Massachusetts is full of stories written on aged stone buildings, along streets as old as time.

It’s not just for history buffs, although a visit to Boston and the hallowed grounds of Cambridge should be high on every traveler’s list. Massachusetts has an incredibly diverse horticulture scene, with cideries and wineries, as well as cranberry bogs and endless orchards, that makes their official Wine and Cheese Trail a worthy venture.

The Massachusetts coastline is a great place to stop off, and is the home of Cape Cod. With over 40 miles of protected coastlines, there is a sense of history thanks to the cute small towns that are dotted along, and the literary gems that were born here. The coast is one of the best spots in the US to go whale watching.

There are many amazing holiday rentals in Massachusetts where you can get cozy and make a home base.

Airbnbs in Massachusetts will give you insider access to beautiful, yet mostly unknown neighborhoods. You can stay by the coastline or in the mountains.

Read on to find out more on why Airbnbs are the perfect option before we dive into the best Airbnbs in Massachusetts.

Winchester Massachusetts

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Quick Answer: These are the Top 5 Airbnbs in Massachusetts

Overall Best Value Airbnb in Massachusetts
Farm Stay
Overall Best Value Airbnb in Massachusetts

Farm Stay

  • > $$
  • > 5 Guests
  • > Working farm
  • > Private access
Best Budget Airbnb in Massachusetts
Little Paris
Best Budget Airbnb in Massachusetts

Little Paris

  • > $
  • > 2 Guests
  • > Great location
  • > Shared kitchen
Over-the-Top Luxury Airbnb in Massachusetts
Cape Cod Estate
Over-the-Top Luxury Airbnb in Massachusetts

Cape Cod Estate

  • > $$$$
  • > 16 Guests
  • > Beautiful views
  • > On-site concierge
For Solo Travelers in Massachusetts
Sun-Filled Apartment
For Solo Travelers in Massachusetts

Sun-Filled Apartment

  • > $$
  • > 2 Guests
  • > Central location
  • > Clean and modern
Ideal Digital Nomad Airbnb
Private Country Retreat (1)
Ideal Digital Nomad Airbnb

Private Country Retreat

  • > $$
  • > 2 Guests
  • > 23-Acre property
  • > Work desk views

What to Expect from Airbnbs in Massachusetts

Airbnbs throughout Massachusetts always fit in with the vibe of the town, the city, or the nature surrounding it.

If you head for downtown Boston, you will find apartments and studios with skyline views and easy access to public transport and local attractions.

On the coastline, looking out over the Atlantic Ocean, you will find romantic getaways in the form of beachfront homes, and family cottages steps from Main Street.

What to Expect from Airbnbs in Massachusetts

In the woods, you can discover tiny homes, cabins, and estates with rustic charm and fire pits. Be close to the mountains, and rural towns for classic homestyle cooking.

Prices range from budget private rooms in a bed and breakfast in Massachusetts up to expensive oceanfront mansions. But crafty travelers can use Airbnb to find themselves a great deal and get even closer to where they want to explore.

The homes, cabins, and apartments are run with a mom-and-pop-type vibe by people that are excited to show off their homes and where they live. You should expect a welcoming experience, cozy bedrooms, and hopefully, a lovely view.

The Top 15 Airbnbs in Massachusetts

Ok folks, now it is time to dive into the fun stuff. Here are the best Airbnbs in Massachusetts!

Farm Stay | Overall Best Value Airbnb in Massachusetts

Farm Stay

Get away from the hustle and bustle of the city and soak in a quiet country setting at this Airbnb in Massachusetts. The home has its own separate entrance and a large living room with multiple bedrooms.

This Airbnb experience is a little bit different from others as it is located on a working farm. Come and meet cows, horses, pigs, chickens, ducks, and more!

Ideal for a group of friends, or a family with kids, you can take in the views from the private patio, or light up the fire pit and relax under the stars.

Little Paris | Best Budget Airbnb in Massachusetts

Little Paris

Save some pennies without venturing too far out of Boston with this Airbnb in Massachusetts. The large and cozy room will be waiting for you each night after a day of adventures.

