TOP 10 Vacation house rentals in Stockbridge, Massachusetts

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Located in the charming town of West Stockbridge, Massachusetts, the Pleasant Valley Motel offers comfortable and affordable lodging for those looking to explore the beautiful Berkshires region. Situated at 42 West Stockbridge Road, this cozy motel provides a peaceful retreat for visitors seeking a relaxing getaway. With its convenient location and friendly staff, Pleasant Valley Motel is the perfect choice for travelers looking for a comfortable stay in West Stockbridge.

The Cottage B and B is a charming lodging establishment located at 14 Prospect Hill Road in the picturesque town of Stockbridge, Massachusetts. This historic bed and breakfast offers cozy accommodations in a beautifully restored cottage, providing guests with a peaceful and relaxing retreat. In addition to its comfortable rooms, The Cottage B and B also features a small museum showcasing local artifacts and history, adding a unique touch to the overall guest experience. Whether you are looking for a romantic getaway or a cultural escape, The Cottage B and B is the perfect destination for your next visit to Stockbridge.

The Stockbridge Country Inn is a charming bed and breakfast located at 26 Glendale Road in Stockbridge, Massachusetts. Nestled in the heart of the picturesque Berkshires, this cozy inn offers beautifully appointed guest accommodations, each with its own unique character and style. Guests can enjoy a peaceful and relaxing atmosphere, surrounded by stunning gardens and a cozy fireplace room. Conveniently located just 1 mile away from the Norman Rockwell Museum and Chesterwood, The Stockbridge Country Inn is the #1 closest Berkshires Bed and Breakfast to these popular attractions. This makes it an ideal choice for visitors looking to explore the museum while enjoying the serene surroundings of the Berkshires.

Located at 30 East Street in Stockbridge, Massachusetts, The Inn at Stockbridge is a charming Georgian-style bed and breakfast nestled on six beautifully landscaped acres in the tranquil Berkshires. Offering three distinct lodging options to cater to every traveler's preferences, guests can choose between the elegant Main House, the cozy Cottage House, or the rustic-chic Barn. Immerse yourself in the thriving arts and culture scene of the Berkshires, with world-class museums and entertainment venues just minutes away. Explore attractions like the Norman Rockwell Museum, MASS MoCA, and Tanglewood, or enjoy exclusive offerings such as tee times at Stockbridge Golf Club and deals at local ski resorts.

Holiday Inn Express & Suites Great Barrington - Lenox Area is a modern and comfortable lodging option located at 415 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Lenox Area, this hotel offers guests a convenient and relaxing stay with easy access to a variety of attractions and activities. The hotel features spacious and well-appointed guest rooms and suites, each equipped with modern amenities such as flat-screen TVs, free Wi-Fi, and comfortable bedding. Guests can also enjoy complimentary breakfast each morning, as well as access to a fitness center and indoor pool.

Travelodge by Wyndham Great Barrington Berkshires is a cozy and comfortable lodging option located at 400 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the picturesque Berkshires region, this hotel offers convenient access to local attractions, restaurants, and outdoor activities. The rooms are clean and well-appointed, providing guests with a relaxing retreat after a day of exploring. The friendly staff is always ready to assist with any needs or questions, ensuring a pleasant stay for all visitors. Whether you are in town for business or leisure, Travelodge by Wyndham Great Barrington Berkshires is the perfect choice for your accommodations.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is a cozy and modern lodging option located at 249 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Berkshires region, this hotel offers guests a convenient and comfortable stay with close proximity to popular attractions such as Tanglewood, Norman Rockwell Museum, and Ski Butternut. The hotel features spacious and well-appointed rooms and suites, a complimentary hot breakfast buffet, a fitness center, an indoor pool, and free Wi-Fi. Whether you are visiting for business or leisure, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires provides a welcoming and relaxing atmosphere for all guests.

Welcome to Monument Mountain Motel, a budget-friendly lodging option in the heart of Great Barrington, Massachusetts. Located in the beautiful Berkshire Mountains, our motel offers comfortable rooms and family-style amenities. Whether you're in town for business or pleasure, our convenient location puts you near iconic attractions such as Tanglewood Music Festival, Ski Butternut Resort, and the Norman Rockwell Museum. At Monument Mountain Motel, we strive to provide a pleasant and affordable experience for all our guests. Enjoy free wifi, in-room microwaves and fridges, and a spacious patio with barbecue facilities. Family travelers will appreciate our family-friendly amenities, while business travelers will find our simplicity and affordability to be just what they need.

