The 30 Best Countryside retreats in Massachusetts

Located at 512 Main Street in Chatham, Massachusetts, the Chatham Wayside Inn is a unique lodging option that combines a contemporary feel with exceptional service. This boutique hotel offers a restful retreat with amenities such as a heated pool and fitness center. Each room and suite has been carefully restored and offers a different look, with spacious rooms and upscale amenities. Guests can relax on the patio or private balcony and enjoy the sea air. The hotel staff, who are locals, are happy to share their knowledge of the historic town and nearby attractions. Special packages, such as the Birthday & Anniversary package and the Month of Love Package, offer guests the opportunity to enhance their stay with added perks. Don't miss out on the Leap Into Savings promotion, which includes savings of up to 15% and a $50 Food and Beverage credit. Whether you're visiting in the spring, summer, fall, or winter, the Chatham Wayside Inn has something to offer for every season. Book your stay now and experience the charm of this historic hotel in Cape Cod.

The Summer House Cottages is a charming seaside retreat located at 17 Ocean Avenue in Siasconset, Massachusetts. This institution offers a unique combination of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway by the ocean. The cozy cottages provide a comfortable and intimate stay, while the on-site restaurant serves delicious meals made with fresh, local ingredients. Guests can enjoy stunning views of the ocean and easy access to the beach, creating a peaceful and rejuvenating atmosphere. Whether you're looking for a romantic escape or a family vacation, The Summer House Cottages is the ideal choice for a memorable stay on the beautiful island of Nantucket.

Kingfisher Lodging is a pet-friendly accommodation located at 177 Main Street in Dennis, Massachusetts. Since 2001, the Fisher family has been welcoming guests to this historic property on Cape Cod. The recently renovated motel is just a short drive from some of the finest beaches, restaurants, and attractions in the area. Guests can relax at the outdoor pool, one of the largest in the region, or take their four-legged friend to the fenced-in dog run. The hotel prides itself on being one of the few pet-friendly options on Cape Cod.

Wheel In Cottages is a charming lodging establishment located in Eastham, Massachusetts, United States. As a real estate agency and travel agency, we offer cozy and comfortable cottages for your vacation getaway. Our cottages are equipped with all the amenities you need for a relaxing stay, including fully equipped kitchens, private bathrooms, and outdoor seating areas. Whether you're looking for a romantic retreat or a family vacation, Wheel In Cottages has the perfect accommodation for you. Book your stay with us today and experience the beauty of Cape Cod in style and comfort.

Gull Cottage Bed & Breakfast is a charming lodging establishment located at 50 Steele Road in Wellfleet, Massachusetts. Nestled in a picturesque coastal town, this cozy B&B offers a relaxing getaway for visitors looking to unwind and enjoy the beauty of Cape Cod. With comfortable accommodations, delicious homemade breakfasts, and personalized hospitality, Gull Cottage is the perfect home away from home for travelers seeking a peaceful retreat by the sea. Experience the warmth and charm of this quaint bed and breakfast during your next visit to Wellfleet.

Eider Duck Cottages is a charming lodging institution located at 1470 Main Street in the picturesque town of Chatham, Massachusetts, United States. Nestled in a tranquil setting, these cozy cottages offer a perfect retreat for those seeking a peaceful and relaxing getaway. Each cottage is beautifully decorated and equipped with all the modern amenities to ensure a comfortable stay. Guests can enjoy the serene surroundings, explore the nearby attractions, or simply unwind on the porch and take in the breathtaking views. Eider Duck Cottages is the ideal destination for a memorable vacation on Cape Cod.

Culdesac Cottage Bed and Breakfast is a charming lodging located at 49 Glover Square in the picturesque town of Chatham, Massachusetts. Situated in a peaceful cul-de-sac, this cozy cottage offers a serene and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. The accommodations are tastefully decorated and feature modern amenities to ensure a comfortable stay. Guests can enjoy a delicious homemade breakfast each morning, served in the inviting dining area. With its convenient location near beaches, shopping, and dining options, Culdesac Cottage Bed and Breakfast is the perfect choice for a memorable stay on Cape Cod.

