Massachusetts is not merely a city of history books and clam chowder (although we take both of these seriously). Wind-blown beach and a fiery sunset, old-time inns and fireplaces to snuggle, every part of this state has its share of romantic spots that can match any place in New England. My partner and I were able to explore a few weekends and have a lot of giggles, a few direction altercations, and shared ice-cream cones, and after a few of those, here are the top five places that I would recommend to couples, either spending a honeymoon, anniversary, or if you are just in love with life.
Top Romantic Getaways in Massachusetts
1. The Red Lion Inn – Stockbridge (Berkshires)
2. Nantucket Island – Coastal Bliss
3. Boston Beacon Hill – Urban Romantic Retreat
4. Cape Cod & Harwich – Waterfront Romance
5. Martha’s Vineyard – Island Sweethearts Escape
Top 5 Romantic Getaways in Massachusetts
1. The Red Lion Inn – Stockbridge (Berkshires)
It is a magic thing about this old inn. Going out on the porch of The Red Lion Inn is like going out into an old-fashioned New England love affair, with old fireplaces, cozy armchairs, and a dining room in which you can spend long candlelit evenings. I recall how I was sitting before the red wine as I watched snow blow through the window; a complete movie moment.
Stockbridge itself is cute – art galleries, simple hikes, and cozy cafes that are simply crying out to be held hands and stolen kisses. Sometimes the inn provides Inn Love packages, which include wine upon arrival and breakfast in bed (yes, please).
Your reason to love it: The modernity and the olden times at once, the vintage aesthetics and the comfort of a contemporary couple, not to seem too fancy.
Address: 30 Main St, Stockbridge, MA 01262
Price: Approx. $250–$400 per night (seasonal)
Child Friendly: Yes (family-friendly amenities)
2. Nantucket Island – Coastal Bliss
It is a place where you can simply feel romantic about this island. Cobblestone streets, fresh sea breeze, and the views of the seashores make one fall in love at first sight, with his or her partner or with the location. One afternoon, we rented bikes and rode through quiet roads and had seafood rolls and kisses of salt air (we drank wine).
Nantucket provides accommodation to all the vibes, whether it is a luxurious stay at The White Elephant or The Wauwinet, or a cozier stay in Hotel Pippa and Greydon House.
Most appropriate: Sunset strolls along Jetties beach, a couple of dinners, and afternoons window shopping around in boutique shops.
Address: Nantucket, MA (accessible by ferry or air)
Price: Rooms start from about $130–$350+ per night
Child Friendly: Yes — many hotels welcome families
3. Boston Beacon Hill – Urban Romantic Retreat
Provided that your definition of romance involves urban lights and style and elegance, this Beacon Hill hotel is a true treasure. Some of them have big windows, interiors adorned with artwork, and my favorite, fireplaces. One winter when we stayed here, one of the winter nights, we went out onto the balcony and stood and watched the snow falling on the historic brownstones with hot chocolate in our hands. Absolute bliss.
Boston alone has much to offer the couple: go walking in the Public Garden (historically a romantic and pretty location) and have an elegant dinner in the North End, or go sailing in the sunset in the harbor.
Attraction: The city is in love with the gourmet food and cultural experiences right at the door.
Address: XV Beacon Hotel, 15 Beacon St, Boston, MA 02108
Price: ~$400+ per night, depending on season
Child Friendly: Somewhat (great for families, but pricing & vibe skew romantic)
4. Cape Cod & Harwich – Waterfront Romance
Frankly speaking, Cape Cod impressed me with its seashores and sunsets. Something about Cape Cod makes you hunch your shoulders down, hold the hand of your partner, and slack. With the picturesque view of water at the scenic site of Harwich and private beach walks, the cape is couples-friendly.
The Wequassett Resort and Golf Club, among others, is one such place where you can combine romantic fine dining with activities that are fun and exciting, such as paddleboarding and simply lying by an adult pool.
Pro tip: Go during shoulder season (late spring or early fall), so as not to get congested, and to have evenings to walk the beach when the weather is cool and warm.
Why it is magical: Miles of beach, lobster rolls in the evening, or evenings on the fire pit… what’s not to love?
Address: Cape Cod, MA
Price: ~$200–$600+ per night (depends on area & property)
Child Friendly: Yes
5. Martha’s Vineyard – Island Sweethearts Escape
While Cape Cod is the carefree romance, Martha’s Vineyard is the civilized island love. Ride the ferry with your love interest, and before you know it, you are in this mix of serene shores, adorable harbors, and beautiful cedar-shingled houses, including their porch swings, which are ideal for long conversations and wiggling sunsets.
Edgartown is particularly idyllic, with old houses, small-town shopping, and seafood, with an ocean view. Days can be spent cycling across the island, relaxing on hot beaches, or taking local wine tours.
When to go: The mix of a bit of adventure, traditional coastal attractiveness, and easy elegance is best suited to a couple.
Address: Martha’s Vineyard, MA (via ferry)
Price: ~$200–$500+ per night depending on spot
Child Friendly: Yes
So … Which Should You Pick?
Here is the way I deconstruct it through experience:
To spend the night in front of the fire: The Red Lion Inn.
In stylish urban love: The Beacon Hill in Boston.
To watch sunsets on the beach: Cape Cod or Nantucket.
Island Delight: Martha’s Vineyard.
Conclusion
Wherever you go, romance in Massachusetts is factual– and it is every bit as delicious as the clam chowder (nearly). Be it a stroll by the hand on a deserted beach, a glass of wine on a porch at Stockbridge, or a pavement tour around an island, all these places make you feel like a lovey-dovey.
Have you been to any of these? I would be happy to know which of you is looking forward to the most!
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