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The Coolest Airbnbs In Massachusetts


Modified: December 28, 2023

by Gayel Escobar



Massachusetts, also known as the Bay State, is a captivating destination that offers a myriad of attractions, from historic landmarks and picturesque landscapes to vibrant cities and charming coastal towns. With its rich history, diverse culture, and stunning natural beauty, it comes as no surprise that Massachusetts is a popular choice for travelers seeking a unique and memorable experience.


One of the key aspects of planning a trip to Massachusetts is finding the perfect accommodation. While hotels and resorts are the traditional choices, many travelers are opting for a more personalized and immersive experience by booking stays at unique and stylish Airbnbs throughout the state. These properties provide not only a comfortable place to rest but also a glimpse into the local lifestyle and a chance to create lasting memories.


In this article, we will explore some of the coolest Airbnbs in Massachusetts, ranging from urban lofts with skyline views to secluded treehouses in the serene countryside. Whether you are planning a romantic getaway, a family vacation, or a solo adventure, these accommodations will elevate your stay and make it truly unforgettable.


Boston Loft with Skyline View

If you’re looking for a sleek and modern accommodation with stunning views of the Boston skyline, this loft is the perfect choice. Located in the heart of the city, this Airbnb boasts floor-to-ceiling windows that offer panoramic vistas of the bustling streets below and the iconic cityscape beyond.


The loft features a contemporary design with stylish furniture, sleek finishes, and an open-concept layout. The living area is spacious and comfortable, with a cozy sofa and a large flat-screen TV. The fully equipped kitchen offers everything you need to whip up a delicious meal, and the dining area provides a perfect spot to enjoy it while taking in the breathtaking views.


The bedroom is a haven of tranquility, with a plush bed, soft linens, and blackout curtains to ensure a restful night’s sleep. The bathroom is equally sophisticated, with modern fixtures and a luxurious shower.


One of the highlights of this Airbnb is the rooftop terrace, where you can unwind with a glass of wine while admiring the glittering city lights. It’s also an ideal spot for morning yoga or enjoying a cup of coffee as the city comes alive below.


In addition to its prime location and stunning views, this loft is within walking distance of renowned attractions such as Fenway Park, the Boston Common, and the historic Freedom Trail. You’ll also find an array of restaurants, shops, and entertainment options right at your doorstep.


Whether you’re a solo traveler, a couple seeking a romantic getaway, or a family looking for a stylish urban retreat, this Boston loft with its skyline view is sure to exceed your expectations and provide an unforgettable stay in one of America’s most vibrant cities.


Quaint Cottage in Cape Cod

Escape to the idyllic shores of Cape Cod and immerse yourself in the charm of this cozy and quaint cottage. Nestled in a picturesque setting, this Airbnb offers a peaceful retreat away from the hustle and bustle of everyday life.


The cottage features a classic Cape Cod design with shingled siding, a charming front porch, and a beautifully landscaped yard. Step inside, and you’ll find a welcoming and tastefully decorated interior. The living area is adorned with comfortable furnishings and a fireplace, creating a cozy ambiance for relaxing after a day of exploring.


The kitchen is fully equipped with modern appliances, allowing you to prepare your own meals, and the dining area offers a lovely space to enjoy them. The cottage also has a private backyard with a BBQ grill and outdoor seating, perfect for al fresco dining or simply unwinding in the fresh coastal air.


With its convenient location in Cape Cod, you’ll have easy access to pristine beaches, charming seaside towns, and all the outdoor activities the area has to offer. Spend your days sunbathing on the sandy shores, exploring the scenic bike trails, or indulging in delicious seafood at local restaurants.


For those seeking a tranquil escape, the Cape Cod National Seashore is just a short drive away, where you can wander through coastal dunes, take a refreshing swim in the ocean, or simply enjoy a peaceful picnic surrounded by nature’s beauty.


Whether you’re planning a romantic getaway or a family vacation, this quaint cottage in Cape Cod will make you feel right at home. Experience the relaxed coastal lifestyle and create lasting memories as you unwind in this charming retreat.


Historic Brownstone in Beacon Hill

Step back in time and experience the elegance of Boston’s historic Beacon Hill neighborhood by staying in this charming Airbnb. Housed in a beautifully restored brownstone, this accommodation offers a unique blend of old-world charm and modern comfort.


The brownstone features exquisite architectural details, including ornate moldings, high ceilings, and hardwood floors. The interior is tastefully decorated with a mix of antique and contemporary furnishings, creating a warm and inviting atmosphere.


The living area is spacious and cozy, with comfortable seating and a fireplace, perfect for relaxing after a day of exploring the city. The fully equipped kitchen provides all the necessary amenities for preparing meals, and the dining area offers a beautiful space for enjoying them.


