Chester Hotels

Top reasons to visit Chester

• Outdoor Adventures: Chester is ideal for nature lovers, offering skiing, hiking, and scenic beauty.
• Charming Atmosphere: The city centre features delightful shopping and local eateries to explore.
• Romantic Getaways: Perfect for couples, Chester offers tranquil spots for a romantic retreat.
• Vibrant Nightlife: Enjoy live music and various activities that enhance the lively evening scene.
• Welcoming Accommodation: A range of charming bed and breakfasts and hotels cater to diverse preferences.

Find great hotels near Chester

Discover a delightful range of accommodation options in Chester, Massachusetts, where charming bed and breakfasts and inviting hotels cater to every traveler's desires. Whether you're seeking family-friendly facilities, pet-friendly services, or an adventurous getaway, Chester's hotels offer a variety of amenities to enhance your stay. Experience the best of hospitality in this picturesque locale, with options suited for all budgets and preferences.

• Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the picturesque Berkshires, this 3.5-star resort is a haven for those seeking adventure and family-friendly experiences. Located 24.1km from Chester, the resort is LGBTQIA welcoming, making it a diverse choice for all travellers. Guests can delight in a variety of outdoor activities, including skiing, hiking, and snowboarding, with rental options available nearby. The resort also offers amenities tailored for children, such as a free crib service, an arcade game room, and an onsite mini-golf course, ensuring a fun-filled stay for families.
• The Black Swan Lee - Lenox, an Ascend Collection Hotel: This charming 3-star hotel, situated 24.1km from Chester, is perfect for those travelling with pets and looking for an adventurous family getaway. The Black Swan offers a range of recreational activities, including onsite fishing and various skiing options nearby. Families will appreciate the thoughtful amenities for children, such as a free crib service and first aid kits. With a pet-friendly policy that allows dogs and service animals, this hotel ensures that no family member is left behind, making it a welcoming choice for all.
• Quality Inn: Located 22.5km from Chester, Quality Inn caters primarily to business travellers seeking comfort and convenience. This hotel provides essential amenities for a productive stay, including a business centre and complimentary Wi-Fi. While it may not offer the extensive recreational options of other hotels, its strategic location makes it an ideal base for exploring the surrounding area or attending meetings. Guests can expect a practical, no-frills stay focused on their professional needs.

Where to stay near Chester

Chester, Massachusetts, offers a delightful blend of outdoor adventures and romantic getaways, perfect for families and couples alike. Explore charming spots in the city centre, where you can enjoy shopping and local eateries. Venture into the scenic surroundings for breathtaking views and relaxing recreational activities. With its inviting atmosphere, Chester is an ideal base to discover nearby picturesque towns and natural landscapes that enhance your travel experience.

• Lenox: Nestled 27.4km from Chester, Lenox is a charming city that thrives on its rich cultural offerings. Visitors flock here primarily from June to August for a delightful blend of entertainment and romantic experiences. The city is renowned for its music concerts and theatre performances, making it a cultural hub. Outdoor enthusiasts will appreciate its picturesque mountains and serene lakes, while those seeking spiritual solace can visit local places of worship. Lenox is an ideal spot for travellers looking to immerse themselves in the arts while enjoying stunning natural landscapes.
• The Berkshires: Just 19.3km away from Chester, The Berkshires is a remarkable region that offers year-round appeal, especially during the peak summer months. This area is perfect for outdoor adventurers and nature lovers, featuring numerous ski fields and resorts that attract visitors seeking thrilling activities. The breathtaking scenery, characterised by lush mountains and serene lakes, provides a stunning backdrop for hiking, skiing, and other outdoor pursuits. Additionally, The Berkshires hosts various events and conferences, making it a vibrant destination for both relaxation and social engagement.
• Becket: Located a mere 9.7km from Chester, Becket is a beautiful city that invites couples and outdoor enthusiasts alike to explore its scenic beauty. With a steady influx of visitors from June to August, Becket offers a romantic atmosphere complemented by its proximity to a national state park. Popular activities here include theatre performances, dance events, and skiing in the winter months. The surrounding landscapes, featuring tranquil lakes and majestic mountains, create a perfect setting for a peaceful retreat or an adventurous getaway, making Becket a hidden gem worth visiting.

