TOP 30 Charming retreat inn in Massachusetts

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The Inn at Freeman Elms Farm B&B is a charming and welcoming lodging establishment located in the picturesque town of New Marlborough, Massachusetts. Situated at 566 Mill River Great Barrington Road, this historic bed and breakfast offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of city life. Surrounded by the natural beauty of the Berkshires, the Inn at Freeman Elms Farm B&B provides a cozy and comfortable atmosphere for guests to unwind and recharge. The property boasts beautifully appointed rooms, each uniquely decorated to provide a home away from home experience. Guests can enjoy a delicious homemade breakfast each morning, made with locally sourced ingredients.

The Wainwright Inn Bed & Breakfast is a charming and historic lodging establishment located at 518 South Main Street in the picturesque town of Great Barrington, Massachusetts, United States. This cozy inn offers comfortable accommodations in a beautiful Victorian-style setting, perfect for a relaxing getaway or romantic retreat. Guests can enjoy a delicious homemade breakfast each morning and explore the nearby attractions, including the Berkshire Mountains and quaint shops and restaurants in the town center. With its warm hospitality and inviting atmosphere, The Wainwright Inn Bed & Breakfast is the perfect choice for a memorable stay in the Berkshires.

Thornewood Inn is a charming and historic lodging located at 453 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, this cozy inn offers a tranquil escape for guests looking to relax and unwind. The beautifully appointed rooms are elegantly furnished and offer modern amenities for a comfortable stay. Guests can enjoy a delicious breakfast each morning and explore the surrounding area, which is known for its scenic beauty and cultural attractions. Whether you are seeking a romantic getaway or a peaceful retreat, Thornewood Inn is the perfect destination for your next vacation.

The Egremont Village Inn is a charming and historic lodging establishment located at 17 Main Street in the picturesque town of Egremont, Massachusetts, United States. This cozy inn offers a comfortable and welcoming atmosphere, perfect for a relaxing getaway in the Berkshires. Guests can enjoy beautifully appointed rooms, delicious meals at the on-site restaurant, and easy access to the area's many attractions and outdoor activities. Whether you're looking for a romantic retreat, a family vacation, or a solo adventure, The Egremont Village Inn is the perfect choice for your stay in the Berkshires.

Located in the quaint village of New Marlborough in Massachusetts, The Old Inn On The Green is a historic institution offering both bar services and lodging. The inn, originally a stagecoach relay, features beautifully restored guest rooms, fine dining in candlelit rooms, and seasonal outdoor dining on the garden terrace. The Southfield Store, open for takeout daily, is also part of the institution. Whether you are visiting for business or pleasure, for dinner or an overnight stay, The Old Inn On The Green provides a charming and authentic experience in the heart of the Berkshire region. With its picturesque surroundings of rolling fields and meadows, this historic inn is a perfect destination for those seeking a peaceful retreat in New England. Visit us at 134 Hartsville-New Marlborough Rd, New Marlborough, MA 01230 or contact us at 413-229-7924 or [email protected]. Feel the love and experience the best of the oldest at The Old Inn On The Green.

Located in the picturesque town of Sandisfield, Massachusetts, Hillside Garden Inn offers a charming and relaxing Bed and Breakfast experience. Housed in the historic Elijah Twining House, dating back to 1785, guests can enjoy immaculate accommodations and gracious hospitality. The inn boasts a spacious wrap-around porch overlooking the Farmington River, as well as a screened-in patio and hilltop gazebo with stunning panoramic views of the distant hills. Sandisfield, with its beautiful landscapes and thriving arts scene, is the perfect destination for outdoor enthusiasts and culture lovers alike. The Berkshires region offers plenty of activities year-round, from skiing and hiking to water sports and cultural events. For those who enjoy shopping, Prime Outlets are just a short drive away.

Welcome Inn is a charming lodging establishment located at 2041 Riverdale Street in West Springfield, Massachusetts. Our cozy rooms and welcoming atmosphere make us the perfect choice for travelers looking for a comfortable and affordable place to stay. Conveniently located near local attractions and dining options, Welcome Inn offers a convenient and pleasant stay for all guests. Our friendly staff is dedicated to providing excellent customer service and ensuring that your stay is enjoyable. Book your stay with us today and experience the warm hospitality of Welcome Inn.

Bel Air Inn is a cozy lodging facility located at 387 Riverdale Street in West Springfield, Massachusetts. This charming inn offers comfortable accommodations and a welcoming atmosphere for guests looking for a relaxing stay. Conveniently situated in a prime location, Bel Air Inn is the perfect choice for travelers visiting the area for business or pleasure. With its friendly staff, clean rooms, and affordable rates, Bel Air Inn is a top choice for those seeking a comfortable and convenient place to stay in West Springfield.

