You’ve packed your bags, booked your flight (or Uber), and now all that’s left is to find the perfect Massachusetts spot to spend your precious vacation days. If you’re looking to venture outside the ordinary and have an incredible experience, take a look at these jaw-dropping places to stay in Massachusetts.
- Silo Cottage
Airbnb/Denise
Airbnb/Denise What do you get when you mix a cozy woodland cottage with a lily pond and a babbling brook? One of the most unique places to stay in Massachusetts, this fairytale retreat in Tyringham will become your new favorite home away from home. Available through Airbnb, this whimsical getaway might even inspire you to kiss a frog or two. Tyringham, MA, USA
- Hotel at MIT
Le Meridien-Cambridge Also called Le Meridien Cambridge, this hotel is designed to reflect the spirit of the nearby Massachusetts Institute of Technology. Robots in the lobby, equations on the sheets, and a pool area that is just plain wacky all add up to a very unique experience. Le Méridien Boston Cambridge, 20 Sidney St, Cambridge, MA 02139, USA
- Longfellow’s Wayside Inn
Longfellow’s Wayside Inn The longest continually operated inn in the country, these rooms have a haunted history. Reports of ghostly guests date back to the 19th century and some male visitors have even stated that spectral women have slipped into their beds for a snuggle. So if you’re looking for one of the most haunted places to stay in Massachusetts, you’ve found it. Longfellow’s Wayside Inn, 72 Wayside Inn Rd, Sudbury, MA 01776, USA
- The Starlight Llama B&B
Starlight Llama B&B, Michael Aquino
Flickr/Marcia O’Conner For the discerning conspiracy theorist or environmentally responsible holidaymaker, we have the Starlight Llama B&B. This unique place to stay in Massachusetts is completely solar-powered and off the grid. Food comes straight from the garden and they can accommodate vegan, gluten-free, and other special diets. “What about the ’llama’ part,” you ask. They have those, too! Along with peacocks, emus, and other farm animals. Grab a cup of coffee and have breakfast with the herd.
- Blantyre
Blantyre
Blantyre Conde Nast, Forbes, and U.S. News agree: Blantyre is the height of Gilded-Age luxury. Combining Massachusetts-style easy elegance with rooms that any duke or duchess would appreciate, this property offers something for each of the senses. Between the spa, the manicured grounds, and the splendor of the Great House, you may just forget you’re not actually an aristocrat. Blantyre Road, Blantyre Rd, Lenox, MA 01240, USA
- Nickerson State Park
Flickr/Lizard10979
Flickr/London Permaculture Fancy staying in a yurt? This is the place for you. For a no-frills vacation experience, this gigantic Massachusetts state park offers a variety of different camping options including the aforementioned native-style dwelling. There’s nothing like waking up to a campfire breakfast. Nickerson State Park, 3488 Main St, Brewster, MA 02631, USA
- Chatham Bars Inn
Chatham Bars Inn
Chatham Bars Inn If you want all the frills with extra frills on the side, this is the hotel you’ve been waiting for. Right on the water? Yes. Gourmet dining with ingredients sourced from the resort’s own farm? For sure. In-room saunas, fireplaces, and espresso makers? Naturally. This is one of the best places to stay in Massachusetts when you want to feel like royalty at the seashore. Chatham Bars Inn, 297 Shore Rd #1, Chatham, MA 02633, USA
- Green Turtle Floating B&B
Facebook/Green Turtle We all have those days when we feel like life on dry land is more trouble than it’s worth. Before you trade in your landlocked home for an aquatic abode, however, take one for a test float at this unique bed and breakfast in Massachusetts. Stay on an actual houseboat or a luxurious yacht and let your terrestrial worries drift away. Green Turtle, 1 Pier 8, 13th St, Charlestown, MA 02129, USA
- The Encore B&B
Encore B&B Editor’s Note: Unfortunately this bed and breakfast in Boston has closed its doors.
Located in Boston’s fashionable and historic South End, this bed and breakfast was co-created by the director of Boston’s Zeitgeist Stage Company, David Miller. The colorful details and personality of these lodgings are perfect for a guest who appreciates a little dramatic flair.
