Sometimes you just need a little mini-vacation to reset, and weekend getaways from Boston are perfect for that! If you’re looking to plan the perfect adventure away from Boston, then check out this list of easy weekend trips from Boston that will have you returning to the city recharged and ready to jump back into the grind!
Best of all, with the driveability of New England, you can head to destinations all around the region for your weekend escape.
Weekend Getaways from Boston
Make a beeline for the Berkshires
This one is a no-brainer, right? If you’re looking to get away from The City on a Hill for a little weekend reset, you don’t even need to leave the state because the Berkshires can offer both fun and relaxation! If you’re looking for a weekend getaway in the fall, there are multiple choices for prime leaf-peeping and apple-picking, and if you’re looking for a little more adventure, there are several options for that too, including some of the coolest hikes in New England!
If it’s more of a romantic getaway you’re after, consider renting a cozy Berkshires cabin during your weekend trip from Boston. Whether you’re into action, respite, or romance, the Berkshires is an ideal weekend getaway from Boston.
If you’re looking for a modern, romantic place to stay, book a room at 33 Main!
Check in and check out for the weekend in Old Saybrook
Saybrook Point Resort and Marina in Old Saybrook, CT means a weekend getaway of rest and relaxation on the lovely Long Island Sound with amenities and accommodations to die for. Room options include stellar views over the Long Island Sound, fireplaces, and private balconies.
If you are planning a romantic weekend getaway from Boston, the Lighthouse Suite was voted the “Most Romantic Place to Stay” by Connecticut Magazine and features 360-degree views of the coastal oasis of Old Saybrook, CT, so hint, hint on that…
Spend the weekend sampling all Portland has to offer
Portland, ME is well-known as a foodie destination, and is an interesting and eclectic mix of trendy hipster vibes and historical sophistication; you can find breweries, museums, lighthouses, shopping, coffee shops, bakeries, sailing, and cruises in Casco Bay, nearby hiking trails, and so much more. In fact, you can find a ready-made itinerary of all the must-do, must-see, must-eat & drink spots to visit for a perfect weekend getaway in Portland here, including recommendations for the best hotels and Airbnbs in Portland.
Portland Harbor Hotel has a very cool vibe.
Stay in stunning Stowe
A must-add to any weekend getaway list, the gorgeous ski town of Stowe, VT is perfect for a weekend trip from Boston! Travel + Leisure named Stowe as one of America’s Best Ski Towns, and Stowe has a lot more to offer beyond just their spectacular ski slopes.
There are many things to do in Stowe, including hiking and checking out the top restaurants, breweries, and breakfast places and if you’re looking for a spot to rev up the romance, well, Stowe also made it on this list of romantic getaways in Vermont, too! There are lots of cool Stowe hotel and Airbnb options to pick from, but a stay at the Trapp Family Lodge is quintessential Stowe!
Venture into North Conway
If you are looking for a weekend getaway from Boston to enjoy a variety of adventurous outdoor activities, then North Conway might just be the perfect destination for you! In the winter, you can hop on a snowmobile as the snow falls softly all around you, and in the summer, you can kayak or tube down the river as the sun glistens off the water with highly-rated Northern Extremes.
There are plenty of fun things to do here, but don’t forget to check out one of the region’s favorite outlet malls, Settlers Green, where you can shop at all 60+ retailers TAX-FREE! There are lots of solid options for where to stay and where to eat in North Conway, too, and North Conway Grand Hotel is a cool place to stay.
Indulge in some Gilded Age glory in Newport
Newport, RI is one of the most beautiful cities on the New England coast, and one of the top weekend getaways from Bostson sure to make anyone feel like they have stepped into another world far, far away from the hustle and bustle of the city.
Newport is well-known for its beautifully preserved Gilded Age era mansions, gorgeous beaches, delicious restaurants, and the scenic Cliff Walk, and it’s hard not to get swept away in the romance of this enchanting city, so if you are looking for a romantic getaway, check out these cool hotels and Airbnbs in Newport, too. If you’re looking to splurge, check out Castle Hill Inn!
Retreat to Rockport
Just about an hour up the road, lovely Rockport, MA makes for a great quick weekend getaway from Boston! You’ll love the stunning natural scenery of Cape Ann and the man-made charm that includes the row of rainbow houses and Motif #1, the bright red fishing shack that attracts artists from all around the world to capture its essence.
Whether you spend your weekend in Rockport checking out the local art on Bearskin Neck or lounging on the beach, this picturesque seaside village offers plenty of options for anything a person might need to relax and unwind for the weekend, including interesting inns, amazing restaurants, and some of the best breakfast options on Cape Ann! Plus, with Rockport being such a short trip from Boston, it can be the perfect overnight trip spot.
Check out our review of Emerson Inn; definitely a cool place to stay in Rockport!
Go for a wild weekend in Acadia National Park
Okay, so spending the weekend visiting Acadia National Park doesn’t necessarily mean you will be going “wild,” but it’s the perfect place to enjoy the wild beauty of coastal Maine. It is just under 5 hours drive to get to Acadia from Boston, so this one is probably best reserved for a long weekend from Boston trip.
Whether you stay in one of these beautiful Airbnbs, charming inns, cute cabins, or you decide to rough it by camping on your own, there are so many ways to enjoy the stunning scenery of Acadia National Park. Hiking is a given, but leave the plan loose with plenty of time to explore other activities too (like whale watching!) and you can even use this thoughtfully planned 3 Day Itinerary to guide you.
Consider booking a room at Bar Harbor Manor for its convenient downtown location!
