Find hotels in Chester, MA from $78

Top reasons to visit Chester

• Stunning Outdoor Scenery: Chester boasts beautiful landscapes with numerous parks and nature reserves, perfect for outdoor enthusiasts.
• Vibrant Arts Scene: Enjoy live music and engaging theater performances, contributing to a lively nightlife experience.
• Charming Local Shopping: Explore unique boutiques and artisan shops, offering a delightful shopping experience.
• Cozy Accommodations: Choose from a range of charming bed and breakfasts and hotels tailored for various preferences.
• Family-Friendly Activities: Chester provides fun and educational experiences for visitors of all ages, ensuring memorable moments.

Find great hotels near Chester

Discover the charm of Chester, Massachusetts, where a variety of accommodations await to enhance your getaway. From cozy bed and breakfasts to delightful hotels, there’s something for everyone. Whether you're seeking pet-friendly options, family-friendly experiences, or thrilling adventures, Chester's hotels cater to all your needs. Explore the best available hotels and find the perfect star-rated stay for your vacation in this picturesque town.

• Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the heart of the Berkshires, this family-friendly 3.5-star resort offers a perfect blend of adventure and relaxation. Situated 15 miles from Chester, the resort features a wide array of outdoor activities, including snowboarding, skiing, and hiking. Families will appreciate amenities like a mini-golf course, arcade game room, and a playground designed for children. With spacious accommodations and a focus on recreational fun, this resort is ideal for those looking to create unforgettable family memories in a stunning natural setting.
• The Black Swan Lee - Lenox, Ascend Hotel Collection: Experience a unique blend of adventure and comfort at The Black Swan Lee - Lenox, located 15 miles from Chester. This 3-star hotel is perfect for families and pet owners alike, offering activities such as fishing and mountain climbing nearby. With pet-friendly policies and amenities like cribs and first aid kits for children, it caters to families traveling with fur companions. The hotel’s charming atmosphere and proximity to outdoor recreation make it a fantastic choice for those seeking adventure without sacrificing comfort.
• Quality Inn Westfield - Springfield: Conveniently located 16 miles from Chester, the Quality Inn Westfield - Springfield is a versatile option for both business and leisure travelers. This hotel offers essential amenities for business guests, including a business center, making it a practical choice for work-related stays. Families will find comfort in the welcoming environment, with cribs available for little ones. Pet-friendly policies also allow guests to bring their furry friends along, ensuring that everyone can enjoy their stay in this comfortable and accommodating setting.

Where to stay near Chester

Chester, Massachusetts, offers a delightful blend of outdoor adventures and charming scenery perfect for a romantic getaway or family-friendly vacation. Explore the picturesque landscapes in nearby parks, or enjoy leisurely strolls through the city center. Don't miss the shopping scene, where local boutiques and artisan shops await. With its relaxing atmosphere and scenic spots, Chester is an ideal destination for those seeking both recreation and tranquility in a beautiful setting.

• Lenox: Nestled 17 miles from Chester, Lenox is a charming city that attracts visitors year-round, with peak travel from June to August. Known for its romantic ambiance and family-friendly activities, Lenox offers a plethora of entertainment options. Enjoy a night at the theater, attend a live music concert, or take advantage of the nearby ski resorts in winter. Nature lovers will appreciate the scenic beauty of local lakes and mountains, while conference venues host various events throughout the year, making it a versatile destination.
• The Berkshires: Located just 12 miles from Chester, The Berkshires is a year-round outdoor paradise that invites adventure seekers and nature enthusiasts alike. With travel peaking in the summer months, visitors flock to the area for its stunning scenery and outdoor activities, such as skiing at the local resorts. The Berkshires is known for its breathtaking lakes and majestic mountains, providing ample opportunities for hiking, skiing, and relaxation amidst nature. Whether you’re exploring the great outdoors or enjoying a quiet retreat, this region offers something for everyone.
• Lee: Just 14 miles from Chester, Lee is a delightful city that draws visitors with its romantic charm and vibrant entertainment scene. Like its neighboring towns, Lee sees peak travel from June to August, featuring a mix of family-friendly fun and cultural experiences. Enjoy an evening at the theater or a lively music concert, and don’t miss the nearby ski fields for winter sports enthusiasts. With picturesque lakes, stunning mountains, and historical monuments, Lee offers a well-rounded getaway for travelers seeking both adventure and relaxation.