Riverdale Inn is a charming lodging located at 1500 Riverdale Street in West Springfield, Massachusetts. Situated in a picturesque setting, this cozy inn offers a relaxing and comfortable stay for guests visiting the area. The rooms are tastefully decorated and equipped with modern amenities to ensure a pleasant stay. The friendly staff at Riverdale Inn are dedicated to providing exceptional service and making guests feel right at home. Whether you are in town for business or leisure, this welcoming inn is the perfect place to unwind and enjoy a peaceful retreat.

The Wilbraham Inn is a charming lodging establishment located at 2009 Boston Post Road in Wilbraham, Massachusetts. Situated in a picturesque town in the United States, the inn offers comfortable and cozy accommodations for guests looking to relax and unwind. With its convenient location and welcoming atmosphere, the Wilbraham Inn is the perfect choice for travelers seeking a peaceful retreat in the heart of New England.

Sturbridge Country Inn is a charming lodging establishment located at 530 Main Street in the historic town of Sturbridge, Massachusetts, United States. This quaint inn offers a cozy and welcoming atmosphere, perfect for a relaxing getaway or a romantic weekend retreat. Guests can enjoy comfortable accommodations, delicious breakfast options, and personalized service from the friendly staff. The inn's convenient location provides easy access to local attractions such as Old Sturbridge Village, restaurants, and shops. Whether you're looking for a peaceful escape or a convenient base for exploring the area, Sturbridge Country Inn is the ideal choice for your next stay in Sturbridge.

Publick House Historic Inn is a charming and cozy establishment located at 277 Main Street in Sturbridge, Massachusetts. This historic inn offers a unique combination of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway or a delicious meal. With its quaint New England charm and warm hospitality, Publick House Historic Inn provides guests with a truly memorable experience. Whether you're looking for a comfortable place to stay, a delectable meal, or a cozy spot to relax, this institution has everything you need for a delightful stay in Sturbridge.

Hamilton Inn is a charming lodging establishment located at 172 Main Street in the heart of Sturbridge, Massachusetts. This cozy inn offers comfortable accommodations and a warm, inviting atmosphere for guests looking to relax and unwind. With its convenient location, guests can easily explore the nearby attractions, shops, and restaurants in the area. Whether you are visiting for business or pleasure, Hamilton Inn provides a peaceful retreat for travelers seeking a home away from home.

The Old Sturbridge Inn & Reeder Family Lodges is a charming lodging option located at 369 Main Street in Sturbridge, Massachusetts. Nestled in the heart of historic Sturbridge, this institution offers a cozy and comfortable stay for guests looking to experience the beauty and charm of New England. The inn and lodges provide a warm and welcoming atmosphere, with beautifully appointed rooms and modern amenities. Whether you are visiting for a weekend getaway or a longer stay, the Old Sturbridge Inn & Reeder Family Lodges is the perfect choice for a memorable and relaxing stay in Massachusetts.

River Inn is a charming lodging establishment nestled in the heart of Springfield, Massachusetts. Located in the United States, this cozy inn offers comfortable accommodations and a warm, inviting atmosphere for guests to relax and unwind. With a picturesque setting along the river, guests can enjoy scenic views and a peaceful environment. Whether you are traveling for business or leisure, River Inn provides a convenient and welcoming place to stay during your time in Springfield.

Old Inn Associates is a charming establishment located at 100 Stone Manor Dr in New Marlborough, Massachusetts. As a renowned food, lodging, and restaurant institution, we pride ourselves on providing top-notch service and comfortable accommodations for our guests. Whether you're looking for a delicious meal at our restaurant, a cozy stay in our well-appointed rooms, or a relaxing retreat in the beautiful Massachusetts countryside, Old Inn Associates has everything you need for a memorable experience. Come visit us and experience the warm hospitality and exceptional amenities that have made us a favorite destination for travelers near and far.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires is a charming lodging destination nestled in the picturesque town of Lee, Massachusetts. Surrounded by the stunning beauty of the Berkshires, this resort offers a perfect retreat for families and couples looking to relax and unwind in a peaceful setting. The resort features spacious accommodations, including comfortable rooms and suites, all equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a range of on-site facilities, including indoor and outdoor pools, a fitness center, tennis courts, and a game room. There are also organized activities and events for guests of all ages to enjoy.

The Inn At Richmond is a charming lodging establishment located at 802 State Road in the picturesque town of Richmond, Massachusetts, United States. Nestled in the heart of the Berkshires, this historic inn offers a peaceful retreat for guests seeking a relaxing getaway. With cozy rooms, elegant decor, and modern amenities, The Inn At Richmond provides a comfortable and inviting atmosphere for visitors to enjoy. Whether you're looking to explore the nearby attractions or simply unwind in a tranquil setting, this institution is the perfect choice for your stay in the Berkshires.

