TOP 30 Best Romantic getaways in Massachusetts

Candleberry Inn Cape Cod Bed and Breakfast is a charming and cozy establishment located on Main Street in Brewster, Massachusetts. This historic inn offers comfortable accommodations and a warm, inviting atmosphere for guests looking to relax and unwind on Cape Cod. The inn features beautifully decorated rooms, a delicious breakfast served each morning, and a restaurant offering delectable meals made with locally sourced ingredients. Whether you are visiting for a romantic getaway or a family vacation, Candleberry Inn is the perfect choice for a memorable stay on the Cape.

A Little Inn on Pleasant Bay is a charming and romantic boutique Bed & Breakfast located in Orleans, Massachusetts. Winner of the 2023 LuxLife Hospitality Awards for Most Charming Bed & Breakfast in MA, our inn offers guests quintessential European hospitality in an all-American setting. Situated between the historic villages of Chatham and Orleans on Cape Cod, our nine-room inn overlooks the picturesque Pleasant Bay. Each room is named after sailboats that sail the waters of Cape Cod, with a strong New England identity and beautifully designed by interior designer Matthew Yee.

The Old Harbor Inn is a charming lodging establishment located at 22 Old Harbor Road in the picturesque town of Chatham, Massachusetts. Nestled in a tranquil and historic setting, this inn offers guests a cozy and welcoming atmosphere with comfortable accommodations. Whether you are looking for a romantic getaway or a relaxing retreat, The Old Harbor Inn provides the perfect home away from home. With its convenient location near the harbor and local attractions, guests can easily explore the beauty and charm of Chatham. Experience exceptional hospitality and personalized service at The Old Harbor Inn for a memorable stay in Cape Cod.

D.A. Luxury Travel, Inc. is a premier travel agency located on the iconic Newbury Street in Boston, Massachusetts. Our agency specializes in providing high-end, personalized travel experiences for discerning clients looking for luxury vacations and unforgettable adventures. With a team of experienced travel experts, we offer a wide range of services including customized itineraries, exclusive accommodations, private tours, and VIP access to top attractions around the world. Whether you're planning a romantic getaway, a family vacation, or a corporate retreat, D.A. Luxury Travel, Inc. is dedicated to creating memorable and stress-free travel experiences tailored to your unique preferences and desires. Contact us today to start planning your next dream vacation.

Sunset Sail Salem is a premier travel agency located in the historic city of Salem, Massachusetts. Our agency is dedicated to providing unforgettable experiences on the water, offering scenic sunset sails along the picturesque coast of Salem. Our expert crew ensures a safe and enjoyable journey as you relax and take in the stunning views of the sunset over the Atlantic Ocean. Whether you're looking for a romantic evening out or a fun adventure with friends and family, Sunset Sail Salem is the perfect choice for your next nautical excursion. Book your sail today and create lasting memories on the water.

Located at 10 MacMillan Pier in Provincetown, Massachusetts, the Schooner Hindu and the Cutter Bloodhound travel agency offers unique and exciting sailing experiences. Step aboard these historic vessels and set sail on the waters of Cape Cod Bay for a memorable adventure. Whether you're looking for a relaxing cruise or a thrilling racing experience, the Schooner Hindu and the Cutter Bloodhound have something for everyone. Book your voyage today and discover the beauty of the Massachusetts coastline from a whole new perspective.

Cape Cod Catamaran Sailing Charters is a travel agency located at 255 Commercial Street in Wellfleet, Massachusetts, United States. Offering morning and afternoon charters as well as sunset cruises from Wellfleet Harbor, this institution provides an authentic Cape Cod experience on their catamaran, Discovery. Escape the crowds and immerse yourself in the serene beauty of Cape Cod with a private daytime charter, where you can explore the bay, watch seals, or simply relax and enjoy the tranquility of the local waters. The experienced captain ensures a smooth and comfortable ride as you navigate Wellfleet Harbor and Cape Cod Bay.

Rekindled Home is a charming home goods store located at 9 South Main Street in Middleborough, Massachusetts, United States. Our store offers a curated selection of unique and stylish home decor items, furniture, and accessories to help you create a cozy and inviting space. Whether you're looking to refresh your living room, update your kitchen, or add a touch of elegance to your bedroom, Rekindled Home has everything you need to transform your house into a home. Visit us today and let us help you bring new life to your living space.

Summer Village on the Pond Westford is a charming lodging institution located at 6 Summer Village Road in Westford, Massachusetts. Nestled in a picturesque setting by a serene pond, this institution offers a peaceful and idyllic retreat for guests looking to escape the hustle and bustle of everyday life. The accommodations are cozy and comfortable, providing a perfect home away from home for visitors. With a range of amenities and activities available on-site, including swimming, fishing, and hiking, guests can enjoy a relaxing and rejuvenating stay in the heart of nature. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Summer Village on the Pond Westford is the perfect destination for your next trip.

