Hotels in Chester

Chester: Where Tranquil Waters Meet Nature's Embrace

Nestled along the picturesque Connecticut River, Chester, Connecticut, is a charming gem that captures the essence of New England's quaint beauty. This idyllic town boasts a vibrant marina, perfect for boating and fishing enthusiasts, while its lush natural parks offer serene trails and stunning views. Stroll through the historic center, where art galleries, unique boutiques, and cozy cafés invite leisurely exploration. Chester’s blend of scenic landscapes and rich cultural experiences makes it an enchanting destination for nature lovers, romantic getaways, or anyone seeking a peaceful retreat off the beaten path. Discover the magic of Chester, where adventure meets tranquility. 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, Connecticut offers a variety of accommodations, from cozy bed and breakfasts to charming boutique hotels. Visitors can find comfortable stays with a mix of luxury and quaint charm, often situated near the picturesque town center, making it easy to explore local attractions and enjoy the area's natural beauty. Here are some of the best hotels in Chester that our travelers love:

1. Copper Beech InnOpens in a new window: Nestled in the picturesque setting of Chester, Connecticut, Copper Beech Inn is a charming 4.0-star hotel that offers a delightful blend of comfort and New England charm. With an array of dining options, including a complimentary breakfast and an inviting restaurant for dinner, guests can indulge in culinary experiences that elevate their stay. The property boasts various recreational activities nearby, such as hiking, sailing, and kayaking, making it perfect for leisure travelers seeking adventure. The elegant rooms, beautifully decorated interiors, and attentive service create a warm and welcoming atmosphere, ensuring an unforgettable getaway.
2. James Pharmacy Bed & BreakfastOpens in a new window: James Pharmacy Bed & Breakfast is a delightful 4.0-star bed and breakfast located in a prime area of Chester, Connecticut, perfect for travelers who appreciate a cozy and intimate experience. With complimentary daily breakfast and a charming décor, this inn provides a home-like ambiance that caters to the needs of discerning guests. The clean and comfortable rooms promise a restful stay, while the property's proximity to local attractions and scenic views enhances the overall experience. This hotel is ideal for those looking for charm and convenience in a serene setting.
3. Madison Beach HotelOpens in a new window: Madison Beach Hotel is an inviting 4.0-star hotel offering a vibrant blend of adventure and relaxation in Chester, Connecticut. Perfectly suited for leisure travelers, this property features direct access to the beach and provides ample opportunities for outdoor activities, including hiking and biking. The welcoming atmosphere is complemented by attentive service, ensuring that guests feel pampered throughout their stay. With stylish accommodations and a focus on creating memorable experiences, this hotel is an excellent choice for those seeking an enjoyable escape with a touch of New England charm.

Top locations to stay in Chester

Some great areas to stay in when visiting Chester, Connecticut, are Westbrook Center, Madison Center, and Old Saybrook Center. Westbrook Center offers charming shops and beautiful beaches, while Madison Center is known for its vibrant downtown and local eateries. Old Saybrook Center boasts rich history and scenic views. For first-time visitors, Madison Center is the best choice for its lively atmosphere and convenience.

1. Westbrook CenterOpens in a new window: Westbrook Center is a charming spot to stay, offering a delightful mix of coastal charm and local character. Known for its beautiful beaches, you can enjoy sunbathing or a leisurely stroll along the shoreline. The area is also home to unique shops and boutiques where you can find one-of-a-kind items, making it perfect for a bit of shopping. Don’t miss the chance to explore the local cultural attractions, including art galleries and seasonal events that highlight the vibrant community spirit.
2. Old Saybrook CenterOpens in a new window: Old Saybrook Center is a historic gem with a picturesque waterfront that makes it a desirable base for your travels. The town is rich in history, featuring landmarks and cultural attractions that give you insight into its storied past. Take a walk along Main Street to discover charming shops and cozy cafes. The nearby beaches offer a perfect retreat for relaxation, while the scenic views make for great photo opportunities, especially at sunset.
3. Madison CenterOpens in a new window: Madison Center is a delightful destination known for its quaint New England charm. This area boasts a vibrant shopping scene, featuring a mix of local boutiques and specialty shops. You can enjoy a leisurely day exploring the attractive town green, where community events often take place. The nearby beaches and parks offer beautiful spots for outdoor relaxation and recreation, enhancing your stay with a touch of nature. Madison Center also hosts cultural attractions, making it a well-rounded choice for travelers.

