The Coolest Airbnbs in Massachusetts

This post has been updated to include a roundup of my favorite boutique properties and vacation rentals in Massachusetts.

Whether you are looking to take in those autumnal vibes or want to soak in the sun on the Atlantic coastline, Massachusetts is the place to be. It’s a dream destination for digital detoxes and swanky city breaks alike.

From rustic cabins to urban oases, there are so many unique accommodation options that will elevate your experience.

Here are the coolest Airbnbs in Massachusetts!

And don’t miss my round-up of the best hotels in Boston, if you’re spending some time in the city!

Modern Waterfront Getaway

With space for nine, this sunny waterfront is a picture-perfect space for a retreat. Whether you’re traveling with kids or planning a girlfriend’s getaway, this property ticks all of the boxes.

BOOK HERE

Chatham Cottage

Chatham, Massachusetts

This studio cottage is fitted with a queen bed, a full bath, and a charming kitchenette. The backyard area is an ideal hangout spot with a brick patio and pergola—complete with a grill—and an outdoor shower for after the beach.

BOOK HERE

Riverfront Getaway

Chester, Massachusetts

This two-bedroom tranquil oasis in Chester overlooks the river and will make you feel right at home. Lounge on the deck, soak in the warmth of a hot tub, then just lie in bed and listen to the water flowing by.

BOOK HERE

Seaside Haven

New Seabury, Massachusetts

This classy beach house has been completely renovated and has magnificent views of the ocean. It’s also just steps away from a private beach—doesn’t get much better than that, does it?

BOOK HERE

Seaside Haven

New Seabury, Massachusetts

This classy beach house has been completely renovated and has magnificent views of the ocean. It’s also just steps away from a private beach—doesn’t get much better than that, does it?

BOOK HERE

The Writer’s Retreat

Orange, Massachusetts

This cottage for two on the shores of Tully Pond was made for rustic retreats. Cook your dinner over the fire, grab a book from the ample library, and simply unplug.

BOOK HERE

Nature Reserve Tiny House

North Adams, Massachusetts

Standing on the highest peak of the Hoosac Range, this unique space for two was is perfect for romantic escapes. Get the barbeque started, uncork that wine, and sit back to admire the breathtaking view.

BOOK HERE

Octagonal Glass Treehouse

Otis, Massachusetts

This treehouse in the Berkshires is truly breathtaking. From the jaw-dropping vistas to cozy fireplaces to the chic designer touches, this place impresses at every turn.

BOOK HERE

Eliza Cottage

Nantucket, Massachusetts

Dream of a Nantucket getaway? This quintessential Nantucket home overlooks the harbor, along with Children’s Beach and Park. It’s located next door to White Elephant and just a five-minute stroll to Main Street.

BOOK HERE

Secluded Cabin Next to a Babbling Brook

Monterey, Massachusetts

This three-bedroom cabin, with its wood-burning fireplace and professional kitchen, has all of the modern amenities in a picturesque forest by a bubbling stream.

BOOK HERE

Cottage off Main Street

Nantucket, Massachusetts

This charming cottage in the heart of the historic district on Main Street in Nantucket sleeps up to 6.

With the outside blooming with roses and hydrangeas and a lovely patio dining area, you’ll want to spend hours in the garden after days wandering the town.

BOOK HERE

Rustic Berkshire Getaway

Otis, Massachusetts

Just outside of Jacob’s Pillow, this two-bedroom rustic space has stunning views from the spacious outdoor porch.

BOOK HERE

High Tide Cottage

Ipswich, Massachusetts

Would you take a look at this hidden gem! Located on a small island (or rather a peninsula) called Little Neck in Ipswich, this place is such a dream.

Little Neck is a gated, private community where you can step back in time and relax with your family.

The 100-year-old cottage sleeps up to 8 and has been updated with all modern amenities. Plus, the beach is just about 100 yards away! You’ll have access to a kayak, a dock, and two kids’ playgrounds, along with views of the beach and sand dunes from every room.