Chatham Seaside Cottages is a charming lodging institution located at 439 Ridgevale Road in the picturesque town of Chatham, Massachusetts. Nestled along the stunning coastline of Cape Cod, this quaint retreat offers guests a peaceful and relaxing getaway by the sea. The cozy cottages provide a comfortable and cozy atmosphere, perfect for a romantic weekend escape or a family vacation. With easy access to the beach and nearby attractions, Chatham Seaside Cottages is the ideal destination for those looking to experience the beauty of the Massachusetts coast.

Located at 94 Washington Street in Weymouth, Massachusetts, Bra-Wey Florist is your go-to destination for the freshest flowers and plants for any occasion. As a local florist and home goods store, we offer a wide variety of floral arrangements and gift baskets expertly designed by our talented florists. Whether you need flowers for a birthday, anniversary, Valentine's Day, or sympathy funeral, Bra-Wey Florist has the perfect bouquet to brighten someone's day. At Bra-Wey Florist, we provide flower delivery in Weymouth and surrounding areas, as well as nationwide delivery through our network of trusted florists. You can trust us to deliver the perfect floral gift with the best customer service. With same-day delivery available, you can count on us for any last-minute gift needs.

Welcome to the Cuttyhunk Fishing Club, a charming retreat nestled in the picturesque town of Gosnold, Massachusetts. Located at 1 Road to the Landing, our establishment offers a unique blend of food, lodging, and dining experiences that capture the essence of New England's coastal charm. At Cuttyhunk Fishing Club, we pride ourselves on providing a warm and inviting atmosphere where guests can escape the hustle and bustle of everyday life. Our cozy accommodations offer the perfect sanctuary for relaxation, with comfortable furnishings and stunning views of the surrounding natural beauty.

Welcome to Experience the Dream Travel, your gateway to unforgettable journeys and remarkable adventures! Nestled in the heart of Topsfield, Massachusetts, at 3 Beech Place, our travel agency is dedicated to crafting personalized travel experiences that turn your dreams into reality. At Experience the Dream Travel, we specialize in curating bespoke itineraries that cater to your unique preferences and desires. Whether you're seeking a relaxing beach getaway, an exhilarating adventure tour, or an immersive cultural exploration, our team of experienced travel experts is here to guide you every step of the way.

Welcome to East Rock Inn, your charming getaway nestled in the heart of the Berkshires. Located at 304 State Road, Great Barrington, Massachusetts, our inn offers a perfect blend of comfort and tranquility, making it an ideal destination for both relaxation and adventure. At East Rock Inn, we pride ourselves on providing a warm and inviting atmosphere where guests can unwind and enjoy the natural beauty of the surrounding area. Our elegantly appointed rooms are designed to offer a cozy retreat, complete with modern amenities to ensure a comfortable stay. Whether you're here for a romantic escape, a family vacation, or a solo journey, you'll find the perfect accommodation to suit your needs.

Granville House is a charming lodging institution located at 98 Division Street in the picturesque town of New Marlborough, Massachusetts. This cozy and inviting establishment offers comfortable accommodations for visitors looking to experience the beauty and tranquility of the Berkshires region. With its convenient location and warm hospitality, Granville House is the perfect choice for a relaxing getaway in New England.

Laurel Ridge Bed and Breakfast is a charming lodging establishment located at 648 Southbridge Road in Warren, Massachusetts, United States. Nestled in a picturesque setting, this cozy B&B offers guests a peaceful and relaxing retreat. With comfortable accommodations and personalized service, Laurel Ridge Bed and Breakfast is the perfect choice for a weekend getaway or a romantic escape. Experience the beauty of the New England countryside while enjoying modern amenities and warm hospitality at this lovely inn.

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 Lakehouse Inn is a charming lodging located at 615 Laurel Street in the picturesque town of Lee, Massachusetts, United States. This cozy inn offers a peaceful retreat for guests looking to relax and unwind by the lake. With comfortable accommodations, beautiful views, and friendly staff, The Lakehouse Inn is the perfect destination for a tranquil getaway. Whether you're looking to explore the surrounding area or simply enjoy a peaceful escape, this charming inn provides a warm and inviting atmosphere for guests to enjoy.

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 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.

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.

The Lake House Guest Cottages of the Berkshires is a charming retreat nestled on the shores of Pontoosuc Lake in Lanesborough, Massachusetts. This picturesque institution offers cozy and beautifully appointed cottages for overnight stays, providing guests with a peaceful and serene atmosphere to relax and unwind. The on-site restaurant serves delicious meals made with locally sourced ingredients, offering a taste of the region's culinary delights. Whether you're looking for a romantic getaway, a family vacation, or a solo escape, The Lake House Guest Cottages of the Berkshires is the perfect destination for a memorable and rejuvenating experience.

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.

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.

Rose and Goat Retreat is a charming and cozy real estate and travel agency located in the picturesque town of North Adams, Massachusetts. Situated at 25 Moores Road, this institution offers a unique blend of services that cater to both property buyers and travelers looking for a peaceful escape. Whether you are in search of a dream home nestled in the scenic beauty of North Adams or planning a relaxing getaway to rejuvenate your soul, Rose and Goat Retreat has got you covered. With a team of experienced professionals and a wide range of properties and travel packages to choose from, you can trust that your needs and preferences will be taken care of with utmost care and attention to detail.

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.

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.

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.