Find hotels in Chester, MA from AED 256

Top reasons to visit Chester

• Outdoor Adventures: Enjoy skiing at local resorts and explore scenic nature reserves, perfect for adventure seekers.
• Charming Town Atmosphere: Discover the quaint charm of Chester with its welcoming shopping scene and historic houses.
• Vibrant Nightlife: Experience a lively nightlife that adds a romantic touch to your visit.
• Family-Friendly Activities: Engage in fun activities that cater to families and create lasting memories.
• Diverse Accommodations: Choose from cozy bed and breakfasts to pet-friendly hotels for a delightful stay.

Find great hotels near Chester

Discover the charm of Chester, Massachusetts, with a variety of hotel accommodations tailored to adventurous travelers and families alike. From cozy bed and breakfasts to well-equipped hotels, you’ll find the perfect place to stay. Enjoy pet-friendly options and a welcoming atmosphere that makes your visit unforgettable. Explore the best hotels in Chester and experience a delightful vacation surrounded by natural beauty.

• Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This 3.5-star resort is a perfect haven for adventure seekers and business travelers alike. Nestled 24.1km from Chester, it offers easy access to ski lifts and shuttles, making it ideal for winter sports enthusiasts. Guests can indulge in a variety of outdoor activities, from snowboarding and skiing to hiking and biking, all within proximity. The resort features spacious accommodations equipped with modern amenities, ensuring a cozy retreat after a day of adventure. With on-site recreational options, it's an excellent choice for those looking to blend relaxation with excitement.
• Quality Inn Westfield - Springfield: Located 25.7km from Chester, this welcoming hotel caters to families and business travelers, offering a pet-friendly environment. The Quality Inn provides essential amenities for children, including complimentary cribs, ensuring a comfortable stay for families with little ones. Its pet policy allows certain pets, making it easy for travelers to bring their furry friends along. The property’s strategic location also provides guests with easy access to local attractions, making it an ideal base for exploring the Westfield area while enjoying modern comforts.
• The Black Swan Lee - Lenox, an Ascend Collection Hotel: Also situated 24.1km from Chester, this 3-star hotel combines a family-friendly atmosphere with adventure-driven activities. The Black Swan Lee - Lenox offers various outdoor experiences, including motorboating, kayaking, and fishing right on-site, as well as nearby skiing lessons for winter sports lovers. The hotel is equipped with amenities for children, ensuring a safe and enjoyable environment for families. With a pet-friendly policy, it welcomes guests traveling with dogs, making it a versatile choice for all types of travelers.

Where to stay near Chester

Chester, Massachusetts, offers a delightful blend of outdoor adventures and charming getaways, ideal for families and couples alike. Explore scenic spots and enjoy a relaxing atmosphere in nearby neighborhoods. The city center boasts a welcoming shopping scene, while the surrounding regions provide opportunities for recreation and picturesque landscapes. Whether you're seeking adventure or a tranquil retreat, Chester and its vicinity promise an unforgettable vacation experience.

• Lenox: Nestled 27.4km from Chester, Lenox is a charming town that captivates visitors with its blend of culture and natural beauty. Known for its vibrant arts scene, travelers flock here for entertainment-themed experiences, especially during the summer months. Enjoy live music concerts and captivating theater performances while surrounded by stunning lakes and majestic mountains. Ideal for romantic getaways, Lenox offers scenic spots perfect for a cozy picnic or a peaceful walk. Don’t miss the nearby historical landmarks and places of worship that add to the town's unique character.
• The Berkshires: Located a mere 19.3km from Chester, The Berkshires is an outdoor paradise that beckons adventure enthusiasts year-round. With a strong focus on outdoor activities, visitors can engage in thrilling skiing at various ski resorts and take in breathtaking scenery along the way. The region is less seasonal than others, making it a fantastic choice for those seeking to enjoy nature's beauty in any season. Lakes and mountains provide stunning backdrops for hiking, fishing, and other outdoor adventures, while event venues host a variety of cultural events throughout the year.
• Becket: Just 9.7km from Chester, Becket is a picturesque town that offers a romantic atmosphere combined with outdoor adventures. Visitors can immerse themselves in the stunning natural landscape, which includes lakes and mountains, perfect for hiking or relaxing. The town hosts various artistic performances such as theater and dance, making it a cultural gem as well. Becket is also home to a national state park, providing endless opportunities for exploration and connection with nature. Whether you’re seeking a cozy retreat or an active outdoor experience, Becket has something for everyone.

