TOP 30 Countryside retreats in Massachusetts

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.

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.

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.

Conroy's Bed & Breakfast is a charming lodging establishment located at 11 East Street in the picturesque town of Stockbridge, Massachusetts, United States. Nestled in a quaint and peaceful neighborhood, this cozy bed and breakfast offers comfortable accommodations and warm hospitality for guests looking to relax and unwind in a homely atmosphere. With its convenient location near local attractions, shops, and restaurants, Conroy's Bed & Breakfast is the perfect choice for travelers seeking a memorable stay in the heart of Stockbridge.

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.

Green Valley Motel Williamstown is a charming lodging option located at 1214 Simonds Road in the picturesque town of Williamstown, Massachusetts. Surrounded by lush greenery and offering stunning views of the surrounding countryside, this motel provides a peaceful and relaxing retreat for guests. The rooms are cozy and comfortable, with modern amenities to ensure a pleasant stay. Whether you're visiting for business or pleasure, Green Valley Motel Williamstown is the perfect choice for your accommodation needs.

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.

Ingalls Crossing Farm Bed and Breakfast is a charming lodging establishment located at 175 Blair Road in the picturesque town of Williamstown, Massachusetts, United States. Situated on a beautiful farm with scenic views of the surrounding countryside, this bed and breakfast offers a peaceful and relaxing retreat for guests. The cozy rooms are tastefully decorated and feature modern amenities for a comfortable stay. Guests can enjoy a delicious homemade breakfast each morning made with fresh ingredients from the farm. Whether you are looking for a romantic getaway or a peaceful escape, Ingalls Crossing Farm Bed and Breakfast is the perfect destination.

The Becket Motel is a cozy lodging establishment located at 29 Chester Road in Becket, Massachusetts, United States. Nestled in the serene countryside, this charming motel offers comfortable accommodations for travelers seeking a peaceful retreat. With its convenient location and warm hospitality, The Becket Motel is the perfect choice for those looking to relax and unwind in a picturesque setting.

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.

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.

Canterbury Farm is a charming lodging institution located at 1986 Fred Snow Road in Becket, Massachusetts, United States. Surrounded by picturesque countryside, this cozy retreat offers a peaceful escape from the hustle and bustle of city life. Guests can enjoy comfortable accommodations, delicious meals, and a range of outdoor activities such as hiking, fishing, and horseback riding. Whether you're looking for a romantic getaway or a family vacation, Canterbury Farm is the perfect destination for relaxation and rejuvenation.

Maple House Bed & Breakfast is a charming lodging establishment located at 51 Middletown Hill Road in Rowe, Massachusetts, United States. Nestled in a picturesque countryside setting, this cozy B&B offers guests a peaceful retreat surrounded by nature. The well-appointed rooms are tastefully decorated and provide a comfortable stay for visitors looking to relax and unwind. Guests can enjoy a delicious homemade breakfast each morning, made with locally sourced ingredients. The friendly staff at Maple House Bed & Breakfast are dedicated to providing exceptional hospitality and ensuring that guests have a memorable and enjoyable stay. Whether you are looking for a romantic getaway or a peaceful escape from the hustle and bustle of city life, Maple House Bed & Breakfast is the perfect destination for your next vacation.

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.

Upland Meadows Farm B&B is a charming bed and breakfast located in the picturesque town of Cummington, Massachusetts. Situated at 338 West Cummington Road, this institution offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of city life. Surrounded by lush meadows and rolling hills, Upland Meadows Farm B&B provides comfortable accommodations and warm hospitality. Guests can enjoy the beauty of the countryside, explore nearby hiking trails, or simply relax on the porch and take in the stunning views. Whether you're looking for a romantic getaway or a quiet weekend retreat, Upland Meadows Farm B&B is the perfect destination for your next escape.

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.

