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11 Top-Rated Weekend Getaways from Boston

Written by Alison Abbott and Shandley McMurray
Updated Jun 23, 2021

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Boston packs a whole lotta fun and entertainment within its borders. Offering easy access to some of the country's best art, culture, restaurants, shops, and sporting events, this East Coast gem has become a well-loved hub for travelers. Sometimes, though, all of that excitement can get to be a bit much. That's when it's time to plan a great weekend getaway from Boston - one that will help you destress in nature, enjoy a scenic boat cruise, or simply sit back and sip a coffee on a quiet outdoor patio in a charming small town.

Within a few hours' drive from Boston, tourists can reach a wide variety of destinations. Whether you are looking for outdoor adventure, fantastic beaches, or great food, all are within easy reach. Explore the best places to visit with our list of the top weekend getaways from Boston.

Note: Some businesses may be temporarily closed due to recent global health and safety issues.

1. Portland, Maine

Portland, Maine
Portland, Maine

Portland has undergone a renaissance of late, becoming a hot spot for travelers looking for a refreshing weekend getaway from Boston. New restaurants are opening, and their chefs are winning awards. With that in mind, it's a particularly popular spot for those looking for a foodie destination.

This coastal town goes a lot deeper than its remarkable food scene and, depending on your interests, Portland has a little something for everyone. Outdoor enthusiasts can take advantage of a multitude of water sports. Hiking trails surround the area. Art lovers should head to the Portland Museum of Art, where an impressive number of works from both local and international artists are on display.

Another must-see is the Victoria Mansion, an 1800s-era mansion with a remarkable period interior. The historic "Old Port" is a cobbled-street neighborhood on the waterfront, with plenty of shops and restaurants, many housed in repurposed warehouses.

Outside the city center, excursions to the Casco Bay Islands or Cape Elizabeth are worthy of additional time. Pack a towel, as you'll want to spend some time at the beach, especially if you're visiting during summer.

For an overnight stay, good value can be found at the Holiday Inn Portland by the Bay, which offers free Wi-Fi and a pool. Directly on the waterfront is the Portland Harbor Hotel, a boutique property with luxury amenities.

2. Provincetown, Massachusetts

Provincetown, Massachusetts
Provincetown, Massachusetts

Provincetown is a fun and vibrant city located at the tip of Cape Cod's "hook." Chock-full of art galleries, ice-cream stores, eclectic shops, and unique murals, this one-of-a-kind destination is one you really must visit.

While this is a great year-round destination for a weekend getaway from Boston, the best months to visit are July and August. This is when the water is at its warmest and the beaches at their most luxurious, and it's the time when the town comes alive with tourists of all ages, shapes, and sizes. This is an uber popular spot for a summer vacay, and it's best to book early if you're hoping to spend a night or two.

The Pilgrim Monument
The Pilgrim Monument

The Pilgrim Monument is a must-see. This iconic landmark can be spotted from pretty much every place in town. From the water, it serves as an opulent white blip on the landscape, marking the landing of the pilgrims in 1620. A climb to the top rewards visitors with remarkable vistas. Looking for some adventure? Rent a kayak or paddleboard in town.

Provincetown is about two hours from Boston, but in the summer, it could take much longer (we're talking four hours or more) to reach your destination. Travel on a weekday (not including Friday) for a faster drive or, better yet, leave the crowds behind by taking a seasonal ferry. Boston Harbor offers ferries that run to Provincetown in only one hour.

For your weekend stay, the Lands End Inn offers luxurious accommodations with majestic views of the Atlantic Ocean and the region's soft, sandy beaches. Additional Provincetown accommodations can be found at the Cape Colony Inn, boasting an above-ground pool among its many amenities.

Read More: Top-Rated Things to do in Provincetown, MA

3. Martha's Vineyard, Massachusetts

Martha's Vineyard, Massachusetts
Martha's Vineyard, Massachusetts

Martha's Vineyard is the perfect getaway to leave the hustle and bustle of Beantown behind. This island has long been a prized vacation spot for Boston's elite and others just wanting to get away, recharge, or enjoy a romantic couples retreat.

While you are here, rent a bicycle so you can explore the island at your leisure. On the southwestern tip of the island is Aquinnah Cliffs, a popular tourist spot, where you can see the impressive clay cliffs. From the top, you can view the Gay Head Light or the Elizabeth Islands.

For animal lovers, head to Island Alpaca, where you can meet one of the friendly Huacaya alpacas and tour the beautiful farm. The main draw to Martha's Vineyard is the beach, so be sure to enjoy the ocean, sand, and sunshine on your trip.

Martha's Vineyard is a few hours from Boston, but well worth the drive. If you want to bring your car, make sure to have a ferry reservation booked well in advance (we're talking months, not days). You can also reach it via plane. In all, there are six main ways to get from Boston to Martha's Vineyard.

Centrally located in Edgartown, the Vineyard Square Hotel and Suites is a boutique property with modern décor and seaside charm.