Boston is an easy 10-minute drive away, so you don’t have to trade away proximity to save some money. Check out all the best things to do in Boston with a cozy home to return to.

Right down the road are local grocery stores and restaurants, and the spacious shared kitchen is open to be used.

Beyond your own private space, you will also have access to the patio, backyard, and grill. Cook a nice meal and relax in the backyard after a big day on the move.

If you picked up some marshmallows, feel free to start a campfire! Budget traveling doesn’t get much better!

Is This the Best Backpack EVER???
Aether Backpack

We’ve tested countless backpacks over the years, but there’s one that has always been the best and remains the best buy for adventurers: the broke backpacker-approved Osprey Aether and Ariel series.

Want more deetz on why these packs are so damn perfect? Then read our comprehensive review for the inside scoop!

View on Osprey View on REI

Cape Cod Estate | Over-the-Top Luxury Airbnb in Massachusetts

Cape Cod Estate

Pool together all the cash you have, gather your friends, and head to this incredible Cape Cod Estate. It features luxury you can only dream of.

There is a huge 8,000 square feet of living space, and multiple lush outdoor areas. With over two acres of lawns to yourself, this is the perfect spot for games. Soak in beautiful views of the pond located in the Lower Cape.

With eight bedrooms and 5.5 baths, each guest or couple will have their own private room. Meanwhile, the massive dining space will mean everyone has plenty of space to gorge.

During the day, you can head down to the sand bottom pond, and relax on the floating swimming dock.

Sun-Filled Apartment | Perfect Massachusetts Airbnb for Solo Travelers

Sun-Filled Apartment

At this airy, open-concept apartment, you can enjoy a sun-filled start to each day. This Airbnb in Massachusetts is placed nearby to many local amenities. Enjoy a lovely walk along the river to reach restaurants, shopping, bars, cinema, and even kayaking.

Have easy access to public transport that will take you to Cambridge, the home of Harvard University. Alternatively, stay on the bus to reach downtown Boston.

Each night, make use of the brand new kitchen and take your meal out to the patio to enjoy a cool breeze. End your day relaxing on the sofa with Netflix, or having a nightly stroll around the beautiful neighborhood.

Private Country Retreat | Perfect Short Term Airbnb in Massachusetts for Digital Nomads

Private Country Retreat (1)

For all digital nomads and remote workers, taking a trip away doesn’t mean signing off from work. Upon arrival, you will immediately feel at ease as the fresh country air fills your lungs.

The simple, one-bedroom cottage features a great work desk that overlooks the meadows. With no distractions, noisy neighbors, or crazy traffic, you can fly through your workday with ease.

Take your lunch breaks strolling through the 23 acres of rolling meadows, which boast an abandoned orchard. Alternatively, you can simply relax in the walled gardens.

For adventures beyond, head to Shelburne Falls or grab a beer in Northampton.

Travel with peace of mind. Travel WITH a security belt.
Active Roots Security Belt

Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.

It looks exactly like a normal belt except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)

Hide Yo’ Money!

More Epic Airbnbs in Massachusetts

Here are a few more of my favorite Airbnbs in Massachusetts!

Annisquam Village Cottage | Most Romantic Airbnb for Couples

Annisquam Village Cottage

Renovated by two artists, you will immediately appreciate the passion and style that has gone into the Bunny Cottage. But even more importantly, this home is perfect for walking around to explore.

Just a five-minute walk from the lighthouse and Cambridge beaches, as well as the wonderful Market Restaurant, you can stroll around town and enjoy the sights.

Wake up each morning with a French press coffee in hand as you take in the views from the private patio. Overlooking the garden on the lounge chairs, you can begin to plan the day.

The cottage has private access from the main house, so you can come and go as you please.

Cottage in Harwichport | Best Airbnb in Massachusetts for Families

Cottage in Harwichport

Take your family on a perfect Cape Cod vacation by heading to this beautiful cottage, which features three bedrooms, including a bunk-bed room.

