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 that make every moment feel unforgettable.
There’s something undeniably romantic about Massachusetts. From charming coastal inns and historic towns to cozy mountain retreats and boutique hotels tucked away in the Berkshires, the state offers endless opportunities for couples to escape the everyday.
Whether you’re looking for a seaside stroll with ocean views, a fireside glass of wine in a centuries-old inn, or a chic boutique stay surrounded by art and culture, Massachusetts has the perfect setting for your love story.
Best Romantic Weekend Getaways in Massachusetts:
The Inn at Scituate Harbor
Just under an hour along the coastline from Boston, The Inn at Scituate Harbor gives you the best mix of New England coastal beauty and small-town comfort.
I loved waking up in a cozy room with big windows that opened up to sparkling water views, the kind of view that instantly makes you slow down and appreciate the moment.
What makes it even better is the location. You can stroll right out the front door and find yourself surrounded by some of Scituate’s best local restaurants, shops, and cafés.
In the summer, nothing beats grabbing an ice cream cone and walking along the harbor at sunset, it feels like pure magic. For me, it’s the perfect place for a weekend getaway without the crowds of Cape Cod or the hustle of the city.
The inn itself feels warm and personal. The staff go out of their way to make you feel at home, and little touches like fresh coffee in the morning and a welcoming lounge, make the stay extra special.
If you’re looking for a true New England coastal escape, The Inn at Scituate Harbor is absolutely one of the best places to experience it. It’s a hidden gem I’ll always recommend.
To book, check availability or prices for The Inn at Scituate Harbor .
What I loved best:
My favorite feature has to be the indoor pool overlooking the harbor. It’s the kind of spot where you can swim, relax, and still soak up those amazing views no matter the weather.
Harbor Light Inn
Nestled in the historic district, Harbor Light Inn is set within two beautifully preserved Federal-style mansions, which instantly give it that timeless New England feel.
I loved how every detail inside the inn, from the antique furnishings and cozy fireplaces to the elegant four-poster beds, made me feel like I had stepped into a storybook setting.
Yet at the same time, it had all the modern comforts that make a getaway feel seamless.
What I think makes the Harbor Light Inn so special is not just the inn itself, but its location.
Marblehead is an absolute treasure of a town, with winding streets, historic homes, and sweeping harbor views that make every walk feel memorable.
Staying here meant I could wander to local shops, art galleries, and some of the town’s best restaurants in just minutes.
It felt like the perfect blend of relaxation and discovery.
One of my favorite features at the inn is its intimate tavern, a true hidden gem.
The Harbor Light Inn is warm, welcoming, and romantic, making it one of the best-kept secrets for anyone looking for a quintessential New England escape.
To book, check availability or prices for Harbor Light Inn.
What I loved best:
In the summer, the outdoor pool tucked away in the courtyard feels like a private oasis.
The Platinum Pebble Boutique Inn - West Harwich, MA
Nestled in West Harwich 90 minutes from Boston, the adults-only Platinum Pebble Boutique Inn immediately feels like a luxurious coastal hideaway filled with modern charm and heartfelt warmth.
Every morning, I loved waking up in a plush bed with premium linens in a beautifully designed room, some even have fireplaces, patios, or soaking tubs that feel like pure indulgence. What makes this place truly special is the all-inclusive experience.
From gourmet breakfasts crafted with fresh, local ingredients to complimentary bikes, beach gear, and even thoughtful extras like EV charging, I felt cared for in every detail.
There were no hidden fees, just pure relaxation and comfort. One of my favorite parts of the stay was the personal touch.
The property itself is stunning, with beautifully landscaped grounds perfect for lounging by the heated pool or gathering around the outdoor fireplace in the evenings. It’s romantic, serene, and welcoming all at once.
The Platinum Pebble Boutique Inn combines New England charm with modern luxury, and it’s one of the best underrated escapes I’ve ever found.
To book, check availability or prices for The Platinum Pebble.
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. 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.
From the moment I arrived, I was taken by the charm of The Captain’s House Inn. The white clapboard exterior, manicured gardens, and inviting front porch made me feel instantly welcome.
Inside, the inn is cozy yet elegant, with fireplaces, canopy beds, and antique touches that add so much character. My room had a whirlpool tub and a little sitting area where I could curl up with a book.
It felt like the perfect retreat after a day exploring Cape Cod. Every detail made me feel spoiled, from the soft linens to the thoughtful amenities that made the space feel like home.
Breakfast was a highlight for me. Each morning, I loved starting the day with a gourmet meal that felt more like dining in a fine restaurant than a traditional inn. The homemade pastries, seasonal specials, and fresh coffee made it one of my favorite parts of the stay.
What makes the Captain’s House Inn even better is its location. Nestled in Chatham, I could easily walk to shops, restaurants, and the harbor, yet still felt tucked away in a peaceful oasis.
To book, check availability or prices for The Captain’s House Inn.
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.
My room was light and airy, with crisp white linens, nautical touches, and a private balcony that looked straight out onto the Atlantic.
Waking up to the sunrise over the water was hands-down my favorite part of the stay. It felt private, refreshing, and completely rejuvenating.
In the afternoon, I loved lounging by the pool, strolling the seaside path, or just sitting in one of the Adirondack chairs that dot the lawn, soaking in the view.
What makes this hotel especially underrated is the location. It’s close to downtown Gloucester and Rockport, so I could explore shops, seafood shacks, and art galleries with ease, yet still return to a peaceful oceanfront retreat.
To book, check availability or prices for Ocean House Hotel at Bass Rocks.
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. 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.
Designed by Annie Selke, this charming inn combines the warmth of a historic New England home with chic, modern style.
From the moment I stepped inside, I loved the clean lines, cheerful patterns, and vibrant touches of color.
My room was a perfect mix of comfort and style, with a plush bed dressed in premium linens, thoughtful details like fresh flowers, and spa-like amenities in the bathroom.
Every corner of the inn had a cozy, curated feel, from the elegant lounge with its inviting fireplace to the sunny dining area where I enjoyed coffee each morning.
I also loved being right in the heart of Lenox, you can stroll to shops, art galleries, and some of the town’s best restaurants within minutes.
In the summer, outdoor concerts at Tanglewood are just around the corner, and in the winter, the Berkshires turn into a snowy wonderland.
For me, 33 Main is the best blend of stylish design and cozy New England hospitality. It’s a true gem for anyone seeking a chic yet homey Berkshires escape.
To book, check availability or prices for 33 Main.
What I loved best:
One of my favorite parts of staying here was how personal the experience felt.
The inn is small enough to feel intimate, and the staff go out of their way to make you feel at home.
Final Thoughts on Romantic Getaways in Massachusetts
What I love most is the variety. You can spend one weekend exploring sandy beaches on Cape Cod, the next wandering around cobblestone streets in Salem, and another discovering the rolling hills and cultural gems of the Berkshires.
Each destination feels like a hidden treasure, offering its own unique blend of beauty, history, and intimacy.
More to Explore
- Weekend Getaways from Boston
- Day Trips from Boston
- Massachusetts Day Trips
- Places to Visit in Massachusetts
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
