TOP 10 Best Rental cottages in Lenox, Massachusetts

Canyon Ranch Lenox is a renowned institution located at 165 Kemble Street in Lenox, Massachusetts, United States. This institution offers a unique combination of health, lodging, and spa services for guests looking to improve their overall well-being. One of the special offers at Canyon Ranch Lenox is the Best Friends Bonus Offer, where guests can save on double occupancy and receive extra services. The institution also hosts events such as The Canyon Ranch Weight Loss Program, designed to help guests achieve long-term weight loss goals.

Welcome to Seranak Cottage, a charming retreat nestled in the heart of Lenox, Massachusetts. Located at the picturesque address of Lenox, Massachusetts 01240, our cottage offers a serene escape for those seeking tranquility and comfort in the beautiful Berkshires. Seranak Cottage is steeped in history and surrounded by natural beauty, providing an ideal setting for relaxation and rejuvenation. Whether you're planning a romantic getaway, a family vacation, or a solo retreat, our cottage promises a cozy and inviting atmosphere.

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.

Welcome to Tonia Scalise, William Pitt Sotheby's International Realty, located in the heart of Lenox, Massachusetts at 34 Church Street. As a prominent real estate agency, we specialize in providing exceptional service and expertise in the picturesque Berkshires region. Our dedicated team, led by Tonia Scalise, is committed to helping you find your dream home or the perfect investment property. With a deep understanding of the local market and a passion for delivering personalized experiences, we offer a seamless and rewarding real estate journey. Whether you're buying, selling, or exploring the area's rich culture and stunning landscapes, Tonia Scalise and William Pitt Sotheby's International Realty are your trusted partners in Lenox. Visit us today and discover the unique charm and elegance that define the Berkshires lifestyle.

Stonover Farm is a charming lodging institution located at 169 Under Mountain Road in Lenox, Massachusetts, United States. Surrounded by picturesque countryside, this tranquil farm offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. The property features beautifully appointed rooms, a cozy fireplace, and stunning views of the rolling hills. Guests can enjoy a relaxing stay in this idyllic setting, with opportunities for hiking, biking, and exploring the nearby attractions. Whether you're seeking a romantic getaway or a peaceful weekend retreat, Stonover Farm provides a warm and welcoming atmosphere for a memorable stay.

The Dewey is a charming lodging establishment located at 7 Hubbard Street in Lenox, Massachusetts. This cozy inn offers comfortable accommodations in a picturesque setting, perfect for those looking to relax and unwind in the heart of the Berkshires. The Dewey's convenient location allows guests to easily explore the many attractions and activities in the area, including historic sites, art galleries, and outdoor adventures. With its warm hospitality and inviting atmosphere, The Dewey is the ideal destination for a peaceful getaway in the beautiful New England countryside.

Wyndhurst Golf & Club is a premier destination located at 55 Lee Road in Lenox, Massachusetts. This institution offers a luxurious experience with top-notch amenities including a golf course, lodging accommodations, and a gourmet restaurant. Guests can enjoy a round of golf on the beautifully landscaped course, relax in the comfortable lodging options, and indulge in delicious meals at the on-site restaurant. Whether you are looking for a weekend getaway, a golf retreat, or a fine dining experience, Wyndhurst Golf & Club has everything you need for a memorable stay.

The Ponds at Foxhollow is a secluded resort located in the heart of the Berkshire Mountains at 3 Fox Hollow Drive, Lenox, Massachusetts. The resort offers one and two bedroom condominiums for timesharing or rental purposes, each with a master bedroom, fully equipped kitchen, living area with a double sleeper sofa, and a deck overlooking a picturesque pond. The property spans 223 acres, perfect for hiking in the warmer months and cross country skiing in the winter. The resort also offers outdoor activity equipment and canoes for guests to use. With breathtaking mountain views and a variety of recreational and cultural activities nearby, The Ponds at Foxhollow is the perfect destination for a relaxing getaway. Please note that the hot tub is temporarily out of service, but a new one is on the way.

