The best deals on hotels when visiting Cheshire Harbor in Massachusetts.

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Top 24 Hotels In Cheshire Harbor, Massachusetts 01220

Hotel Downstreet

40 Main St North Adams, MA

Enjoy a relaxing environment at Hotel Downstreet near Cheshire Harbor, with inviting rooms designed for comfort and value, all beginning at an affordable $130.99 per night. Relax in accommodations that provide a touch of luxury and comfort, making your stay both enjoyable and affordable.

Guests staying at Hotel Downstreet will appreciate the calm atmosphere, with downtown Cheshire Harbor just a short drive away for easy city access. Take advantage of a Cheshire Harbor hotel that elevates your travel experience—lock in today!

  Call (855) 234-2997 to book with an agent.
  7.4 miles from Cheshire Harbor, MA 01220

Starting at

$130.99

per night

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The Porches Inn at Mass MoCA

231 River Street North Adams, MA

Explore comfort and charm at The Porches Inn at Mass MoCA as you travel to Cheshire Harbor, where refined rooms provide relaxation, with rates starting from $203.99 per night. Find comfort in luxury with rooms that offer sophisticated decor and a high level of amenities for your pleasure.

At The Porches Inn at Mass MoCA, visitors can enjoy the peace and tranquility of the location, while downtown Cheshire Harbor remains within reach for all their sightseeing needs. Discover the beauty of Cheshire Harbor with accommodations that offer style and value—secure now!

  Call (855) 239-4019 to book with an agent.
  7.6 miles from Cheshire Harbor, MA 01220

Starting at

$203.99

per night

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Howard Johnson by Wyndham Williamstown

213 Main St Williamstown, MA

With rooms beginning at $97.99, Howard Johnson by Wyndham Williamstown provides affordable accommodations for guests headed to Cheshire Harbor, creating a hospitable and comfortable space perfect for relaxation. Choose Howard Johnson by Wyndham for your next journey, where you'll find a cheerful and comfortable base for your adventures.

The peaceful location of Howard Johnson by Wyndham Williamstown allows guests to unwind, with downtown Cheshire Harbor a convenient drive away for a day of sightseeing. Plan your Cheshire Harbor getaway smartly with budget-savvy lodging—reserve your room today!

  Call (855) 234-5074 to book with an agent.
  7.7 miles from Cheshire Harbor, MA 01220

Starting at

$97.99

per night

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Williamstown Motel

295 Main Street Williamstown, MA

With rooms starting at $79.99, Williamstown Motel offers budget-friendly accommodations for guests visiting Cheshire Harbor, creating a pleasant space ideal for a relaxing stay. Find value in rooms that offer reliable comfort, ensuring a pleasant and worry-free stay at an economical price.

From Williamstown Motel, the drive into downtown Cheshire Harbor is simple and convenient, making it easy for guests to explore the city while enjoying a more relaxed stay. Stay affordably and comfortably on your Cheshire Harbor adventure—reserve today!

  Call (855) 233-7850 to book with an agent.
  7.9 miles from Cheshire Harbor, MA 01220

Starting at

$79.99

per night

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Fairfield Inn & Suites by Marriott Williamstown

430 Main St Williamstown, MA

At Fairfield Inn & Suites by Marriott Williamstown, guests bound for Cheshire Harbor will find restful accommodations with rates beginning at $159.99, creating a warm and welcoming environment. Enjoy Fairfield’s seasonal outdoor equipment rentals, such as bicycles in the summer and snow gear in the winter.

Guests at Fairfield Inn & Suites by Marriott Williamstown will love the calm atmosphere, with downtown Cheshire Harbor just a drive away for easy access to the city’s top destinations. Settle in and enjoy your Cheshire Harbor stay with amenities that make all the difference—reserve now!

  Call (855) 235-0725 to book with an agent.
  8.1 miles from Cheshire Harbor, MA 01220

Starting at

$159.99

per night

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Willows Motel Williamstown

480 Main St Williamstown, MA

Guests bound for Cheshire Harbor can enjoy affordable comfort at Willows Motel Williamstown, where rooms start at $83.00, creating a heartwarming, welcoming environment perfect for unwinding. Experience dependable comfort in well-appointed rooms that provide everything you need for a relaxing and budget-friendly stay.

From Willows Motel Williamstown, downtown Cheshire Harbor is still within reach by car, allowing guests to explore the city while retreating to a quieter setting afterward. Book an inviting, budget-friendly hotel for your Cheshire Harbor travels and relax—reserve now!

