Best 20 Hotels in Cheshire (MA) to Visit in 2024

Cheshire (MA) Hotels (city in United States)

1. Harbour House Inn B&B

Nestled in the charming town of Cheshire, Massachusetts, the Harbour House Inn B&B offers a cozy and intimate retreat for travelers seeking a unique and personalized experience. This independently owned bed and breakfast boasts a picturesque setting along North State Road, providing easy access to the area's natural beauty and outdoor activities. The property exudes historical charm and warmth, making guests feel right at home from the moment they arrive. Although the star rating is not available, the personalized service and attention to detail elevate the guest experience. With a total of rooms available, the inn promises a peaceful escape with comfortable accommodations and modern amenities. The Check-in Time is 3:30 PM and the Check-out Time is 10:30 AM, allowing guests to relax and unwind at their own pace. Experience the tranquility and charm of Cheshire at the Harbour House Inn B&B.

Checkin : 3:30 PM

Checkout : 10:30 AM

2. The Springs Motel

4.91 Km from Cheshire (MA)

Rated 9.4 /10 (2 reviews)

Checkin : 4:00 PM

Checkout : 11:00 AM

3. Weathervane Motel Lanesboro

6.72 Km from Cheshire (MA)

Discover the charm of Lanesboro, MA with a stay at the Weathervane Motel. This 2-star independent property offers a cozy and comfortable accommodation option in a picturesque setting. Located at 475 South Main Street, the motel provides easy access to the area's attractions and outdoor activities. With a total of spacious rooms, guests can enjoy a peaceful retreat during their visit. The check-in time is 1:00 PM and check-out is at 11:00 AM, allowing for a hassle-free stay. Whether you're exploring the Berkshires or simply passing through, the Weathervane Motel is a welcoming choice for your accommodation needs.

Checkin : 1:00 PM

Checkout : 11:00 AM

4. Vacation Village in the Berkshires

7.1 Km from Cheshire (MA)

Rated 8.9 /10 (18 reviews)

Escape to Vacation Village in the Berkshires, a luxurious 5-star resort located in the charming city of Hancock, Massachusetts. Nestled in the heart of the United States, this property boasts top-notch amenities and impeccable service. With 18 glowing reviews and an impressive average rating of 8.9, guests can expect nothing but the best during their stay. The resort offers a variety of accommodation types, ensuring a comfortable and unforgettable experience for all visitors. Check-in time is at 4:00 PM, allowing guests to settle in and start their vacation with ease. Check-out is at 10:00 AM, giving guests ample time to enjoy all the resort has to offer. Plan your next getaway at Vacation Village in the Berkshires for a truly exceptional experience.

Checkin : 4:00 PM

Checkout : 10:00 AM

5. Club Wyndham Bentley Brook

7.12 Km from Cheshire (MA)

Rated 8.5 /10 (21 reviews)

At Club Wyndham Bentley Brook, exceptional service and top-notch amenities create a memorable experience for guests. Complimentary internet access is available in the hotel to ensure you stay connected during your visit.Complimentary parking is available for guests. Chilly nights become more delightful than balmy ones, as you snuggle near the hotel's inviting hearth.Due to health concerns, smoking is strictly prohibited within the entire premises of hotel. Allow your journey to be free from the pangs of hunger! On-site eateries offer delicious and accessible meal choices.At Club Wyndham Bentley Brook, guests can take pleasure in the delightful recreational amenities provided for their entertainment. At Club Wyndham Bentley Brook, a wide array of amenities guarantees a fulfilling experience throughout your visit. Make your holiday truly memorable by taking a rejuvenating plunge into the pool.At the hotel fitness center, you have the option to engage in your daily exercise routine or simply alleviate your jet lag by breaking a sweat.