The bedrooms in the brownstone are elegantly appointed, with luxurious bedding, ample storage space, and charming decorative touches. The bathrooms are modern and well-appointed, ensuring a comfortable stay for guests.


Perhaps the most enticing aspect of this Airbnb is its location in Beacon Hill. This historic neighborhood is known for its cobblestone streets, gas-lit lamps, and classic architecture. Take a leisurely stroll through the neighborhood and explore the charming shops, quaint cafes, and historic sites that line the streets.


Just a short walk from the brownstone, you’ll find the iconic Massachusetts State House, the Boston Common, and the Charles River Esplanade, where you can enjoy scenic walks and beautiful views of the city skyline.


Immerse yourself in the rich history of Boston by staying in this historic brownstone in Beacon Hill. Experience the timeless charm of the neighborhood and enjoy the convenience of being in close proximity to all that Boston has to offer.


Secluded Treehouse in the Berkshires

Escape the ordinary and embrace the tranquility of nature by staying in this secluded treehouse tucked away in the picturesque Berkshires region of Massachusetts. Surrounded by towering trees and breathtaking views, this Airbnb offers a unique and unforgettable getaway.


The treehouse is an architectural marvel, crafted with care to blend seamlessly with its natural surroundings. Built high up in the trees, this accommodation provides a sense of being completely immersed in the forest. The interior is cozy and rustic, with wooden accents and large windows that offer panoramic views of the lush greenery.


The treehouse features a comfortable sleeping area with a plush bed, allowing you to fall asleep to the soothing sounds of nature. There is also a small seating area where you can relax and enjoy a cup of coffee or read a book. A private outdoor deck provides the perfect spot to take in the serene surroundings and enjoy the fresh air.


While the treehouse offers a peaceful retreat, it is also conveniently located near popular attractions in the Berkshires. Explore the nearby hiking trails and discover hidden waterfalls, or visit the quaint towns and charming art galleries that dot the region.


For a truly memorable experience, opt for a stay in the treehouse during the fall months, when the foliage transforms into a vibrant display of colors. Imagine waking up to a breathtaking panorama of red, orange, and gold leaves, creating a picturesque and unforgettable backdrop.


Whether you’re seeking a romantic escape or a nature-filled adventure, this secluded treehouse in the Berkshires is the perfect choice. Reconnect with nature, unwind, and create lasting memories amidst the beauty and serenity of the forest.


Oceanfront Villa on Martha’s Vineyard

Indulge in the ultimate seaside retreat by staying at this luxurious oceanfront villa on Martha’s Vineyard. With its stunning location and exquisite design, this Airbnb offers a truly unforgettable experience on this iconic island off the coast of Massachusetts.


The villa boasts breathtaking panoramic views of the ocean, with large windows that flood the living spaces with natural light. The interior is elegant and sophisticated, with high-end furnishings, beautiful décor, and all the modern amenities you could desire.


The living area is spacious and tastefully decorated, providing a comfortable space to relax and unwind. The fully equipped kitchen is a chef’s dream, featuring top-of-the-line appliances and ample counter space for preparing meals. The dining area offers a stunning backdrop for enjoying meals with family and friends while gazing out at the spectacular ocean views.


The bedrooms in the villa are luxurious havens of comfort, with plush bedding, stylish furnishings, and private en-suite bathrooms. Wake up to the sound of waves crashing and step onto your own private balcony to take in the fresh ocean breeze.


Outside, the villa features a sprawling deck with ample seating, a BBQ grill, and a private infinity pool overlooking the ocean. Spend your days lounging by the pool, soaking up the sun, or venture down to the nearby private beach for a refreshing swim or a leisurely stroll along the shoreline.


Martha’s Vineyard is renowned for its stunning natural beauty, charming towns, and picturesque beaches. From exploring the charming streets of Edgartown and Oak Bluffs to enjoying the seaside attractions and delicious seafood, there’s something for everyone on this enchanting island.


Whether you’re planning a romantic escape, a family vacation, or a gathering with friends, this oceanfront villa offers a luxurious and unforgettable experience on Martha’s Vineyard. Bask in the beauty of the island, savor the serenity of the ocean, and create cherished memories that will last a lifetime.


Rustic Cabin in the North Shore

Escape the hustle and bustle of everyday life by retreating to a rustic cabin in the peaceful North Shore region of Massachusetts. Tucked away in a secluded setting, this Airbnb offers a cozy and enchanting getaway surrounded by nature’s beauty.


The cabin exudes charm and rustic elegance, with its wooden beams, stone fireplace, and cozy furnishings. The interior is warm and inviting, providing a comfortable space to relax and reconnect with nature. Curl up by the fire with a good book or enjoy a board game with loved ones.


