Romantic Escapes: Perfect Weekend Anniversary Trips in Massachusetts

If your vibe is all about romance, your perfect weekend getaway is to The Platinum Pebble Boutique Inn. The Couples Romance Package ensures that everything is taken care of, encouraging you to focus on relaxing with your best friend by your side. Sip complimentary wine, sample gourmet chocolates, dine at your choice of a local restaurant, and unwind during your 60-minute couples massage. It’s time to simply enjoy the company of one another.

Finally just the two of you again? Explore all that Boston has to offer including the Empty Nesting in the Lap of Luxury Package at XV Beacon. Reconnect with your lover as you savor complimentary wine, dine using a $100 Amex gift card, and get flirty with the help of some seasonal bath salts—the makings for a seriously romantic weekend away.

First thing’s first, congratulations! Your perfect babymoon is waiting to prepare you for the beautiful chaos that is to come, allowing you to connect more deeply with your partner, and encouraging you to relax before your daily routine shifts. The Babymoon Getaway Package at The Platinum Pebble Boutique Inn is the most fitting place to start. To ensure your trip is special, you’ll receive a 60-minute pre-natal therapy massage voucher for mom-to-be, fresh flowers in your room, a bottle of sparkling cider upon arrival, access to a body pillow for support while you sleep, and a Platinum Pebble teddy bear or coffee mug. There’s so much to celebrate—but don’t forget to cheers the thing that started it all: your love! 

It’s not every day that you welcome a little one into the world. Celebrate the growing of your little family with the Celebrations Package at The Verve Hotel, Tapestry Collection by Hilton. Take a weekend away with your partner to explore Natick, dine on local flavors, and enjoy a change of scenery before your bundle of joy blesses your life.

Marriage isn’t always a breeze. But talking things out over a delicious meal always helps. If you agree, the Bubbles, Blossoms, and Bites Package at Woods Hole Inn is for you. It includes a delicious homemade Woods Hole Inn breakfast each morning (queue the conversation!), a bottle of bubbly to welcome you to your room, assorted hand-made chocolates from their local chocolate emporium, and a beautiful welcome bouquet of seasonal flowers. Happy dining!  

For couples that particularly value health, wellness, and relaxation, you’ll want to book a room at Chatham Bars Inn, but don’t wait long—they book up relatively far out (and for good reason). Request the Spa Retreat Package to treat yourself to a truly luxurious getaway including two nights’ accommodations and a $600 credit for spa services. Choose from a menu of indulgent massages, facials, manicures, and pedicures before sinking into your seat and recharging your body and mind.  

When it comes to anniversary getaways in Massachusetts, the stunning views of Martha’s Vineyard stay top of mind. Opt for the Island Romance Package at Harbor View Hotel, the perfect setting for a couples getaway. Before hitting the beach, venturing to town, or touring the area, you’ll receive a special delivery including a chilled bottle of champagne and signature island strawberries. Then, the day is yours for exploring.

Interested in spending the day exploring the local sights of Plum Island with your best friend? The Couple’s Retreat Package at Blue - Inn on the Beach makes it easy to combine romance and adventure. By sunset, you’ll be ready to retire to your suite and enjoy a locally curated charcuterie board and a bottle of wine. See? The perfect balance does exist.

Here’s to the next 50 years! Congratulations on finding the person you’re willing to share your life with. There’s no better feeling than having a partner you can count on through the good and the bad. Let’s celebrate! 

New England Inns and Resorts was founded in 1907 and has been devoted to providing unforgettable experiences ever since. With over 300 hotels, inns, and resorts located across New England, we support exceptional hospitality with a dedication to keeping it local at every location.