- The Liberty Hotel
Facebook/The Liberty Hotel
Facebook/The Liberty Hotel This establishment has played host to Malcolm X and former Boston mayor James Curley. They didn’t stay as guests though: they were inmates. This massive Boston hotel is a former PRISON. This jailhouse has been transformed into luxury accommodations. Some of their services include overnight shoe-shining and running concierges to help you keep in shape. You know…for when you want to make a break for it. The Liberty, a Luxury Collection Hotel, Boston, 215 Charles St, Boston, MA 02114, USA
- The Scargo Manor
The Scargo Cafe
The Scargo Cafe This quaint manor in Massachusetts has three main big things going for it: 1) An absolutely beautiful pond. 2) Ghosts, allegedly. 3) Award-winning, incredible, I-need-a-vat-of-this grape nut pudding. If you don’t know what grape nut pudding is, we’re not going to spoil the surprise. It’s a Massachusetts favorite and you should go visit the Scargo Manor to taste it for yourself. Scargo Manor Bed & Breakfast, 909 Main St, Dennis, MA 02638, USA
- Herreshoff Castle
Wikimedia Commons/Daderot Massachusetts isn’t really known as “castle country,” but that’s exactly why this little-known B&B in Marblehead is such a cool destination. The castle was built in the 1920s by a wealthy and obviously rather fanciful artist. It doesn’t have a moat, but it does have buckets of old-world charm. 2 Crocker Park Ln, Marblehead, MA 01945, USA
Sometimes the destination definitely trumps the journey. If you’re looking to spend a few nights sleeping under the stars, here are some of the most beautiful campsites in Massachusetts to do just that.
Airbnb/Denise
What do you get when you mix a cozy woodland cottage with a lily pond and a babbling brook? One of the most unique places to stay in Massachusetts, this fairytale retreat in Tyringham will become your new favorite home away from home. Available through Airbnb, this whimsical getaway might even inspire you to kiss a frog or two.
Tyringham, MA, USA
Le Meridien-Cambridge
Also called Le Meridien Cambridge, this hotel is designed to reflect the spirit of the nearby Massachusetts Institute of Technology. Robots in the lobby, equations on the sheets, and a pool area that is just plain wacky all add up to a very unique experience.
Le Méridien Boston Cambridge, 20 Sidney St, Cambridge, MA 02139, USA
Longfellow’s Wayside Inn
The longest continually operated inn in the country, these rooms have a haunted history. Reports of ghostly guests date back to the 19th century and some male visitors have even stated that spectral women have slipped into their beds for a snuggle. So if you’re looking for one of the most haunted places to stay in Massachusetts, you’ve found it.
Longfellow’s Wayside Inn, 72 Wayside Inn Rd, Sudbury, MA 01776, USA
Starlight Llama B&B, Michael Aquino
Flickr/Marcia O’Conner
For the discerning conspiracy theorist or environmentally responsible holidaymaker, we have the Starlight Llama B&B. This unique place to stay in Massachusetts is completely solar-powered and off the grid. Food comes straight from the garden and they can accommodate vegan, gluten-free, and other special diets. “What about the ’llama’ part,” you ask. They have those, too! Along with peacocks, emus, and other farm animals. Grab a cup of coffee and have breakfast with the herd.
Blantyre
Conde Nast, Forbes, and U.S. News agree: Blantyre is the height of Gilded-Age luxury. Combining Massachusetts-style easy elegance with rooms that any duke or duchess would appreciate, this property offers something for each of the senses. Between the spa, the manicured grounds, and the splendor of the Great House, you may just forget you’re not actually an aristocrat.
Blantyre Road, Blantyre Rd, Lenox, MA 01240, USA
Flickr/Lizard10979
Flickr/London Permaculture
Fancy staying in a yurt? This is the place for you. For a no-frills vacation experience, this gigantic Massachusetts state park offers a variety of different camping options including the aforementioned native-style dwelling. There’s nothing like waking up to a campfire breakfast.
Nickerson State Park, 3488 Main St, Brewster, MA 02631, USA
Chatham Bars Inn
If you want all the frills with extra frills on the side, this is the hotel you’ve been waiting for. Right on the water? Yes. Gourmet dining with ingredients sourced from the resort’s own farm? For sure. In-room saunas, fireplaces, and espresso makers? Naturally. This is one of the best places to stay in Massachusetts when you want to feel like royalty at the seashore.
Chatham Bars Inn, 297 Shore Rd #1, Chatham, MA 02633, USA
Facebook/Green Turtle
We all have those days when we feel like life on dry land is more trouble than it’s worth. Before you trade in your landlocked home for an aquatic abode, however, take one for a test float at this unique bed and breakfast in Massachusetts. Stay on an actual houseboat or a luxurious yacht and let your terrestrial worries drift away.
Green Turtle, 1 Pier 8, 13th St, Charlestown, MA 02129, USA
Encore B&B
Editor’s Note: Unfortunately this bed and breakfast in Boston has closed its doors.
Located in Boston’s fashionable and historic South End, this bed and breakfast was co-created by the director of Boston’s Zeitgeist Stage Company, David Miller. The colorful details and personality of these lodgings are perfect for a guest who appreciates a little dramatic flair.
Facebook/The Liberty Hotel
This establishment has played host to Malcolm X and former Boston mayor James Curley. They didn’t stay as guests though: they were inmates. This massive Boston hotel is a former PRISON. This jailhouse has been transformed into luxury accommodations. Some of their services include overnight shoe-shining and running concierges to help you keep in shape. You know…for when you want to make a break for it.