Number of Rooms : 80

Checkin : 4:00 PM

Checkout : 10:00 AM

6. Berkshire Valley Inn

7.26 Km from Cheshire (MA)

Checkin : 3:00 PM

Checkout : 11:00 AM

7. Jiminy Peak Mountain Resort

7.4 Km from Cheshire (MA)

Rated 7.9 /10 (4 reviews)

Welcome to Jiminy Peak Mountain Resort in beautiful Hancock, Massachusetts! This 3-star resort is the perfect destination for a relaxing getaway surrounded by stunning natural beauty. With many rooms spread across multiple floors, this resort offers a cozy and comfortable stay for all visitors. Check-in is available starting at 4:00 PM, and guests are able to check-out by 10:30 AM. Renowned for its excellent service and breathtaking views, Jiminy Peak Mountain Resort has received an average rating of 7.9 based on 4 reviews. Don't miss out on the chance to experience the charm and hospitality of this lovely resort during your next trip to Hancock!

Checkin : 4:00 PM

Checkout : 10:30 AM

8. FairBridge Inn Express Pittsfield

8.02 Km from Cheshire (MA)

Rated 4 /10 (2 reviews)

9. Stay Berkshires

8.57 Km from Cheshire (MA)

Rated 3 /10 (1 reviews)

Experience the charm of Stay Berkshires located in the picturesque town of Williamstown, MA. This 2-star hotel offers cozy accommodations and inviting ambiance for a delightful stay. Check-in time is at 2:00 PM and check-out time is at 11:00 AM. With a total of rooms, guests can expect personalized attention and comfort during their visit. Conveniently situated on Cold Spring Road, this hotel is the perfect base for exploring the beauty of the Berkshires. Embrace the tranquility and warmth of Stay Berkshires for a memorable getaway.

Checkin : 2:00 PM

Checkout : 11:00 AM

10. Hotel Downstreet

8.61 Km from Cheshire (MA)

Indulge in luxury and comfort at InterContinental Hotels Group's esteemed Hotel Downstreet located in the charming city of North Adams, MA. With a 3-star rating, this hotel offers a warm and inviting atmosphere for guests to relax and unwind. Situated at 40 Main Street, Hotel Downstreet provides easy access to nearby attractions and activities. Boasting a total of spacious rooms, guests are treated to modern amenities and impeccable service throughout their stay. Whether you're visiting for business or leisure, the hotel's convenient check-in at 3:00 PM and check-out at 11:00 AM allows for a seamless experience. Although the year opened and renovated are unavailable, Hotel Downstreet promises a memorable stay with its top-notch accommodations and prime location in the United States. Don't miss out on the opportunity to experience unparalleled hospitality at this exceptional hotel.

Checkin : 3:00 PM

Checkout : 11:00 AM

11. Howard Johnson by Wyndham Williamstown

8.72 Km from Cheshire (MA)

Rated 8.9 /10 (9 reviews)

At Howard Johnson by Wyndham Williamstown, exceptional service and top-notch amenities create a memorable experience for guests. Complimentary internet access is available in the hotel to ensure you stay connected during your visit.Complimentary parking is available for guests. Due to health concerns, smoking is strictly prohibited within the entire premises of hotel. At Howard Johnson by Wyndham Williamstown, each day commences with a scrumptious breakfast offered at no additional cost. Allow your journey to be free from the pangs of hunger! On-site eateries offer delicious and accessible meal choices.At Howard Johnson by Wyndham Williamstown, guests can take pleasure in the delightful recreational amenities provided for their entertainment. At Howard Johnson by Wyndham Williamstown, a wide array of amenities guarantees a fulfilling experience throughout your visit. Make your holiday truly memorable by taking a rejuvenating plunge into the pool.

Number of Rooms : 35

Checkin : 3:00 PM

Checkout : 11:00 AM

12. Williamstown Motel

8.83 Km from Cheshire (MA)

Rated 8 /10 (3 reviews)

Located in the picturesque town of Williamstown, MA, the Williamstown Motel is a charming 3-star accommodation that promises a comfortable stay. With its convenient location on Main Street Route 2, guests can easily explore the surrounding attractions. The motel offers cozy rooms with modern amenities, perfect for a relaxing getaway. Check-in is at 2:00 PM and check-out at 11:00 AM, ensuring a hassle-free experience. Despite its small size, the Williamstown Motel has received glowing reviews from guests, with an average rating of 8. Whether you're visiting for business or pleasure, this quaint motel is a great choice for your stay in Williamstown.

