Romantic Weekend Getaways in Massachusetts

Whether you are looking for a historical inn, country estate or a cozy bed & breakfast, there are many beautiful romantic places to stay in Massachusetts.

“We needed something small, something quiet,” I thought as we crossed into Massachusetts, coastal towns ahead, winding roads between us and somewhere softer. We weren’t looking for grand hotels or fancy itineraries. Just harbor views, porches with two chairs, and the kind of mornings that let us stay in our robes a little longer.

Massachusetts gave us all of that. From sea breezes to Berkshires stillness, we found inns tucked beside harbors, historic homes with creaky floors, and lighthouses that blinked steady through fog. These were places made for two, where breakfast is delivered in a basket, where fireplaces flicker at night, and where time stretches just enough to let you remember each other.

Best Romantic Weekend Getaways in Massachusetts:

The Inn at Scituate Harbor

We drove south from Boston, just under an hour along the coastline. The road narrowed as we neared Scituate, the air turning salty and cool, the harbor opening suddenly into view with boats bobbing in the water. The inn sat right at the edge of the docks, its windows looking out to sea.

I was planning to check into The Inn at Scituate Harbor with my husband, settle into the harbor’s slower rhythm, and enjoy the small-town charm that defines New England’s coast. I wanted a place where the water was never far from sight or sound.

Scituate was like a moving postcard with fishing boats pulling in with the tide, gulls calling overhead, and pastel houses stacked neatly against the shoreline. The inn carried that same spirit, cozy and nautical without losing its elegance.

I set my bag down in the room, opened the curtains to the harbor view, and thought, “This is the kind of place where you let time drift.”

I enjoyed sitting on the deck as the sun dipped low, the masts of sailboats cutting into a sky brushed pink and orange. The harbor lights flickered on one by one, and the quiet lapping of waves carried into the night.

Local Tip: Walk down the street to Mill Wharf Restaurant, a local favorite.

A downside? Parking near the harbor was limited, especially on weekends.

Harbor Light Inn

We drove north from Boston, a quick 45-minute ride along winding coastal roads. As we entered Marblehead, the streets narrowed into a maze of colonial homes, their clapboard siding and weathered shutters glowing in the afternoon sun. Tucked into the heart of the historic district, the Harbor Light Inn welcomed us like a secret retreat.

My plan was to settle into the inn, walk through Marblehead’s old streets, and let the harbor itself set the rhythm. I wasn’t chasing attractions. I wanted to feel the character of this seafaring town.

Marblehead felt storied and intimate with cobblestone lanes, church steeples rising above rooftops, and the ocean always within reach. The inn carried that same grace, its antique furnishings and fireplaces grounding me in New England history.

I dropped my bag in the room, the window cracked open to let in the scent of salt air, and thought, “This is the kind of place where history feels like it’s still alive.”

I enjoyed wandering down to Marblehead Harbor, sailboats rocking gently at anchor while gulls wheeled overhead. Returning to the inn in the evening, I settled into one of the common rooms, where soft lamplight and polished wood made the space feel timeless.

Where We Ate: For dinner, I walked to The Landing Restaurant by the water. The harbor lights outside made the evening feel cinematic.

A downside? Marblehead’s narrow streets made parking tricky.

The Platinum Pebble Boutique Inn - West Harwich, MA

We drove from Boston to Cape Cod in about 90 minutes, the road carrying us over the bridge and into the Cape’s slower rhythm. By the time we reached West Harwich, the neighborhoods grew quieter, shaded by oaks and pines, the ocean breeze carrying across the streets. The Platinum Pebble stood tucked back from the road, elegant and understated, its white clapboard framed by gardens.

My plan was to make the inn the anchor. Then spend time unwinding, explore the nearby beaches, and let Cape Cod’s relaxed charm take over.

West Harwich felt calm and coastal. We admired beach cottages and antique shops, harbors dotted with small boats, the Atlantic never far away. The inn itself carried that same balance, polished and stylish without losing the warmth of a classic Cape stay.

I dropped my bag in the room, the bed turned down in crisp white linens, and thought, “This is the kind of place where rest becomes part of the itinerary.”

I enjoyed lounging by the pool in the afternoon. The gardens were rustling with summer breeze. I took the short walk down to Belmont Beach, where the tide left smooth stretches of sand and seagrass. Returning to the inn, the evening felt quiet, the kind of quiet you can only find near the ocean.

A downside? The boutique setting meant fewer rooms, so availability was limited. Booking well in advance was necessary, especially in summer, when Cape Cod fills quickly.