4. Nantucket, Massachusetts

Nantucket, Massachusetts
Nantucket, Massachusetts

Thirty-six miles out to sea, there is an island off Cape Cod that is committed to preserving it's past while moving into the future. Rose-covered cottages, cobblestone streets, and white picket fences are the norm. Many of the roads are unpaved, and a good portion of the island is devoted to conservation land. It's a beaut!

Although Nantucket is known for its beaches, culture and history play a big role in the social scene here. The remoteness and simple beauty just adds to the abundance of charm.

For just a weekend visit, leave your car at home and rent a bicycle to get around and see the island's beauty. There are many spots to do so right off the ferries. Stop by the Brandt Point Lighthouse or one of the many pristine beaches like Ladies or Jetties Beach.

A large selection of restaurants offers many choices, but on summer weekends, make sure to have a reservation. You could also load up on the amazing bounty of seafood or readily prepared sandwiches at Bartlett Farm and have a picnic on the beach.

The easiest way to get to Nantucket is to fly from Boston via Cape Air, or you can drive to Hyannis and take the ferry over. It will take a few hours either way, so this trek is best made on a long weekend.

Most hotels on Nantucket are located in town. The Veranda House along with the historical Jared Coffin House are centrally located and within walking distance to the harbor and a wide selection of restaurants in all price ranges.

Read More: Top-Rated Attractions & Things to Do in Nantucket

5. Block Island, Rhode Island

Block Island, Rhode Island
Block Island, Rhode Island

Located just off the coast of mainland Rhode Island and Long Island, New York, this nine-square-mile isle is only accessed by ferry from the mainland. Getting here from Boston is easy. Take the hour-and-a-half drive to Kingston and then hop on the Block Island ferry, which takes approximately 15 minutes port to port.

Once there, rent a moped or bike and explore the 17-mile perimeter of some of the most pristine sandy beaches in Rhode Island. Even though Block Island is small, it's filled with dozens of charming specialty shops, art galleries, and more.

Nature enthusiasts will enjoy the Clayhead Nature Trail, Rodman's Hollow, and Settlers Rock. Pack comfy shoes, snacks, and plenty of water and sunblock as you'll want to hit these trails for hours.

The Block Island Maritime Institute is a fun stop, and you'll likely learn something new about the diverse marine life in this area. If you are looking for a little more adventure, try a fishing excursion with Block Island Fishworks.

National Hotel, within walking distance from the ferry docks, is the epitome of a classic Victorian-styled hotel. The large structure has a front porch made for rocking chairs and binoculars. Breakfast is included in your stay.

6. Berkshires, Massachusetts

Berkshires, Massachusetts
Berkshires, Massachusetts

There are few views as beautiful as those from atop the Berkshire Hills. This gorgeous region, one of the most popular getaways from Boston and New York, spans western Massachusetts and parts of Connecticut. It's packed with some of Mother's Nature's best creations, a natural wonderland begging to be explored and photographed.

This area offers a lot to those who choose it for a weekend getaway from Boston: visiting quaint towns, eating great food, and hiking lush trails top the list of things to do in the Berkshires. Depending on your mood, you can enjoy relaxing during a class at the world famous Kripalu Center for Yoga and Health in Stockbridge, or indulge your inner adventurer by white water rafting or flying high through the trees on a zipline. Alternatively, you may simply choose to relax at one of the beautiful resorts in the Berkshires.

History buffs will particularly love this area as it's home to places like Historic Deerfield and museums like the Norman Rockwell Museum and Susan B. Anthony Birthplace Museum. One of the best things to do here is eat! Farm to table has taken up residence within the Berkshires' borders, with plenty of great restaurants taking advantage of the artisan food suppliers and makers in the area.

In the heart of the Berkshires, the chic Hotel on North is a loft-style boutique hotel, with modern conveniences, exposed brick, and high ceilings. Located in Lee, the Black Swan Inn Berkshires is a lakefront property with balcony rooms overlooking the water.

7. Providence, Rhode Island

Providence, Rhode Island
Providence, Rhode Island

Pretty Providence lies about an hour's drive from Boston. This small city is busting at the seams with charm and a rich history, making it a wonderful and very romantic spot to spend a weekend getaway from Beantown.

Check out some of the town's beautiful architecture, from the historic homes that line Benefit Street to the dome of the State House, which is home to the fourth-largest self-supporting marble dome in the world. If you are an art lover, the Rhode Island School of Design has an impressive body of work on display. More than 90,000 pieces of art are here for your viewing. You won't want to miss a show at the Providence Performing Arts Center.

Those traveling with family should definitely take in one of the many kid-friendly venues like the Roger Williams Park Zoo. With so many things to do, Providence will hit every item on your weekend getaway bucket list.

Providence Marriott Downtown has a resort-type atmosphere and a great outdoor pool. It's also one of the few places in town to offer free parking. In the heart of downtown, The Dean Hotel has been tastefully restored to reflect its past and is convenient to the Convention Center.

