The 30 Best Countryside inn in Massachusetts

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.

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 info@oldinn.com. Feel the love and experience the best of the oldest at The Old Inn On The Green.

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.

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.

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.

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.

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.

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.

Country Inn is a charming lodging establishment located at 37 Corey Road in Hancock, Massachusetts, United States. Nestled in the picturesque countryside, this quaint inn offers a cozy and inviting atmosphere for guests looking to relax and unwind. With comfortable accommodations, warm hospitality, and beautiful surroundings, Country Inn is the perfect destination for a peaceful getaway in the heart of nature. Whether you are visiting for a romantic weekend escape or a family vacation, you will feel right at home at this idyllic retreat.

THE 1896 House Inn and Country Lodgings is a charming accommodation located at 910 Cold Spring Road in the picturesque town of Williamstown, Massachusetts. This historic institution offers a cozy and comfortable stay in a beautiful countryside setting. With a range of accommodations to choose from, including rooms in the main inn and private cottages, guests can enjoy a peaceful retreat surrounded by nature. The inn also features a delicious on-site restaurant, perfect for enjoying a meal after a day of exploring the nearby attractions such as the Williams College Museum of Art or the Clark Art Institute. Whether you are looking for a romantic getaway or a family vacation, THE 1896 House Inn and Country Lodgings provides a welcoming and relaxing atmosphere for all guests.

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.

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.

Whistler's Inn is a charming lodging establishment located at 5 Greenwood Street in the picturesque town of Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and personalized service to make guests feel right at home. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Whistler's Inn is the perfect choice for travelers looking to experience the beauty and culture of the Berkshires. Whether you're visiting for a romantic getaway or a family vacation, Whistler's Inn provides a peaceful retreat in the heart of Lenox.

The Goldenrod Country Inn is a charming bar and lodging establishment located at 144 Huntington Road in the picturesque town of Worthington, Massachusetts. Nestled in the heart of the countryside, this cozy inn offers a warm and inviting atmosphere for guests looking to relax and unwind. With comfortable accommodations, a well-stocked bar, and friendly staff, The Goldenrod Country Inn is the perfect destination for a weekend getaway or a peaceful retreat in the New England countryside.

Warfield House Inn is a charming lodging option located at 200 Warfield Road in the picturesque town of Charlemont, Massachusetts. This historic inn offers a cozy and inviting atmosphere, perfect for a relaxing getaway in the beautiful New England countryside. Guests can enjoy comfortable accommodations, delicious meals, and warm hospitality during their stay. Whether you're looking for a romantic retreat or a family vacation, Warfield House Inn provides a peaceful and tranquil setting for your next escape.

The Dancing Bear Guest House, also known as Blooming Inn, is a charming accommodation option located in the heart of Shelburne Falls, Massachusetts. Housed in the historic Moses W. Merrill homestead dating back to 1852, this inn offers comfortable lodgings in a setting that exudes historic elegance. Each room is equipped with a private bathroom for convenience, and guests can enjoy spacious living and dining rooms for relaxation. The inn also provides self-serve coffee, tea, and toast-making facilities, as well as access to a refrigerator for storing personal food items. Guests can customize their breakfast with English Muffins and special bread, adding to the flexibility of their morning routine. Additionally, the lovely garden and outdoor breakfast option enhance the overall guest experience, providing a serene setting for a memorable stay. The cozy guest sitting rooms and dining room offer inviting spaces for socializing, reading, or enjoying a quiet moment. With amenities like fireplaces and scenic views, these common areas enhance comfort and relaxation. Whether visiting for a short-term stay or longer duration, the Dancing Bear Guest House AKA Blooming Inn offers a convenient and pleasant lodging option within a historic setting.

Sugar Maple Trailside Inn is a cozy and charming lodging located at 62 Chestnut Street in the picturesque town of Northampton, Massachusetts. Nestled in a serene and scenic setting, this inn offers a peaceful retreat for guests looking to unwind and relax. With comfortable accommodations, friendly staff, and a warm and inviting atmosphere, Sugar Maple Trailside Inn is the perfect place to stay for a weekend getaway or a longer vacation. Whether you're exploring the nearby trails and outdoor activities or simply enjoying the local shops and restaurants, this inn provides a comfortable and convenient home base for your adventures in the beautiful Pioneer Valley.