BOOK HERE

Modernized Historic Home

North Adams, Massachusetts

Built in 1875, this two-bedroom home has been lovingly restored. With vintage touches throughout (and modern updates where it matters), this is the perfect base for exploring swanky restaurants or hiking through the waterfalls.

BOOK HERE

Dogtown Cabin at Applecart Farm

Rockport, Massachusetts

This quaint cabin has room for five (and your four-legged friends) in the woods of Cape Ann. Meet the neighboring miniature horses, walk to Rockport, or spend the day exploring the secluded hiking paths.

BOOK HERE

Quaint Private Garden Cottage

Uxbridge, Massachusetts

With room for three in the historic Uxbridge, this teeny tiny house will transport you back to the days you dreamt of having a secret fort in the backyard.

BOOK HERE

Enchanted Tiny Tower at Santarella Gardens

Lee, Massachusetts

This whimsical tiny house in the Berkshires looks straight out of a fairytale. If you’re looking to take your knight in shining arming away for the weekend, look no further.

BOOK HERE

Gorgeous Oceanfront Penthouse

Swampscott, Massachusetts

This tastefully designed penthouse has breathtaking views of the ocean. Perfect for couples, this studio space has luxe touches like a jetted tub, quartzite kitchen, and cozy space.

BOOK HERE

Ocean View Unit with Private Roof Deck

Rockport, Massachusetts

In Rockport, you’ll find this two-bedroom apartment with a sweeping sea view. Kayak in the harbor, sample the ultra-fresh seafood, then come back and lounge on your roof deck and take in the beautiful vista.

BOOK HERE

Authentic Rustic Single Family Home in Old Town

Marblehead, Massachusetts

This thoughtfully restored nineteenth-century home offers room for four in Old Town Marblehead. Barbeque on the backyard patio, then explore the very best of Salem right outside of your doorsteps.

BOOK HERE

Two-Bedroom Cape Cod Cottage

Denis, Massachusetts

Featured in Boston Globe Magazine, this modern and minimalist space is within walking distance of the beach. Grab the canoe and kayaks provided by the host, and start exploring.

BOOK HERE

Central Boston One-Bedroom

Boston, Massachusetts

In the swanky Back Bay neighborhood, this one-bedroom apartment is perfect for two. Explore the designer boutiques, galleries, and cool cafes right outside of your door from this dream base.

BOOK HERE

Quintessential Salem Gothic Home

Salem, Massachusetts

Just off Essex street, you’ll feel like you’ll like you’ve stepped back in time. With room for four, this quirky space is inspired by a Victorian British library.

BOOK HERE

Pet-Friendly Cottage

Provincetown, Massachusetts

This cozy Victorian cottage has a dream location amongst the best restaurants and shops in Provincetown and, within less than five minutes’ driving, you can be on some of the most beautiful beaches in Massachusetts.

BOOK HERE

Charming Lake Cottage

Wrentham, Massachusetts

This lovely three-bedroom cottage is just 35 minutes from Boston and 30 minutes from Providence. Constructed in 1905, this home will have you in her center of all the best options.

BOOK HERE

Want to keep on exploring? Keep on driving north then check out the Ultimate Guide to Visiting the Maine Coast.

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Max

Thank you for sharing amazing information and photos. I love your all blogs. This place is so beautiful.

February 25, 2021 at 1:12 am · Reply

The Blonde Abroad

Thanks so much!

March 2, 2021 at 5:39 pm · Reply

Instagram

🎶 The hills are alive with the sound of music 🎶
••••••••••••••••••••••••••••
Love the Sound of Music? What if I told you that you can visit the real Von Trapp family’s lodge from the famed musical starring Julie Andrews in the quiet town of Stowe, Vermont?

Day 7 of my Autumn New England Road Trip (with a toddler) started the day by driving through Smuggler’s Notch—it’s a short and super windy drive through a mountain pass that’s seriously beautiful.

Helpful Tip: Get started on the drive as easy as possible. Traffic is notorious during foliage season so we hit the road at 7am and had it to ourselves!