  Call (855) 235-6136 to book with an agent.
  8.2 miles from Cheshire Harbor, MA 01220

Starting at

$83.00

per night

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The Williams Inn

101 Spring Street Williamstown, MA

Step into elegance at The Williams Inn as you explore Cheshire Harbor, where refined rooms create comfort and warmth, with budget-friendly rates beginning at $223.99. Relax in spaces where luxury and functionality meet, providing a haven of comfort and style for every guest.

The calm atmosphere at The Williams Inn makes for a restful stay, with downtown Cheshire Harbor just a drive away for easy access to the city’s highlights. Discover the beauty of Cheshire Harbor with accommodations that turn comfort into an art form—secure now!

  Call (855) 235-6136 to book with an agent.
  8.6 miles from Cheshire Harbor, MA 01220

Starting at

$223.99

per night

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Blue Vista Motor Lodge

229 Mohawk Trail North Adams, MA

For a calm stay near Cheshire Harbor, Blue Vista Motor Lodge offers inviting accommodations with rooms beginning at $157.99, creating a warm and welcoming environment ideal for rest. Find value in clean, comfortable rooms that provide dependable comfort and a welcoming environment.

The calm atmosphere at Blue Vista Motor Lodge provides a restful stay, with downtown Cheshire Harbor still within easy reach for those wanting to explore the city. Enjoy Cheshire Harbor to the fullest with a welcoming, cost-effective hotel—reserve now!

  Call (855) 234-2997 to book with an agent.
  8.9 miles from Cheshire Harbor, MA 01220

Starting at

$157.99

per night

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FairBridge Inn Express

16 Cheshire Road Pittsfield, MA

For a warm-hearted and affordable stay near Cheshire Harbor, FairBridge Inn Express offers comfortable accommodations with rates beginning at $79.99, providing a warm environment. Find a balance of comfort and value in rooms that provide a straightforward, clean, and comfortable environment.

Guests staying at FairBridge Inn Express can appreciate the calm surroundings, with downtown Cheshire Harbor still within reach for a day of exploring the city’s highlights. Stay in Cheshire Harbor with accommodations that balance luxury and affordability—book today!

  Call (855) 234-7135 to book with an agent.
  9.2 miles from Cheshire Harbor, MA 01220

Starting at

$79.99

per night

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Cozy Corner Motel

284 Sand Springs Rd. Rte 7 Williamstown, MA

With affordable rooms starting at $75.05, soft Corner Motel provides budget-conscious comfort for guests visiting Cheshire Harbor, creating a welcoming and relaxing space. Rest easy in clean, comfortable rooms that offer standard amenities, ensuring a worry-free stay at a great price.

Guests staying at Cozy Corner Motel will love the calm environment, while downtown Cheshire Harbor remains a convenient drive away for a day of exploration. Book an inviting, budget-friendly hotel for your Cheshire Harbor travels and relax—reserve now!

  Call (855) 235-0725 to book with an agent.
  10.3 miles from Cheshire Harbor, MA 01220

Starting at

$75.05

per night

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The Villager Motel

953 Simonds Rd Williamstown, MA

With rates from $69.00, The Villager Motel provides budget-conscious comfort for travelers visiting Cheshire Harbor, creating a warm and inviting atmosphere ideal for relaxation. Stay in accommodations that deliver reliable comfort and value, ensuring a pleasant and budget-conscious visit.

A calm atmosphere and proximity to downtown Cheshire Harbor make The Villager Motel ideal for travelers who want to balance city exploration with rest. Book now and make your Cheshire Harbor stay both cozy and cost-effective—reserve today!

  Call (855) 234-2997 to book with an agent.
  10.5 miles from Cheshire Harbor, MA 01220

Starting at

$69.00

per night

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Hotel on North

297 North Street Pittsfield, MA

Relax in the warmth of Hotel on North as you visit Cheshire Harbor, where refined accommodations provide a charming stay, with budget-friendly rates from $145.99. Enjoy accommodations that provide a rich blend of luxury and practicality, ensuring a satisfying and restful stay.

Guests staying at Hotel on North will enjoy the tranquil surroundings, while downtown Cheshire Harbor remains easily accessible by car. Get the most out of Cheshire Harbor with a hotel that’s dedicated to your happiness—lock in today!