Lantern House Motel is a charming lodging establishment located at 256 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts, United States. Offering comfortable and affordable accommodations, this quaint motel is the perfect choice for travelers looking to explore the beautiful Berkshires region. With its convenient location and friendly staff, Lantern House Motel provides a cozy home away from home for guests looking to relax and unwind during their stay. Whether you are visiting for business or pleasure, you are sure to enjoy your time at this welcoming institution.

Briarcliff Motel is a charming lodging establishment located at 506 Stockbridge Road in Great Barrington, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy motel offers comfortable and affordable accommodations for travelers looking to explore the beauty of the region. With its convenient location and friendly staff, Briarcliff Motel is the perfect choice for a relaxing getaway in the heart of New England.

Located at 30 Main Street in Stockbridge, Massachusetts, The Red Lion Inn is a historic landmark of hospitality that has been welcoming guests for 250 years. The property includes the original Main Inn, a contemporary guest house, and unique lodging options like the turn-of-the-century Firehouse. Enjoy the heated outdoor pool, Hot Tub, and Pool House stocked with fresh towels and games. The culinary experience at The Red Lion Inn is top-notch, with seasonal menu items sourced from local farmers, craft cocktails, and an award-winning wine selection. Live music at The Lion’s Den adds to the vibrant atmosphere. Guests rave about the cozy rooms, delicious food, and exceptional service. Don't miss out on the curated packages and experiences to make the most of your stay in the Berkshires. The Red Lion Inn is a proud member of Historic Hotels of America and the National Trust for Historic Preservation. Come experience the charm and history of The Red Lion Inn for yourself.

Located in the charming town of West Stockbridge, Massachusetts, the Shaker Mill Inn offers a cozy and comfortable lodging experience. Situated at 2 Oak Street, this historic inn provides a peaceful retreat for guests looking to relax and unwind. The beautifully decorated rooms and friendly staff make for a memorable stay. With its convenient location and warm hospitality, the Shaker Mill Inn is the perfect choice for travelers visiting the Berkshires region.

Tanglewood Suites is a charming lodging establishment located in Stockbridge, Massachusetts, United States. Nestled in the overgrown woods, this peaceful retreat offers cozy and comfortable suites for guests seeking a tranquil escape from the hustle and bustle of city life. With its rustic charm and serene surroundings, Tanglewood Suites is the perfect destination for nature lovers and those looking to unwind and relax in a picturesque setting. Enjoy the beauty of the Berkshires while staying at Tanglewood Suites, where hospitality and comfort meet in perfect harmony.

Devonfield Inn is a charming lodging establishment located at 85 Stockbridge Road in Lee, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy inn offers a peaceful and serene retreat for guests seeking a relaxing getaway. The beautifully appointed rooms and suites are tastefully decorated and provide all the comforts of home. Guests can enjoy a delicious homemade breakfast each morning, as well as afternoon tea and snacks. The inn also features a lovely garden area, perfect for unwinding and taking in the natural beauty of the surrounding landscape. Whether you're looking for a romantic escape or a peaceful retreat, Devonfield Inn is the perfect destination for your next vacation.

The Kemble Berkshires is a historic lodging institution located at 2 Kemble Street in Lenox, Massachusetts, United States. Originally built in the 1880s for a U.S. Secretary of State and New Jersey State Senator, the property has been newly renovated by Shared Estates with modern finishes and luxurious amenities. The estate features manicured landscaping with stunning views of the Stockbridge Bowl. Guests can enjoy various spaces within the property, including a library room, music room, private bar, and seven fireplaces. The Kemble is 100% carbon neutral and can accommodate events for up to 175 guests. The property offers a dining room, professional kitchen, herb and vegetable garden, fire pit, and multi-level stone patios and decks. Guests can enjoy a wide range of amenities, including a virtual reality gaming room, retro arcade, outdoor sports equipment, and more. The Kemble Berkshires is owned by 143 investors through Shared Estates' equity crowdfunding model, making it a unique social equity vehicle in the real estate industry.