Blue Heron Farm in Charlemont, Massachusetts is a charming lodging destination nestled on 250 acres of pristine countryside. This unique institution offers a tranquil retreat for visitors looking to escape the hustle and bustle of city life. The farm also serves as a real estate agency, helping clients find their dream homes in the picturesque New England landscape. Additionally, Blue Heron Farm operates as a travel agency, providing personalized itineraries for those looking to explore the beauty of western Massachusetts. Whether you're seeking a peaceful getaway or looking to invest in a piece of paradise, Blue Heron Farm is the perfect destination for all your lodging, real estate, and travel needs.

Bourke Shire Farm Bed & Breakfast is a charming lodging located at 15 South Road in the picturesque town of Heath, Massachusetts. Nestled in the heart of the United States, this cozy B&B offers guests a peaceful and relaxing retreat surrounded by the beauty of the countryside. The property features comfortable rooms, delicious home-cooked meals, and friendly hospitality. Whether you're looking for a romantic getaway or a weekend escape, Bourke Shire Farm Bed & Breakfast is the perfect destination for a memorable stay.

Norton Hill BnB is a charming bed and breakfast located at 10 Norton Hill Road in the picturesque town of Ashfield, Massachusetts. This cozy institution offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind in the beautiful New England countryside. With its convenient location and attentive staff, Norton Hill BnB is the perfect choice for travelers seeking a peaceful retreat in the United States.

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.

Cavalier Cottage Bed & Breakfast is a charming lodging establishment located at 236 East Oxbow Road in the picturesque town of Charlemont, Massachusetts. This cozy retreat offers guests a peaceful and comfortable stay in a beautiful countryside setting. The cottage-style accommodations are tastefully decorated and feature modern amenities to ensure a relaxing experience. Guests can enjoy a delicious homemade breakfast each morning and take advantage of the convenient location near outdoor recreational activities such as hiking, skiing, and river rafting. Whether you are looking for a romantic getaway or a relaxing escape, Cavalier Cottage Bed & Breakfast is the perfect destination for your next vacation.

Shelburne Springs is a charming lodging institution located at 904 Mohawk Trail in the picturesque town of Shelburne Falls, Massachusetts. Nestled in the heart of the scenic Berkshires, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests looking to unwind and relax. With its convenient location near local attractions such as the Bridge of Flowers and the Mohawk Trail State Forest, Shelburne Springs is the perfect destination for a weekend getaway or a longer stay in the beautiful New England countryside. Whether you're seeking a romantic retreat or a family vacation, Shelburne Springs provides a welcoming and memorable experience for all who visit.

Located on 60 Masterson Road in the picturesque town of Whately, Massachusetts, Hillside House Bed & Breakfast offers a charming and cozy retreat for travelers looking for a peaceful and relaxing stay. This quaint lodging institution is nestled on a hillside, providing stunning views of the surrounding countryside. Guests can enjoy comfortable accommodations, delicious homemade breakfasts, and warm hospitality from the friendly staff. Whether you are visiting for a weekend getaway or a longer vacation, Hillside House Bed & Breakfast is the perfect place to unwind and recharge in the heart of New England.

Rainbow Motel is a charming and cozy campground located at 68 State Road in Whately, Massachusetts. Nestled in the beautiful countryside of Massachusetts, this institution offers a peaceful and serene environment for guests to relax and unwind. Whether you are looking for a place to stay while exploring the nearby attractions or simply want to enjoy a quiet retreat in nature, Rainbow Motel has everything you need. The motel offers a variety of lodging options, including comfortable rooms and spacious RV sites. Guests can enjoy the park-like setting with lush greenery and scenic views. The on-site amenities include picnic areas, playgrounds, and hiking trails, making it the perfect destination for outdoor enthusiasts.

At Poetry Ridge B&B is a charming bed and breakfast located at 55 Stone Ridge in Greenfield, Massachusetts. Nestled in the beautiful countryside, this cozy retreat offers a peaceful and relaxing atmosphere for guests to unwind and recharge. The B&B features comfortable accommodations, delicious breakfasts, and a warm and welcoming staff. Guests can enjoy exploring the nearby hiking trails, visiting local attractions, or simply relaxing on the porch with a good book. Whether you're looking for a romantic getaway or a quiet escape from the hustle and bustle of everyday life, At Poetry Ridge B&B is the perfect destination.

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.