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Cheshire Hotels

Cheshire
Jan 19, 2025 - Jan 20, 2025
2 adults, 1 room
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United States Hotels
Massachusetts Hotels
Cheshire Hotels
Price per night:
Up to 100$
$100 - 200
From $200
Rating:
Excellent 9+
Very good 8+
Good 7+
All ratings
Star rating:
5-stars
4-stars
3-stars
Unrated
8.4
Very good (6)
Harbour House Inn B&B
3
View map · 1.2 mi City Centre
From
273US$ /per night

Discover Your Perfect Stay

Nestled in the scenic Berkshires of Massachusetts, Cheshire is a charming town that offers a delightful blend of natural beauty and local charm. Whether you're drawn to its picturesque landscapes or the rich history permeating the area, Cheshire serves as the perfect backdrop for a relaxing getaway. To fully immerse yourself in this quaint community, choosing the right accommodations is essential, and there are several outstanding hotels in Cheshire MA that cater to every traveler's needs.

When exploring the hotels in Cheshire MA, visitors can expect to find a variety of options, from cozy inns to more modern establishments that combine comfort with style. You can enjoy stunning views of the surrounding mountains while kicking back after a day of hiking or sightseeing. Many of these hotels also provide easy access to local attractions, ensuring you make the most of your stay.

In addition to comfortable lodging, the hospitality in Cheshire is second to none, with friendly staff eager to help you discover the area's hidden gems. Don’t miss out on sampling the local cuisine at nearby restaurants, where you can fetch a delicious meal after a day of adventure. With its welcoming atmosphere and the promise of unforgettable experiences, staying at one of the hotels in Cheshire MA will surely enhance your visit to this lovely destination.

Name of hotel Accommodation Rating Price, $
The Williams Inn

9.4 / 10

(163 Reviews)

 From 188US$
The Hotel on North

9.1 / 10

(189 Reviews)

 From 135US$
Inn at Kenmore Hall

9.5 / 10

(8 Reviews)

 From 594US$
Berkshire Mountain Lodge

8.4 / 10

(601 Reviews)

 From 168US$
The Porches Inn at Mass MoCA

8.7 / 10

(93 Reviews)

 From 169US$
9.4
Excellent (163)

The Williams Inn

4
101 Spring Street
The Williams Inn is a quintessential boutique hotel that combines modern luxury with a charming New England aesthetic. Nestled amidst the picturesque Berkshire Mountains, it offers plush accommodations with stunning views and tailored experiences for guests. The hotel's restaurant serves locally sourced cuisine, allowing visitors to savor the flavors of the region. Additionally, you'll find thoughtfully curated guest rooms that reflect the character and warmth of Cheshire MA. With easy access to hiking trails and cultural attractions, this hotel captures the essence of a Berkshire escape. Whether you're planning a romantic getaway or an adventure-filled family trip, The Williams Inn is a fantastic choice.

From

188US$ /per night
9.1
Excellent (189)

The Hotel on North

3
297 North Street
Situated just a short drive from Cheshire on North provides an ideal blend of modern amenities and vintage charm. This stylish boutique hotel features a unique decor that pays homage to the area’s history, making it an exciting place to discover. Each guest room is thoughtfully furnished with comfortable bedding and local artwork, ensuring you feel connected to Cheshire MA's artistic community. Guests can indulge in a relaxing atmosphere with complimentary breakfast and a cozy lounge to unwind. The Hotel on North is also conveniently located near several cultural landmarks, making it easier for you to explore the fascinating art scene surrounding Cheshire. This hotel exemplifies the boutique experience with its focus on personal touches and neighborhood vibes.

From

135US$ /per night

Charming Boutique Hotels in Cheshire MA

For travelers seeking a unique experience that blends comfort and style, charming boutique hotels in Cheshire MA present an inviting choice. These accommodations often reflect the local culture and provide personalized service that makes you feel at home. Visitors can enjoy thoughtful design and locally sourced amenities, highlighting the town's rich heritage and artistic flair. With close proximity to various attractions, boutique hotels are perfect for those looking to explore the countryside while enjoying the comforts of home. Each of these hotels showcases the spirit of Cheshire, providing an intimate setting that larger chains simply can't replicate. Here are some top picks for boutique hotels in Cheshire MA that will make your stay unforgettable.

