The 7 Best Weekend Getaways from Boston

The Press Hotel is just under two hours drive from Boston and conveniently located in the Old Port district, home to Portland’s best bars, restaurants, pubs, and shops. The historic area with cobblestone streets and red brick buildings winds down to the pier, where you’ll find a lively waterfront area with traditional seafood spots and ferries to Casco Bay Islands.

The boutique hotel previously housed Maine‘s largest newspaper, the Portland Press Herald, and the decor plays off the building’s journalistic past with a wall of typewriters in the lobby, news copy on the walls, and typewritten letters on the carpet. That theme also extends to the Inkwell lobby bar, which serves complimentary coffee each morning and hand-crafted vintage cocktails during their “off the record” happy hour.

Guest rooms are inspired by 1920’s writer’s offices — and come with a journalist-style desk, thought-provoking quotes and a number of in-room amenities, including Frette bedding to make for a good night’s sleep. Marble-tiled bathrooms with glass showers come with a rain head, and others with bathtubs.

From Boston, head west on the Massachusetts Turnpike, I-90, for two and a half hours and you’ll hit the Berkshires, a series of small towns in the hills of western Massachusetts known for their natural beauty. This is a popular vacation spot for those who love the outdoors and the arts.

The Porches Inn is a row of 19th century refurbished Victorian houses, walking distance from MASS MoCA, a contemporary art museum set in large former factory. Over the years, MASS MoCA has attracted international acclaim for its cutting edge exhibits, cultural programming, music concerts and festivals. It is also credited with revitalizing North Adams and the surrounding area.

The Porches takes its cue from MASS MoCA, blending new and old. This modern B&B is decorated with vintage and retro furniture, and includes cutting-edge technology. In fact, The Porches has its own recording music studio called The Studio at Building 9, where musicians come to record.

Breakfast should not be missed – it includes croissants, locally made granola, fruit, homemade jams, banana bread, cheese and meats. You won’t go hungry here but if you do feel peckish, the front desk has coffee and seasonal treats in the afternoon, like apple cider donuts in the fall, watermelon plus iced tea and lemonade in the summer, and chocolate chip cookies with Harney & Sons teas in the winter.

The front desk can help you get tickets to MASS MoCA or, if you prefer more traditional art, to the Clark Art Institute in Willamstown. The Clark is best known for its French Impressionist collection and its extensive system of walking trails. Don’t miss a trip to North Adams, a small walkable town with plenty of galleries and restaurants to choose from.

The Red Lion Inn is one of the grand dames of the Berkshires, located in the heart of the region — Stockbridge, Massachusetts. This historic hotel dates back to 1773. Its guest rooms and common areas are decorated with early American furnishings, antiques, and china — making it the quintessential New England inn.

The Red Lion is a great place for families and couples, who often gather on its wide front porch to sit, relax, and people watch. You might recognize its style – Stockbridge resident Norman Rockwell painted it in 1967. There are 125 rooms and suites in the main building, four restaurants serving locally sourced food, and a terrific pub, the Lion’s Den, that has live entertainment.

It’s centrally located, near many of the Berkshire’s cultural and historical sites, including the Norman Rockwell Museum, Tanglewood outdoor music venue and Jacob’s Pillow, an internationally acclaimed dance and performance space.

Follow the Massachusetts Turnpike I-90 to the end of Massachusetts, and you’ll cross the border into New York state, home of the Hudson Valley. Hudson is a popular tourist destination for Bostonians and New Yorkers who love to shop — especially at its antique and furniture shops. On Warren street, you’ll find small boutiques, clothing shops, food markets, and many home furnishing stores.

William Farmer & Sons is located at the end of town near the river, and a short walk from the main shopping district. With only 15 rooms and suites, it has the intimate feel of a bed and breakfast and guests stay in the main building and next door.

Couples will find the setting romantic and the furnishings comfy, rustic and charming. While all rooms have king sized beds and well stocked mini-bars, they do vary in size, price and amenities. Some come with their own living room, like The Pennington; others cater to couples who want a bit of privacy, like The Abigail.

Rooms in the main inn are on the second and third floors located over the barroom (an old Americana term for a bar that serves food). It includes a restaurant serving farm-to-table dining and craft cocktails. The barroom serves classic American fare with a fine dining twist. The smaller bites and larger plates are meant to be shared family style. Try the sea scallop crudo, caste iron cabbage with foie gras and the Tivoli mushroom pot pie.

Guests can purchase coffee and pastries in the morning from The Mercantile, a coffee shop that doubles as a rum room at night. Across the street, at Promenade Park, are 180 degree views of the Catskills and the Hudson River.

Cape Cod is an ideal weekend getaway from Boston for those who love the beach.

Located mid-Cape, Chatham Bars Inn is a large property overlooking the Atlantic Ocean, with a lot of activities for families with kids. This high-end resort also caters to couples looking for a romantic weekend away.

In addition to having its own private beach, Chatham Bars Inn has an ocean-side pool area, tennis courts, and STARS – an outstanding formal dining restaurant that serves freshly caught seafood and organic produce from its garden. Parents might opt to eat at The Sacred Cod Tavern, a bar and restaurant serving burgers, sandwiches and salads.

Another reason to stay here is the hotel’s extensive shuttle service. Drivers are happy to pick you up at your room or cottage and drive you to the main clubhouse building, the spa, downtown Chatham, or even the National Seashore. If you do venture into town, walk to the lighthouse or visit Buffy’s for a post-dinner ice cream.

The Compass Rose Inn is a hidden treasure in the center of Newburyport, a beautiful seaside town just 45 minutes north of Boston. It’s perfect for those who want to escape Beantown, but don’t want to travel too far. Plus, it’s right on the ocean and close to many beaches.

The small downtown area has a lot of charm – quaint New England federal style buildings, lovely little shops, and a waterfront area. The inn is also a federal style mansion, a sophisticated nod to the town’s historic roots.

All five suites include a charming living room with a fireplace, a dressing alcove, bedrooms with king sized beds and deluxe bathrooms. Breakfast in the dining room includes a hot entree, like eggs or pancakes, plus fresh pastries, fruits, cereals, juices, coffee, and teas. The garden patio is an oasis of flowers and plants, perfect for solo travelers to enjoy.Nearby, Plum Island has miles of sandy beaches and serves as a wildlife refuge to 800 types of birds, animals and plants. Head to Sandy Point on the southern tip of the island to swim and sun bathe on the beach.

If you want to stay close to Boston, head northwest to Concord, Massachusetts, a mere 30 miles away. A town prominent in both literary and revolutionary history, some of the first battles of the American Revolution were fought here and in neighboring Lexington.

The Colonial Inn dates back to 1716 and is a perfect spot for travelers who love history. Its 56 spacious rooms and suites have hardwood floors, exposed beams, and Colonial period details – along with modern amenities, including flat-screen HD TVs.

Located on Monument Square road in downtown Concord, the inn is just 15 minutes from the revolutionary battlefields at Old North Bridge and the Minute Man National Historical Park. There are also a number of historic homes and sites to visit in Concord, including Louisa May Alcott’s Orchard House, the Ralph Waldo Emerson House, and Walden Pond — the inspiration for author Henry David Thoreau’s “Walden.”

Eat at the inn’s Merchants Row, a dining room with Colonial charm and a local hotspot. Highlights include afternoon tea and Sunday’s buffet brunch.