TOP 10 Vacation house rentals in Pittsfield, Massachusetts

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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.

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.

Nocher Realty is a reputable real estate agency located at 152 Main Street in Great Barrington, Massachusetts. Whether you are buying or selling a property, our experienced team is here to guide you through the process and provide you with the best possible experience. From condos to mansions, we have a wide range of properties available for you to explore. Visit us at our second location at 48 Elm Street in Pittsfield, Massachusetts for more options. Don't let the property adventure make you nervous - trust Nocher Realty to help you every step of the way.

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.

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.

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.

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.

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.

Howard Johnson by Wyndham Lenox is a charming lodging facility located at 462 Pittsfield Road in Lenox, Massachusetts. Situated in the beautiful Berkshires region, this hotel offers comfortable and affordable accommodations for travelers looking to explore the area. Guests can enjoy spacious rooms, complimentary breakfast, free Wi-Fi, and a seasonal outdoor pool. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Howard Johnson by Wyndham Lenox is the perfect choice for a relaxing getaway in Massachusetts.

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.

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.

Bellco Realty Inc is a well-established real estate agency located at 656 North Street in Pittsfield, Massachusetts. With years of experience in the industry, our team of dedicated professionals is committed to helping clients buy, sell, and rent properties in the area. Whether you are looking for a new home, investment property, or commercial space, we are here to assist you every step of the way. Contact us today to learn more about our services and how we can help you achieve your real estate goals.

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.

DiRon Realty is a leading real estate agency located at 674 Tyler Street in Pittsfield, Massachusetts. With a reputation for excellence and a commitment to exceptional customer service, our team of experienced agents are dedicated to helping clients buy, sell, and rent properties in the greater Pittsfield area. Whether you are looking for your dream home, investment property, or rental, DiRon Realty is here to guide you every step of the way. Visit us today and let us help you achieve your real estate goals.

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.

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.

Royal Property Group is a multifaceted institution located at 392 Merrill Road in Pittsfield, Massachusetts. As a finance company, general contractor, and real estate agency, we offer comprehensive services to meet all your property needs. Whether you are looking to buy, sell, or renovate a property, our team of experts is dedicated to providing unparalleled service and expertise. Trust Royal Property Group to help you navigate the complex world of real estate with confidence and ease.

Nocher Realty is a reputable real estate agency located at 100 Summer Street in Adams, Massachusetts, United States. Whether you are buying, selling, or simply looking for information, our experienced team is here to guide you through the property adventure. From condos to mansions, we have a wide range of properties available for you to explore. Visit us at 48 Elm Street in Pittsfield, Massachusetts 01201, United States, and let us help you find your dream home.

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.

Jan Perry Realty & Associates, LLC TheBerkshires.com is a reputable real estate agency located at 431 North Street in Pittsfield, Massachusetts, United States. Specializing in buying, selling, and renting properties in the beautiful Berkshires region, our team of experienced and knowledgeable agents are dedicated to helping clients find their dream home or investment property. With a strong focus on customer service and attention to detail, we strive to make the buying or selling process as smooth and stress-free as possible. Contact us today to learn more about how we can assist you in your real estate needs in the Berkshires.

Berkshire Hathaway HomeServices Barnbrook Realty is a reputable real estate agency located at 77 East Street in Pittsfield, Massachusetts, United States. With a team of experienced and dedicated real estate professionals, they specialize in helping clients buy and sell properties in the Berkshire County area. Whether you are looking for a new home, investment property, or commercial real estate, their knowledgeable agents are here to assist you every step of the way. Trust Berkshire Hathaway HomeServices Barnbrook Realty to provide top-notch service and expert guidance in all your real estate transactions.