Checkin : 2:00 PM

Checkout : 11:00 AM

13. The Porches Inn at Mass MoCA

8.84 Km from Cheshire (MA)

Rated 9.3 /10 (2 reviews)

Indulge in luxury at the 4-star rated The Porches Inn at Mass MoCA in North Adams, Massachusetts. Nestled on 231 River Street, this charming inn offers a unique and cozy retreat for guests. Check-in at 3:00 PM and immerse yourself in the artistic surroundings of Mass MoCA. With a total of 0 rooms spread across 0 floors, each space is thoughtfully designed for comfort and style. Enjoy the modern amenities and personalized service that make this accommodation a top choice for travelers. Don't miss the chance to experience the warm hospitality and exceptional comfort of The Porches Inn at Mass MoCA during your next visit.

Checkin : 3:00 PM

Checkout : 11:00 AM

14. The 1896 House Country Inn - Brookside & Pondside

8.86 Km from Cheshire (MA)

Rated 5.8 /10 (7 reviews)

Nestled in the picturesque town of Williamstown, MA, The 1896 House Country Inn - Brookside & Pondside is a charming 4-star inn that exudes historic charm and modern comfort. With a serene location on Cold Spring Road, this former bed and breakfast offers a peaceful retreat for travelers seeking relaxation. Boasting a total of beautifully appointed rooms, each designed with guests' comfort in mind, this inn is perfect for a weekend getaway or a longer stay. The check-in time at 3:00 PM and check-out at 11:30 AM ensure a seamless experience for guests. With an average rating of 5.8 based on 7 reviews, this accommodation promises a delightful stay in the heart of the United States.

Checkin : 3:00 PM

Checkout : 11:30 AM

15. 1896 House Country Inn - Barnside Inn

8.93 Km from Cheshire (MA)

Rated 10 /10 (1 reviews)

Nestled in the charming town of Williamstown (MA), the 1896 House Country Inn - Barnside Inn is a 5-star gem that exudes historic charm and modern luxury. Check-in at 3:00 PM and immerse yourself in the elegant ambiance of this inn with no chain affiliation. With personalized service and attention to detail, this accommodation is perfect for discerning travelers seeking a unique stay. The Barnside Inn offers a cozy retreat with beautifully appointed rooms, each designed for comfort and relaxation. Enjoy a leisurely check-out at 11:00 AM and explore the scenic surroundings of the Berkshires. Discover why guests rave about this hidden gem with a perfect average rating of 10.

Checkin : 3:00 PM

Checkout : 11:00 AM

16. Fairfield Inn & Suites Williamstown

9.06 Km from Cheshire (MA)

Rated 7.8 /10 (5 reviews)

Fairfield Inn & Suites Williamstown provides flawless service and all the necessary facilities for visitors. Share your photos and respond to emails at your convenience, thanks to the free Wi-Fi internet access offered by hotel.Visitors can take advantage of complimentary parking directly at the hotel. Relax and feel the warmth in the hotel's inviting lobby, featuring an enchanting on-site fireplace.The hotel maintains a completely smoke-free zone, providing a breathable atmosphere. Embark on your holiday experience in the most ideal manner. Commence each morning of your visit with an on-site breakfast.Indulge in the numerous pursuits available at Fairfield Inn & Suites Williamstown. Each day at hotel, immerse yourself in the invigorating waters of the pool, perfect for a rejuvenating plunge or a series of revitalizing laps.Bypass the formal attire and choose a laid-back mixed drink or brew at hotel's waterside lounge. For individuals who don't want to skip their exercise routine, visiting the hotel fitness center ensures you maintain your vitality and wellness.