The Black Walnut Inn is a charming lodging establishment located at 1184 North Pleasant Street in Amherst, Massachusetts. Nestled in the heart of the historic town, this inn offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. The inn's cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a delicious breakfast in the quaint dining area or relax in the beautiful garden courtyard. With its convenient location and welcoming atmosphere, The Black Walnut Inn is the perfect choice for travelers seeking a memorable stay in Amherst.

Clamber Hill Inn & Restaurant is a charming establishment located at 111 North Main Street in Petersham, Massachusetts. This quaint inn offers cozy lodging accommodations and a top-rated restaurant all under one roof. Guests can enjoy a peaceful retreat in the heart of the New England countryside, with beautifully appointed rooms and delicious meals made with locally sourced ingredients. Whether you're looking for a weekend getaway or a special dining experience, Clamber Hill Inn & Restaurant is the perfect destination for food and lodging in Massachusetts.

Countryside Motel is a charming lodging establishment located at 662 Spring Street in the picturesque town of Winchendon, Massachusetts. Nestled in the heart of the countryside, this cozy motel offers comfortable and affordable accommodations for travelers looking to explore the natural beauty and charm of the New England region. With clean and spacious rooms, friendly staff, and convenient amenities, Countryside Motel is the perfect home away from home for your next getaway. Experience the tranquility and serenity of the countryside at Countryside Motel.

Nestled in the picturesque town of Sudbury, Massachusetts, the Inn On The Horse Farm offers a unique and tranquil lodging experience. Located at 277 Old Sudbury Road, this charming inn is surrounded by acres of beautiful farmland and rolling hills. Guests can enjoy a peaceful retreat in a cozy room, each uniquely decorated with a country charm. The Inn On The Horse Farm also offers horseback riding opportunities for guests to explore the scenic countryside. Whether you are looking for a relaxing getaway or a romantic escape, this charming inn is the perfect destination.

The Inn at Woburn is a charming lodging establishment located at 14 Hill Street in the picturesque town of Woburn, Massachusetts. This historic inn offers a cozy and inviting atmosphere for guests looking for a comfortable stay in a beautiful New England setting. The Inn features well-appointed rooms with modern amenities, a delicious breakfast served daily, and friendly staff who are dedicated to ensuring a memorable experience for every visitor. Whether you are in town for business or pleasure, The Inn at Woburn is the perfect choice for your next stay in Massachusetts.

The Hampton Inn Boston/Marlborough is a cozy and comfortable lodging option located at 277 Boston Post Road West in Marlborough, Massachusetts. This charming hotel offers a convenient location for travelers looking to explore the vibrant city of Boston or the picturesque New England countryside. With spacious rooms, modern amenities, and friendly staff, guests can enjoy a relaxing stay while visiting the area. Whether you are traveling for business or pleasure, the Hampton Inn Boston/Marlborough is the perfect choice for your next trip to Massachusetts.

Located at 101 Main Street in Rowley, Massachusetts, Briar Barn Inn is a charming lodging institution just 30 miles from the bustling city of Boston. Offering a blend of laid-back luxury and heartfelt hospitality, Briar Barn Inn provides a quintessential country inn experience with a modern twist. The farmhouse setting of the inn features 30 guest rooms that combine rustic charm with contemporary finishes, creating a serene retreat or romantic getaway. The Spa at Briar Barn Inn offers a tranquil escape with three treatment rooms for massages, facials, wax treatments, and more. The intimate spa provides a relaxing environment for guests to indulge in personalized wellness treatments.

The Old Red Farm Inn is a charming lodging establishment located at 20 Stockton Short Cut Street in Wareham, Massachusetts. This historic inn offers cozy accommodations in a picturesque setting, perfect for a relaxing getaway. Guests can enjoy comfortable rooms, delicious breakfast options, and a warm, welcoming atmosphere. Whether you're looking for a romantic retreat or a peaceful escape, the Old Red Farm Inn is the perfect choice for your next stay in Massachusetts.

Located at 854 Scenic Highway in Bourne, Massachusetts, the Bournedale Village Inn offers a variety of room types to cater to different visitor needs. From Standard rooms with kitchenettes to Full Kitchen Rooms and a charming Cape Cod style Cottage Suite, there is something for everyone at this cozy inn. The Standard rooms feature two double beds with comfortable bedding, a dresser, closet, and bedside tables for personal belongings. The room has a studio apartment feel with a separate dining space and a full kitchen equipped with utensils, dishes, mugs, pots, and pans. Guests can cook full meals and store groceries for extended stays.