Each evening, gather around the wood-burning fireplace inside the huge family room with vaulted ceilings. The galley-style kitchen is ideal for preparing home cooked meals on the nights you don’t fancy going out. Meanwhile, the lovely backyard patio will be great for relaxing in the sun and watching the kids run around.

When you wake up in the morning, the fresh sea breeze will float through the home, reminding you that a mere two-minute walk is all that stands between you and an exciting day at the beach.

Meanwhile, the town of Harwichport, with restaurants and family fun, is right down the road.

Graham Cracker House | Best Cottage on Airbnb in Massachusetts

Graham Cracker House

At the Graham Cracker House you can say goodbye to the world, and immerse yourself in beautiful nature. This newly renovated cottage is located on the crystal clear White’s Pond.

Enjoy private access to the pond, for swimming, fishing, and boating, and a spacious outdoor area perfect for eating alfresco and having a campfire each evening.

The home is within walking distance of the Cape Cod Rail Trail which will take you up and down the peninsula, while many of the best local beaches are a short drive away.

When you don’t feel like heading far, have fun on the kayaks provided with the home!

Traditional Log House | Best Cabin on Airbnb in Massachusetts

Traditional Log House

A cabin experience is always memorable. It is the kind of place you can immediately feel at home, so much so, that it will be the best part of your holiday.

This beautiful log cabin offers exactly that.

Perfectly located to explore the surrounding towns such as historic Plymouth, the beaches, and Cape Cod, this home is ideal for those who want to wander around. However, there is also much to see and do on the property itself. Private and heavily wooded, you can enjoy an escape to nature.

Across the street, you’ll discover cranberry bogs which are a constant hit with guests.

The rustic interior comes with a certain charm that you will never forget. It is warm, cozy, and has unforgettable views.

Rooftop Retreat | Best Condo on Airbnb in Massachusetts

Rooftop Retreat

Have wonderful views of the Boston skyline as you grill up a storm on the rooftop patio. This Airbnb in Massachusetts is a beautiful, renovated historic brownstone, decorated with an artistic vibe.

The condo is filled with records, art, and books along with all the trappings of home. All the while, the quiet neighborhood is waiting for you to come and explore.

Make the most of the short walk to public transport for easy access to downtown Boston and Cambridge. After a big day of exploring, relax and watch the sun go down from the rooftop.

Away from the excitement of the city, you can rest each night in peace, ready to explore again the following day!

Historic One Bedroom Airbnb in Town | Best Airbnb with Jacuzzi

Historic One Bedroom Airbnb in Town

A beautifully restored historic home, this Airbnb has one of the best Jacuzzis in the state of Massachusetts. When you aren’t admiring the beautiful streets of Plymouth, rest your weary legs in this Jacuzzi with a view.

The home is situated in town, just steps away from the Pilgrim’s first settlement. Plymouth is also home to a variety of award-winning restaurants, shops, nightlife, and numerous tours to historic landmarks.

Relax in the evenings on the plush king bed, and take your time getting ready in the morning. After all, you have this spacious home all to yourself. Make some coffee, and take in the brook views from the back deck.

Waterfront Condo | Best Airbnb for a Weekend in Massachusetts

Waterfront Condo

Get away for 48 hours and enjoy breathtaking views of the Provincetown Bay. This condo Airbnb opens up to the waterfront giving you easy access to the bay.

The condominium community is the only one in Provincetown that has its own grass area and a private beach with lounge chairs. When you aren’t admiring the views from your deck, enjoy a slice of luxury down by the water.

This home features one spacious bedroom with a queen size bed, and also a single bed if you have an extra guest, or small child.

Restaurants, nightlife, and the gallery district are all within walking distance. Enjoy stunning sunset views as you explore the bay on breezy evenings.