Number of Rooms : 94

Checkin : 4:00 PM

Checkout : 11:00 AM

17. Willows Motel Williamstown

9.14 Km from Cheshire (MA)

Rated 9.7 /10 (5 reviews)

At Willows Motel Williamstown, exceptional service and top-notch amenities create a memorable experience for guests. Complimentary internet access is available in the motel to ensure you stay connected during your visit.Arrange your trips to and from the airport using the motel's convenient transportation services booking. Complimentary parking is available for guests.Chilly nights become more delightful than balmy ones, as you snuggle near the motel's inviting hearth. Due to health concerns, smoking is strictly prohibited within the entire premises of motel. At Willows Motel Williamstown, each day commences with a scrumptious breakfast offered at no additional cost. Allow your journey to be free from the pangs of hunger! On-site eateries offer delicious and accessible meal choices.At Willows Motel Williamstown, affordable refreshments are available 24/7 through the convenient vending machines on-site.

Number of Rooms : 17

Checkin : 1:30 PM

Checkout : 10:30 AM

18. The Williams Inn

9.51 Km from Cheshire (MA)

Rated 10 /10 (1 reviews)

Experience the true essence of New England charm at The Williams Inn, located in the picturesque town of Williamstown, Massachusetts. Nestled on Spring Street, this hotel offers a cozy and inviting atmosphere where guests can unwind and relax. With a perfect rating of 10, this accommodation is a true hidden gem for those seeking a peaceful getaway. Boasting an ideal location near museums, theaters, and hiking trails, guests can immerse themselves in the rich culture and natural beauty of the Berkshires. The Williams Inn features a variety of comfortable rooms, providing a home away from home for every traveler. Although this hotel is not part of a chain, it stands out for its exceptional service and attention to detail. Whether you are visiting for a weekend escape or a longer stay, The Williams Inn promises a memorable and enjoyable experience for all. Discover the charm of New England hospitality at this quaint and welcoming hotel in the heart of Williamstown.

Checkin : 3:00 PM

Checkout : 12:00 PM

19. Hotel on North

10.07 Km from Cheshire (MA)

Rated 10 /10 (2 reviews)

Discover the charm of Hotel on North located on North Street in Pittsfield, MA. This hidden gem offers a unique experience for every traveler, whether you are here for business or leisure. The hotel boasts a stellar average rating of 10, showcasing its commitment to excellence in hospitality. With a prime location in the heart of the city, guests have easy access to nearby attractions, restaurants, and shops. Although the hotel does not belong to a chain, its independent spirit shines through in its personalized service and attention to detail. The check-in and check-out times are convenient for guests, allowing for a seamless stay. With a variety of room options available, guests can choose the perfect accommodation to suit their needs. Come experience the warmth and hospitality of Hotel on North during your next visit to the United States.

Checkin : 4:00 PM

Checkout : 11:00 AM

20. Blue Vista Motor Lodge

10.1 Km from Cheshire (MA)

Checkin : 3:00 PM

Checkout : 11:00 AM

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Top 20 Cheshire (MA) Hotels (city in United States)

Cheshire (MA) Hotels (city in United States)

1. Harbour House Inn B&B

2. The Springs Motel

3. Weathervane Motel Lanesboro

4. Vacation Village in the Berkshires

5. Club Wyndham Bentley Brook

6. Berkshire Valley Inn

7. Jiminy Peak Mountain Resort

8. FairBridge Inn Express Pittsfield

9. Stay Berkshires

10. Hotel Downstreet

11. Howard Johnson by Wyndham Williamstown

12. Williamstown Motel

13. The Porches Inn at Mass MoCA

14. The 1896 House Country Inn - Brookside & Pondside

15. 1896 House Country Inn - Barnside Inn

16. Fairfield Inn & Suites Williamstown

17. Willows Motel Williamstown

18. The Williams Inn

19. Hotel on North

20. Blue Vista Motor Lodge

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