The Liberty, a Luxury Collection Hotel, Boston, 215 Charles St, Boston, MA 02114, USA
The Scargo Cafe
This quaint manor in Massachusetts has three main big things going for it: 1) An absolutely beautiful pond. 2) Ghosts, allegedly. 3) Award-winning, incredible, I-need-a-vat-of-this grape nut pudding. If you don’t know what grape nut pudding is, we’re not going to spoil the surprise. It’s a Massachusetts favorite and you should go visit the Scargo Manor to taste it for yourself.
Scargo Manor Bed & Breakfast, 909 Main St, Dennis, MA 02638, USA
Wikimedia Commons/Daderot
Massachusetts isn’t really known as “castle country,” but that’s exactly why this little-known B&B in Marblehead is such a cool destination. The castle was built in the 1920s by a wealthy and obviously rather fanciful artist. It doesn’t have a moat, but it does have buckets of old-world charm.
2 Crocker Park Ln, Marblehead, MA 01945, USA
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The OIYS Visitor Center
places to stay in Massachusetts October 04, 2022 Jackie Ann What are the best scenic campgrounds in Massachusetts? When you’re looking for places to stay in Massachusetts, campgrounds are often overlooked but they can be some of the most beautiful places you’ll ever rest your head. While primitive tent camping is always an option, you can always choose to rent a cabin or go with a hybrid solution where you can go yurt camping in Massachusetts. With 150 state parks in Massachusetts, you’re never too far away from a scenic campground. Can I stay in a treehouse in Massachusetts? For one of the most unique places to stay in the Bay State, consider renting a treehouse for a night or two. There are actually a handful of treehouses in Massachusetts that each offer the rare opportunity to live out your childhood fantasy of living in an enchanting treehouse. These aren’t small treehouses, either! This treehouse near Lee, Massachusetts features two bedrooms and a whimsical gingerbread house look that’ll make you feel like you’ve stepped into a fairy tale. What are the most unique places to spend the night in Massachusetts? One of the most unique places to spend the night in Massachusetts will take you straight to the top of the Berkshire Mountain Range. This cozy cabin in Massachusetts is ideal for two people on the hunt for a little peace and quiet. Not only will you have a panoramic view of North Adams and the surrounding mountains and valleys, but you’ll have complete privacy and feel like you’re a million miles away from everything.
The OIYS Visitor Center
places to stay in Massachusetts
October 04, 2022
Jackie Ann
What are the best scenic campgrounds in Massachusetts? When you’re looking for places to stay in Massachusetts, campgrounds are often overlooked but they can be some of the most beautiful places you’ll ever rest your head. While primitive tent camping is always an option, you can always choose to rent a cabin or go with a hybrid solution where you can go yurt camping in Massachusetts. With 150 state parks in Massachusetts, you’re never too far away from a scenic campground. Can I stay in a treehouse in Massachusetts? For one of the most unique places to stay in the Bay State, consider renting a treehouse for a night or two. There are actually a handful of treehouses in Massachusetts that each offer the rare opportunity to live out your childhood fantasy of living in an enchanting treehouse. These aren’t small treehouses, either! This treehouse near Lee, Massachusetts features two bedrooms and a whimsical gingerbread house look that’ll make you feel like you’ve stepped into a fairy tale. What are the most unique places to spend the night in Massachusetts? One of the most unique places to spend the night in Massachusetts will take you straight to the top of the Berkshire Mountain Range. This cozy cabin in Massachusetts is ideal for two people on the hunt for a little peace and quiet. Not only will you have a panoramic view of North Adams and the surrounding mountains and valleys, but you’ll have complete privacy and feel like you’re a million miles away from everything.
The OIYS Visitor Center
The OIYS Visitor Center
When you’re looking for places to stay in Massachusetts, campgrounds are often overlooked but they can be some of the most beautiful places you’ll ever rest your head. While primitive tent camping is always an option, you can always choose to rent a cabin or go with a hybrid solution where you can go yurt camping in Massachusetts. With 150 state parks in Massachusetts, you’re never too far away from a scenic campground.
Can I stay in a treehouse in Massachusetts?
For one of the most unique places to stay in the Bay State, consider renting a treehouse for a night or two. There are actually a handful of treehouses in Massachusetts that each offer the rare opportunity to live out your childhood fantasy of living in an enchanting treehouse. These aren’t small treehouses, either! This treehouse near Lee, Massachusetts features two bedrooms and a whimsical gingerbread house look that’ll make you feel like you’ve stepped into a fairy tale.
What are the most unique places to spend the night in Massachusetts?
One of the most unique places to spend the night in Massachusetts will take you straight to the top of the Berkshire Mountain Range. This cozy cabin in Massachusetts is ideal for two people on the hunt for a little peace and quiet. Not only will you have a panoramic view of North Adams and the surrounding mountains and valleys, but you’ll have complete privacy and feel like you’re a million miles away from everything.