9.5
Excellent (8)

Inn at Kenmore Hall

3
1385 State Road
The Inn at Kenmore Hall is a historic charming hotel known for its traditional design and captivating surroundings. Once an iconic family estate, this structure has been lovingly restored to provide a refined yet cozy experience for guests. The rooms showcase delightful historical details, and the property includes beautifully landscaped gardens that invite guests to relax. Located just outside Cheshire, this hotel is an excellent launching pad for exploring local historic sites and attractions. With its elegant atmosphere and connection to history, The Inn at Kenmore Hall exemplifies the allure of historic hotels in the Cheshire MA area, providing an experience steeped in nostalgia and charm.

From

594US$ /per night
8.4
Very good (601)

Berkshire Mountain Lodge

8 Dan Fox Drive
The Berkshire Mountain Lodge is designed with families in mind, offering spacious suites with full kitchens for the ultimate home-away-from-home experience. Located near Cheshire MA, this hotel provides a variety of amenities, including an outdoor pool and game room that kids will love. Families can explore the surrounding area, filled with lovely hiking trails and local attractions that cater to all ages. The hotel also features a picnic area, encouraging families to enjoy meals outside while soaking up the natural beauty of the Berkshires. With its focus on creating enjoyable, engaging experiences for families, the Berkshire Mountain Lodge is a fantastic choice among hotels in Cheshire MA. Your family will feel right at home during your visit!

From

168US$ /per night

Budget-Friendly Hotels in Cheshire MA

For travelers looking to enjoy the beauty of Cheshire MA without breaking the bank, budget-friendly hotels offer comfortable accommodations at accessible prices. These hotels focus on delivering essential amenities and services that ensure a pleasant stay while keeping costs down. Affordability doesn’t mean compromising on comfort, as many budget options still provide a welcoming atmosphere and convenient access to local attractions. This makes them perfect for families, solo adventurers, or couples seeking an economical getaway. Here are some top budget-friendly hotels in Cheshire MA that won’t empty your wallet while still providing a pleasant experience.

Berkshire Valley Inn

5
2541 Hancock Road
The Berkshire Valley Inn is a quaint, cozy option for couples seeking a peaceful and budget-friendly escape in the very heart of the Berkshires. This small inn offers romantic rooms with a rustic charm, complete with fireplaces and beautiful views of the surrounding countryside. Enjoy leisurely breakfasts served each morning, and unwind in front of the fireplace after a day of exploring the local area together. The inn is within a short drive from local attractions, including charming shops and stunning parks for a day full of adventures. At Berkshire Valley Inn, couples can revel in a romantic atmosphere that feels both intimate and secluded. This hotel is a warm and inviting spot for any couple looking to create lasting memories in Cheshire MA.

From

160US$ /per night
8.7
Excellent (93)

The Porches Inn at Mass MoCA

4
231 River Street
Located just a short drive from Cheshire MA, The Porches Inn at Mass MoCA offers a unique blend of contemporary art and vintage charm, perfect for art-loving couples. Accommodations are inspired by the region's historic mill buildings, providing a cozy yet stylish environment for romantic retreats. Guests can explore the nearby Massachusetts Museum of Contemporary Art, adding an exciting cultural element to their stay. The inviting atmosphere encourages leisurely afternoons spent in charming common areas or enjoying local dining options. At The Porches Inn, you'll immerse yourselves in a vibrant artistic community while savoring quality time together. This hotel stands out as one of the most romantic hotels in Cheshire MA, offering the perfect backdrop for your love story.

From

169US$ /per night
7.3
Good (413)

Berkshire Inn

2
150 W Housatonic St
The Berkshire Inn serves as another excellent budget option for travelers exploring the Cheshire area. This comfortable inn provides spacious rooms with essential amenities while maintaining a relaxed and welcoming atmosphere. Guests will appreciate the friendly staff dedicated to ensuring a pleasant stay, along with the amenities like free breakfast and Wi-Fi. The Berkshire Inn is conveniently located near shopping venues and local attractions, allowing visitors to make the most of their time in the beautiful Berkshires. This inn proves that travelers can enjoy hotels in Cheshire MA without a significant financial commitment, providing exceptional value along with comfort.

From

80US$ /per night

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