The Constance is a charming lodging located at 11 Old Stockbridge Road in Lenox, Massachusetts. This historic institution offers cozy accommodations in a picturesque setting, perfect for a relaxing getaway in the heart of the Berkshires. Guests can enjoy comfortable rooms, beautiful gardens, and personalized service during their stay. Whether you're looking for a weekend retreat or a longer vacation, The Constance is the perfect choice for a memorable experience in this idyllic New England town.

Henderson House is a reputable real estate and travel agency located at 39 Main Street in the charming town of Stockbridge, Massachusetts, United States. Our experienced team of professionals is dedicated to helping clients find their dream homes or plan the perfect getaway. With a focus on personalized service and attention to detail, Henderson House is your go-to destination for all your real estate and travel needs. Whether you're looking to buy or sell a property, or seeking assistance with booking a vacation, we are here to assist you every step of the way. Visit us today and experience the difference Henderson House can make in your real estate and travel endeavors.

Taggart House is a unique institution located at 18 Main Street in the charming town of Stockbridge, Massachusetts. As a health center, Taggart House offers a range of services aimed at promoting wellness and holistic healing. Whether you're looking for acupuncture, massage therapy, or nutritional counseling, their team of experienced professionals is dedicated to helping you achieve optimal health. In addition to their health services, Taggart House also operates as a real estate agency, assisting clients in finding their dream home in the picturesque Berkshires region. With a deep knowledge of the local market and a commitment to personalized service, their team can help you navigate the real estate process with ease.

Stone House Properties LLC is a reputable real estate agency located at 38 Main Street in West Stockbridge, Massachusetts, United States. The agency is known for providing exceptional service to their clients, as evidenced by glowing testimonials from satisfied customers. Whether you are looking to buy or sell a property, the team at Stone House Properties LLC, led by experienced realtors Katie Soules and Jeff Astore, will guide you through the process with professionalism and expertise. Their attention to detail, excellent communication skills, and dedication to client satisfaction make them a top choice for anyone in the Berkshire County area looking to navigate the real estate market. Trust Stone House Properties LLC to help you find your dream home or successfully sell your property with ease.

Katie Soules, REALTOR - Stone House Properties LLC is a reputable real estate agency located at 38 Main Street in West Stockbridge, Massachusetts. Katie Soules is the Managing Broker, overseeing a team of 32 agents and managing the commercial division, marketing design, and training programs. With a background in International Studies and French, Katie brings a unique perspective to the real estate industry. She is actively involved in professional organizations and conferences, ensuring she stays up-to-date with industry trends. Clients praise Katie for her thoroughness, knowledge, and excellent customer service skills. She is described as a true professional who goes above and beyond to provide top-notch service. Whether it's selling a difficult property or navigating a challenging market, Katie and her team at Stone House Properties are dedicated to helping clients achieve their real estate goals.

Welcome to Mezze Guesthouse, a serene retreat nestled above the renowned Mezze Bistro in the picturesque town of Williamstown, Massachusetts. Located at 777 Cold Spring Road, our guesthouse offers a harmonious blend of contemporary comfort and classic Mezze hospitality. Our guesthouse features five uniquely designed units, each adorned with custom finishes such as Grohe rain showers, K-Fee coffee-makers, and locally sourced treats. Choose from three elegant queen-sized units, a spacious two-bedroom suite with a queen bedroom and twin room, or indulge in our luxurious King suite complete with a separate sitting room and an oversized bathroom.

Welcome to Alexis J. Prisendorf | Find Berkshire Properties Today With Berkshire County's Best Realtor, located at 271 Main Street, Great Barrington, Massachusetts. With over three decades of expertise in customer service and marketing, Alexis J. Prisendorf stands as a beacon of reliability and excellence in the Berkshire County real estate market. Whether you're seeking your dream home or planning to sell your property, Alexis offers unparalleled service and insight. Explore stunning properties like 26 Pine Crest Hill Road in Egremont, a luxurious 4-bedroom estate set on 4.3 acres, or the sophisticated 165 Kemble Street in Lenox, a refined 1-bedroom residence at Canyon Ranch Living. Discover the charm of North Egremont with the beautifully maintained home at 11 Hickory Hill Road, offering 3 bedrooms and 3 baths on 3.3 acres.

