Romantic Weekend Getaways in Massachusetts
Massachusetts is made for romance with charming seaside towns, historic inns, and rolling countryside that feels straight out of a postcard. Whether you’re planning a cozy retreat by the fire, a culture-filled city escape, or a seaside stroll hand in hand, the Bay State has the perfect spot for two. Here are a few romantic weekend getaways that stood out most during my three weeks of travels, and I think you’ll fall for them, too.
1. Scituate Harbor & The Inn at Scituate Harbor
This is a charming and romantic New England seaside escape and one of the best weekend getaways in Massachusetts! Why? I love how Scituate has preserved its quaint harbor-town character by emphasizing its maritime heritage, local art, and natural coastal beauty rather than giving in to over-commercialization.
Located about 45 minutes from Boston on Massachusetts’ South Shore, Scituate is known for its historic lighthouses, sandy beaches, and a bustling harbor lined with fishing boats, boutiques, and cozy seafood spots.
I thought that staying at The Inn at Scituate Harbor was absolutely perfect. The inn sits directly on the harbor, offering sweeping water views and a warm, intimate vibe. The rooms are bright and coastal-inspired, many with private balconies overlooking the sailboats. The indoor heated pool was a delightful surprise, and the sense of being so close to the water made it a truly romantic retreat. Waking up to the sight of the harbor coming alive in the morning was unforgettable.
- Location: Map & Directions
- Check prices at The Inn at Scituate Harbor
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.
2. Harbor Light Inn
I love how Marblehead has held onto its historic charm with winding streets, colonial-era homes, and a strong connection to its maritime roots, rather than giving in to tourist over-commercialization.
Part of Massachusetts’ scenic North Shore, just under an hour from Boston, Marblehead is famous for its picturesque harbor dotted with sailboats, its Revolutionary War history, and its charming old-town center filled with boutiques, art galleries, and waterfront dining.
I think that The Harbor Light Inn is once of the best romantic weekend getaways in Massachusetts. Why? Tucked into the historic district, the inn is a romantic blend of colonial character and modern comfort. The rooms are individually decorated with fireplaces, canopy beds, and elegant details that make it feel like you’re stepping back in time. The courtyard pool and intimate tavern add to the warm, welcoming vibe. It felt incredibly romantic!
- Location: Map & Directions
- Check prices at Harbor Light Inn
In the summer, the outdoor pool tucked away in the courtyard feels like a private oasis.
3. The Platinum Pebble Boutique Inn - West Harwich, MA
West Harwich offers a more peaceful, intimate side of the Cape, with its quiet beaches, scenic bike trails, and charming village atmosphere, rather than being overrun by crowds and commercialization.
Part of Massachusetts’ beloved Cape Cod, West Harwich is nestled along Nantucket Sound, just a short drive from both Chatham and Hyannis. It’s known for its soft sandy beaches, historic sea captain’s homes, and its slower-paced charm that invites you to relax and soak in the coastal beauty. Stroll down Main Street, bike the Cape Cod Rail Trail, or spend a lazy afternoon watching the sun sparkle on the water.
The Platinum Pebble Boutique Inn is an adults-only luxury inn that feels like a hidden gem, set in a beautifully restored 19th-century sea captain’s house. The rooms are chic and romantic, with plush beds, soaking tubs, and fireplaces that make it feel indulgent and private. The landscaped grounds and outdoor pool add to the serene atmosphere, and the attentive hospitality made the stay unforgettable.
- Location: Map & Directions
- Check prices at 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.
4. Captain's House Inn
This is a quintessentially romantic Cape Cod escape! I love how Chatham has preserved its seaside charm with historic architecture, pristine beaches, and a lively yet sophisticated village center, rather than giving in to overdevelopment.
Part of Massachusetts’ Lower Cape, Chatham is celebrated for its white-sand beaches, iconic lighthouse, and vibrant Main Street filled with boutiques, galleries, and seafood restaurants. With its windswept dunes, harbor views, and timeless New England character, it feels like a postcard-perfect setting for a coastal getaway.
When I stayed at the Captain’s House Inn this month, it was absolutely perfect. Set in a beautifully restored 19th-century sea captain’s estate, this bed-and-breakfast blends historic elegance with modern luxury. The rooms are warm and romantic, many with fireplaces, four-poster beds, and soaking tubs. The landscaped gardens and afternoon tea add to the refined yet cozy atmosphere, making it feel like a private retreat.
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.
5. Ocean House Hotel at Bass Rocks, Gloucester
Gloucester blends its rich maritime history with dramatic coastal scenery, retaining its authentic fishing-town character rather than turning into something overly commercialized.
Part of Massachusetts’ rugged Cape Ann coastline, Gloucester is known for its working harbor, sweeping sandy beaches, and striking rocky shores. Artists have long been drawn here for the luminous light and ocean views, and you’ll find galleries, seafood shacks, and historic sites that make the town both vibrant and timeless. The combination of rugged headlands and charming New England streets gives it a truly unforgettable atmosphere.
Staying at the Ocean House Hotel at Bass Rocks was a wonderful idea. Perched right on the water’s edge, this historic boutique hotel offers panoramic views of the Atlantic. The rooms are airy and coastal-chic, many with balconies that open to the sound of crashing waves. The saltwater pool, firepits, and wraparound porch create a romantic seaside ambiance, while the inn’s attentive hospitality makes the experience feel both refined and relaxed.
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.
6. 33 Main, Lenox, MA
This is a romantic and sophisticated Berkshires escape! I love how Lenox has preserved its historic charm and artistic soul, offering a refined yet welcoming small-town atmosphere rather than becoming overly commercialized.
Nestled in the heart of Massachusetts’ Berkshire Hills, Lenox is celebrated for its cultural treasures—like Tanglewood, summer home of the Boston Symphony Orchestra—as well as its historic mansions, boutique shops, and farm-to-table dining. Surrounded by rolling hills, forest trails, and mountain vistas, it’s the perfect balance of natural beauty and cultural richness.
I thought that staying at 33 Main was absolutely perfect. This elegant boutique inn, designed by lifestyle maven Annie Selke, feels like stepping into a modern, stylish retreat with a dash of New England charm. The rooms are chic and individually decorated, with luxurious bedding, fireplaces, and thoughtful details that make the experience indulgent yet cozy. The intimate atmosphere and designer touches make it a wonderfully romantic setting.
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.
Conclusion
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.
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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.
