TOP 30 Best Vacation house rentals in Pittsfield, Massachusetts

The Hilton Garden Inn Lenox Pittsfield is a comfortable and modern lodging establishment located at 1032 South Street in Pittsfield, Massachusetts. This hotel offers a convenient location for guests looking to explore the beautiful Berkshires region. The hotel features spacious and well-appointed rooms, a fitness center, an indoor pool, and a delicious on-site restaurant. Whether you are traveling for business or leisure, the Hilton Garden Inn Lenox Pittsfield provides a relaxing and enjoyable stay for all guests.

Welcome to Cory Evangelisto - Pittsfield, MA Realtor, your trusted partner in real estate and finance located at 48 Elm Street, Pittsfield, Massachusetts. With over 11 years of diverse experience in the real estate industry and a Bachelor of Business Administration in Accounting from the University of Massachusetts, Cory Evangelisto is dedicated to helping clients achieve their real estate goals. As a proud Berkshire County native, Cory began his real estate journey in 2010 by purchasing and rehabilitating distressed properties. This hands-on experience laid the foundation for his expertise in real estate investment. In 2013, Cory became a licensed Realtor, focusing on educating clients about the potential of real estate investing. His commitment to the community was further demonstrated by purchasing his first rental property, aimed at stabilizing neighborhoods and providing safe, well-maintained homes for local residents.

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, is a charming lodging option located at One West Street in Pittsfield, Massachusetts, United States. This hotel offers comfortable accommodations and a range of amenities for both business and leisure travelers. Guests can enjoy spacious rooms and suites, a fitness center, on-site dining options, and convenient access to local attractions such as Tanglewood, Norman Rockwell Museum, and the Berkshire Museum. With its prime location and excellent service, Holiday Inn & Suites Pittsfield-Berkshires is the perfect choice for a relaxing stay in the heart of the Berkshires.

Welcome to Margaret Apkin, TUCKER REAL ESTATE, your trusted partner in real estate located at 17 Leroi Drive, Pittsfield, Massachusetts. We are dedicated to providing exceptional service to our clients, whether you're buying, selling, or renting a property. Our team of experienced professionals understands the local market dynamics and is committed to helping you find the perfect home or investment opportunity that meets your needs. At Margaret Apkin, TUCKER REAL ESTATE, we believe in building lasting relationships based on trust, transparency, and personalized attention. Explore our website to discover a wide range of properties and learn more about how we can assist you in achieving your real estate goals. Your dream home awaits in the heart of the Berkshires!

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.

Courtyard by Marriott Lenox Berkshires is a charming lodging option located at 70 Pittsfield Road in Lenox, Massachusetts, United States. Situated in the beautiful Berkshires region, this hotel offers modern amenities and comfortable accommodations for guests looking to explore the area's cultural attractions, outdoor activities, and scenic landscapes. With spacious rooms, a fitness center, indoor pool, and on-site dining options, Courtyard by Marriott Lenox Berkshires is the perfect choice for travelers seeking a relaxing and convenient stay in this picturesque New England town.

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.

Hotel on North is a charming and sophisticated institution located in the heart of Pittsfield, Massachusetts. Situated at 297 North Street, this unique establishment offers a combination of luxurious lodging, a vibrant bar, and a lively night club all under one roof. Guests can enjoy stylish accommodations, delicious cocktails, and exciting entertainment all in one convenient location. Whether you're looking for a relaxing retreat or a fun night out, Hotel on North has something for everyone. Experience the best of Pittsfield at this one-of-a-kind destination.

Located in Lenox, Massachusetts, the Hampton Inn & Suites Berkshires-Lenox offers comfortable and modern lodging for travelers looking to explore the beautiful Berkshires region. The hotel is conveniently situated at 445 Pittsfield Road, providing easy access to local attractions, shopping, and dining options. Guests can enjoy spacious rooms and suites, complimentary breakfast, a fitness center, and an indoor pool. Whether visiting for business or leisure, the Hampton Inn & Suites Berkshires-Lenox is a great choice for a relaxing stay in the heart of the Berkshires.

Berkshire Mountain Lodge is a charming lodging institution located at 8 Dan Fox Drive in Pittsfield, Massachusetts. Situated in the beautiful Berkshires region, the lodge offers a perfect blend of cultural attractions, historical sites, and natural beauty. Guests can explore nearby attractions such as The Mount, the former estate of American author Edith Wharton, and Tanglewood, the summer home of the Boston Symphony Orchestra. Berkshire Mountain Lodge is a family-friendly vacation destination that offers a variety of amenities and activities for guests of all ages. The resort has received numerous awards, including the RCI Gold Crown Status, Tripadvisor's Travelers' Choice Award, and the Hotels.com Loved by Guests Award, all of which recognize the exceptional service and hospitality provided by the lodge.