We then spent the entire day exploring nature trails and hanging with animals at @trappfamilylodge, an Austrian-inspired mountain lodge with 300 acres of farmland in the middle of Stowe.

The Von Trapps, made famous from the movie The Sound of Music, fled Austria during WWII and ultimately landed in Stowe, VT where their hospitality lives on today. Did you know the Sound of Music is one of the top 10 highest-grossing films of all time??

Had we had a little more time, we also would have added:

🥾 Moss Glen Falls
⛪️ Stowe Community Church
🍻 @alch3mistb33r
☕️ @blackcapvermont
🥞 @butlers_pantry_stowe

We did manage to catch a glimpse of the famed Stowe Community Church from afar, but any closer meant fighting traffic and huge crowds.

Come back for day 8 and the final video of the series as we explore the beautiful and family-friendly parts of Boston!
••••••••••••••••••••••••••••
@vermonttourism @visitnew_england
#vermont #newenglandroadtrip #stowevermont

668 10

🎶 The hills are alive with the sound of music 🎶
••••••••••••••••••••••••••••
Love the Sound of Music? What if I told you that you can visit the real Von Trapp family’s lodge from the famed musical starring Julie Andrews in the quiet town of Stowe, Vermont?

Day 7 of my Autumn New England Road Trip (with a toddler) started the day by driving through Smuggler’s Notch—it’s a short and super windy drive through a mountain pass that’s seriously beautiful.

Helpful Tip: Get started on the drive as easy as possible. Traffic is notorious during foliage season so we hit the road at 7am and had it to ourselves!

We then spent the entire day exploring nature trails and hanging with animals at @trappfamilylodge, an Austrian-inspired mountain lodge with 300 acres of farmland in the middle of Stowe.

The Von Trapps, made famous from the movie The Sound of Music, fled Austria during WWII and ultimately landed in Stowe, VT where their hospitality lives on today. Did you know the Sound of Music is one of the top 10 highest-grossing films of all time??

Had we had a little more time, we also would have added:

🥾 Moss Glen Falls
⛪️ Stowe Community Church
🍻 @alch3mistb33r
☕️ @blackcapvermont
🥞 @butlers_pantry_stowe

We did manage to catch a glimpse of the famed Stowe Community Church from afar, but any closer meant fighting traffic and huge crowds.

Come back for day 8 and the final video of the series as we explore the beautiful and family-friendly parts of Boston!
••••••••••••••••••••••••••••
@vermonttourism @visitnew_england
#vermont #newenglandroadtrip #stowevermont

Arguably the MOST “autumnal” day of the trip: 🍎 🍂 🍩
•••••••••••••••••••••••••••••
Welcome back to my Autumn New England Road Trip (with a toddler) series! We’re over halfway through our road trip on Day 6 and this was the perfect day of all things autumn.

After a slow morning leaving @woodstock.inn, we were on our way to the famous town of Stowe, Vermont!

I had originally created a jam-packed itinerary, but traveling with a toddler can definitely call for some readjusting and going with the flow. We made 2 of the stops I had planned:

🍎🌳 Hunger Mountain Orchard
🍎🍩 @coldhollowcidermillvt

If we had a little more time, a lot of people add the 🍦 @benandjerrys factory tour on this day.

We ended our day by checking into the @trappfamilylodge —owned by the real family from the Sound of Music where we enjoyed the lodge and property before dinner and bedtime.

Be sure to come back for Day 7 with more on this amazing property and all the furry friends that live here!
•••••••••••••••••••••••••••••
@vermonttourism @visitnew_england
#vermont #newenglandroadtrip #stowevermont

559 21

Arguably the MOST “autumnal” day of the trip: 🍎 🍂 🍩
•••••••••••••••••••••••••••••
Welcome back to my Autumn New England Road Trip (with a toddler) series! We’re over halfway through our road trip on Day 6 and this was the perfect day of all things autumn.

After a slow morning leaving @woodstock.inn, we were on our way to the famous town of Stowe, Vermont!