Captain's House Inn

Next day, we drove from West Harwich to Chatham, just fifteen minutes along tree-lined roads where hydrangeas bloomed in blue and pink. As we entered town, the streets narrowed into a picture-perfect Cape Cod village—white steeples, clapboard homes, and shopfronts flying American flags. The Captain’s House Inn sat tucked just off the main road, a stately 1839 sea captain’s estate surrounded by gardens.

Our plan was to enjoy the inn’s charm, and then wander through Chatham’s shops and harbor. This wasn’t about sightseeing as much as it was about sinking into Cape Cod life.

Chatham felt refined and timeless with fishing boats moving in and out of the harbor, the lighthouse standing tall, and the Atlantic stretching endlessly beyond. The inn carried that same elegance, blending historic detail with quiet luxury.

I set my bag in the room, sunlight filtering through lace curtains onto antique wood furniture, and thought, “This is the kind of place that makes history feel like home.”

I enjoyed the afternoon tea service offered at the inn. Small sandwiches, scones with clotted cream, and delicate pastries were served on china, and sitting by the window, I felt the day slow down. The inn offered both comfort and ritual, a rare combination.

For dinner, we went to Impudent Oyster in downtown Chatham. I ordered the swordfish special, grilled and topped with citrus butter, served with roasted potatoes. The fish was meaty and fresh, carrying the flavor of the sea, while the sauce was bright and fragrant. Dessert was a crème caramel, smooth and caramel-sweet. The cozy, space made it feel like dining in a historic tavern.

A downside? Chatham’s popularity meant crowds, especially in summer. The streets grew busy, and parking downtown was tight. It took patience to find the quiet corners I had hoped for.

Ocean House Hotel at Bass Rocks, Gloucester

We drove north from Boston in under an hour, following Route 128 until the road spilled us into Gloucester. The town’s fishing boats rocked in the harbor, and then the road curved out along the coastline, where the Atlantic opened wide. The Ocean House Hotel at Bass Rocks sat on the bluff, its white clapboard exterior glowing against a backdrop of sea and sky.

In Gloucester, fishing trawlers pulling in, gulls wheeling overhead, and the salt spray carried on the wind. The inn matched that character. I thought it was elegant but not overdone, with rocking chairs set on porches facing the endless blue.

I opened the window in my room, the sound of waves rolling in steady, and thought, “The ocean never needs an invitation to fill a room.”

I enjoyed walking along the rocky shore at sunset, the light turning the waves gold as they broke against the cliffs. Back at the inn, the fire pit crackled, and guests lingered with blankets, letting the night settle slowly.

For dinner, we headed into town to Roy Moore Lobster Co. I ordered a lobster roll served in a buttered bun, overflowing with sweet lobster meat. We sat at a picnic table outside, the salt air mixing with the smell of drawn butter.

A downside? The popularity of Cape Ann meant summer weekends were busy. The coastal road filled with cars, and reservations at local restaurants were hard to snag without planning ahead.

33 Main, Lenox, MA

We drove west from Boston, a little over two hours into the Berkshires. The highway gave way to winding country roads, where rolling hills were patched with forest and stone walls marked old farmland. As we entered Lenox, the town felt tucked into the landscape with boutique shops, historic homes, and a quiet main street. At its center stood 33 Main, a stately white inn framed by gardens and shaded trees.

Lenox felt both sophisticated and unhurried with music drifting from Tanglewood rehearsals, antique shops filled with treasures, and the mountains wrapping the town in green. 33 Main carried that same balance, its design elegant yet welcoming, with soft colors and modern touches inside a historic frame.

I enjoyed sitting on the inn’s porch in the evening, watching the town quiet down as the sky turned lavender over the hills. The stillness felt restorative, the kind of quiet that comes only in small mountain towns.

A downside? The inn’s boutique size meant fewer rooms and higher prices, and in high season (summer and fall foliage), availability was scarce. It was worth it, but planning ahead was essential.

Final Thoughts on Romantic Getaways in Massachusetts

What stayed with us wasn’t the thread count or the breakfast menu, it was how each place made space for stillness. A harbor view that didn’t rush you. A fireplace that felt like an invitation. Rooms that let you read or nap or say nothing at all. From quiet Cape Cod porches to window-lit Berkshires suites, Massachusetts gave us a kind of romance that lingered gently and didn’t ask for much, just time, together.

We returned rested, not just in body but in rhythm. These weren’t just weekend getaways. They were small reminders of how good it can feel to pause in the same place, at the same time, with someone you love.

More to Explore

• Weekend Getaways from Boston
• Day Trips from Boston
• Massachusetts Day Trips
• Places to Visit in Massachusetts

Howdy!

Let me help you plan your next authentic and truly unique getaway. I've been a travel professional for nearly 30 years. I've been featured on abc6 Morning Show, Best of the Web, USAToday, and many other media outlets, government and educational institutions. Click for more.