Find hotels in Chester, MA from CA $94

Top reasons to visit Chester

• Outdoor Adventures: Chester offers stunning scenery perfect for hiking, golfing, and exploring nature reserves.
• Historic Attractions: Don't miss the iconic Chester Castle and the charming city centre steeped in history.
• Live Performances: Enjoy a variety of theatre performances and music concerts for an engaging cultural experience.
• Family-Friendly Activities: Chester provides a welcoming atmosphere with options for both relaxation and recreation.
• Diverse Accommodations: Choose from cozy bed and breakfasts to comfortable hotels, catering to every traveller's needs.

Find great hotels in Chester

Discover the charm of Chester, Massachusetts, with a variety of hotel accommodations to suit every traveller's needs. Whether you're seeking a cozy bed and breakfast, a budget-friendly option, or a comfortable 4-star hotel, Chester has it all. Enjoy pet-friendly amenities, adventure-themed experiences, and business-friendly facilities, ensuring a memorable stay in this picturesque town.

• The Black Swan Lee - Lenox, Ascend Hotel Collection: Nestled 24.1km from Chester, The Black Swan Lee - Lenox is a charming 3-star hotel that caters to families, adventure seekers, and pet lovers alike. This property is an excellent choice for those looking to immerse themselves in outdoor activities, offering a range of adventure sports such as onsite fishing and nearby skiing lessons. Families will appreciate the thoughtful amenities designed for children, including first aid kits and cribs available upon request. Moreover, pets are welcome with certain restrictions, ensuring that your furry friends can join in on the fun.
• Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This 3.5-star resort, located 24.1km from Chester, is perfect for families, skiing enthusiasts, and adventure lovers. With convenient access to ski shuttles and lifts, guests can easily explore the snowy slopes. The resort boasts a variety of recreational activities, including onsite mini-golf and an arcade game room for children. For those seeking outdoor thrills, skiing, snow tubing, and hiking options are available nearby. The welcoming environment and family-friendly amenities make this resort a fantastic home base for your Berkshires adventure.
• Hampton Inn & Suites Berkshires-Lenox: Situated 27.4km from Chester, Hampton Inn & Suites Berkshires-Lenox offers a blend of adventure, business amenities, and pet-friendly options. This hotel is ideal for business travellers, featuring a well-equipped 24-hour business centre and conference space. Adventure awaits with nearby skiing, snowshoeing, and biking trails. The welcoming atmosphere extends to furry companions, accommodating dogs and cats with designated exercise areas. Guests will enjoy the modern comforts alongside attentive service, making it a great choice for both work and relaxation.

Where to stay in Chester

Chester, Massachusetts, is a charming destination ideal for outdoor enthusiasts and romantic getaways. Explore the picturesque Chester city centre, steeped in history and surrounded by beautiful scenery. Nearby regions offer a family-friendly atmosphere perfect for relaxation and recreation. Don't miss the chance to visit historic sites and enjoy the serene vibes of this delightful town. Whether you're seeking adventure or tranquility, Chester has something special for every type of traveller.

• Lenox: Nestled 27.4km from Chester, Lenox is a charming city renowned for its vibrant cultural scene. With seasonal visitor peaks from June to August, this destination offers a delightful mix of entertainment, romance, and family experiences. Visitors can enjoy live music concerts, captivating theatre performances, and winter skiing adventures. Nature enthusiasts will appreciate the stunning lakes and mountains that surround the area, making it a perfect spot for outdoor activities year-round. Don't miss the local event conference venues that host various exciting gatherings throughout the year.
• Sherwood Forest: A serene neighborhood located 8.0km from Chester, Sherwood Forest is an idyllic escape with a relaxed atmosphere. While visitor numbers peak in July to August and October, this area offers year-round allure for those seeking romance, outdoor activities, and beautiful scenery. Enjoy the recreational areas and nearby theatres that offer captivating performances. The local highlights include picturesque lakes, a lively stadium, and a thrilling theme park, providing ample opportunities for fun and relaxation amidst nature’s beauty.
• Becket: Situated a mere 9.7km from Chester, Becket is a delightful city that attracts visitors with its blend of romance, outdoor adventures, and entertainment. Peak travel periods occur from June to August, making it an ideal summer getaway. Becket boasts a variety of engaging activities, including theatre productions, live music concerts, and skiing at local fields. Nature lovers will enjoy the stunning lakes, majestic mountains, and the nearby national state park, offering plenty of opportunities for hiking and exploring the great outdoors.

Things to do in Chester

Chester, Massachusetts, is perfect for an outdoor, romantic getaway surrounded by stunning scenery. Enjoy activities like theatre performances and music concerts, or explore local educational experiences. Don't miss a visit to Chester Castle, a round of golf at the local course, and the convenience of tour buses for trips from Chester. Plan an exciting day filled with exploration, making the most of your time in this charming town.

Shopping

For a delightful shopping experience in Chester, visit the Berkshire Mountain Country Store or explore Guido's Marketplace for unique finds. If you're up for a drive, the Lee Premium Outlets offer a variety of brand-name deals just 20.9km away, perfect for gift shopping.

Recreation

Experience the artistry of dance at Jacob's Pillow, a cultural gem located 11.3km from Chester, where romance and entertainment meet. For a serene escape, visit Goose Pond Reservation, 17.7km away, offering wellness and relaxation amidst nature's beauty. Enjoy outdoor sports at Wyndhurst Golf & Club, 24.1km distant.

Adventure

Experience the thrill of skiing at Blandford Ski Area, located 11.3km from Chester, where you can enjoy invigorating slopes. For a scenic hike, the Skyline Trail offers outdoor adventure and captivating views, only 11.3km away. For more skiing excitement, head to Berkshire East Ski Resort, 38.6km from Chester.

Nightlife

Experience the charm of Chester's nightlife by catching a performance at Shakespeare and Company, only 25.7km away, or enjoy family fun at Spare Time Bowling, 29.0km away. For a romantic evening, visit the Academy of Music Theater, also 29.0km from Chester.

Booking tips and Expedia advantages for Chester

To save money during your visit to Chester, Massachusetts, consider exploring free attractions like Chester Town Hall, Pyramid Lake, and the Becket Land Trust Historic Quarry. The most affordable months to visit are March and December to January, while Tuesdays typically offer the lowest hotel rates. Use Expedia's search tool to find budget accommodations and consider package deals that combine flights, hotels, and activities for additional savings. Look for eco-friendly hotels to ensure sustainable options that fit your budget.

• 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: Expedia's search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring you see the most affordable hotels first. Additionally, you have the option to narrow down your choices by hotel type; for instance, selecting the "Eco-certified" filter will showcase sustainable and environmentally friendly hotels that you can book.
• Consider bundling your trip: You can save money by combining your Chester hotel reservation with your flights and activities through an Expedia package.

Best time to go to Chester

Visitor numbers in Chester is generally unchanged in popularity throughout the year. 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

To visit Chester, Massachusetts, the nearest major airports are Hartford, CT (BDL-Bradley Intl.), Albany, NY (ALB-Albany Intl.), and Worcester, MA (ORH-Worcester Regional). Bradley International Airport is approximately 45.1km away, with nearby hotels such as the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. Albany International Airport is 85.3km from Chester, offering options like The Landing Hotel at Rivers Casino & Resort, 12.9km away. Worcester Regional Airport is situated 91.7km from Chester, with accommodations like the Beechwood Hotel, located 8.0km from the airport. All these hotels provide accessible transportation to their respective airports.