Want to plan a dreamy weekend escape? I’ve done a few quick getaways around Massachusetts over the years, and they always leave me feeling refreshed and reconnected. Whether you’re planning something romantic or just want a change of scenery, these Massachusetts getaways are some of my absolute favorites. You’ll find cozy inns, charming towns, and little moments that turn into sweet memories.

Highlights:

  • I always feel relaxed after a seaside escape in Cape Cod—think sandy strolls, lighthouses, and salty breezes.
  • You’ll love the cozy, charming bed-and-breakfast stays in Martha’s Vineyard. I’ve stayed in a few, and they’re as peaceful as they are picturesque.
  • When I want a little history, I head to Salem or Marblehead. The walks here are beautiful and full of stories.
  • I’ve spent crisp fall weekends tucked away in a mountain cabin in the Berkshires. You can hike, nap, and repeat.
  • And if you're staying near Boston, treat yourself to a romantic dinner along the waterfront. I’ve had a few unforgettable evenings watching the city lights dance on the harbor.

Best Romantic Weekend Getaways in Massachusetts:

The Inn at Scituate Harbor

The Inn at Scituate Harbor

The Inn at Scituate Harbor - Look at harbor views and stroll the waterfront on an easy weekend trip.                                    

Ocean Edge Resort and Golf Club, Cape Cod

Ocean Edge Resort and Golf Club

Ocean Edge Resort and Golf Club, Cape Cod - Golf oceanside and enjoy beach days on an exciting summer vacation.                                    

Harbor Light Inn

Harbor Light Inn

Harbor Light Inn - Admire colonial charm and relax by the fire on a romantic couples getaway.                                    

Brook Farm Inn

Brook Farm Inn

Brook Farm Inn - Explore literary history and unwind in quiet surroundings on a peaceful spring retreat.                                    

The Platinum Pebble, Massachusetts

The Platinum Pebble

The Platinum Pebble, Massachusetts - Walk to the beach and enjoy boutique comfort on an affordable summer escape.                                    

Captain's House Inn

Captain's House Inn

Captain's House Inn - Savor gourmet breakfasts and relax in cozy luxury on a romantic fall trip.                                    

The Marblehead Inn

The Marblehead Inn

The Marblehead Inn - Discover seaside charm and admire historic homes on an easy weekend escape.                                    

Ocean House Hotel at Bass Rocks, Gloucester

Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks, Gloucester - Gaze at crashing waves and stroll rocky shores on a relaxing retirement trip.                                    

33 Main

33 Main

33 Main -                                    

The Captain Farris House Bed & Breakfast

The Captain Farris House Bed & Breakfast

The Captain Farris House Bed & Breakfast - Savor homemade treats and admire elegant décor on a romantic spring retreat.                                    

In Summary...

(and if you want to revisit my photo journey)