TOP 30 Best Quaint countryside inn in Massachusetts

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.

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.

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.

The Old Manse Inn is a charming and historic bed and breakfast located at 1861 Main Street in Brewster, Massachusetts. This cozy inn offers a warm and welcoming atmosphere, with beautifully decorated rooms and exceptional hospitality. Guests can enjoy a delicious homemade breakfast each morning, relax in the peaceful garden, or explore the nearby beaches and attractions of Cape Cod. Whether you're looking for a romantic getaway or a relaxing retreat, the Old Manse Inn is the perfect choice for your stay in Brewster.

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.

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.

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 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 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.

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.

The West Tisbury Inn is a charming lodging establishment located at 1070 State Road in the picturesque town of West Tisbury, Massachusetts. This historic inn offers a cozy and welcoming atmosphere for guests looking to relax and unwind in the heart of Martha's Vineyard. With comfortable accommodations, friendly staff, and convenient access to local attractions, the West Tisbury Inn is the perfect choice for a memorable getaway. Whether you're exploring the island or simply enjoying a peaceful retreat, this quaint inn provides the ideal home away from home.

The Shady Hollow Inn is a charming lodging establishment located at 370 Main Street in Dennis, Massachusetts, United States. Nestled in a tranquil and picturesque setting, this cozy inn offers a peaceful retreat for travelers seeking a relaxing getaway. Guests can enjoy comfortable accommodations, friendly service, and a warm atmosphere that makes them feel right at home. Whether you're visiting for a weekend escape or an extended vacation, The Shady Hollow Inn is the perfect place to unwind and recharge in the heart of Cape Cod.

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 Manor House Inn is a charming lodging establishment located at 31 Centre Street in the picturesque town of Nantucket, Massachusetts. This historic inn offers a cozy and inviting atmosphere for guests looking to experience the beauty and charm of Nantucket. The Manor House Inn features comfortable rooms, delicious breakfast options, and friendly staff to ensure a memorable stay for all visitors. With its convenient location in the heart of Nantucket, guests can easily explore the island's beaches, shops, and attractions. Whether you're visiting for a weekend getaway or a longer vacation, the Manor House Inn is the perfect place to relax and unwind in Nantucket.

The Bursley Manor is a charming lodging located at 651 Main Street in the picturesque town of Barnstable, Massachusetts. This historic institution offers a unique and cozy atmosphere for guests looking to relax and unwind in a beautiful setting. With its comfortable accommodations and welcoming staff, The Bursley Manor provides a perfect retreat for travelers seeking a peaceful getaway. Enjoy the tranquility of the surrounding area, explore the nearby attractions, or simply relax in the comfort of this charming establishment. Experience the charm and hospitality of The Bursley Manor during your next visit to Barnstable.

Cedar Hill Farm Bed & Breakfast offers a charming and cozy retreat in the heart of Essex, Massachusetts. Situated at 22 John Wise Avenue, this quaint lodging establishment provides a peaceful and relaxing atmosphere for guests looking to escape the hustle and bustle of city life. Surrounded by picturesque landscapes and scenic views, Cedar Hill Farm Bed & Breakfast is the perfect destination for a romantic getaway or a weekend of rest and rejuvenation. With comfortable accommodations, delicious breakfast options, and friendly hospitality, this charming bed and breakfast is sure to make your stay unforgettable.

The Chestnut House is a charming lodging establishment located at 3 Chestnut Street in the picturesque town of Nantucket, Massachusetts. This cozy inn offers a warm and inviting atmosphere, perfect for a relaxing getaway or a romantic escape. The Chestnut House features comfortable accommodations, friendly staff, and a convenient location near local attractions and amenities. Guests can enjoy a peaceful stay in one of the well-appointed rooms, each designed with comfort and style in mind. Whether you're visiting Nantucket for business or pleasure, The Chestnut House is the perfect place to call home during your stay.

The Cora Needham House is a charming lodging establishment located at 48 Main Street in Wales, Massachusetts, United States. This historic house offers a cozy and comfortable atmosphere for guests looking to relax and unwind in a picturesque New England setting. With its quaint decor and warm hospitality, The Cora Needham House provides a unique and memorable experience for those seeking a peaceful getaway in the heart of the countryside. Whether you're visiting for a weekend retreat or an extended stay, this institution is the perfect place to call home during your time in Wales.

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.

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.

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.

Ahh Qua Bed and Breakfast is a charming lodging facility located at 164 Wapping Road in Kingston, Massachusetts, United States. This cozy establishment offers a peaceful and relaxing atmosphere for guests looking for a comfortable stay. The beautifully decorated rooms and friendly staff ensure a warm and inviting experience for all visitors. With its convenient location, guests can easily explore the nearby attractions and enjoy a memorable stay at Ahh Qua Bed and Breakfast.

Hillcrest Bed & Breakfast is a charming New England residence located at 70 Gosnold Street in Barnstable, Massachusetts. Originally built in 1899, the Hillcrest has a rich history as a guest house, family residence, and now as a weekly rental. The property offers four beautifully decorated guest rooms named The Blueberry Patch, The Ocean Breeze, The Sand Dunes, and Bayberry Brambles. Guests can enjoy their breakfast on the porch, front or back patio, or small deck off the kitchen while listening to the birds and feeling the cool ocean breezes just two blocks away. For those who prefer not to cook, there are plenty of dining options within walking distance, including the Landing Cafe at the nearby ferry dock.

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.

Gilbert's Bed & Breakfast is a charming and cozy lodging located at 30 Spring Street in Rehoboth, Massachusetts, United States. Nestled in a peaceful and picturesque setting, this welcoming B&B offers comfortable accommodations and warm hospitality to guests looking for a relaxing getaway. With well-appointed rooms, delicious breakfast options, and personalized service, Gilbert's Bed & Breakfast is the perfect choice for travelers seeking a home away from home experience. Whether you are visiting for business or pleasure, you are sure to enjoy your stay at this delightful establishment.

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.

Wholesome Hearth B & B is a charming bed and breakfast located at 100 Pleasant Street in Barre, Massachusetts. This cozy establishment offers comfortable accommodations in a quaint and peaceful setting. Guests can enjoy a delicious homemade breakfast each morning, prepared with fresh, locally sourced ingredients. The friendly staff at Wholesome Hearth B & B provide personalized service to ensure a relaxing and enjoyable stay for all visitors. Whether you are looking for a weekend getaway or a longer stay, this welcoming B & B is the perfect choice for travelers seeking a home away from home.

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.

Village Landing Bed & Breakfast is a charming lodging establishment located at 13 South Street in the picturesque town of Marion, Massachusetts. This cozy bed and breakfast offers a comfortable and inviting atmosphere for guests looking to relax and unwind in a tranquil setting. The quaint rooms are tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can enjoy a delicious homemade breakfast each morning and take advantage of the convenient location near local attractions such as beaches, shops, and restaurants. Whether you are visiting for a romantic getaway or a peaceful retreat, Village Landing Bed & Breakfast provides a warm and welcoming experience for all guests.