Whether you’re looking for a sleepy New England town or big city excitement, you’ll find what you crave in Massachusetts. This New England state is packed with romantic attractions and activities for couples. Enjoy an exciting getaway exploring Boston’s restaurants, museums, shops, and entertainment venues. Treat yourselves to a leisurely excursion to Martha’s Vineyard. Massachusetts boasts a huge variety of vacation rentals ranging from quaint rowhomes to luxurious beachfront cottages. With so many options available, it’s easy to find a Massachusetts vacation rental located minutes from the area’s most romantic destinations. Of course, Massachusetts is quite chilly during February, so make sure to pack warm clothing. Here are seven of the best Massachusetts towns and cities to visit this Valentine’s Day.

Source: Pixabay/tpsdave

1. Boston

Boston is Massachusett’s flagship city, and it has something to offer vacationers of all ages. The New England Aquarium is one of Boston’s most popular attractions. Enjoy a leisurely hand-in-hand stroll with your valentine while looking at the huge variety of marine life. Experience a breathtaking 360-degree bird’s eye view of Boston at the Skywalk Observatory, and then treat yourself to some pampering at the Bella Sante Boston Day Spa. The spa has nine different treatment rooms, including plenty of couples options. For dinner, head to the South End and get a table at Mistral, a lovely French restaurant that is both elegant and comfortable.

Find vacation rentals in Boston

2. Martha’s Vineyard

Martha’s Vineyard is an island paradise that’s synonymous with luxury. It’s the perfect place to travel if you and your sweetheart really want to go all out. The island tends to be quiet during the winter, so your trip should be quite relaxing. Start by heading to the Barn Bowl & Bistro. It’s a wonderfully renovated barn that features 10 bowling lanes, a luxurious-yet-casual atmosphere, and some fantastic food and drink options. For dinner, it’s hard to beat l’etoile, an elegant, contemporary French-inspired restaurant that’s highly regarded among culinary enthusiasts. For a traditional romantic dinner, visit The Terrace at the Charlotte Inn, where you can enjoy exquisite American cuisine with French and Italian influences by candlelight.

Find vacation rentals in Martha’s Vineyard

Find the perfect Massachusetts vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

3. Nantucket

Nantucket is a quaint town known for its charming downtown with cobblestone streets, eclectic shops, and exceptional eateries. During the summer, the beaches are very popular, but you can still enjoy a shoreline stroll if you bundle up. Nantucket has some great antique shops to explore, many with one-of-a-kind nautical-themed items. If you’re interested in antiquing and don’t know where to go in Nantucket, start with Nantucket Country Antiques and Val Maitino Antiques. For authentic, fresh-caught New England seafood, go to Brant Point Grill and enjoy a meal by the water. For a more upscale dining experience, reserve a table in one of Dune’s three distinct dining rooms. The menu includes a variety of mouthwatering seasonal dishes, as well as a variety of unique cocktails, fine wines, and tantalizing desserts.

Find vacation rentals in Nantucket

4. The Berkshires

The Berkshires is a rural region in Western Massachusetts that’s speckled with multiple quaint towns and villages. Regardless of where you get a vacation rental in the area, you will have plenty of places nearby to explore. If the weather allows, you must visit Sweet Brook Farm in Williamstown for a horse-drawn sleigh ride through a winter wonderland. Enjoy a live performance together at Mahaiwe Performing Arts Center, one of the country’s oldest surviving theaters. The Berkshires area is home to many excellent wineries, with Furnace Brook Winery in Richmond and Balderdash Cellars in Pittsfield being two of the most popular. For dinner, head to Lee and get a table at Chez Nous. It’s a lovely French bistro with a welcoming, romantic atmosphere.

Find vacation rentals in The Berkshires

5. Rockport

Located on Cape Ann, Rockport is a sleepy seaside village that’s just an hour from Boston, giving you the best of both worlds — rural tranquility and big city amenities. Exploring the village’s many one-of-a-kind shops, galleries, and restaurants is sure to be a treat for couples. One must-visit destination is the Shalin Liu Performance Center. Far from an ordinary concert hall, the building is known for its extraordinary acoustics and a massive window that serves as a backdrop to the stage, providing an absolutely stunning view of the coast. While the venue was originally created to showcase chamber music, today it hosts classical, jazz, folk, world, and pop concerts. For dinner, go to My Place by the Sea, an award-winning restaurant that overlooks the Atlantic Ocean and serves American cuisine with a focus on fresh seafood.

Find vacation rentals near Rockport

6. Ipswich

Ipswich is a quaint coastal town that’s famous for its Great Marsh clams, historical architecture, and serene beaches. Take a hike or snow shoe through Castle Hill’s beautifully landscaped grounds, and then stop in the Great House for a tour of an actual castle. While you’re in town, make sure you try some of Ipswich’s famous fried clams at Clam Box or Ipswich Clam Bake. For a more elegant dining experience, try 1640 Hart House. It’s an atmospheric early American farmhouse that services delicious American cuisine. Ithaki Modern Mediterranean is another great option for a romantic meal, featuring Greek-Mediterranean served in an upscale yet comfortable environment.

Find vacation rentals near Ipswich

7. Cape Cod

Although Cape Cod tends to be a summer vacation rental destination, there is plenty to do and see all year round. The Cape boasts a wide variety of movie and performance theaters, including The Academy Playhouse, Chatham Orpheum, Cotuit Center for the Arts, and Cape Cinema, so check some local calendars and plan a dinner-and-a-show outing. Captain Linnell House is one of the best dinner spots, featuring elegant cuisine in a stunning 1840 mansion. The prime rib is sure to melt in your mouth. Cape Cod is also home to a variety of museums for you and your sweetheart to explore together, including the Cape Cod Museum of Art and Cape Cod Museum of Natural History.

Find vacation rentals near Cape Cod

 
Ready to go?  Check out these amazing Massachusetts vacation rentals on Tripping.com.