Things to do near Chester

Chester, Massachusetts, is ideal for outdoor and romantic getaways, boasting beautiful scenery. Visitors can enjoy live music and engaging theater performances, making for a vibrant nightlife experience. Whether you're looking for fun activities or educational experiences, Chester has something for everyone. A trip to this charming town promises memorable moments and a delightful atmosphere perfect for relaxation and entertainment.

Shopping

If you're up for a drive, visit the Lee Premium Outlets, located 13 miles away, offering a variety of retail options for gifts. The Berkshire Mountain Country Store, 14 miles away, provides unique local items, while Guido's Marketplace, 17 miles away, features fresh produce and gourmet goods.

Recreation

At Jacob's Pillow, immerse yourself in the vibrant world of dance surrounded by picturesque landscapes, offering a unique cultural experience. Goose Pond Reservation invites you to unwind with serene hiking trails and tranquil waters, perfect for relaxation. For outdoor enthusiasts, Bas Ridge Golf Course offers a challenging game amidst beautiful scenery.

Adventure

At Blandford Ski Area, located 7 miles from Chester, experience thrilling skiing on its well-groomed slopes. For hiking enthusiasts, the Skyline Trail, also 7 miles away, offers breathtaking outdoor scenery. Additionally, Otis Ridge, 9 miles from Chester, provides fantastic skiing opportunities amid a vibrant sports atmosphere.

Nightlife

Experience the charm of Chester's nightlife by visiting Shakespeare and Company for a captivating theater performance. For some adventure, check out Spare Time Bowling, where fun awaits. Don't miss the Academy of Music Theater for an enchanting evening of culture and entertainment, just a short drive away.

Booking tips and Expedia advantages for Chester

To save money on your trip to Chester, consider visiting during the cheaper months of March or December to January, avoiding the peak season in summer. Book your stay on a Tuesday for the best rates and utilize Expedia's search tool to find budget-friendly accommodations, including eco-certified hotels. Combine hotel and flight bookings for added savings, and join the One Key membership for exclusive discounts. Don't forget to explore free activities and take advantage of Chester's public transport options to keep travel expenses low.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are March and December to January, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia's search tool to customize your preferences, such as budget, desired location, and type of hotel. For instance, selecting the Eco-certified option will show you a range of sustainable and environmentally friendly hotels available at this moment. To find the best prices and deals, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your Chester hotel reservation with your flights and activities through an Expedia package.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Chester

Chester, Massachusetts, is perfect for outdoor and romantic getaways, offering stunning scenery and a variety of attractions. Visitors can explore urban parks, nature reserves, and historic houses, making it a great destination for families and culture enthusiasts. Don't miss the opportunity to visit Chester's charming local spots for a memorable experience.

• Chester Town Hall: This historic civic government building captures the rich culture of Chester. Its charming architecture and community vibe make it a perfect spot to appreciate local history and governance.
• Pyramid Lake: Located 6 miles from Chester, Pyramid Lake is a serene escape with beautiful beach areas and stunning scenery. Perfect for outdoor activities or a romantic picnic, it offers a peaceful retreat amidst nature.
• Glendale Falls: Just 5 miles away, Glendale Falls is a breathtaking waterfall that invites adventure seekers. Enjoy hiking trails and the romantic ambiance of cascading water, making it a fantastic spot for photography and nature lovers.

Best time to go to Chester

The best time to visit Chester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	23.5°F (-4.7°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	25.3°F (-3.7°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
March	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	44.8°F (7.1°C)	Light Rain	Mostly Cloudy	Average	Average
May	56.5°F (13.6°C)	Light Rain	Mostly Sunny	Average	Average
June	64.4°F (18.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	70.5°F (21.4°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	68.7°F (20.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	61.9°F (16.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	50.7°F (10.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	30.2°F (-1.0°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low

The nearest major airports for your trip to Chester

To visit Chester, Massachusetts, you have several airport options. Hartford, CT (BDL-Bradley Intl.) is located 28 miles away, with nearby hotels like the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport, and the 4-star Marriott Hartford Downtown, 12 miles away. Albany, NY (ALB-Albany Intl.) is 53 miles from Chester, featuring hotels such as the 4-star Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 8 miles away. Worcester, MA (ORH-Worcester Regional) is 57 miles away, with good options like the 4-star Beechwood Hotel and AC Hotel by Marriott Worcester, both 4-5 miles from the airport.