Welcome to Victoria Standring of Stone House Properties, your premier real estate partner located in the charming town of West Stockbridge, Massachusetts. Situated at 38 Main Street, our office is at the heart of the Berkshires, a region renowned for its natural beauty and vibrant cultural scene. At Victoria Standring of Stone House Properties, we are dedicated to providing personalized and professional real estate services to meet all your buying and selling needs. Our team of experienced agents is committed to helping you find the perfect home or investment property in this picturesque area. Whether you are looking for a serene country retreat, a historic home with character, or a modern family house, we have the local expertise and market knowledge to guide you every step of the way.

Welcome to Stephen Schoenfeld, Stone House Properties, LLC, your premier real estate partner located in the heart of West Stockbridge, Massachusetts. Nestled at 38 Main Street, our office is perfectly positioned to serve the vibrant community and picturesque surroundings of the Berkshires. With a deep-rooted commitment to excellence, we specialize in providing personalized real estate services that cater to both buyers and sellers. Whether you're looking to find your dream home, sell your property, or explore investment opportunities, our experienced team is dedicated to guiding you through every step of the process. At Stephen Schoenfeld, Stone House Properties, LLC, we pride ourselves on our local expertise, integrity, and a client-focused approach. Discover the charm and beauty of West Stockbridge and beyond with us as your trusted real estate advisor. Visit us today and let us help you turn your real estate dreams into reality.

Welcome to Suzanne Crerar at Stone House Properties, your premier real estate partner located at 38 Main Street, West Stockbridge, Massachusetts. Serving the beautiful regions of Berkshire County, Massachusetts, and Columbia County, New York's Upper Hudson Valley, we are a well-established brokerage firm dedicated to providing exceptional services for both buyers and sellers. Our region is renowned for its breathtaking natural beauty, with the Berkshires and Upper Hudson Valley offering picturesque landscapes of rolling hills and expansive valleys. In addition to the stunning scenery, our area is rich in cultural landmarks, including Tanglewood, MASS MoCA, and the Olana State Historic Site, making it a truly desirable location for your next home.

Welcome to Wheeler & Taylor Realty, your trusted partner in real estate since 1871. Conveniently located at 10 Elm Street in the charming town of Stockbridge, Massachusetts, we are proud to serve the vibrant communities of Southern Berkshire County. Our experienced team is dedicated to helping you find the perfect property, whether you're searching for a single-family home, a vacation retreat, or a commercial investment. At Wheeler & Taylor Realty, we specialize in a diverse range of real estate options to meet your needs. From single-family homes priced up to $750,000 to luxurious estates over $1,000,000, we cover the entire spectrum from Lenox/Richmond south to the Connecticut border. Explore beautiful homes located on or near the water, or find the perfect condo in any price range. We also offer parcels of land and commercial listings for those looking to build or invest.

Welcome to The Constance, The Whitlock, & The Dewey by The Lenox Collection, your premier lodging destination nestled in the heart of Lenox, Massachusetts. Located at 11 Old Stockbridge Road, our exquisite collection of inns offers a unique blend of historical charm, modern comfort, and serene surroundings, perfect for every traveler seeking a memorable escape in the Berkshires. The Dewey: Discover our most intimate inn, featuring 12 uniquely designed guestrooms that capture the essence of historical elegance amidst peaceful natural surroundings. Situated just north of downtown Lenox, The Dewey offers a harmonious balance of accessibility to local dining and shopping, and the tranquility of Pleasant Valley. Each room, surrounded by lush treetops, invites you to relax and rejuvenate in a beautifully preserved historic setting. Ideal for the discerning traveler, The Dewey promises a serene retreat.

Welcome to Barb Hassan Realty, Inc. Nestled in the heart of the beautiful Berkshires, Barb Hassan Realty, Inc. is your premier full-service real estate agency located at 31 Wendell Avenue, Pittsfield, Massachusetts. With over 35 years of dedicated service to the Northern, Central, and Southern Berkshire areas, we pride ourselves on offering professional, courteous, and responsive real estate services.

Welcome to Barb Hassan Realty, Inc. – Your Trusted Real Estate Partner in the Berkshires Located at 69 South Main Street, Lanesborough, Massachusetts, Barb Hassan Realty, Inc. is your local, full-service real estate agency dedicated to serving the vibrant community of the Berkshires. With over 35 years of experience in the real estate industry and more than $155 million in career sales, our team is committed to providing professional, courteous, and responsive services for all your real estate needs.