TOP 10 Pet friendly bed and breakfasts in Massachusetts

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.

Rosie's B's in Holland is a charming institution located at 70 Allen Hill Road in Holland, Massachusetts. Our cozy and inviting space offers a wide range of delicious baked goods, including cakes, cookies, and pastries. Whether you're looking for a sweet treat to enjoy with a cup of coffee or a custom cake for a special occasion, Rosie's B's has you covered. Our friendly staff is dedicated to providing top-notch service and ensuring that every customer leaves satisfied. Stop by Rosie's B's in Holland today to indulge in some of the best baked goods in the United States.

The Carriage House is a prestigious university located in the charming town of Great Barrington, Massachusetts, United States. Situated in a historic building, the institution offers a unique and inspiring learning environment for students. With a focus on academic excellence and innovation, the Carriage House provides a wide range of programs and resources to help students succeed in their chosen fields. The university's beautiful campus and dedicated faculty make it a top choice for those seeking a quality education in a picturesque setting.

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.

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.

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 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 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.

The Guest House at Field Farm is a charming lodging establishment located at 554 Sloan Road in beautiful Williamstown, Massachusetts. Nestled in the picturesque countryside, this guest house offers a peaceful and serene retreat for visitors looking to escape the hustle and bustle of city life. With comfortable accommodations, stunning views of the surrounding landscape, and warm hospitality, The Guest House at Field Farm is the perfect destination for a relaxing getaway. Whether you're looking to explore the nearby attractions or simply unwind in a tranquil setting, this institution provides a welcoming and cozy atmosphere for all guests.

33 Main offers a luxurious lodging experience curated by renowned designer Annie Selke. Located in the charming town of Lenox, Massachusetts, this upscale accommodation combines modern amenities with classic New England charm. Each room is elegantly decorated with Selke's signature style, creating a cozy and inviting atmosphere for guests to relax and unwind. With its prime location on Main Street, guests can easily explore the local shops, restaurants, and cultural attractions that Lenox has to offer. Whether you're visiting for a romantic getaway or a weekend retreat, 33 Main promises a memorable and indulgent stay in the heart of the Berkshires.

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 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.

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.

Welcome to Brook Farm Inn, a charming lodging establishment located at 15 Hawthorne Street in Lenox, Massachusetts. Our Victorian Inn offers 15 guest rooms, including a carriage house with three luxury accommodations, perfect for a relaxing getaway in the beautiful Berkshires. Surrounded by trees and award-winning gardens, our inn provides a serene and secluded atmosphere, while still being just a short walk from historic Lenox village. Built in 1882 and furnished with antiques, our elegant inn features a library filled with poetry, history, and literature, where guests can enjoy the soothing sounds of classical music. Each room at Brook Farm Inn includes a full plated breakfast, providing a perfect start to the day before exploring all that the Berkshires have to offer. From skiing and hiking to theater and antiquing, there is something for everyone to enjoy in the area.

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.

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 Cornell Inn is a charming lodging establishment located at 203 Main Street in Lenox, Massachusetts, United States. This historic inn offers cozy accommodations, friendly service, and a convenient location in the heart of the Berkshires. Guests can relax in comfortable rooms, enjoy a delicious breakfast, and explore the nearby shops, restaurants, and attractions. Whether you're visiting for a romantic getaway, a family vacation, or a business trip, the Cornell Inn is the perfect place to stay in Lenox.

Stay Berkshires is a charming lodging institution located at 1146 Cold Spring Road in the picturesque town of Williamstown, Massachusetts. Nestled in the heart of the Berkshires, our cozy accommodations offer a peaceful retreat for visitors looking to relax and unwind in a beautiful natural setting. Whether you're exploring the nearby cultural attractions or simply seeking a tranquil escape, Stay Berkshires provides a comfortable and inviting home away from home. Experience the warmth and hospitality of our friendly staff as you enjoy all that the Berkshires have to offer.

Villager Motel is a cozy lodging establishment situated at 953 Simonds Road in the picturesque town of Williamstown, Massachusetts, United States. Nestled in a tranquil setting, this charming motel offers comfortable accommodations for travelers looking for a peaceful retreat. With its convenient location near local attractions and amenities, Villager Motel is the perfect choice for visitors seeking a relaxing stay in the heart of the Berkshires. Experience warm hospitality and excellent service at Villager Motel during your next trip to Williamstown.