  Call (855) 235-6136 to book with an agent.
  11.3 miles from Cheshire Harbor, MA 01220

Starting at

$145.99

per night

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Holiday Inn & Suites Pittsfield Berkshires an IHG Hotel

One West Street Pittsfield, MA

Find the perfect mix of comfort and value at Holiday Inn & Suites Pittsfield Berkshires an IHG Hotel near Cheshire Harbor, where gentle accommodations start from an affordable rate of $124.00 per night. Manage your stay with ease using Holiday Inn’s mobile app, from digital room keys to local area guides.

For those looking for relaxation, Holiday Inn & Suites Pittsfield Berkshires an IHG Hotel provides peaceful surroundings with downtown Cheshire Harbor still accessible for sightseeing. Make your Cheshire Harbor visit memorable with a hotel that blends elegance and affordability—book today!

  Call (855) 234-5074 to book with an agent.
  11.6 miles from Cheshire Harbor, MA 01220

Starting at

$124.00

per night

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Berkshire Inn

150 West Housatonic St Pittsfield, MA

With rooms beginning at $88.99, Berkshire Inn provides inviting accommodations for guests headed to Cheshire Harbor, creating a comfortable, welcoming atmosphere for rest. Find value in rooms that offer dependable comfort, making your stay both enjoyable and economical.

For travelers looking to relax, Berkshire Inn offers quiet surroundings while keeping downtown Cheshire Harbor within easy driving distance. Make your Cheshire Harbor travel experience cost-effective and cozy—secure your room today!

  Call (855) 235-6136 to book with an agent.
  12.1 miles from Cheshire Harbor, MA 01220

Starting at

$88.99

per night

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Best Western Plus Berkshire Hills Inn & Suites

1350 West Housatonic St Pittsfield, MA

Guests bound for Cheshire Harbor will find welcoming accommodations at Best Western Plus Berkshire Hills Inn & Suites, with rooms beginning at $97.99, creating a welcoming, comfortable atmosphere ideal for relaxation. Relax in the stylish and comfortable lounge areas at Best Western Plus, perfect for casual meetings or unwinding after a long day.

A relaxing drive takes guests from Best Western Plus Berkshire Hills Inn & Suites into downtown Cheshire Harbor, offering a blend of city adventure and tranquil retreat. Step into an unforgettable Cheshire Harbor adventure with lodging that offers more for less—lock in today!

  Call (855) 234-2997 to book with an agent.
  14.0 miles from Cheshire Harbor, MA 01220

Starting at

$97.99

per night

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Hilton Garden Inn Lenox Pittsfield

1032 South Street Pittsfield, MA

Unwind at Hilton Garden Inn Lenox Pittsfield as you explore Cheshire Harbor, where restful rooms offer relaxation and comfort, with affordable rates starting at $141.99 per night. Appreciate the convenience of Hilton Garden Inn's on-site parking, perfect for guests who prefer easy access to their vehicles.

Guests staying at Hilton Garden Inn Lenox Pittsfield will enjoy the calm setting, with the excitement of downtown Cheshire Harbor still a smooth drive away. Choose accommodations that turn your Cheshire Harbor travels into a relaxing and memorable experience—book today!

  Call (855) 234-7135 to book with an agent.
  14.3 miles from Cheshire Harbor, MA 01220

Starting at

$141.99

per night

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Wagon Wheel Inn

484 Pittsfield Rd Lenox, MA

Guests traveling to Cheshire Harbor can unwind at Wagon Wheel Inn, where inviting rooms start at $69.00, creating a clean and comfortable environment perfect for relaxation. Relax in accommodations that balance comfort and practicality, offering a comfortable environment at a great price.

Unwind in the serene environment of Wagon Wheel Inn, where peaceful surroundings meet easy access to the heart of downtown Cheshire Harbor. Enjoy Cheshire Harbor with a hotel that makes affordability feel effortless—reserve your room today!

  Call (855) 235-6136 to book with an agent.
  14.6 miles from Cheshire Harbor, MA 01220

Starting at

$69.00

per night

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The Yankee Trademark Collection by Wyndham

461 Pittsfield Rd Lenox, MA

With rooms beginning at $100.99, The Yankee Trademark Collection by Wyndham provides affordable comfort for travelers to Cheshire Harbor, creating a warm and welcoming space perfect for relaxation. Stay in accommodations where each detail tells a story of the region, from the artwork to the furnishings and beyond.

Guests staying at The Yankee Trademark Collection by Wyndham can enjoy a quiet retreat, with downtown Cheshire Harbor still within reach for all their city adventures. Maximize your Cheshire Harbor adventure with inviting, well-appointed lodging—secure your room now!