Things to do near Chester

Chester, Massachusetts, is perfect for outdoor and adventure seekers, offering exciting activities like skiing at local resorts and ski fields. Visitors can enjoy live music, explore the charming town, and partake in fun activities that make for a memorable vacation. Don't miss the vibrant nightlife, which adds a romantic touch to your stay in this picturesque destination.

Shopping

In Chester, you can shop at the nearby Berkshire Mountain Country Store for unique gifts. If you're up for a drive, head to Lee Premium Outlets for a wide selection of brands, or explore Guido's Marketplace for a local shopping experience filled with fresh produce and goods.

Recreation

Jacob's Pillow, just 11.3km from Chester, offers a captivating dance experience infused with romance and culture. For a tranquil retreat, visit Goose Pond Reservation, 17.7km away, where you can unwind amidst nature's beauty. Wyndhurst Golf & Club, 24.1km distant, provides a perfect setting for outdoor sports enthusiasts.

Adventure

Experience thrilling skiing at Blandford Ski Area, located 11.3km from Chester, where you can embrace the winter sports vibe. For hiking enthusiasts, the Skyline Trail offers breathtaking outdoor scenery, also 11.3km away. Otis Ridge, 14.5km from Chester, provides another fantastic ski experience for adventure seekers.

Nightlife

Experience the charm of Chester's nightlife by catching a show at Shakespeare and Company, just 25.7km away, or enjoy a fun-filled evening at Spare Time Bowling, located 29.0km from town. For a romantic vibe, the Academy of Music Theater, also 29.0km away, offers captivating performances.

Booking tips and Expedia advantages for Chester

To save money during your visit to Chester, consider traveling in March or between December and January for lower accommodation rates. Tuesdays are typically the cheapest days to book a stay, while Saturdays are the most expensive. Use Expedia to find the best hotel deals by filtering prices from lowest to highest, and consider package deals that combine your hotel, flights, and activities for additional savings. Additionally, take advantage of free local attractions and explore Chester on foot or through its affordable public transportation options to keep travel costs down.

• 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 options based on your budget, preferred location, and desired hotel type. 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 hotel stay in Chester with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chester

Chester, Massachusetts, is perfect for outdoor and romantic getaways, featuring attractions like urban parks, nature reserves, and historic houses. Visitors can immerse themselves in family-friendly activities and cultural experiences. Don’t miss a visit to Chester, CT, for additional exploration. Whether you’re seeking adventure or a relaxing retreat, Chester offers a variety of points of interest that cater to all types of travelers.

• Chester Town Hall: This historic civic building embodies the charm and culture of Chester. Its architecture reflects the town's rich history, making it a perfect spot for history enthusiasts to appreciate the local heritage.
• Glendale Falls: Located 8.0km from Chester, this picturesque waterfall offers a romantic setting for couples and adventure seekers alike. The serene environment is perfect for a day of outdoor exploration and capturing stunning photographs.
• Becket Land Trust Historic Quarry: Just 4.8km from Chester, this reserve invites families and adventurers to explore its rich geological history. With options for both luxury and budget experiences, it’s a trendy spot for nature lovers and those seeking a unique outing.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, 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

Chester, Massachusetts is conveniently accessible via several major airports. Hartford, CT (BDL-Bradley Intl.) is located 45.1km away, with nearby hotels such as the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and the Marriott Hartford Downtown, 19.3km away. Albany, NY (ALB-Albany Intl.) is 85.3km from Chester, featuring options like the Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from the airport. Lastly, Worcester, MA (ORH-Worcester Regional) lies 91.7km away, with accommodations including the Beechwood Hotel and AC Hotel by Marriott Worcester, both 6.4km from the airport.