Things to do near Chester

Chester, Massachusetts, is a charming destination perfect for outdoor enthusiasts and those seeking adventure or romance. Visitors can enjoy skiing at local resorts and explore the scenic beauty of the surrounding area. Additionally, Chester offers a lively atmosphere with live music and various fun activities, ensuring an enjoyable nightlife experience. A trip to Chester promises memorable moments and delightful experiences amidst nature's splendour.

Shopping

In Chester, you can visit the Berkshire Mountain Country Store, a charming shop located 22.5km away. If you're up for a drive, the Holyoke Mall, situated 30.6km from Chester, offers a vast selection of stores and entertainment options. Guido's Marketplace is another great choice, located 27.4km away.

Recreation

Jacob's Pillow, a renowned dance venue, offers a rich cultural experience just 11.3km from Chester, blending romance and entertainment. For a tranquil day, visit Goose Pond Reservation, 17.7km away, where you can unwind in nature's embrace. Golf enthusiasts will enjoy Wyndhurst Golf & Club, located 24.1km away, featuring splendid outdoor sports.

Adventure

Blandford Ski Area, located 11.3km from Chester, offers exhilarating skiing experiences amidst stunning winter sports vibes. For a scenic adventure, hike the Skyline Trail, also 11.3km away, where breathtaking outdoor views await. Alternatively, enjoy the slopes at Otis Ridge, situated 14.5km from Chester, for more skiing thrills.

Nightlife

The nightlife in Chester offers a delightful mix of romance and entertainment at Shakespeare and Company and the Academy of Music Theater, both 16 and 29.0km away respectively. For family fun, Spare Time Bowling provides an adventurous arcade experience, perfect for an evening of laughter and excitement.

Booking tips and Expedia advantages for Chester

To save money on your visit to Chester, consider travelling during the off-peak months of March and December to January, when accommodation prices are lower. Avoid weekends, particularly Saturdays, as these tend to be the most expensive days to stay. Use Expedia to find budget-friendly options and refine your search for eco-certified hotels. For further savings, book a package that combines flights, accommodation, and activities. Additionally, explore the town on foot to minimise transport costs and take advantage of free local attractions.

• 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: Utilise Expedia’s search tool to refine your options based on your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase hotels that are both sustainable and environmentally friendly, available at this moment. To find the best prices and offers, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel reservation in Chester with your flights and activities by opting for an Expedia package.

Find the best attractions in and around Chester

Chester, Massachusetts, is perfect for outdoor and romantic getaways, offering attractions such as urban parks, nature reserves, and historic houses. Ideal for families and adventure seekers, visitors can enjoy a range of outdoor activities. Don't miss the opportunity to visit Chester, CT, to explore its charming scenery and local culture, enhancing your vacation experience in this delightful region.

• Becket Land Trust Historic Quarry: This unique reserve offers a blend of adventure and family-friendly activities, set in a picturesque landscape just 4.8km from Chester. Explore the historic quarry and enjoy the trendy atmosphere while reconnecting with nature. Ideal for both budget-conscious and luxury seekers.
• Chester Town Hall: A charming civic building located in the heart of Chester, the Town Hall is steeped in history and showcases the local culture. Its architecture and surrounding area provide a delightful experience for visitors interested in the town's heritage.
• Glendale Falls: Situated 8.0km from Chester, this stunning waterfall is perfect for those seeking romance and outdoor adventure. Hike the scenic trails and enjoy the tranquil sounds of cascading water amidst a beautiful natural setting.

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

For your visit to Chester, Massachusetts, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is approximately 45.1km away. Nearby hotels include the 4-star Simsbury 1820 House, 11.3km from the airport, and the 3.5-star Marriott Hartford/Windsor Airport, just 6.4km away. Albany International Airport (ALB) in New York is about 85.3km from Chester, with hotels such as the 4-star The Landing Hotel at Rivers Casino & Resort, 12.9km away. Worcester Regional Airport (ORH) is 511.3km from Chester, offering hotels like the 4-star Beechwood Hotel, 8.0km from the airport. Each airport has convenient transport access from its nearby hotels.