Quality Inn, located at 170 Housatonic Street in Lee, Massachusetts, offers comfortable and affordable lodging for travelers visiting the United States. With spacious rooms, modern amenities, and friendly staff, guests can enjoy a relaxing stay in a convenient location. Whether you are traveling for business or leisure, Quality Inn provides a welcoming atmosphere and top-notch service to ensure a memorable experience. Book your stay today and experience the comfort and quality that Quality Inn has to offer.

Sunset Inn is a charming lodging facility located at 150 Housatonic Street in the picturesque town of Lee, Massachusetts, United States. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind. With its convenient location near popular attractions and scenic views, Sunset Inn is the perfect choice for a peaceful getaway in the heart of the Berkshires. Whether you're visiting for business or pleasure, you'll find everything you need for a comfortable stay at Sunset Inn.

Chambery Inn is a charming lodging and spa located at 199 Main Street in Lee, Massachusetts. This historic inn offers a tranquil and luxurious retreat for guests seeking a peaceful getaway in the heart of the Berkshires. The beautifully appointed rooms feature elegant decor and modern amenities, creating a cozy and inviting atmosphere for relaxation. Guests can indulge in rejuvenating spa treatments, unwind in the serene garden courtyard, or explore the nearby attractions and activities in the picturesque town of Lee. With its convenient location and exceptional service, Chambery Inn is the perfect destination for a memorable and rejuvenating stay.

Morgan House Inn & Restaurant is a charming establishment located at 33 Main Street in Lee, Massachusetts, United States. This institution offers a cozy and inviting atmosphere perfect for enjoying a meal or drinks with friends and family. The restaurant serves delicious food made with fresh, locally sourced ingredients, while the bar offers a variety of cocktails, wines, and beers. Whether you're looking for a casual meal or a special occasion dinner, Morgan House Inn & Restaurant is the perfect place to relax and indulge in good food and drinks.

Lanesborough Country Inn is a charming lodging located at 499 South Main Street in Lanesborough, Massachusetts, United States. This cozy inn offers a peaceful retreat in the picturesque Berkshire Mountains, surrounded by beautiful nature and just a short drive from cultural attractions such as Tanglewood and the Norman Rockwell Museum. Guests can relax in comfortable rooms, enjoy delicious breakfasts, and unwind in the serene setting of the inn's grounds. Whether you're looking for a romantic getaway or a relaxing escape, Lanesborough Country Inn provides a warm and welcoming atmosphere for your stay.

Welcome to Blackinton Manor, a charming lodging establishment located at 1391 Massachusetts Avenue in North Adams, Massachusetts. This historic manor offers a unique and luxurious experience for guests looking to escape the hustle and bustle of everyday life. With its elegant architecture, beautifully landscaped grounds, and top-notch amenities, Blackinton Manor is the perfect destination for a relaxing getaway. Whether you're looking to explore the nearby attractions or simply unwind in a tranquil setting, our friendly staff is dedicated to ensuring your stay is comfortable and memorable. Experience the timeless elegance of Blackinton Manor during your next visit to Massachusetts.

Netherwood is a charming lodging institution located at 253 Kemp Avenue in the picturesque town of North Adams, Massachusetts, United States. Nestled in a serene and peaceful setting, Netherwood offers comfortable accommodations and a warm hospitality experience for guests seeking a relaxing getaway. With its convenient location and cozy atmosphere, Netherwood is the perfect place to unwind and enjoy the beauty of the surrounding area. Whether you are visiting for business or pleasure, Netherwood welcomes you with open arms and promises a memorable stay.

Harbour House Inn B&B is a charming lodging establishment located at 725 North State Road in the picturesque town of Cheshire, Massachusetts, United States. This cozy bed and breakfast offers comfortable accommodations in a historic building, with a warm and inviting atmosphere. Guests can enjoy a delicious homemade breakfast each morning, as well as access to a peaceful garden and relaxing common areas. Whether you are looking for a romantic getaway or a peaceful retreat in the Berkshires, Harbour House Inn B&B is the perfect choice for your stay.

Berkshire Lakeside Lodge is a charming lodging located at 3949 Jacobs Ladder Road in Becket, Massachusetts. Situated in the stunning Berkshire Mountains, this cozy retreat offers guests a peaceful and serene escape surrounded by nature. With comfortable accommodations and beautiful views of the nearby lake, Berkshire Lakeside Lodge is the perfect destination for those looking to relax and unwind. Whether you're seeking a romantic getaway or a family vacation, this lodge provides a warm and welcoming atmosphere for all guests to enjoy.