The best deals on hotels when visiting Chester in Massachusetts.

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Top 24 Hotels In Chester, Massachusetts 01050

Quality Inn Westfield Springfield

2 Southampton Rd Westfield, MA

For a delightful and inviting stay, Quality Inn Westfield Springfield offers budget-friendly accommodations with rates from $96.99, creating a warm and comfortable environment. Trust in Quality Inn's dedication to cleanliness, providing a safe and welcoming environment for every guest.

Relax in the peaceful surroundings of Quality Inn Westfield Springfield, knowing that downtown Chester is still within easy reach for a day of exploration. Rest easy in Chester with accommodations that deliver value and quality—secure your room today!

  Call (855) 235-6136 to book with an agent.
  14.7 miles from Chester, MA 01050

Starting at

$96.99

per night

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Hampton Inn Westfield

39 Southampton Rd Westfield, MA

With rates starting at $137.99, Hampton Inn Westfield provides budget-conscious accommodations for travelers visiting Chester, creating a warm-hearted atmosphere perfect for relaxation. Gather by the fireplace in select Hampton lobby areas, a cozy spot for meeting friends or winding down after a busy day.

Rest in the quiet surroundings of Hampton Inn Westfield, while downtown Chester remains a comfortable drive away for city adventures. Experience Chester in style and on budget with accommodations tailored for you—lock in today!

  Call (855) 234-7135 to book with an agent.
  14.9 miles from Chester, MA 01050

Starting at

$137.99

per night

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Pilgrim Inn

165 Housatonic St Lee, MA

Guests traveling to Chester will find soft accommodations at Pilgrim Inn, where rooms begin at $89.99, creating a warm, inviting environment ideal for relaxation. Enjoy a little extra comfort and convenience in rooms that offer upgraded amenities at an economical price.

For a peaceful retreat, Pilgrim Inn offers quiet surroundings, with the convenience of downtown Chester still being nearby. Find the right balance between affordability and quality during your Chester trip—lock in today!

  Call (855) 235-0725 to book with an agent.
  15.4 miles from Chester, MA 01050

Starting at

$89.99

per night

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Quality Inn

170 Housatonic Street Lee, MA

With rates from $93.99, Quality Inn is ideal for travelers bound for Chester, providing cozy-like, budget-friendly accommodations perfect for relaxation. Keep up with your fitness routine in Quality Inn's well-equipped exercise rooms, helping you stay active while on the road.

Guests staying at Quality Inn will love the peaceful retreat, with downtown Chester just a convenient drive away for easy access to all the city's attractions. Plan your Chester getaway with a hotel that knows how to make you feel at home—reserve today!

  Call (855) 239-4019 to book with an agent.
  15.5 miles from Chester, MA 01050

Starting at

$93.99

per night

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Sunset Inn

150 Housatonic Street Lee, MA

With rates starting at $90.99, Sunset Inn provides budget-conscious comfort for travelers to Chester, creating a clean and harmonious space ideal for relaxation. Stay in rooms that provide dependable amenities and straightforward comfort, perfect for budget-conscious travelers.

For those looking to unwind, Sunset Inn offers a quiet retreat, while the convenience of downtown Chester is within reach. Book a welcoming hotel for your Chester travels that fits your budget—secure today!

  Call (855) 233-0132 to book with an agent.
  15.5 miles from Chester, MA 01050

Starting at

$90.99

per night

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Fairfield Inn & Suites Springfield Northampton / Amherst

115A Conz Street Northampton, MA

Relax in the warm ambiance of Fairfield Inn & Suites Springfield Northampton / Amherst on your trip to Chester, where restful rooms provide a welcoming retreat, with rates beginning at just $189.99 per night. Experience the Fairfield 100 percent Guarantee, ensuring your satisfaction with every aspect of your stay.

For those seeking a balance of relaxation and city exploration, Fairfield Inn & Suites Springfield Northampton / Amherst offers tranquility with downtown Chester still close by. Plan a relaxing Chester getaway with accommodations that prioritize your needs—book today!