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.

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.

Located in the picturesque town of Pittsfield, Massachusetts, the Best Western Plus Berkshire Hills Inn & Suites offers comfortable and modern lodging for travelers looking to explore the beautiful Berkshires region. Situated at 1350 West Housatonic Street, this hotel provides guests with a convenient location near popular attractions such as Tanglewood, Hancock Shaker Village, and the Norman Rockwell Museum. The hotel features spacious rooms and suites equipped with amenities such as free Wi-Fi, flat-screen TVs, and mini fridges. Guests can also enjoy a complimentary hot breakfast, a fitness center, and an indoor pool. Whether visiting for business or leisure, the Best Western Plus Berkshire Hills Inn & Suites provides a welcoming and relaxing atmosphere for all guests.

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.

Evergreen Home Real Estate is a reputable real estate agency located at 1040 West Street in Pittsfield, Massachusetts. With a team of experienced and knowledgeable agents, they are dedicated to helping clients find their dream homes or sell their properties quickly and efficiently. Whether you are a first-time homebuyer or a seasoned investor, Evergreen Home Real Estate offers personalized service and expert guidance every step of the way. Trust them to make your real estate experience smooth and successful.

S.N.O. Real Estate, Rentals & Development is a registered real estate agency located at 250 East Street in Pittsfield, Massachusetts, United States. Our experienced staff is dedicated to helping you find the perfect apartment rental or property to buy or lease. We understand that finding the right home is important, and we prioritize our clients' best interests above all else. Whether you are looking to buy, sell, lease, or rent residential or commercial properties, our team is here to assist you every step of the way. We pride ourselves on delivering exceptional service and have a diverse portfolio of properties available for you to choose from. Our listings include detailed descriptions and photographs, with more available upon request.

Evergreen Buyer Brokers is a reputable real estate agency located at 1040 West Street in Pittsfield, Massachusetts, United States. With a team of experienced and dedicated buyer brokers, we specialize in helping clients find their dream homes in the Berkshire County area. Our personalized approach ensures that each client receives individualized attention and expert guidance throughout the home buying process. Whether you are a first-time homebuyer or looking to upgrade to a new property, Evergreen Buyer Brokers is committed to helping you find the perfect home to suit your needs and budget. Contact us today to start your journey towards finding your forever home.

Welcome to Cindy Carrigan, GREYLOCK REALTY, your trusted partner in real estate located in the heart of Pittsfield, Massachusetts. Situated at 395 North Street, our office is dedicated to serving the diverse property needs of the Berkshire community with professionalism, integrity, and personalized service. At Cindy Carrigan, GREYLOCK REALTY, we specialize in residential and commercial real estate, offering a comprehensive range of services to buyers, sellers, and investors. Our team of experienced agents is committed to guiding you through every step of the real estate process, ensuring a seamless and stress-free experience.

Welcome to Natalie Rose, located at 137 North Street, Pittsfield, Massachusetts. We are proud to be part of the vibrant Berkshire community, offering unparalleled real estate services through All Seasons Realty Group. With a proven track record of assisting over 1,600 families and closing over $276 million in real estate, we are the trusted choice for buyers and sellers in the Berkshires. Explore our exclusive "Little Black Book," a curated list of trusted professionals to support your buying, selling, and homeowning needs. At Natalie Rose, we believe in not only providing exceptional real estate services but also giving back to the community where we live, work, and play.

Welcome to Harmony Edwards, your trusted real estate agency located in the heart of Pittsfield, Massachusetts. Situated at 150 North Street, our agency is dedicated to helping you find your dream home or investment property in the beautiful Berkshires region. At Harmony Edwards, we pride ourselves on offering personalized and professional service to each of our clients. Our team of experienced real estate agents is passionate about the local community and has an in-depth understanding of the Pittsfield area and its surrounding neighborhoods. Whether you are buying, selling, or renting, we are committed to guiding you through every step of the real estate process with integrity and expertise.

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.

Welcome to John Ciepiela, ALL SEASONS REALTY GROUP, your trusted partner in navigating the real estate landscape in Pittsfield, Massachusetts, and the surrounding areas. Conveniently located at 306 South Street, our dedicated team is committed to providing exceptional service for all your real estate needs. Whether you're buying, selling, or renting, we offer personalized solutions tailored to your unique requirements. With a deep understanding of the local market and a passion for helping clients achieve their real estate goals, we ensure a seamless and rewarding experience. Discover the difference with ALL SEASONS REALTY GROUP—where your real estate journey is our top priority. Visit us today and let us help you find your perfect home or investment opportunity.

