TOP 10 Vacation house rentals in Sheffield, Massachusetts

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Sheffield Lodge is a charming lodging located at 400 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests looking to escape the hustle and bustle of city life. Whether you're seeking a romantic getaway or a relaxing vacation in nature, Sheffield Lodge provides a tranquil setting for all guests to unwind and rejuvenate. With its convenient location near local attractions and outdoor activities, this institution is the perfect destination for those seeking a peaceful retreat in the heart of Massachusetts.

Race Brook Lodge is a charming institution nestled in the beautiful countryside of Sheffield, Massachusetts. Located at 864 South Undermountain Road, this unique establishment offers a blend of health, lodging, and park amenities for guests to enjoy. From cozy accommodations to wellness retreats, Race Brook Lodge provides a tranquil escape from the hustle and bustle of everyday life. Explore the lush surroundings, unwind in the peaceful atmosphere, and rejuvenate your mind, body, and soul at this idyllic retreat in the heart of the Berkshires.

Birch Hill Bed & Breakfast is a charming lodging located at 254 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshires region, this cozy B&B offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. With comfortable accommodations, delicious homemade breakfasts, and warm hospitality, Birch Hill Bed & Breakfast is the perfect place to relax and unwind during your stay in the Berkshires.

The Race Mountain House is a unique institution located at 894 South Undermountain Road in Sheffield, Massachusetts, United States. As a real estate agency and travel agency, The Race Mountain House specializes in providing exceptional services for those looking to buy or rent properties in the picturesque Berkshires region. Whether you're searching for your dream home or planning a relaxing getaway, our dedicated team is here to assist you every step of the way. Experience the beauty and tranquility of the Berkshires with The Race Mountain House.

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 Sandra M Preston Real Estate, your trusted partner in navigating the dynamic real estate market of Sheffield, Massachusetts, and the surrounding areas. Conveniently located at 575 Sheffield Plain, Sheffield, MA 01257, our agency is committed to providing exceptional service, whether you are buying, selling, or renting a property. With a deep understanding of the local market and a passion for helping clients achieve their real estate goals, our experienced team offers personalized services tailored to meet your unique needs. We pride ourselves on our integrity, transparency, and dedication to ensuring a smooth and successful real estate experience.

Welcome to Wilder House Berkshires, your serene escape nestled in the heart of the picturesque Berkshires. Located at 48 South Main Street, Sheffield, Massachusetts, our charming lodging offers a perfect blend of comfort, tranquility, and rustic elegance. Whether you're seeking a peaceful retreat or an adventurous getaway, Wilder House provides the ideal base for exploring the natural beauty and cultural richness of the area. Our accommodations are thoughtfully designed to provide a cozy and inviting atmosphere, ensuring a restful stay for all our guests. Each room is equipped with modern amenities while retaining the charm and warmth of a classic Berkshire residence. Wake up to the stunning views of the surrounding landscapes and enjoy a delicious breakfast to start your day.