphere.

1. GoshenOpens in a new window: Goshen is a charming destination known for its rich architectural heritage and beautiful landscapes. It's home to the stunning Storm King Art Center, where you can stroll through impressive outdoor sculptures against a backdrop of rolling hills. The town's historical vibe, coupled with attractions like Algonquin Park, makes it perfect for leisurely explorations. For those looking to enjoy some evening entertainment, the cultural offerings at venues like Castle Fun Center and Paramount Theatre provide engaging experiences. Plus, with shopping options at Monroe Federal Plaza Shopping Center and Galleria at Crystal Run, you can easily find unique items to bring back home.
2. MiddletownOpens in a new window: Middletown offers a delightful mix of architecture and nature, making it a great spot for travelers seeking a balance between city life and outdoor experiences. The Orange County Arboretum is a lovely place to appreciate local flora, while the Neversink River offers picturesque views. Cultural attractions like Castle Fun Center and Paramount Theatre add to the local charm with various shows and events. Shoppers will enjoy the Galleria at Crystal Run and Mamakating Farmers Market, where you can discover local goods and delicious treats.
3. WarwickOpens in a new window: Warwick is a picturesque getaway nestled in the countryside, perfect for those wanting to escape the hustle and bustle. The area is known for its scenic trails, such as those at Harriman State Park, which offer fantastic hiking opportunities. Cultural experiences can be enjoyed at the Penguin Rep Theatre and Castle Fun Center, providing fun for the whole family. For shopping enthusiasts, Woodbury Common Premium Outlets is just a short drive away, featuring a variety of stores and brands. Whether you're seeking adventure in nature or a quiet retreat, Warwick has something for everyone.

Things to do in Chester

Chester invites travelers to explore its charming streets, where you can enjoy delightful shopping experiences and indulge in cozy cafés. For the adventurous, there are opportunities for hiking along scenic paths and even trying your hand at boating. Whether you crave relaxation or excitement, Chester offers something for everyone!

• Harness Racing Museum and Hall of FameOpens in a new window – Step into the thrilling world of harness racing! Explore the history and impact of this exciting sport through engaging exhibits and memorabilia. Don’t miss the chance to see beautiful horses and learn about the important figures who shaped harness racing over the years.
• Museum VillageOpens in a new window – Travel back in time at Museum Village, where you can experience life in the 19th century. Walk through authentic buildings, enjoy interactive demonstrations, and discover how people lived, worked, and played in a bygone era. It’s a delightful outing for families and history enthusiasts alike!
• Orange County FairgroundsOpens in a new window – Experience the vibrant atmosphere of the Orange County Fairgrounds, where events and activities abound. From seasonal fairs to farmer’s markets and craft shows, there’s always something happening. Sample local treats, browse unique crafts, and soak up the lively ambiance.
• Goosepond Mountain State ParkOpens in a new window – Escape to nature at Goosepond Mountain State Park! With its scenic trails, picnic areas, and beautiful views, it’s an ideal spot for hiking, birdwatching, or simply unwinding in the great outdoors. Bring your camera to capture the stunning landscapes.
• Storm King Art CenterOpens in a new window – Discover a harmonious blend of art and nature at Storm King Art Center. Wander through expansive outdoor galleries showcasing impressive sculptures set against the backdrop of rolling hills. It’s a peaceful retreat where art inspires and nature soothes, perfect for a leisurely stroll or a thoughtful exploration.

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 from January to March, when hotel prices are typically lower. For a great value for money experience, staying for at least 2 to 3 days allows you to fully explore the city's key historical landmarks and cultural attractions. Enjoy the rich history and vibrant culture while sticking to a budget-friendly plan, as prices may drop during this off-peak season.
2. Look for last-minute deals on Hotels.com: To uncover last-minute deals to Chester, head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section on Hotels.com, where you may discover discounted hotel rates as your travel date approaches. Consider enabling email alerts or push notifications to stay updated on flash sales and special promotions, so you’re more likely to see opportunities for great savings on hotels. Additionally, use Smart ShoppingOpens in a new window in the app to compare room rates and amenities, ensuring you can act quickly if prices drop or rooms become available 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 in a Chester hotel. If you're in search of something distinctive, boutique hotels often provide a more personalized experience and can sometimes offer better value. When you book through Hotels.com, we’ll inform you whether the price for your chosen dates is above or below the average. If the price appears to be on the higher side, we’ll suggest alternative dates that could be more affordable, helping you find the best deal.
4. Consider your location: Hotels near the city center usually tend to be more expensive, but thanks to Chester's outstanding public transportation options, you might discover a more affordable independent hotel a bit farther out that still offers convenient access. For those interested in exploring alternative, less crowded neighborhoods or even lesser-known nearby towns, there’s often great value to be found. Opting for these alternative destinations could provide 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 Chester. 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 Chester

Chester experiences its lowest average temperature in January, at 28.0°F (-2.2°C), while July is the hottest month, with an average temperature of 73.9°F (23.3°C). July is usually the wettest month. June, July, and September are the peak travel months in Chester, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, with light rainfall. On the other hand, February, November, and December tend to be quieter times to visit, marked by light rainfall and mostly sunny conditions.