Cottage Grove At Eastham is a charming lodging institution located at 1975 State Highway in Eastham, Massachusetts, United States. Nestled in a serene and picturesque setting, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests to relax and unwind. With its convenient location near popular attractions such as the Cape Cod National Seashore and Nauset Light Beach, Cottage Grove At Eastham provides the perfect base for exploring the beauty of Cape Cod. Whether you're looking for a romantic getaway or a family vacation, this charming establishment is sure to provide a memorable and enjoyable stay.

Jacob's Tanglewood Ranch is a charming lodging institution located at 560 Stockbridge Road in Lee, Massachusetts, United States. Nestled in the picturesque countryside, this ranch offers a peaceful and tranquil retreat for guests looking to escape the hustle and bustle of city life. The rustic yet cozy accommodations provide a comfortable stay, while the surrounding Tanglewood forest offers plenty of opportunities for outdoor activities such as hiking, horseback riding, and birdwatching. Whether you're seeking a romantic getaway or a family vacation, Jacob's Tanglewood Ranch is the perfect destination for a relaxing and rejuvenating experience.

Freeland Brook Farm is a charming lodging located at 63 Russell Stage Road in Blandford, Massachusetts, United States. Nestled in a picturesque countryside setting, this institution offers a peaceful and tranquil retreat for guests looking to escape the hustle and bustle of city life. The farm boasts comfortable accommodations, beautiful gardens, and scenic views of the surrounding landscape. Whether you're seeking a relaxing weekend getaway or a romantic escape, Freeland Brook Farm provides a cozy and welcoming atmosphere for all visitors to enjoy.

Ashley Hills Condominiums is a premier residential complex located at 150 Hillside Road in Westfield, Massachusetts, United States. Nestled in a picturesque setting, this institution offers luxurious condominium living with stunning views of the surrounding hills and countryside. Residents can enjoy a range of amenities including a fitness center, swimming pool, and beautifully landscaped grounds. With spacious and modern units, Ashley Hills Condominiums provides a comfortable and convenient living experience for those seeking a peaceful retreat in a desirable location.

The Cottage @ Round Hill is a charming lodging located at 44 Round Hill Road in the picturesque town of Northampton, Massachusetts, United States. Nestled in a serene and peaceful setting, this cozy cottage offers a relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With its comfortable accommodations and beautiful surroundings, The Cottage @ Round Hill is the perfect destination for a weekend getaway or a longer stay in the scenic New England countryside. Experience tranquility and comfort at this hidden gem in Northampton.

Olde English Village in Gardner, Massachusetts is a charming transit station that transports visitors back in time to a quaint English village. With its cobblestone streets, Tudor-style buildings, and traditional shops, this unique institution offers a delightful experience for travelers passing through Gardner. Step off the train and immerse yourself in the old-world charm of Olde English Village, where you can explore the shops, enjoy a cup of tea, or simply take in the picturesque surroundings. Whether you're a history buff or just looking for a one-of-a-kind stop on your journey, Olde English Village is sure to leave a lasting impression.

Birchwood Hills is a real estate agency located at 54 Junction Square Drive in Concord, Massachusetts, United States. This institution is a community of 68 townhomes developed in 3 villages, surrounded by over 120 acres of stunning scenery and 250 acres of conservation land. Residents can enjoy walking trails, picnics, and beautiful sunsets over the hills. Birchwood Hills offers a peaceful and picturesque living environment for those seeking a tranquil retreat in nature.

Chestnut Farm Apartments is a charming rural community located at 100 Chestnut Farm Way in Raynham, Massachusetts. Our one, two, and three bedroom apartments offer attractive amenities and a picturesque setting that will capture your heart. Situated near Bridgewater and Taunton, and just 30 miles from Boston and Providence, our location provides the perfect blend of countryside tranquility and city convenience. Our resort-style pool with pergola and chaise lounge seating, along with sprawling green spaces and garden-style buildings, create a peaceful and inviting atmosphere. Please note that floor plan images are representations and layouts may vary slightly.