Romantic Ocean Views | Stunning Airbnb for Honeymooners in Massachusetts

Romantic Ocean Views

It’ll be hard to find a more romantic oceanfront Airbnb for your honeymoon to Massachusetts. Over two levels, this home has stunning views of the Atlantic Ocean, as well as the Boston skyline.

Enjoy an easy stroll to the beach each day, and in the evenings you can walk along the sand and have your choice of delightful oceanside restaurants.

Post dinner, wind down in hot tub, or stoke up the wood burning fireplace.

The morning sunrise will have the home glowing, adding another layer of romance. Cook a tasty brunch in the chef’s kitchen, and admire the gorgeous views from the comfort of the wrap-around patio.

Oceanfront Compound | Most Beautiful Airbnb in Massachusetts

Oceanfront Compound

This home incredibly beautiful and surrounded by coastal nature, earning its spot in our list of the best Airbnbs in Massachusetts. This oceanfront compound is one of the most spectacular homes on the exclusive island of Martha’s Vineyard.

Located on the precipice of Chilmark Bluff, the views are as intimidating as they are spectacular. You will feel on the edge of the world.

The immaculate property features four bedrooms including two master suites across a total of three homes. The large deck that connects them will be the perfect gathering place for your family and friends.

At night have your choice of an indoor or outdoor fire, or simply head up to the viewing platform and admire the stars.

Octagonal Glass Treehouse | Most Unique Airbnb in Massachusetts

Octagonal Glass Treehouse

Pack your bags and head to the Berkshires to stay at this incredible Airbnb. This home manages to combine the whimsical vibe of a treehouse with a spectacular circular home featuring floor-to-ceiling windows.

Regardless of where you stand, you can enjoy unobstructed views of the woods, while being elevated high up in the canopy.

The large back deck has outdoor dining and seating as well as a BBQ, so you can grill among the trees.

The seven private acres that surround the home are yours to explore every day. Meanwhile, the end of day activities will no doubt include lighting up the wood-burning fireplace.

What to Pack for Massachusetts

Pants, socks, underwear, soap?! Take it from me, packing for an Airbnb stay is not always quite as straightforward as it seems. Working out what to bring and what to leave at home is an art I have perfected over many years.

Don’t Let Snorers Keep You Awake!
Don’t Let Snorers Keep You Awake!

Ear Plugs

Snoring dorm-mates can ruin your nights rest and seriously damage the hostel experience. This is why I always travel with a pack of decent ear plugs.

Keep your laundry organized and stink free
Keep your laundry organized and stink free

Hanging Laundry Bag

Trust us, this is an absolute game changer. Super compact, a hanging mesh laundry bag stops your dirty clothes from stinking, you don’t know how much you need one of these… so just get it, thank us later.

Stay Dry With a Micro Towel
Stay Dry With a Micro Towel

Sea To Summit Micro Towel

Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight, and can be used as a blanket or yoga mat if need be.

Make Some New Buddies…
Make Some New Buddies…

Monopoly Deal

Forget about Poker! Monopoly Deal is the single best travel card game that we have ever played. Works with 2-5 players and guarantees happy days.

Reduce Plastic – Bring a Water Bottle!
Reduce Plastic – Bring a Water Bottle!

Grayl Geopress Water Bottle

Always travel with a water bottle! They save you money and reduce your plastic footprint on our planet. The Grayl Geopress acts as a purifier AND temperature regulator. Boom!

Don’t Forget Your Massachusetts Travel Insurance

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing.

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

Final Thoughts on Massachusetts Airbnbs

As you can see, one of the best ways to get around is by staying at an Airbnb in Massachusetts. Whether you want a unique vacation full of memories or a well-located studio to catch a red-eye flight, there’s a perfect Airbnb for you.

The best Airbnbs in Massachusetts will bring your destination to life. Budget travelers can snag themselves an ocean view, couples can have romantic retreats, and families can have entire homes to themselves.

One thing is for sure, your accommodation will be remembered as much as the adventure itself. The unique properties will be hard to leave, and you just might find yourself clicking the button for round two.

Looking for more info on visiting Massachusetts and USA?