TOP 30 Cozy cottages in Pittsfield, Massachusetts

The Berkshire Inn is a charming lodging establishment located at 150 West Housatonic Street in the picturesque town of Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to enjoy during their stay. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's many attractions, including cultural venues, outdoor activities, and charming shops and restaurants. Whether visiting for business or pleasure, the Berkshire Inn is the perfect home away from home for travelers seeking a relaxing and enjoyable experience in the beautiful Berkshires region.

Yankee Inn, Trademark Collection by Wyndham is a charming lodging establishment located at 461 Pittsfield Road in Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and top-notch amenities, making it the perfect place to relax and unwind during your stay in the beautiful Berkshires. With its convenient location and warm hospitality, Yankee Inn is the ideal choice for travelers looking for a memorable and enjoyable experience in Lenox.

Life House, Berkshires is a charming lodging located at 194 Pittsfield Road in Lenox, Massachusetts. Nestled in the picturesque Berkshires region, this institution offers a peaceful and serene retreat for guests looking to escape the hustle and bustle of everyday life. The accommodations are cozy and comfortable, providing a welcoming atmosphere for visitors to relax and unwind. With its convenient location and warm hospitality, Life House, Berkshires is the perfect destination for a memorable getaway in the heart of the Berkshires.

Wagon Wheel Inn is a charming lodging located at 484 Pittsfield Road in Lenox, Massachusetts. Nestled in the heart of the beautiful Berkshire Mountains, this cozy inn offers comfortable accommodations and a warm, welcoming atmosphere. Guests can relax in well-appointed rooms, enjoy a delicious complimentary breakfast, and take advantage of convenient amenities such as free Wi-Fi and onsite parking. Whether you're visiting for a weekend getaway or a longer stay, Wagon Wheel Inn is the perfect home base for exploring all that Lenox has to offer.

The Heart of the Berkshires Motel is a charming lodging option located at 970 West Housatonic Street in Pittsfield, Massachusetts. Situated in the heart of the picturesque Berkshires region, this motel offers cozy and comfortable accommodations for travelers looking to explore the natural beauty and cultural attractions of the area. With a convenient location and friendly staff, the Heart of the Berkshires Motel is the perfect place to relax and unwind during your visit to the United States.

Berkshire Yankee Suites is a charming lodging establishment located at 20 West Housatonic Street in the picturesque city of Pittsfield, Massachusetts. Our suites offer a cozy and comfortable stay for travelers looking to explore the beautiful Berkshire region. Each suite is tastefully decorated and equipped with modern amenities to ensure a relaxing stay. Our convenient location allows guests easy access to local attractions, dining options, and outdoor activities. Whether you are visiting for business or pleasure, Berkshire Yankee Suites is the perfect home away from home in the heart of the Berkshires.

Berkshire Inns is a charming lodging institution located at 461 Pittsfield Road in Lenox, Massachusetts, United States. Offering comfortable and cozy accommodations, Berkshire Inns provides a peaceful retreat for guests looking to explore the beautiful Berkshires region. With its convenient location and welcoming atmosphere, Berkshire Inns is the perfect choice for travelers seeking a relaxing stay in the heart of New England.

FairBridge Inn Express is a cozy and convenient lodging option located at 16 Cheshire Road in Pittsfield, Massachusetts. Whether you are visiting for business or pleasure, our inn offers comfortable accommodations at an affordable price. With easy access to nearby attractions and amenities, including shopping, dining, and outdoor activities, FairBridge Inn Express is the perfect home base for your stay in the beautiful Berkshires. Our friendly staff is dedicated to ensuring that your visit is enjoyable and stress-free. Book your stay with us today and experience the comfort and convenience of FairBridge Inn Express.

Bonnie Brae Campground is a picturesque retreat nestled in the heart of Pittsfield, Massachusetts. Located at 108 Broadway Street, this charming campground offers a peaceful escape for nature lovers and outdoor enthusiasts. With spacious campsites, cozy lodging options, and beautiful park amenities, Bonnie Brae Campground is the perfect destination for a weekend getaway or extended vacation. Whether you prefer hiking through the lush forests, fishing in the nearby lakes, or simply relaxing by the campfire, this campground has something for everyone. Come experience the beauty and tranquility of Bonnie Brae Campground in Pittsfield, Massachusetts.

Stone House Properties LLC is a reputable real estate agency located in Pittsfield, Massachusetts, United States. Specializing in buying, selling, and renting residential properties, our experienced team of professionals is dedicated to providing top-notch services to our clients. Whether you are looking for a cozy starter home or a luxurious estate, we have the expertise to help you find the perfect property to suit your needs. With a focus on customer satisfaction and attention to detail, Stone House Properties LLC is the go-to agency for all your real estate needs in the Pittsfield area.

Nocher Realty is a premier real estate agency located at 48 Elm Street in Pittsfield, Massachusetts. Whether you are buying, selling, or simply exploring your options, our team of experts is here to guide you through the process with ease. We have a wide range of properties available, from cozy condos to luxurious mansions. Trust in our top-notch skills to ensure you have the best real estate experience possible. Visit us at our convenient location in Pittsfield or contact us today to start your property adventure.

Welcome to Berkshire County Realty Co Inc. - Your Trusted Partner in Real Estate Located at 338 South Street, Pittsfield, Massachusetts, Berkshire County Realty Co Inc. is your premier destination for all real estate needs in the Berkshires and Eastern New York. With over 30 years of experience, we specialize in commercial and residential real estate, land and building lots, and investment properties.