  Call (855) 234-5074 to book with an agent.
  14.6 miles from Cheshire Harbor, MA 01220

Starting at

$100.99

per night

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Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox, MA

At Howard Johnson by Wyndham Lenox, travelers to Cheshire Harbor can find hospitable, affordable rooms beginning at $77.99, creating a clean and inviting environment perfect for unwinding. Spend time outdoors in our beautifully maintained spaces, perfect for relaxing or enjoying a leisurely evening.

For a relaxing stay, Howard Johnson by Wyndham Lenox offers quiet surroundings, with the added convenience of downtown Cheshire Harbor being within easy reach. Stay comfortable and budget-savvy on your Cheshire Harbor visit—lock in your room today!

  Call (855) 239-5277 to book with an agent.
  14.6 miles from Cheshire Harbor, MA 01220

Starting at

$77.99

per night

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Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd Lenox, MA

Guests traveling to Cheshire Harbor will appreciate the inviting comfort at Hampton Inn & Suites Berkshires Lenox, where budget-friendly rooms start at $135.99, creating a warm, welcoming environment. Explore with confidence, knowing that Hampton by Hilton's locations are conveniently situated near local attractions and business centers.

A peaceful stay awaits at Hampton Inn & Suites Berkshires Lenox, where tranquil surroundings combine with easy access to downtown Cheshire Harbor. Discover the joy of Cheshire Harbor with a hotel that pairs convenience with affordability—lock in today!

  Call (855) 233-0132 to book with an agent.
  14.8 miles from Cheshire Harbor, MA 01220

Starting at

$135.99

per night

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Life House Berkshires

194 Pittsfield Rd Lenox, MA

Relax in the elevated comfort of Life House Berkshires near Cheshire Harbor, where quality rooms offer a welcoming environment, with rates starting at an accessible $108.99. Stay in rooms that redefine comfort and luxury, offering a wealth of amenities to make your visit exceptional.

Guests staying at Life House Berkshires will love the serene atmosphere, while downtown Cheshire Harbor remains close by for all their city adventures. Get the most out of Cheshire Harbor with a hotel that knows how to treat guests right—book today!

  Call (855) 233-0132 to book with an agent.
  15.8 miles from Cheshire Harbor, MA 01220

Starting at

$108.99

per night

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Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd Lenox, MA

Find a peaceful escape at Courtyard by Marriott Lenox Berkshires near Cheshire Harbor, where mellifluous rooms create a welcoming stay, with affordable rates starting at $161.99 per night. Maintain your fitness routine with ease in Courtyard's well-equipped gym, ensuring you stay energized and active during your travels.

For guests seeking both tranquility and city access, Courtyard by Marriott Lenox Berkshires offers the best of both worlds, with downtown Cheshire Harbor within reach. Make every moment of your Cheshire Harbor visit special with accommodations that impress—book today!

  Call (855) 234-7135 to book with an agent.
  16.4 miles from Cheshire Harbor, MA 01220

Starting at

$161.99

per night

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South Shire

124 Elm St Bennington, VT

Enjoy a welcoming experience at South Shire as you explore Cheshire Harbor, where refined accommodations offer warmth, with budget-friendly rates beginning at $198.99. Enjoy a stay that combines timeless elegance with modern luxury, where rooms are designed to provide an unparalleled level of comfort.

Guests staying at South Shire will appreciate the balance of easy city access and the calming retreat offered by the hotel. Choose a hotel in Cheshire Harbor that transforms your visit into a world-class experience—book today!

  Call (855) 233-0132 to book with an agent.
  19.7 miles from Cheshire Harbor, MA 01220

Starting at

$198.99

per night

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The Black Swan Lee Lenox Ascend Hotel Collection

435 Laurel St Lee, MA

Stay at The Black Swan Lee Lenox Ascend Hotel Collection as you explore Cheshire Harbor, where comfortable rooms create a welcoming atmosphere, with nightly rates starting at a friendly $98.99. Experience a delightful stay in rooms that are thoughtfully equipped with modern amenities and extra comfort features.

With a relaxing drive into downtown Cheshire Harbor, guests at The Black Swan Lee Lenox Ascend Hotel Collection can explore the city’s best spots before retreating to the peaceful surroundings of their stay. Make your Cheshire Harbor trip unforgettable with well-appointed, budget-conscious accommodations—reserve now!

  Call (855) 239-5277 to book with an agent.
  19.7 miles from Cheshire Harbor, MA 01220

Starting at

$98.99

per night

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