  Call (855) 239-5277 to book with an agent.
  16.1 miles from Chester, MA 01050

Starting at

$189.99

per night

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Quality Inn & Suites Northampton Amherst

117 Conz St Northampton, MA

Guests bound for Chester can enjoy harmonious comfort at Quality Inn & Suites Northampton Amherst, where rooms start at $132.99, creating a welcoming environment ideal for relaxation. Enjoy a refreshing swim in Quality Inn's indoor or outdoor pools, suitable for relaxation or family fun.

For travelers seeking a peaceful retreat, Quality Inn & Suites Northampton Amherst offers a calm environment while keeping downtown Chester within a convenient drive. Settle into Chester with lodging that keeps costs low and comfort high—reserve today!

  Call (855) 239-5277 to book with an agent.
  16.1 miles from Chester, MA 01050

Starting at

$132.99

per night

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Econo Lodge Lee Great Barrington

980 Pleasant Street Lee, MA

Guests bound for Chester will appreciate the delightful accommodations at Econo Lodge Lee Great Barrington, with rates beginning at $55.99, creating a clean and welcoming space for relaxation. Rest comfortably in Econo Lodge's rooms, featuring quality bedding and a selection of pillows for a good night's sleep.

Guests at Econo Lodge Lee Great Barrington can enjoy a calm retreat, with downtown Chester still close enough for a day of city exploration. Enjoy a stress-free Chester trip with affordable, comfortable accommodations—lock in now!

  Call (855) 233-0132 to book with an agent.
  16.5 miles from Chester, MA 01050

Starting at

$55.99

per night

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The Black Swan Lee Lenox Ascend Hotel Collection

435 Laurel St Lee, MA

Enjoy a restful atmosphere at The Black Swan Lee Lenox Ascend Hotel Collection as you explore Chester, where quality accommodations provide comfort, with budget-friendly rates from $98.99 per night. Enjoy a blend of functionality and comfort in rooms that are designed to meet the needs of today’s travelers.

At The Black Swan Lee Lenox Ascend Hotel Collection, guests can unwind in quiet surroundings, with the added convenience of downtown Chester being just a drive away. Enjoy every aspect of your Chester visit with accommodations that never disappoint—reserve now!

  Call (855) 236-8982 to book with an agent.
  16.5 miles from Chester, MA 01050

Starting at

$98.99

per night

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D. Hotel Suites & Spa

1 Country Club Rd Holyoke, MA

Stay comfortably at D. Hotel Suites & Spa when exploring Chester, with restful rooms and a welcoming ambiance, with starting rates from $135.99 per night. Find comfort and convenience in rooms that offer a range of amenities, designed to enhance your experience.

Guests at D. Hotel Suites & Spa can enjoy the peaceful retreat of a quieter stay, with downtown Chester just a scenic drive away. Discover a hotel in Chester that turns your visit into an extraordinary experience—reserve now!

  Call (855) 235-6136 to book with an agent.
  17.1 miles from Chester, MA 01050

Starting at

$135.99

per night

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Fairfield Inn & Suites Springfield Holyoke

229 Whiting Farms Road Holyoke, MA

Guests bound for Chester will find reassuring comfort at Fairfield Inn & Suites Springfield Holyoke, where inviting rooms start at $139.99, creating a welcoming atmosphere ideal for relaxation. Unwind in the evening with Fairfield's custom-designed lounges, perfect for a nightcap or a casual meeting with colleagues.

For a restful stay, Fairfield Inn & Suites Springfield Holyoke offers quiet surroundings with downtown Chester remaining nearby for easy access to city attractions. Discover a Chester experience where comfort and affordability come together—secure now!

  Call (855) 234-7135 to book with an agent.
  17.3 miles from Chester, MA 01050

Starting at

$139.99

per night

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Homewood Suites by Hilton Holyoke Springfield / North

375 Whitney Ave Holyoke, MA

Homewood Suites by Hilton Holyoke Springfield / North is a relaxing choice for travelers visiting Chester, where enveloping rooms offer comfort and quality, with nightly rates beginning at just $142.99. Stay connected with complimentary high-speed Wi-Fi at Homewood Suites, making it easy to work or stay in touch while you're away.

Guests at Homewood Suites by Hilton Holyoke Springfield / North can enjoy a serene escape, with downtown Chester remaining accessible for city exploration. Embrace a Chester visit where luxury meets affordability—lock in your hotel room today!