Copley Gardens is a charming institution located at 105 Market Street in Rockland, Massachusetts, United States. This beautiful garden is a peaceful oasis in the heart of the bustling city, offering a serene escape for visitors to relax and unwind. With meticulously manicured lawns, vibrant flower beds, and tranquil water features, Copley Gardens is a perfect spot for nature lovers and those seeking a moment of tranquility. Whether you're looking for a quiet place to read a book, take a leisurely stroll, or simply enjoy the beauty of the outdoors, Copley Gardens is a must-visit destination in Rockland.

Linden Tree Carriage House is a charming real estate and travel agency located at 252R High Street in the picturesque town of Newburyport, Massachusetts. Our dedicated team of professionals is committed to helping clients find their dream home or plan the perfect getaway. With a focus on personalized service and attention to detail, Linden Tree Carriage House is the go-to destination for all your real estate and travel needs. Visit us today and let us help you turn your dreams into reality.

Terrapin Ridge is a charming institution located in Sandwich, Massachusetts, United States. Nestled in a picturesque setting, this institution offers a unique and enriching experience for visitors. With its serene surroundings and inviting atmosphere, Terrapin Ridge is the perfect destination for those seeking a peaceful retreat. Whether you are looking to relax and unwind or explore the natural beauty of the area, Terrapin Ridge has something for everyone. Come and discover all that this wonderful institution has to offer.

The Pinehills, located at 33 Summerhouse Drive in Plymouth, Massachusetts, is a unique institution that combines the charm of a New England village with modern amenities. As a general contractor and real estate agency, The Pinehills offers inspired new homes and daily adventures just 45 miles from Boston and near Cape Cod. Whether you are an outdoor enthusiast, a food lover, a history buff, or a golf aficionado, The Pinehills has something for everyone. With artfully crafted new homes nestled among towering pines and some with ocean views, the institution offers a range of housing options including custom homes, cottages, townhomes, condominiums, and luxury apartments for rent.

Melpet Farm Residences is a charming retreat located at 812 Massachusetts 134 in Dennis, Massachusetts. Nestled in the heart of Cape Cod, this institution offers a peaceful and serene environment for its residents. The farm features beautifully landscaped grounds, spacious accommodations, and a variety of amenities for a comfortable and enjoyable stay. Whether you are looking for a relaxing getaway or a long-term residence, Melpet Farm Residences provides a welcoming and nurturing community for individuals seeking a tranquil and idyllic setting.

Cassick Valley Cottage is a charming lodging institution located at 75 Cassick Valley Road in Wellfleet, Massachusetts, United States. Nestled in the picturesque Cassick Valley, this cozy cottage offers a peaceful retreat for travelers looking to escape the hustle and bustle of city life. Surrounded by lush greenery and beautiful scenery, guests can relax and unwind in a serene environment. The cottage is equipped with comfortable accommodations and modern amenities to ensure a comfortable stay for all guests. Whether you're looking for a romantic getaway or a family vacation, Cassick Valley Cottage is the perfect destination for a relaxing and rejuvenating experience.

Pie's Cottage is a cozy lodging located at 7 Ellerslie Road in the charming town of Orleans, Massachusetts. This quaint cottage offers a peaceful retreat for guests looking to relax and unwind on Cape Cod. Nestled in a serene neighborhood, Pie's Cottage provides comfortable accommodations and a warm, welcoming atmosphere. Whether you're exploring the nearby beaches, shopping in town, or simply enjoying a quiet evening in, Pie's Cottage is the perfect home away from home during your visit to the United States.

Pleasant Forest Shores cottages is a charming lodging establishment located at 259 Pleasant Street in the picturesque town of Chatham, Massachusetts, United States. Nestled in a tranquil forest setting, the cottages offer a peaceful retreat for guests looking to escape the hustle and bustle of everyday life. Each cottage is tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the serene surroundings, take a leisurely stroll to the nearby beach, or explore the quaint shops and restaurants in the town center. Whether you are seeking a romantic getaway or a family vacation, Pleasant Forest Shores cottages provide the perfect setting for a relaxing and rejuvenating experience.