I had originally created a jam-packed itinerary, but traveling with a toddler can definitely call for some readjusting and going with the flow. We made 2 of the stops I had planned:

🍎🌳 Hunger Mountain Orchard
🍎🍩 @coldhollowcidermillvt

If we had a little more time, a lot of people add the 🍦 @benandjerrys factory tour on this day.

We ended our day by checking into the @trappfamilylodge —owned by the real family from the Sound of Music where we enjoyed the lodge and property before dinner and bedtime.

Be sure to come back for Day 7 with more on this amazing property and all the furry friends that live here!
•••••••••••••••••••••••••••••
@vermonttourism @visitnew_england
#vermont #newenglandroadtrip #stowevermont

Fall fashion is my favorite! What about you? 🍁
••••••••••••••••••••••••••••••••••••••••••••
My recent trip to New England was the perfect opportunity to pack my @meet.nex bags with some cute new styles perfect for any trip!

Nex luggage is super high-quality and will hold up on any adventure. Their Million Mile Care program is also one-of-a-kind. You can trade in your used luggage towards credit for new luggage!

I get so much use out of the Nex crossbody and backpack in Lanikai Amber—they’re my go-to for camera gear and toddler essentials. And you can style them with just about every outfit!
••••••••••••••••••••••••••••••••••••••••••••
Click my link in bio for my luggage and favorite fall styles! #ad

691 16

Fall fashion is my favorite! What about you? 🍁
••••••••••••••••••••••••••••••••••••••••••••
My recent trip to New England was the perfect opportunity to pack my @meet.nex bags with some cute new styles perfect for any trip!

Nex luggage is super high-quality and will hold up on any adventure. Their Million Mile Care program is also one-of-a-kind. You can trade in your used luggage towards credit for new luggage!

I get so much use out of the Nex crossbody and backpack in Lanikai Amber—they’re my go-to for camera gear and toddler essentials. And you can style them with just about every outfit!
••••••••••••••••••••••••••••••••••••••••••••
Click my link in bio for my luggage and favorite fall styles! #ad

Bienvenidos a Oaxaca! 🇲🇽
••••••••••••••••••••••••••••••••••••
I recently visited this vibrant, colorful city just in time for some of the Dia de los Muertos celebrations and it did not disappoint! From walking the cobblestone streets lined with colorful murals to witnessing centuries’ old architectural marvels, this entire city is an UNESCO World Heritage Site with beautiful sites around every corner.

There are tons of epic @vrbo vacation homes in Oaxaca—perfect for a group trip!

One of the major highlights of Oaxaca is the FOOD 🤤 Traditional cuisine like mole, mezcal, tlayuda, quesillo, and even… chapulines (aka fried grasshoppers! 😱) are a must. Foodies and adventurous diners alike will find themselves with more than a few delicious options here in Oaxaca.

Add these highlights to your Oaxaca bucket list:

🇲🇽 Shop at the artisan markets
🇲🇽 Get down on some delicious street food
🇲🇽 Try a traditional cooking class
🇲🇽 Take a day trip to Hierve el Agua
🇲🇽 Experience a temazcal ceremony
🇲🇽 Discover the countless murals
🇲🇽 Visit during Dia de Los Muertos

Did you know you can also book activities with some of the best local, hidden gems, through @expedia?

Try a traditional cooking class, book a local photographer, or enjoy a mezcal and mole tasting with a certified sommelier through the @Expedia app!

Have you been to Oaxaca? What time of year did you go and what was your favorite part??
••••••••••••••••••••••••••••••••••••
#mexico #oaxaca #diadelosmuertos

1162 34

Bienvenidos a Oaxaca! 🇲🇽
••••••••••••••••••••••••••••••••••••
I recently visited this vibrant, colorful city just in time for some of the Dia de los Muertos celebrations and it did not disappoint! From walking the cobblestone streets lined with colorful murals to witnessing centuries’ old architectural marvels, this entire city is an UNESCO World Heritage Site with beautiful sites around every corner.

There are tons of epic @vrbo vacation homes in Oaxaca—perfect for a group trip!