8. Newport, Rhode Island

Newport, Rhode Island
The Breakers mansion in Newport, Rhode Island

Newport is another Rhode Island gem you won't want to miss, and it's only a two-hour drive (without traffic) from Boston. For those of you craving a luxurious couples getaway, this is the place to visit. Its sparkling waterfront views, impeccable restaurants with picturesque outdoor patios, charming pedestrian shopping areas, and romantic boat cruises up the charm factor dramatically.

Speaking of romance, why not tour the opulent mansions that once housed the summer homes of some of this country's richest families; think Vanderbilt. Be sure to check out The Breakers, The Isaac Bell House, and The Elms, which are the most popular estates to visit.

If you are a history buff, a stop at Fort Adams or the National Museum of American Illustration will be top on your list. No matter what sites you choose to visit, don't miss the town's most famous attraction: the Cliff Walk. On a nice day, walking along this famous path with the ocean on one side and the mansions on the other, is wonderful. Let's be honest, this walk is nice on a not-so-nice day as well.

Newport Harbor
Newport Harbor

After a busy day of exploring, grab a bite to eat or enjoy some retail therapy at the waterfront or Thames Street. Ice-cream shops abound, so be sure to partake in some sweet eating. Parking can be a challenge on summer days, but be patient. Something will open up eventually.

An elegant stay reflecting the Gilded Age can be found steps from the Cliff Walk at the The Chanler at Cliff Walk. For a fabulous stay across a small inlet near the harbor, select Gurney's Newport Resort and Marina. The in-house restaurant has some of the best views in town.

9. Kennebunkport, Maine

Kennebunkport, Maine
Kennebunkport, Maine

If you're looking for a coastal retreat where water sports reign, you'll be happy you traveled to the adorable town of Kennebunkport in Maine. A bustling locale in the summer, this popular vacay spot is a mere two hours' drive north of Boston up Route 95. Unlike most of Maine's rocky coastline, Kennebunkport has nice sandy beaches waiting to welcome visitors.

One of the best ways to see Kennebunkport and learn about its rich history is the Intown Trolley Tour. You'll get a full rundown of the notable attractions, from the Bush compound to the Spouting Rock and a local monastery.

Head out of town to enjoy the sights of the lighthouses like the Wood Island Light or Boon Island Light. There are five lights within a 20-mile radius, although some are privately owned and not available to tour, they still make a great photo op.

Before you leave, head to Dock Square. There you will find your fill of unique boutiques, restaurants, and galleries. The town does a good job of incorporating festivals into the shoulder seasons, making the Kennebunks a good year-round destination.

The Nonantum Resort offers plenty of additional activities on their menu, family fun, and an on-site lighthouse. The Rhumb Line Resort offers great value with an in-ground pool and free breakfast and Wi-Fi.

10. Portsmouth, New Hampshire

Portsmouth, New Hampshire
Portsmouth, New Hampshire

Portsmouth's elegant beauty and graceful green spaces entice visitors to unwind, put their feet up, and settle in for a vacation to remember. A big draw for Bostonians looking for a quiet and picturesque weekend getaway, this New Hampshire gem can get crowded in summer. That's not surprising considering its pristine beaches and lush parks, but it's the historic seaport and friendly maritime ambience that charms even the most harried of travelers.

A mere hour's drive north of Boston leads visitors to this historic area located on the picturesque Piscataqua River. While in town, take a leisurely stroll around Prescott Park or Celia Thaxter's Garden to enjoy the beautiful scenery.

Learn more about the area and its history with a visit to the Strawbery Banke Museum. Here, actors reenact what it was like in the waterfront neighborhoods hundreds of years ago. Are you an avid arts lover? Check out a concert at the Music Hall, a historic 895-seat theater, which produces concerts and stage productions.

Convenience and free parking are two benefits that make the Hampton Inn Portsmouth Central hotel a good-value choice for the area. Those looking for a New England bed-and-breakfast experience will find the Sailmaker's House a great choice.

Read More: Top-Rated Tourist Attractions & Things to Do in Portsmouth, NH

11. Stowe, VT

Fall colors in Stowe, VT
Fall colors in Stowe, VT

While most think of Stowe as a winter destination - a haven for skiers and snowboarders, it is best known as an upscale Vermont ski resort - this phenomenal locale is captivating at all times of the year. During fall, Stowe is arguably at its most photogenic, vibrant hues of red, orange, and yellow painting the landscape with such beauty, you'll be left awe-struck.

Luckily for those traveling from Boston, the drive only takes about three hours (without traffic, of course). Once there, lucky weekenders can traipse through mountain trails, enjoy a latte in a cute café, or shop in one of the charming stores. Prepare yourself for a hefty bill, though, as Stowe isn't well suited to those with shallow pockets.

Whether you choose to bike, hike, cross-country ski, snowboard, or whoosh down the mountain on skis, you're sure to find some type of adventure to get your heart-pumping in this gorgeous part of New England.

The Trapp Family Lodge is set within a European-style alpine resort on a sprawling 2,500 acres of incredible landscape. The Lodge at Spruce Peak is another fab spot to rest your weary heads. Also set within a phenomenal mountainous terrain, this lavish spot is the only ski-in, ski-out luxury resort in Stowe.

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