The fully equipped kitchen allows you to prepare your own meals, and the dining area offers a cozy spot to enjoy them. You can also take advantage of the outdoor grill and picnic area, perfect for al fresco dining amidst the tranquility of the forest.


The cabin features comfortable bedrooms adorned with warm, earthy tones and soft bedding, ensuring a restful night’s sleep. Wake up to the sounds of birds chirping and step outside onto the deck to breathe in the fresh forest air.


Surrounded by nature, the North Shore offers a plethora of outdoor activities to enjoy. Explore nearby hiking trails that wind through the forest, take a leisurely bike ride along scenic paths, or venture to the coast for a day at the beach.


In the evenings, make sure to head out and experience the local culture and cuisine. The North Shore is known for its delicious seafood, charming coastal towns, and vibrant arts scene. Whether you’re seeking a romantic dinner overlooking the water or a lively night out at a local pub, you’ll find plenty of options to suit your taste.


Whether you’re seeking a peaceful retreat or an adventurous getaway, this rustic cabin in the North Shore is the perfect choice. Disconnect from the outside world, reconnect with nature, and create lasting memories in this enchanting hideaway.


Modern Farmhouse in Western Massachusetts

Immerse yourself in the charm of the countryside by staying in this modern farmhouse in the picturesque region of Western Massachusetts. Blending contemporary design with rustic elements, this Airbnb offers a unique and stylish retreat surrounded by natural beauty.


The farmhouse features an open and airy layout with large windows that flood the space with natural light. The interior is thoughtfully decorated, combining sleek modern furnishings with warm, natural materials. The living area is cozy and inviting, with comfortable seating and a fireplace, perfect for relaxing after a day of exploring.


The fully equipped kitchen is a chef’s delight, featuring top-of-the-line appliances and a large island for preparing meals. The farmhouse also boasts a spacious dining area, providing the ideal setting for enjoying meals with family and friends.


With its rural location, the farmhouse offers a tranquil and serene atmosphere. Step outside onto the wrap-around porch and savor the fresh country air while taking in the scenic views of meadows and rolling hills.


Western Massachusetts is known for its captivating natural landscapes, charming small towns, and vibrant arts scene. Explore the nearby hiking trails, visit local farms and wineries, or simply embrace the slow pace of country life.


For those seeking cultural experiences, the region is dotted with museums, galleries, and historic sites. From the famous museums of the Berkshires to the renowned Tanglewood Music Center, there’s no shortage of opportunities to immerse yourself in art, history, and music.


Whether you’re planning a romantic getaway, a family vacation, or a friends’ retreat, this modern farmhouse in Western Massachusetts offers a perfect blend of comfort, style, and natural beauty. Recharge in the tranquility of the countryside, explore the surrounding area, and create cherished memories in this idyllic retreat.


Coastal Retreat in Nantucket

Experience the charm and allure of Nantucket by staying in this coastal retreat on the island. Known for its pristine beaches, quaint cobblestone streets, and historic architecture, Nantucket offers a perfect blend of relaxation and sophistication.


This Airbnb is situated in a prime location, just steps away from the beach and within walking distance of the vibrant downtown area. The coastal retreat features a bright and airy interior, with a beach-inspired design that reflects the island’s coastal ambiance.


The living area is tastefully decorated with comfortable furnishings and nautical accents, creating a soothing beachside atmosphere. Relax on the cozy sofa or step out onto the private balcony or patio to enjoy the cool ocean breeze.


The fully equipped kitchen allows you to prepare meals with ease, and the dining area offers a lovely space to enjoy them. In the evenings, make use of the outdoor BBQ grill and have a memorable cookout with friends and family.


After a day of exploring the island, retreat to the cozy bedrooms that provide a comfortable and serene escape. Each bedroom is beautifully appointed, with soft bedding and coastal-inspired décor.


During your stay, take advantage of all that Nantucket has to offer. Spend your days lounging on the sandy beaches, indulging in fresh seafood at local restaurants, or browsing the charming boutiques and art galleries in town.


For outdoor enthusiasts, Nantucket offers ample opportunities for biking, hiking, and kayaking. Explore the island’s scenic trails, paddle along the coastline, or embark on a whale-watching excursion to catch a glimpse of these magnificent creatures.


From its pristine beaches to its rich history and charming atmosphere, Nantucket is a destination that captivates visitors from around the world. And with this coastal retreat as your home base, you’ll have the perfect blend of comfort and convenience to make the most of your Nantucket getaway.


Charming Victorian Home in Salem

Immerse yourself in the bewitching history and charming atmosphere of Salem by staying in this delightful Victorian home. Located in the heart of this historic city, this Airbnb offers a unique and enchanting experience that combines old-world charm with modern comforts.


