7 Weekend Getaways in Massachusetts for Bay State Fun!

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Is it about time for a weekend away somewhere? How about a mini-vacation to the Bay State? There are so many great weekend getaways in Massachusetts, and plenty of fun things to do all over the state. Whether you’re looking for a romantic weekend away or a family-friendly adventure, we’ve got 7 MA weekend getaway options for you right here!

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Nantucket Hotel and Resort on Nantucket

An antique green bus sits in front of the bluish grey Nantucket Hotel and Resort, parked in a drive with grass on one side and trees and blue sky visible above — *Editorial credit: EQRoy / Shutterstock.com*

If you’ve only got one weekend to get out of town, let’s make the most of it with an island stay at Nantucket Hotel and Resort! In addition to the luxury amenities in each room, this gorgeous resort has heated outdoor pools, fire pits and live music in the warmer weather months, and a kids’ day club that will be a hit for the whole family! The onsite restaurant, Breeze, is one of the best restaurants on the island, so really, there’s no need to even leave the resort during your weekend away. Nantucket Hotel and Resort is open year round, so if you’re planning a Nantucket winter trip, this is the place to book.

Of course, Nantucket is full of fun things to see and do, like strolling along the scenic ‘Sconset Bluff Walk that leads to the lovely Sankaty Head Lighthouse; looking for Nantucket photo ops? That’s a good one! And of course, there are plenty of beautiful beaches to choose from if you’re looking to kick back on the sand with a good book for a while, too. When it comes to weekend getaways in Massachusetts, Nantucket is hard to beat!

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The Hawthorne Hotel in Salem

Are you looking for weekend getaways in Massachusetts that offer plenty of unique experiences to talk about back at work on Monday? Then consider booking a room at the Hawthorne Hotel, one of the most haunted hotels in America! This gorgeous hotel is beautifully restored with all of the modern amenities a person could want, but eerie happenings are reported here due to its location on the former apple orchard of one of the poor souls that was tragically hanged under accusation for witchcraft.

Not only may you catch a phantom scent of apples as you move around the hotel, but if you request room 612 or 325, you might get some extra odd instances, like faucets turning themselves on and off. Of course, Salem is full of all kinds of things to do, especially if you decide to visit in October. Check out where Hocus Pocus filmed, take a ghost tour, scope out some of the most haunted places in town (PS you’re staying in one!), and enjoy the fantastic restaurant scene this waterfront town has to offer!

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Cape Codder Resort & Spa in Hyannis

If it’s a splashing around in the water, family fun for everyone kind of Massachusetts weekend getaway you’re looking for, then check out Cape Codder Resort & Spa! There’s an indoor and outdoor water park, so if it’s too cold out to hit the beach, you and yours will still have fun splashing around inside! Family packages are available that include discounted rates at the onsite full service spa, fun family activities like roasting marshmallows at the fire pit and enjoying movies under the stars, and of course, Cape Cod is full of fun things to see and do, especially with kids!

Get out and hike a bit, go on a whale watch tour, get some Vitamin Sea at one of the beautiful Cape Cod beaches, or just hop from cute little beach town to beach town; towns like Provincetown, Chatham, Wellfleet, and Sandwich all have their own vibe about them, so take the time to explore on your weekend getaway in MA! There are also fantastic restaurants and ice cream shops around the Cape, so you really can’t go wrong wherever your explorations take you; can’t leave the Cape without sampling a delicious lobster roll either! PS Cape Cod in the fall is always a great option for lovely scenery and shoulder season rates!

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The Liberty Hotel in Boston

For a hip, trendy, and oh so unique stay, check out The Liberty Hotel in Boston, featuring playful nods to its history as Charles Street Jail from 1851-1990 throughout; cute little reminders that this boutique hotel was one one of the worst places to stay in Boston before it became one of the best places to stay in Boston! In addition to generously appointed rooms and fantastic onsite dining, The Liberty is also in an excellent location for all kinds of great Boston things to do!

Walk the Freedom Trail, visit a museum or three, check out some cool literary sites, go on a ghost tour, a walking tour, a food tour, a brewery tour, in Boston, the sky feels like the limit! Whether you’ve got your kiddos with you, you’re looking for free things to do, or you just need a great cup of coffee or a delicious place to eat, you’ve got soooo many options! Spring, summer, fall, or winter, you’ll find wicked fun (and romance, if you’d like!) in Boston, and plenty of great photo ops, too!

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Red Lion Inn in Stockbridge

The sign of the Red Lion Inn is in the forefront, with the inn itself obscured behind it, with trees and white railing visible — *Editorial credit: T photography / Shutterstock.com*

If you’re looking for weekend getaways in Massachusetts that deliver that quintessentially quaint New England experience, look no further than Red Lion Inn in the beautiful Berkshires! Offering a classic inn stay (with a great outdoor pool!), rooms are comfy, cozy, and beautifully decorated, and the gourmet onsite dining options draw in people from all around the region.

Not only is Stockbridge a fun little area to explore, but the Red Lion Inn is perfectly situated to be your landing spot while you explore all that the Berkshires have to offer! Go hiking, listen to the Boston Symphony Orchestra perform at Tanglewood, visit cool historical sites like Edith Wharton’s The Mount, and explore museums like the Norman Rockwell Museum, located right there in Stockbridge. With cute little towns like Lenox, North Adams, Great Barrington, Pittsfield, and so many more just waiting to be explored, any Berkshires weekend getaway is sure to be a delight!

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Summercamp in Oak Bluffs

For a MA weekend getaway that brings that beach town fun, book a stay at Summercamp on Martha’s Vineyard! This boutique hotel prides itself on bringing the fun back into your weekend getaway by providing lots of cute, kinda campy things to do onsite that might just take you back to your days of summer camp; think kayaking, paddleboarding, and there’s even a cute little canteen where you can score camp snacks like dreamsicles and cracker jacks!

Of course, there’s plenty to do and see on Martha’s Vineyard, especially if you’re looking for fun at the beach. Martha’s Vineyard has some gorgeous beaches, so depending on what you’re looking for (and if you’ve got any little ones with you!), you can find the perfect beach for you and yours. If you’re looking for a weekend getaway in MA that is a little bit nostalgia and a whole lotta fun, Summercamp is for you!

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Hotel 1620 Plymouth Harbor in Plymouth

Delightfully situated overlooking the bay, Hotel 1620 Plymouth Harbor is the perfect place to stay for your next Massachusetts weekend getaway! Not only is this beautiful boutique hotel offering high-quality accommodations and onsite dining, but it is also conveniently located within easy walking distance of all kinds of must-see and do fun in America’s Hometown!

Not only is Plymouth full of great historical sites like Plymouth Rock and Plimouth Plantation, but you’ll also find other neat things to do like going on a cranberry bog tour, a whale watching trip, or just having a little relax time at Plymouth Bay Winery. It’s called America’s Hometown for a reason, a MA weekend getaway to Plymouth makes for a great home away from home experience!

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Massachusetts weekend getaway destinations can be romantic, adventurous, or a nice, low-key relaxing time, so you can plan the perfect mini-vacation for you and yours!

Whether you’re planning your weekend getaway in MA for spring, summer, fall, or winter, you’ll have a blast getting away for the weekend in the beautiful Bay State!

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Amy Hartle

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.