Located at 10 Richmond Mountain Road in Lenox, Massachusetts, the Apple Tree Inn is a charming lodging option that serves as the perfect retreat for those looking to nurture their creativity. Surrounded by the natural beauty of the Berkshires, this institution offers a peaceful escape from the ordinary where guests can unlock new ideas and inspiration. The inn features a picturesque 1885 Victorian main house with 13 rooms that blend historic charm with modern amenities such as Frette linens. Additionally, there is a rustic Lodge with 21 rooms that provide a cozy and tranquil setting overlooking the lush green forests and rolling hills of the Berkshires.

The Chesapeake Inn of Lenox is a charming lodging establishment located at 210 West Street in the picturesque town of Lenox, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind in the heart of the Berkshires. With its convenient location near historic sites, cultural attractions, and outdoor activities, the Chesapeake Inn of Lenox is the perfect destination for a peaceful getaway or romantic retreat. Experience the beauty and hospitality of Lenox at this charming inn.

The Inn at Kenmore Hall is a charming lodging located at 1385 State Road in Richmond, Massachusetts. Nestled in the beautiful countryside of the United States, this institution offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With comfortable accommodations and attentive staff, visitors can enjoy a restful stay surrounded by scenic views and serene surroundings. Whether you're looking for a romantic getaway or a quiet weekend retreat, The Inn at Kenmore Hall is the perfect destination for a memorable stay.

Located in the charming town of Lenox, Massachusetts, the Eastgate Inn Bed & Breakfast offers a cozy and welcoming atmosphere for travelers looking for a peaceful retreat. Situated at 207 West Street, this quaint lodging establishment provides comfortable accommodations with a personal touch. Guests can enjoy a delicious homemade breakfast each morning before exploring the nearby attractions such as Tanglewood, The Mount, and the shops and restaurants of Lenox. Whether you are visiting for a romantic getaway or a relaxing vacation, the Eastgate Inn Bed & Breakfast is the perfect place to stay in the heart of the Berkshires.

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.

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.

Berkshire Valley Inn is a charming lodging located at 2541 Hancock Road in the picturesque town of Williamstown, Massachusetts. Surrounded by the stunning Berkshire Mountains, this cozy inn offers a peaceful retreat for guests looking to relax and unwind. The well-appointed rooms provide a comfortable and inviting atmosphere, perfect for a weekend getaway or a longer stay. Guests can enjoy the beautiful surroundings, explore nearby hiking trails, or visit the many attractions in the area. Whether you're seeking a quiet escape or an adventurous vacation, Berkshire Valley Inn is the perfect destination for your next trip to the Berkshires.

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.

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.

Located at 91 Walker Street in Lenox, Massachusetts, the Hampton Terrace Inn is a historic bed and breakfast that has been rated the #1 place to stay in Lenox on Tripadvisor. Originally built in 1897, this inn was once owned by some of the wealthiest families in the country and was among the first of the "Berkshire cottages" to welcome guests. Today, the inn offers romantic cottages and suites that have been updated with modern amenities while still preserving the property's rich history. Just a 5-minute walk from downtown Lenox, Hampton Terrace Inn is the perfect location for a Berkshires getaway. Guests can enjoy private baths, air conditioning, HDTVs, free Wi-Fi, complimentary cognac and liqueurs, and a full breakfast buffet included in their room rate. The inn also features a heated pool, jetted tubs, and fireplaces for guests to relax and unwind after a day of exploring the Berkshires.

The Lakehouse Inn is a charming lodging located at 615 Laurel Street in the picturesque town of Lee, Massachusetts, United States. This cozy inn offers a peaceful retreat for guests looking to relax and unwind by the lake. With comfortable accommodations, beautiful views, and friendly staff, The Lakehouse Inn is the perfect destination for a tranquil getaway. Whether you're looking to explore the surrounding area or simply enjoy a peaceful escape, this charming inn provides a warm and inviting atmosphere for guests to enjoy.

Garden Gables Inn is a charming lodging establishment located at 135 Main Street in Lenox, Massachusetts, United States. Nestled in the heart of the picturesque town, this historic inn offers a tranquil escape for guests looking to relax and unwind. The beautifully landscaped gardens surrounding the property provide a peaceful setting for guests to enjoy. The inn features elegantly appointed rooms and suites, each uniquely decorated with a blend of modern amenities and classic charm. Guests can start their day with a delicious breakfast served in the cozy dining room or out on the sunny terrace. With its convenient location near local attractions, shops, and restaurants, Garden Gables Inn is the perfect choice for a memorable stay in Lenox.