6 Romantic Airbnbs in Massachusetts, Ideal for a Getaway Any Time of Year

I love vacationing with family and friends, but every once in a while, my partner and I seek out a much-needed trip for two. These vacations are wonderful opportunities to relax and reconnect. If you also need a couples retreat, look no further than these six local Airbnb rentals in Massachusetts. All offer perfect accommodations for romantic getaways all year long.

1. Enchanted Tiny Tower nestled in the Berkshires, Tyringham

Feel like you have stepped into a fairy tale world at one of the most unique and beloved Airbnbs in Massachusetts. The Enchanted Tiny Tower, nestled in the Berkshires, is a long-running guest favorite. This two-story storybook tower sits in a peaceful wooded area, surrounded by a pond, a babbling brook, and gorgeous gardens. The cozy space is the perfect spot for an anniversary trip or a special occasion.

2. Cottage on Whittier, Marblehead

A visit to Marblehead makes a fantastic vacation any time of the year. With so much rich history, a gorgeous shoreline, and fabulous restaurants, this quaint New England town is the perfect spot for romance and fun. Tucked in a cute neighborhood is the modern Cottage on Whittier, a one-bedroom home ideal for couples. The cottage features a wood-burning stove, skylights, and a cozy loft space.     

3. Wings Neck Lighthouse, Pocasset

It has always been my dream to spend the night in a lighthouse, and I have my heart set on this unique Airbnb in Pocasset. A stay at the historic Wings Neck Lighthouse is an unforgettable experience ideal for romance and relaxation. Enjoy comfortable accommodations in the lighthouse keeper’s home and climb to the top of the attached former Coast Guard lighthouse where you will be met with stunning 360-degree ocean views. Private beach access is also included.   

4. The Studio Guesthouse, North Andover

This cozy studio in North Andover is an exquisite place for a two-person retreat. The Studio Guesthouse offers deluxe accommodations in a former art studio. Spend time chilling by the roaring fire or relaxing in the private hot tub. But that’s not all. The guesthouse is located in a local winery. Airbnb guests can explore the gorgeous vineyards and enjoy a complimentary wine tasting. 

5. Salem Waterfront Couples Retreat, Salem

If you plan to go all out on a luxurious romantic getaway, this gorgeous Salem guesthouse might be perfect for you and your partner. The Salem Waterfront Couples Retreat is a magnificent rental with spectacular views of the water, a chef’s kitchen, and a cozy gas fireplace. The property is also within walking distance of many downtown Salem attractions, restaurants, and shops. 

6. Cape Cod Lakefront Vacation Retreat, Sandwich

In my opinion, nothing is more romantic than a waterfront getaway. If you are searching for a Cape Cod property that is perfect for two, check out the Cape Cod Lakefront Vacation Retreat in Sandwich. The gorgeous cottage offers stunning views, a private beach, and a modern kitchen. This highly-rated rental is a beautiful retreat all year round.

Do you know of other vacation rentals that are perfect for two? Tell us about them by filling out a nomination form. If you can't get away but are still looking for romantic destinations, check out these local date spots... or choose your own Massachusetts adventure using our new Travel Planner!