Things to do in Chester

Chester is a delightful blend of scenic beauty and vibrant arts, where lush parks and serene waterways invite exploration. Enjoy outdoor activities like boating and hiking, then unwind with captivating theater performances. This charming city offers a perfect mix of nature and culture, making it a must-visit destination.

• Gillette Castle State ParkOpens in a new window – Step into a whimsical world at Gillette Castle State Park, where the unique architectural design of the castle invites exploration. Wander through the scenic grounds, enjoy a picnic by the river, and take in the breathtaking views of the Connecticut River. The park's hiking trails offer a chance to connect with nature while discovering the history of this remarkable site.
• Hammonasset Beach State ParkOpens in a new window – Spend a delightful day at Hammonasset Beach State Park, Connecticut's largest shoreline park. With over two miles of sandy beach, it's perfect for sunbathing, swimming, and beachcombing. The park also features picnic areas and nature trails, making it a great spot for families and outdoor enthusiasts to unwind and soak up the sun.
• Essex Island MarinaOpens in a new window – Dock your boat or simply enjoy a leisurely stroll at Essex Island Marina. This picturesque marina offers stunning views of the surrounding waters and is an ideal starting point for exploring the nearby islands. Grab a bite at the local eateries and watch the boats sail by for a truly relaxing experience.
• Connecticut Valley Railroad State Park TrailOpens in a new window – Lace up your hiking boots and hit the Connecticut Valley Railroad State Park Trail. This scenic path follows the historic route of the railroad and is perfect for walking, biking, or jogging. The trail’s beautiful landscapes and peaceful surroundings make it an excellent choice for a day of outdoor activity.
• Chester Creek MarinaOpens in a new window – Visit Chester Creek Marina for a taste of the local boating culture. Whether you're looking to rent a kayak or simply enjoy the serene waters, this charming marina is a wonderful place to relax. Take in the sights and sounds of nature as you explore the area, making it a great stop for water lovers.

5 tips for savvy savings when booking a hotel in Chester

1. Book for the cheapest times: For those looking to explore Chester on a budget, the most affordable months to visit are January, February, and December, when hotel prices are lower. A stay of at least 2 to 3 days is recommended to fully appreciate the city's key landmarks and rich cultural history, including its charming marina and beautiful natural parks. This timeframe provides great value for money, allowing visitors to soak in the unique blend of history and nature that Chester has to offer. Plus, prices may drop during these months, making it an even more appealing option for budget-conscious travelers.
2. Look for last-minute deals on Hotels.com: To find last-minute deals to Chester, consider checking the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may discover discounted hotel rates as your travel date approaches. You could also set up email alerts or push notifications to stay informed about flash sales and special promotions. Additionally, the Smart ShoppingOpens in a new window feature in the app allows you to compare room rates and amenities across different hotels, helping you make informed decisions. By using these tools, you're more likely to see the best options for your next stay and secure a great deal.
3. Be flexible with dates: Prices can fluctuate based on various factors such as the hotel's location, star rating, and time of year, so being flexible with your travel dates may help you save on your stay in a Chester hotel. If you’re in search of distinctive accommodations, boutique hotels often provide a more personalized experience and can sometimes offer 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 higher than usual, we’ll suggest alternative dates that could be more budget-friendly, helping you find a great deal.
4. Consider your location: Staying near key attractions or city centers can be convenient, but it often comes with a higher price tag. For more budget-friendly options, you might want to look at hotels in less central neighborhoods, where you can strike a balance between cost and accessibility to the places you want to visit. Additionally, consider exploring independent hotels that are a bit farther away, as they usually tend to be more affordable and can offer a more authentic 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 31.3°F (-0.4°C), while July is the hottest month, with an average temperature of 73.8°F (23.2°C). October tends to be the wettest month. The peak travel months to visit Chester are April, May, and July, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, January, October, and November are ideal if you're looking for a calmer vacation, marked by light rainfall and mostly sunny conditions.