Lose your stress in Litchfield Hills
When you are looking for a laid-back weekend getaway from Boston to escape the stress and pressure of big city life, look no further than the region of Litchfield Hills, CT. known for its scenic backdrop that includes picturesque covered bridges and rushing waterfalls.
In fact, this area is such a perfect example of New England charm that the village of Kent was included in our list of Charming New England Towns to Visit in the Fall. When it is laid-back and restful vibes you are after on your weekend getaway from Boston, consider booking a room at lovely Litchfield Inn for lovely scenery and fantastic service.
Pop in to Providence for a weekend well-spent
Providence is its own unique brand of hip, and because it takes less than an hour to travel to, it make the perfect weekend trip from Boston spot. There are museums, funky outdoor flea markets, cool, historical landmarks, and Waterfire, an internationally known annual art installation event that draws people in from all around the world.
Pack your bags for Portsmouth
Portsmouth is just a quick drive up from Boston, but this weekend getaway destination will still take you worlds away from all the hustle and bustle of the city! This cute coastal New Hampshire town offers a ton of museums and historical monuments, incredible food options, cool breweries, breakfast places, and more. There are plenty of options for where to stay in Portsmouth including some pretty awesome Airbnb stays, too.
Any time of year, Portsmouth is the perfect Seacoast weekend getaway from Boston; consider booking a room at The Hotel Portsmouth for its excellent amenities and location.
Have the best time in Burlington
Burlington is the perfect spot for a Vermont weekend getaway from Boston! This hip and artsy college town has a lot to offer visitors, like some extra cozy coffee shops, unique breweries and bars, excellent restaurants, great breakfast spots, and some fantastic hiking. There are plenty of cool options for where to stay in Burlington, including awesome Airbnbs, and if you are traveling with your pup, Burlington is extra pup-friendly with lots of restaurants, hotels, and activities that welcome you and your pooch, too!
Consider a stay at Hilton Garden Inn Burlington Downtown to be just 2 blocks from Burlington’s famous Church Street!
Lap up luxury in Nantucket
For the ultimate luxury weekend getaway from Boston, look no further than The Wauwinet in Nantucket, MA! Adults only, this stunning seaside resort is the only Relais & Chateaux hotel on the island and when you are there, you will feel like royalty.
There are so many great things to do in Nantucket, from the beaches to the restaurants and beyond, but if it’s a romantic trip from Boston you’re planning, The Wauwinet is one of the most romantic hotels in the US and you will see why from the moment you check in.
Explore the magic of Mystic
The waterfront village of Mystic is less than a 2 hour drive from Boston, making it an ideal weekend vacation near Boston, and not just because you can visit the actual Mystic Pizza that the Julia Roberts movie was based on!
Visit the history, mystery, and intrigue of Salem
Salem remains a hotspot for all intrigued by its infamous past, but there’s more to explore here than just historical drama on its hallowed streets. Of course, there are a lot of activities around Halloween, including ghost tours and checking out all the locations that Hocus Pocus filmed in town, but all year round you can find interesting museums, novelty shops, reputedly haunted places, and psychic encounters that will let you get a bit of a taste of the occult yourself. Salem’s motto is “Still making history,” and when you spend your weekend getaway sampling the tastiest restaurants and staying in the coolest Airbnbs and inns, you’ll see how that’s true!
Want to stay at one of the most haunted hotels in New England? Consider booking a room at Hawthorne Hotel!
Make memories in Manchester, VT
Nestled in the Green Mountains, Manchester is one of those picturesque towns in Vermont and offers something for every kind of visitor.
There’s great hiking, a cute downtown, historical Hildene, the Lincoln Family Home, and more to keep you busy, and with fabulous restaurants and lodging options, Manchester is a great choice for a weekend getaway from Boston that will leave you feeling refreshed and ready to go on Monday.
Check out Kimpton Taconic Hotel for rustic charm within easy walking distance of all kinds of fun downtown Manchester things to do.
Be cool in Cape Cod
A Cape Cod vacation from Boston is nothing short of paradise any time of the year, and just a quick hour drive to get there. Planning your weekend getaway from Boston for warmer weather means you can enjoy the beaches a little more, but Cape Cod in the fall is its own lovely experience, too.
Cape Cod has great dining, hotels, and Airbnb options, wineries to visit, lobster rolls to sample, hikes to take, and more, and the biggest issue you will find on your weekend getaway from Boston will be narrowing down your choices; which Cape Cod towns will you visit? Provincetown? Wellfleet? Chatham? Be sure to scope out some of the best things to do in Cape Cod with kids if you’re planning a family trip from Boston!
We recently stayed at Captain’s House Inn in Chatham and loved it! Check out our experience here.
Slow down on Block Island
Block Island has just about every ingredient to make the perfect summer weekend getaway: beaches, bluffs, lighthouses, and all the amenities you could possibly want. Beautiful Block Island has plenty of options for where to stay, fun things to do, and great restaurants to eat at. Block Island is the perfect spot for a summer weekend trip from Boston!
Consider a stay at Old Town Inn while on Block Island for excellent service, coastal modern rooms, a phenomenal breakfast, and fantastic location for beaches, a lighthouse, and more.
Weekend getaways are always an excellent option for decompressing and letting off a little steam. You work hard all week, hope this list helps you choose the best weekend getaway from Boston for you!
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Amy is the founder of New England with love. A proud Vermonter, she hopes to share her love of New England and help you find the best adventures in the region. Amy is also blogger/founder at Two Drifters, where she writes alongside her husband about romantic and couples travel, relationships, honeymoons, and more. When not working on websites, Amy is probably reading, cuddling with her husband, son, and cats, & drinking a maple latte.