  Call (855) 239-5277 to book with an agent.
  17.3 miles from Chester, MA 01050

Starting at

$142.99

per night

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Hampton Inn Hadley Amherst Area

24 Bay Rd Hadley, MA

With affordable rooms from $138.99, Hampton Inn Hadley Amherst Area is ideal for travelers visiting Chester, creating a comfortable, welcoming environment perfect for unwinding. Kickstart your day with Hampton's complimentary hot breakfast, a hearty and healthy way to start your morning.

For a restful escape, Hampton Inn Hadley Amherst Area provides peaceful surroundings with the convenience of downtown Chester still being nearby. Enjoy a seamless Chester experience with amenities designed for your convenience—reserve now!

  Call (855) 239-4019 to book with an agent.
  17.4 miles from Chester, MA 01050

Starting at

$138.99

per night

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FairBridge Inn Express

16 Cheshire Road Pittsfield, MA

At FairBridge Inn Express, travelers bound for Chester will find cushy rooms with rates beginning at $79.99, creating a warm and welcoming space ideal for relaxation. Find a perfect blend of affordability and comfort in rooms that offer more amenities for a relaxing and enjoyable stay.

For a restful stay, FairBridge Inn Express offers serene surroundings with downtown Chester still close enough for easy access. Enjoy the perfect mix of affordability and comfort during your Chester stay—reserve today!

  Call (855) 233-7850 to book with an agent.
  18.2 miles from Chester, MA 01050

Starting at

$79.99

per night

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Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd Lenox, MA

Stay at Courtyard by Marriott Lenox Berkshires for a restful visit to Chester, where soothing accommodations create a comfortable atmosphere, with nightly rates starting at just $161.99. Relax with Courtyard's selection of herbal teas, available in guest rooms for a soothing beverage before bedtime.

With a relaxing drive into downtown Chester, guests at Courtyard by Marriott Lenox Berkshires can explore the city’s best spots before retreating to the peaceful surroundings of their stay. Stay effortlessly in Chester with a hotel that offers exceptional value and amenities—secure now!

  Call (855) 239-4019 to book with an agent.
  18.2 miles from Chester, MA 01050

Starting at

$161.99

per night

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Life House Berkshires

194 Pittsfield Rd Lenox, MA

Those visiting Chester will find relaxation at Life House Berkshires, where refined accommodations offer warmth, with inviting rates starting at an accessible $108.99. Find your ideal luxury retreat in rooms that combine high-end amenities with impeccable service and style.

Rest in the quiet setting of Life House Berkshires, with downtown Chester still accessible for a blend of rest and city adventure. Make every moment in Chester spectacular with accommodations that prioritize your comfort—secure now!

  Call (855) 235-0725 to book with an agent.
  18.2 miles from Chester, MA 01050

Starting at

$108.99

per night

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Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd Lenox, MA

At Hampton Inn & Suites Berkshires Lenox, travelers bound for Chester will find inviting comfort with rooms beginning at $135.99, creating a clean and welcoming space perfect for relaxation. Experience the warmth of Hampton's community-focused approach, with inviting public spaces designed to bring guests together.

Guests at Hampton Inn & Suites Berkshires Lenox will appreciate the calm environment, while the energy of downtown Chester remains easily accessible. Stay effortlessly in Chester with a hotel that ensures your stay is worry-free—reserve now!

  Call (855) 235-6136 to book with an agent.
  18.3 miles from Chester, MA 01050

Starting at

$135.99

per night

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Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox, MA

For budget-savvy travelers visiting Chester, Howard Johnson by Wyndham Lenox offers inviting rooms with rates starting at $77.99, creating a comfortable, comfortable environment ideal for rest. Kick back in Howard Johnson's outdoor spaces, perfect for enjoying a sunny afternoon or a quiet evening under the stars.

For a more peaceful stay, Howard Johnson by Wyndham Lenox offers a calm atmosphere, with downtown Chester just a convenient drive away. Choose a cost-conscious, inviting stay for your Chester visit—reserve today!