Barnbrook Realty is a reputable real estate agency located at 27 Housatonic Street in Lenox, Massachusetts. With a team of experienced and knowledgeable agents, Barnbrook Realty specializes in helping clients buy and sell residential and commercial properties in the Lenox area. Whether you are looking for a cozy home in the heart of town or a spacious office space for your business, Barnbrook Realty is dedicated to providing top-notch service and helping you find the perfect property to meet your needs. Contact Barnbrook Realty today to start your real estate journey in Lenox, Massachusetts.

Winthrop Estate is a luxurious lodging institution located at 101 Yokun Avenue in the charming town of Lenox, Massachusetts, United States. Nestled in the heart of the Berkshires, this historic estate offers guests a unique and unforgettable experience. The elegant accommodations, stunning gardens, and impeccable service make Winthrop Estate the perfect destination for a romantic getaway, family vacation, or special event. With its rich history and picturesque surroundings, Winthrop Estate truly embodies the essence of New England charm and hospitality.

Welcome to ValleyHead Property Gallery, your premier real estate agency located in the heart of the Berkshires at 79 Reservoir Road, Lenox, Massachusetts. At ValleyHead, we pride ourselves on providing personalized and professional real estate services to the Lenox community and beyond. Whether you’re looking to buy, sell, or invest in property, our dedicated team of experienced realtors is here to guide you through every step of the process. Our extensive knowledge of the local market, coupled with our commitment to client satisfaction, ensures that you receive the best possible service tailored to your unique needs. At ValleyHead Property Gallery, we offer a diverse portfolio of properties, from charming homes and luxurious estates to scenic land and commercial spaces. Our mission is to help you find the perfect property that meets your lifestyle and investment goals.

Welcome to Marie Bourassa, ROBERTS & ASSOC. REALTY, INC., your trusted partner in real estate located in the heart of Lenox, Massachusetts. Situated at 48 Housatonic Street, we are proud to serve the vibrant community of Lenox and the surrounding Berkshire County with exceptional real estate services. Our dedicated team of experienced professionals is committed to providing personalized and comprehensive solutions for all your real estate needs. Whether you're buying, selling, or renting, we offer a wealth of local knowledge and expertise to guide you through every step of the process. At Marie Bourassa, ROBERTS & ASSOC. REALTY, INC., we prioritize building lasting relationships with our clients, ensuring a seamless and rewarding real estate experience. Visit us today to discover how we can assist you in finding your dream home or achieving your real estate goals.

Berkshire Homes and Condos is a reputable real estate agency located at 48 Saint Ann's Avenue in Lenox, Massachusetts, United States. Specializing in luxury homes and vacation condos in the picturesque Berkshire region, this agency offers exclusive listings and full property details for interested buyers and renters. With prices and inventory updated as of April 5, 2024, Berkshire Homes and Condos provides unparalleled service and expertise in the local real estate market. To access their full range of properties and continue your search, simply agree to their Terms of Use.

Piretti Real Estate is a reputable real estate agency located at 22 Walker Street in Lenox, Massachusetts, United States. With a team of experienced and dedicated professionals, Piretti Real Estate is committed to helping clients buy, sell, and rent properties in the Lenox area and beyond. Whether you are looking for a cozy cottage, a luxury estate, or a commercial property, Piretti Real Estate can assist you in finding the perfect property to meet your needs. Contact them today to start your real estate journey!

Welcome to Mark Parsons, ROBERTS & ASSOC. REALTY, INC., your trusted partner in real estate located in the heart of Lenox, Massachusetts. Situated at 48 Housatonic Street, our office is dedicated to providing exceptional real estate services to the Berkshire community and beyond. Whether you are buying, selling, or renting, our experienced team is committed to delivering personalized service tailored to meet your unique needs. At Mark Parsons, ROBERTS & ASSOC. REALTY, INC., we pride ourselves on our deep local knowledge and extensive expertise in the real estate market. Our team of professional agents is here to guide you through every step of your real estate journey, ensuring a seamless and stress-free experience. We offer a comprehensive range of services, including residential and commercial property sales, property management, and rental services.