5 Trending Rentals in Massachusetts That People Book on Repeat (And We See Why)

As someone who loves to travel, one of my favorite aspects of the experience is the planning. More often than not, I find myself researching my next adventure only days after my previous trip has ended. Sights and attractions are easy; nailing down the perfect rental is often more challenging. There are just so many outstanding properties to choose from that it is difficult to decide which is the best. However, one thing I have learned about picking a fantastic Airbnb is that you can’t go wrong with a property where past guests have visited for a second or even third stay. If you are on the search for a top-rated local Airbnb, check out these five trending vacation rentals in Massachusetts, and you may just become a returning vacationer yourself.  

1. Cape Cod Lakefront Cottage - Sandwich, MA

This stunning Cape Cod Lakefront Cottage absolutely warrants a return visit for those who seek a bit of peace and solitude. The trending rental is not only a guest favorite on Airbnb, but one of our top choices for one of the most romantic Airbnbs in Massachusetts. The one-bedroom coastal cottage boasts spectacular lakeside views and has its own private beach.  It is a lovely place to get away with someone you love. 

2. Cider House Cottage - Petersham, MA

It is easy to see why a property this magical and unique is a repeat rental on Airbnb. The Cider House Cottage is a cozy antique retreat set against a beautiful, natural backdrop. The guest house offers privacy, comfort, and many opportunities for outdoor fun. If you are looking for a peaceful country stay, this scenic one-bedroom Petersham cottage should be at the top of your Airbnb wishlist.  

3. Rustic Modern Retreat - West Stockbridge, MA

My family and I stayed at the Rustic Modern Retreat when it first became a rental, and we would absolutely vacation here again. The property’s name is quite fitting, as the home is the ideal blend of a quaint, woodsy cottage with updated amenities and comfortable extras. The luxurious three-bedroom home sleeps up to six guests and is centrally located in the Berkshires, close to ski resorts, hiking, and boating. The rental was perfect for our cozy family winter stay, but it is also a wonderful place to vacation any time of year.

4. Beacon Hill Condo - Boston, MA

When you find a Boston rental as fantastic as this charming Beacon Hill Condo, you stick with it. Located in one of the prettiest neighborhoods in the city, this one-bedroom Airbnb is full of historic charm and modern conveniences. Returning guests love staying in such a safe, convenient location and rave about the helpful host, Lucy.    

5. Chase Hill - North Adams, MA

Hidden inside this gorgeous Victorian mansion in North Adams is a two-story, four-bedroom apartment that books on repeat by guests drawn here for its peaceful environment, unique charm, and proximity to Mass MoCA, Williams College, and local Berkshire ski areas. An outdoor wood-fired sauna, beautiful gardens, and an original 1873 claw-foot tub are bonus perks that will have you anxiously anticipating a return to Chase Hill.

Do you have a favorite vacation rental where you stay year after year? If so, please tell us all about it using our nomination form. And when you plan your next getaway, be sure to use the Only In Your State AI-powered itinerary planner to create a customized trip.