Boston is an incredible city packed with unparalleled history, architecture, and cultural events. But sometimes even those who love the city with all their hearts need a little change of pace.
Fortunately, Boston is located in the compact New England area, which means that it’s easy to take a road trip to see the other cities and states nearby. Whether you live in Boston and need a city break or just are visiting Boston and curious to check out the surrounding areas, many unique destinations are just a couple of hours away by car.
Here are the best weekend getaway destinations from Boston to consider, along with recommended accommodation options to make your stay as comfortable and memorable as possible.
The 1661 Inn - Block Island, Rhode Island
Block Island is known for its towering cliffs, rolling hills, freshwater ponds, and beautiful wildflowers. A popular hotel in Rhode Island, The 1661 Inn is part of a family-run boutique inn that has cozy rooms named after the founding families of Block Island. Some of these rooms have beautiful views of the ocean, so ask for one of those! You can also stay at the Nicholas Ball Cottage, the Guest House, Dewey Cottage, Dodge Cottage, Mitchell Cottage, or Anchor House. The property is very popular in the summertime when the town’s population swells from 1,000 to around 20,000. Popular events are Block Island Race Week with sailboats, fishing tournaments, a summer beach concert series, and the Fourth of July celebration. Since the island only covers about 10 square miles of land, it’s easy to bike around everywhere.
Pomegranate Inn - Portland, Maine
Portland is an amazing town in Maine to visit and a favorite destination among foodies and craft beer lovers. For a unique bed & breakfast, consider staying at the Pomegranate Inn, which is fun, funky, and artsy. This is a perfect getaway destination for romantic couples and art lovers. Inside you’ll find a creative mix of colors and textures in the furniture, fabrics, and artwork. Spend time in the colorful front lounge, play games in the third-floor parlor, and sample complimentary cookies in the dining lounge. Portland is only about 100 miles from Boston via I-95, but it feels like a totally different kind of place. Relax, take in the scenery, and indulge in some retail therapy.
Inn on Putney Road Bed and Breakfast - Brattleboro, Vermont
Vermont is an ideal place to stay at a bed & breakfast, and Inn on Putney Road Bed and Breakfast in Brattleboro is one of the finest. It’s elegant, comfortable, overlooks the water, and is within walking distance to downtown Brattleboro. There’s also a two-course gourmet breakfast each morning, a hot tub, a game room with a pool table, and formal gardens with Japanese Maples. All of the rooms have free Wi-Fi, and guests can enjoy complimentary snacks and drinks all day. Brattleboro is only about two hours west of Boston and surrounded by the woods. Get active by hiking and boating on the Connecticut River, and then wander the streets downtown to find a local restaurant.
Made Inn Vermont - Burlington, Vermont
Made Inn Vermont is an urban-chic B&B that provides a perfect place to stay when you visit Burlington. It’s been voted a “millennials favorite small luxury inn” and very close to the bike path, Church Marketplace, and the city’s art and theater districts. This is a romantic and eclectic spot that’s perfect for celebrating something special with the one you love. The mini-fridges are also stocked with Vermont-themed snacks and complimentary. Lake Champlain is nearby and typically less than four hours from Boston by car. The city of Burlington has an outdoorsy culture, so embrace it and plan to kayak on the lake, climb Mount Mansfield, and bike the Island Line Trail.
Vineyard Square Hotel & Suites - Martha's Vineyard, Massachusetts
One of the most idyllic New England beach destinations is Martha’s Vineyard, and one recommended place to stay here is the Vineyard Square Hotel & Suites. Formerly known as the Colonial Inn, it’s located in the heart of Edgartown, just a short walk from the shops and gourmet restaurants nearby. Here you’ll find a fresh-baked and homemade breakfast served between March and October, a fitness center, afternoon treats, and complimentary bikes for guests to use. Or just sit back and watch the world go by from the top level of the building or on the front porches.
Hotel Portsmouth - Portsmouth, New Hampshire
If you’re traveling to Portsmouth for the weekend, consider staying at Hotel Portsmouth for a boutique, grand, and accommodating experience. It’s a 135-year-old mansion in the downtown area with charming rooms for an intimate experience and personalized attention. Hotel Portsmouth’s historic location is close to all the best coffee shops, lobster restaurants, and local hot spots you’ll want to check out in town. If you time your drive right, you can reach Portsmouth from Boston in about an hour. Come here for a budget-friendly weekend getaway if you only have two days to spend on your trip.
Castle Hill Inn - Newport, Rhode Island
The Castle Hill Inn has accommodations by the beach, on a hill, and that overlooks the harbor. The property spans 40 acres offers amenities like high-speed Wi-Fi, local herbal bath toiletries, and flat-screen televisions. The Dining Room is a Forbes four-star restaurant with a prix fixe menu. Local seafood, seasonal produce, and artisanal cheese are the specialties here. For alfresco dining, The Lawn serves lunch throughout the year with live music for Sunday brunch. While in Newport, you can check out the exquisite mansions, dine at excellent restaurants, and even take a champagne cruise. This is a fun weekend getaway for couples and groups of friends looking for a charming seaside town experience.
Bar Harbor Manor - Bar Harbor, Maine
Bar Harbor is a fun place to visit when you’re coming from Boston, and the Bar Harbor Manor is an elegant hotel in the middle of the city. The manor is made up of historic homes, an inn, and a new hotel that make up a village of their very own. The inn and hotel are very close to the Atlantic Ocean, Acadia National Park, boat tours, whale watching opportunities, shops, and museums. Several package options are available for weekend getaways.
The Inn on Peaks Island - Peak's Island, Maine
Come to Peaks Island for fresh summer breezes, fall foliage, or softly falling snow. At this inn, you can stay in one of the lovely suites. Some suites have fireplaces, Jacuzzi tubs, and private decks. Around 1,000 people are full-time residents here, but that population triples in the summer. The island is two miles long by one mile wide, which makes it perfect for walking and biking. Popular activities here are horseback riding, historic tours, art galleries, ice skating, and ocean kayaking. The Maine Island Kayak Company offers introductory paddling courses if you’re new to the sport. Just hop on a ferry for a 15-minute ride to get here; ferries run daily and year-round.
Berkshire Mountain Lodge - Berkshire Mountains, Massachusetts
Boston residents love to flock to the Berkshire Mountains to get a dose of nature and relaxation. Berkshire Mountain Lodge has comfortable one-bedroom condos with kitchens, living rooms, and dining areas. It’s a family-friendly getaway spot that’s perfect any time of the year. In warm weather, you can spend your days hiking, biking, golfing, and zip-lining. And on cooler ones, there are great theaters, concert halls, museums, and historic homes to check out. The fall season is particularly popular to visit because of the colorful fall foliage. There are several museums here, as well as dance festivals and a music venue called the Tanglewood that’s great for catching a local show.
Kearsarge Inn - North Conway, New Hampshire
The quaint Kearsarge Inn is located in the White Mountains of New Hampshire and known as a modern rendition of a grant hotel. It’s comfortable and cozy, with lots of restaurants, shops, and attractions in walking distance. Come here for a romantic weekend getaway with someone special, and spend your days hiking, biking, skiing, shopping, and sipping coffee. Kids and dogs are also welcome here, so bring the whole family for a weekend away from Boston. Select rooms have queen-sized beds and fireplaces, and luxury rooms have king-sized beds, fireplaces, jetted tubs, and spacious living rooms.