Welcome to Keytoria Jenkins, REALTOR® Located in the heart of Pittsfield, Massachusetts, at 137 North Street, Keytoria Jenkins, REALTOR® is dedicated to providing exceptional real estate services with integrity and a personal touch. Born and raised in Greenville, SC, Keytoria brings a unique blend of Southern hospitality, community connections, and a commitment to service that ensures her clients receive the best experience possible.

Welcome to Paula McLean Realtors Located at 54 King William Road, Lenox, Massachusetts, Paula McLean Realtors is your trusted partner in navigating the dynamic real estate market of Berkshire County. With over four decades of experience since 1981, Paula McLean has established herself as a prominent figure in the real estate industry, proudly holding four prestigious national designations: Accredited Buyers Representative, Certified Residential Specialist, Accredited Staging Professional, and Resort and Second Home Property Specialist.

Welcome to Home Sweet Home Real Estate, your trusted partner in navigating the bustling real estate market of Pittsfield, Massachusetts. Conveniently located at 1404 North Street, we are committed to helping you find the perfect place to call home. Whether you're buying, selling, or renting, our dedicated team of experienced professionals is here to guide you every step of the way. At Home Sweet Home Real Estate, we pride ourselves on offering personalized service tailored to meet the unique needs of each client. Our extensive knowledge of the local market, combined with our passion for real estate, ensures that you receive the best advice and support throughout your property journey.

Welcome to Signature Associates, Inc. Real Estate, your premier real estate agency located in the heart of Pittsfield, Massachusetts. Situated at 127 Elm Street, our agency is dedicated to providing exceptional real estate services to both buyers and sellers in the Berkshire region. With a deep understanding of the local market and a commitment to personalized service, we strive to make your real estate journey smooth and successful. At Signature Associates, Inc., we offer a comprehensive range of services, including residential and commercial property sales, leasing, and property management. Our team of experienced and knowledgeable agents is here to guide you through every step of the process, whether you're looking to find your dream home, sell your property, or invest in commercial real estate.

Welcome to Mark Harris, SIGNATURE ASSOCIATES, your trusted partner in real estate located at 127 Elm Street, Pittsfield, Massachusetts. With a deep commitment to serving the Pittsfield community and surrounding areas, we specialize in providing exceptional real estate services tailored to meet your unique needs. Whether you are buying, selling, or investing in property, our team is dedicated to offering personalized solutions and expert guidance every step of the way. At Mark Harris, SIGNATURE ASSOCIATES, we pride ourselves on our integrity, professionalism, and extensive knowledge of the local market. Visit us today and let us help you turn your real estate dreams into reality.

Welcome to Toni Marie Gage - Signature Associates, Inc., your trusted partner in real estate services located at 127 Elm Street, Pittsfield, Massachusetts. As a premier real estate agency, we specialize in providing personalized and professional services to meet all your property needs. Whether you are buying, selling, or renting, our team is dedicated to delivering exceptional results with integrity and expertise. We pride ourselves on our deep knowledge of the local market and our commitment to client satisfaction. Visit us today and let Toni Marie Gage - Signature Associates, Inc. guide you through your real estate journey with confidence and care.

Welcome to Joseph Jennings at Signature Associates, Inc., your trusted partner in real estate solutions located in the heart of Pittsfield, Massachusetts. Situated at 127 Elm Street, our firm is committed to providing exceptional service and expertise in the real estate industry. Led by Joseph Jennings, we specialize in a comprehensive range of services, including property management, commercial leasing, and residential sales. Our team is dedicated to meeting the unique needs of each client with personalized attention and a deep understanding of the local market. Whether you're buying, selling, or leasing property, we are here to guide you every step of the way with professionalism and integrity. Discover the difference with Joseph Jennings at Signature Associates, Inc., where your real estate goals become our mission. Visit us today to explore how we can assist you in achieving your property aspirations.

Welcome to Dani Giulian Real Estate, where your real estate dreams become a reality. Located at 24 Donna Avenue, Pittsfield, Massachusetts, Dani Giulian is a licensed Realtor who brings years of experience and a deep passion for real estate to the beautiful Berkshires. With a background in sales, finance, and a commitment to excellence, Dani provides a seamless experience for home buyers and sellers alike. Dani is not just a Realtor; she is a dedicated partner in your real estate journey. Known for her honesty, integrity, and innovative problem-solving skills, she excels in helping clients navigate the complexities of buying and selling homes. Her strong referral business is a testament to the trust and satisfaction of her past clients, who frequently describe her as highly responsive, dependable, knowledgeable, and caring.