  Call (855) 235-6136 to book with an agent.
  18.3 miles from Chester, MA 01050

Starting at

$77.99

per night

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Wagon Wheel Inn

484 Pittsfield Rd Lenox, MA

For an affordable stay near Chester, Wagon Wheel Inn offers budget-friendly comfort with rooms from $69.00, creating a clean and easygoing environment. Enjoy a practical approach to travel in rooms that focus on providing essential comforts and straightforward amenities.

Relax at Wagon Wheel Inn, where peaceful surroundings make for a restful stay and downtown Chester is still within driving distance. Choose a reliable hotel for your Chester adventure that won’t break the bank—book now!

  Call (855) 234-5074 to book with an agent.
  18.3 miles from Chester, MA 01050

Starting at

$69.00

per night

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Hilton Garden Inn Lenox Pittsfield

1032 South Street Pittsfield, MA

Hilton Garden Inn Lenox Pittsfield offers a comforting retreat for travelers to Chester, with restful accommodations that provide a warm ambiance, with room rates from $141.99 per night. Relax in the stylish and comfortable seating areas of Hilton Garden Inn's lobby, a welcoming space for casual meetings or relaxation.

At Hilton Garden Inn Lenox Pittsfield, guests can enjoy a quiet environment, with downtown Chester still accessible for a day of exploration or adventure. Get ready to explore Chester with a hotel that checks all the boxes—book today!

  Call (855) 234-5074 to book with an agent.
  18.4 miles from Chester, MA 01050

Starting at

$141.99

per night

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The Yankee Trademark Collection by Wyndham

461 Pittsfield Rd Lenox, MA

At The Yankee Trademark Collection by Wyndham, guests traveling to Chester will find inviting accommodations with rooms starting at $100.99, creating a hospitable, welcoming environment perfect for rest. Stay where tradition meets trend, in rooms that balance classic elements with modern touches, all inspired by the local culture.

At The Yankee Trademark Collection by Wyndham, guests can relax in quiet surroundings while keeping downtown Chester within easy reach for city exploration. Feel at home in Chester with accommodations that keep comfort affordable—reserve now!

  Call (855) 234-7135 to book with an agent.
  18.4 miles from Chester, MA 01050

Starting at

$100.99

per night

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Knights Inn Hadley

208 Russell St Hadley, MA

At Knights Inn Hadley, guests bound for Chester can enjoy inviting accommodations with rooms starting at $109.99, providing a warm and comfortable environment for relaxation. Stay refreshed with Knights Inn’s daily housekeeping service, keeping your room clean and welcoming each day.

With downtown Chester a scenic drive away, guests at Knights Inn Hadley can balance city exploration with the calm and tranquility of their stay. Make the most of your Chester visit with cost-saving, cozy accommodations—book now!

  Call (855) 235-0725 to book with an agent.
  18.7 miles from Chester, MA 01050

Starting at

$109.99

per night

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The Old Inn on the Green

134 Hartsville NE Marlborough Rd Great Barrington, MA

Step into refined relaxation at The Old Inn on the Green as you explore Chester, where inviting rooms create a tranquil escape, with enticing nightly rates from $265.00. Relax in a setting that offers both luxury and comfort, with rooms featuring elegant furnishings and advanced technological conveniences.

Guests staying at The Old Inn on the Green will love the peaceful retreat, with downtown Chester just a convenient drive away for easy access to all the city's attractions. Get ready to be impressed in Chester with accommodations that make every moment memorable—lock in today!

  Call (855) 236-8982 to book with an agent.
  18.9 miles from Chester, MA 01050

Starting at

$265.00

per night

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Riverdale Inn

1500 Riverdale Street West Springfield, MA

For an affordable and restful stay, Riverdale Inn offers inviting accommodations with rooms starting at $107.99, creating a warm, welcoming space ideal for relaxation. Relax in accommodations that offer essential amenities and a welcoming environment, making your stay both pleasant and affordable.

Guests at Riverdale Inn will appreciate the tranquil environment, with downtown Chester nearby for all their city adventures. Enjoy practical savings and added comfort on your Chester trip—reserve now!

  Call (855) 239-5277 to book with an agent.
  18.9 miles from Chester, MA 01050

Starting at

$107.99

per night

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