The Eustis Estate Museum and Study Center is a historic landmark located at 1424 Canton Avenue in Milton, Massachusetts. This beautifully preserved estate offers visitors a glimpse into the lives of the Eustis family, who once called this grand mansion home. The museum features a collection of period furnishings, artwork, and artifacts that provide insight into the history and culture of the region. Visitors can explore the meticulously restored rooms of the estate, including the elegant parlors, dining room, and bedrooms. The surrounding grounds offer a picturesque setting for leisurely strolls and picnics, with lush gardens and scenic views of the surrounding countryside.

Forage is a renowned restaurant located at 5 Craigie Circle in Cambridge, Massachusetts, United States. Known for its farm-to-table approach, Forage sources fresh, seasonal ingredients from local farms and producers to create innovative and flavorful dishes. The restaurant prides itself on its commitment to sustainability and supporting the local community. With a cozy and inviting atmosphere, Forage offers a unique dining experience that celebrates the best of New England cuisine. Whether you're looking for a casual lunch or a special dinner, Forage is the perfect place to enjoy delicious food made with care and passion.

Green River Farms is a picturesque agricultural institution nestled at 2480 Green River Road in Williamstown, Massachusetts. Our farm boasts lush green pastures, rolling hills, and a serene atmosphere that is perfect for reconnecting with nature and enjoying the beauty of the countryside. We specialize in sustainable farming practices and offer a variety of fresh produce, including fruits, vegetables, and herbs. Visitors can also enjoy farm tours, educational workshops, and seasonal events that celebrate the bounty of the land. Come visit us at Green River Farms and experience the magic of rural living in the heart of the United States.

Brookside Farm is a charming institution located on North Main Street in Lanesborough, Massachusetts, United States. Situated in the picturesque countryside, this farm offers a peaceful and serene setting for visitors to enjoy. With its rolling hills, lush green pastures, and babbling brooks, Brookside Farm is the perfect place to escape the hustle and bustle of city life. Visitors can take a leisurely stroll through the farm, visit the animals, or simply relax and take in the beautiful surroundings. Whether you're looking for a fun day out with the family or a quiet retreat in nature, Brookside Farm has something for everyone.

Great Rock Farm is a picturesque institution located at 201 Pond Street in Georgetown, Massachusetts. This charming farm offers visitors the opportunity to experience the beauty of the countryside and get up close and personal with a variety of farm animals. From playful goats to majestic horses, Great Rock Farm is a haven for animal lovers of all ages. In addition to their animal encounters, the farm also offers educational programs, workshops, and events for those looking to learn more about sustainable farming practices and the importance of agriculture. Whether you're looking for a fun day out with the family or a unique learning experience, Great Rock Farm is the perfect destination for anyone interested in connecting with nature and the farming community.

Merrylegs Farm is a charming equestrian facility located at 607 Elm Street in Dartmouth, Massachusetts. Our farm offers a range of services including horse boarding, training, and lessons for riders of all levels. Our experienced staff provide expert care for your equine companions and ensure a safe and welcoming environment for both horses and riders. With spacious pastures, well-maintained facilities, and a peaceful countryside setting, Merrylegs Farm is the perfect place for horse enthusiasts to enjoy their passion for riding and horsemanship. Come visit us and experience the beauty and tranquility of Merrylegs Farm.

Wooly Acres Ranch is a charming farm located at 83 Grove Street in Kingston, Massachusetts, United States. Our ranch is home to a variety of animals, including sheep, goats, and alpacas, all of which are lovingly cared for by our dedicated staff. Visitors to Wooly Acres Ranch can enjoy interactive experiences such as feeding and petting the animals, as well as educational tours to learn more about sustainable farming practices. Whether you're looking for a fun family outing or a peaceful retreat in the countryside, Wooly Acres Ranch is the perfect destination for animal lovers of all ages.