The Victorian home is a architectural gem, boasting intricate detailing, stained glass windows, and a charming wrap-around porch. Step inside, and you’ll be greeted by a beautifully decorated interior that exudes warmth and character.


The living spaces are spacious and filled with natural light, providing a comfortable oasis to relax and unwind. The cozy sitting area is adorned with vintage furnishings and a fireplace, creating a cozy ambiance for chilly evenings.


The fully equipped kitchen allows you to prepare your own meals, and the dining area offers a lovely space to enjoy them. The home also features a private backyard or garden where you can relax and soak up the peaceful atmosphere.


Being in Salem, you’ll have a plethora of attractions and landmarks to explore. Walk along the historic streets lined with charming shops, visit the renowned Salem Witch Museum, or take a tour of the historic homes and sites that tell the tales of Salem’s fascinating past.


During Halloween season, Salem comes alive with festivities, parades, and events. You’ll have a front-row seat to experience the excitement and enchantment of the city during this iconic time of year.


When in Salem, don’t miss the opportunity to indulge in the delicious local cuisine, which includes fresh seafood and classic New England fare. From seafood shacks to upscale restaurants, the city is a food lover’s paradise.


Whether you’re visiting Salem for its rich history, Halloween festivities, or simply to experience its unique charm, this charming Victorian home offers a memorable and comfortable stay. Immerse yourself in the enchanting atmosphere and create cherished memories in this captivating city.


Luxury Condo in Cambridge

Experience the epitome of luxury and sophistication by staying in this exquisite condo in the vibrant city of Cambridge, Massachusetts. Perfectly blending modern design with upscale amenities, this Airbnb offers a luxurious retreat for discerning travelers.


The condo features a sleek and contemporary interior with high-end finishes and stylish furnishings. The open-concept living area is spacious and flooded with natural light, creating an inviting atmosphere. Relax on the plush sofa while enjoying the state-of-the-art entertainment system or take in the city views from the expansive floor-to-ceiling windows.


The fully equipped kitchen is a dream for any culinary enthusiast, with top-of-the-line appliances, granite countertops, and ample workspace. Gather around the elegant dining table for a gourmet meal or enjoy your morning coffee on the private balcony or terrace.


The bedrooms in the condo are beautifully designed with luxurious bedding, ensuring a restful and rejuvenating sleep. The bathrooms are elegant and well-appointed, featuring sleek fixtures and spa-like amenities to enhance your comfort.


Located in vibrant Cambridge, you’ll have access to a plethora of cultural attractions, world-class universities, and renowned dining options. Explore the prestigious campuses of Harvard and MIT, visit the esteemed museums and galleries, or indulge in a culinary adventure at the diverse range of restaurants.


The condo’s prime location also provides easy access to the bustling city of Boston. Hop on the subway or take a leisurely stroll across the Charles River to experience the rich history, vibrant nightlife, and world-class shopping that Boston has to offer.


After a day of exploring, unwind and relax in the condo’s luxurious amenities. Take a dip in the sparkling swimming pool, work out in the state-of-the-art fitness center, or simply bask in the breathtaking views from the rooftop terrace.


For those seeking a sophisticated and indulgent stay in Cambridge, this luxury condo offers the perfect blend of comfort, style, and convenience. Experience the vibrant energy of the city while enjoying the tranquility and comfort of this elegant retreat.



Massachusetts is a state that exudes charm, natural beauty, and rich history, making it a captivating destination for travelers. When it comes to finding accommodation in Massachusetts, opting for unique and stylish Airbnbs can elevate your experience and provide a truly memorable stay.


Whether you’re seeking a sleek loft with skyline views in Boston, a quaint cottage on the shores of Cape Cod, or a historic brownstone in the heart of Beacon Hill, there are Airbnbs that cater to every taste and preference. From secluded treehouses in the Berkshires to oceanfront villas on Martha’s Vineyard, each accommodation offers a distinct and enchanting experience.


When you stay at one of these Airbnbs, you not only get a comfortable place to rest but also a chance to immerse yourself in the local culture and create lasting memories. From exploring the historic neighborhoods of Boston to taking in the natural beauty of the North Shore or indulging in coastal charm on Nantucket, these accommodations serve as a perfect base for your Massachusetts adventures.


No matter which Airbnb you choose, you can expect an inviting and unique experience that goes beyond the traditional hotel stay. These properties showcase the best that Massachusetts has to offer, whether it’s the stunning ocean views, the quaint charm of historic homes, or the tranquil seclusion of rustic cabins.


By opting for an Airbnb, you’ll have the opportunity to live like a local and truly immerse yourself in the state’s culture, cuisine, and natural beauty. So, when planning your next trip to Massachusetts, consider booking one of these cool Airbnbs to enhance your experience and make your stay in the Bay State even more memorable.