One of the major highlights of Oaxaca is the FOOD 🤤 Traditional cuisine like mole, mezcal, tlayuda, quesillo, and even… chapulines (aka fried grasshoppers! 😱) are a must. Foodies and adventurous diners alike will find themselves with more than a few delicious options here in Oaxaca.

Add these highlights to your Oaxaca bucket list:

🇲🇽 Shop at the artisan markets
🇲🇽 Get down on some delicious street food
🇲🇽 Try a traditional cooking class
🇲🇽 Take a day trip to Hierve el Agua
🇲🇽 Experience a temazcal ceremony
🇲🇽 Discover the countless murals
🇲🇽 Visit during Dia de Los Muertos

Did you know you can also book activities with some of the best local, hidden gems, through @expedia?

Try a traditional cooking class, book a local photographer, or enjoy a mezcal and mole tasting with a certified sommelier through the @Expedia app!

Have you been to Oaxaca? What time of year did you go and what was your favorite part??
••••••••••••••••••••••••••••••••••••
#mexico #oaxaca #diadelosmuertos

Is this the cutest town in Vermont? 🍁
••••••••••••••••••••••••••••••••••••••••••••
This is Day 5 of our New England Road Trip with a Toddler Series! We stayed at the @woodstock.inn for 2 nights and set aside a full day to explore Woodstock .

With Woodstock Inn & Resort is situated in the heart of Woodstock, so it gave us the perfect opportunity to explore the town by foot. There are cute shops, cafes, and it’s so festive during foliage season.

My number one tip here is to reserve your room at Woodstock Inn early! Woodstock is a small town, and especially during fall foliage season, it can be fully booked up a year in advance.

BONUS TIP: We booked our room through Amex Travel and got tons of perks like early check-in/late check-out, daily breakfast for 2, a room upgrade, guaranteed 4 pm check-out, and a $100 resort credit (which mama DEF used for a massage at the spa).

We spent our morning at @billingsfarm and got to meet some dairy cows and other farm animals. Kids will love this spot! 
In town, be sure to grab a Maple Creemee (a maple soft serve ice cream) from @woodstockscoops. Visit the F. H. Gillingham & Sons General Store to shop for TONS of local products like maple syrup. And The Village Butcher Shop is a great deli for yummy sandwiches & deli meats & cheese.

We wanted to eat at @simonpearcerestaurant but it was already fully booked (two months in advance!!!) so plan ahead.  Stay tuned for Day 6 for apple picking, cider donuts, and the cutest family-friendly lodge in Vermont! •••••••••••••••••••••••••••••••••••••••••••• Have you been to Woodstock, Vermont?

@vermonttourism @visitnew_england
#vermont #newenglandroadtrip #woodstockvermont

1026 23

Is this the cutest town in Vermont? 🍁
••••••••••••••••••••••••••••••••••••••••••••
This is Day 5 of our New England Road Trip with a Toddler Series! We stayed at the @woodstock.inn for 2 nights and set aside a full day to explore Woodstock .

With Woodstock Inn & Resort is situated in the heart of Woodstock, so it gave us the perfect opportunity to explore the town by foot. There are cute shops, cafes, and it’s so festive during foliage season.

My number one tip here is to reserve your room at Woodstock Inn early! Woodstock is a small town, and especially during fall foliage season, it can be fully booked up a year in advance.

BONUS TIP: We booked our room through Amex Travel and got tons of perks like early check-in/late check-out, daily breakfast for 2, a room upgrade, guaranteed 4 pm check-out, and a $100 resort credit (which mama DEF used for a massage at the spa).

We spent our morning at @billingsfarm and got to meet some dairy cows and other farm animals. Kids will love this spot! 
In town, be sure to grab a Maple Creemee (a maple soft serve ice cream) from @woodstockscoops. Visit the F. H. Gillingham & Sons General Store to shop for TONS of local products like maple syrup. And The Village Butcher Shop is a great deli for yummy sandwiches & deli meats & cheese.

We wanted to eat at @simonpearcerestaurant but it was already fully booked (two months in advance!!!) so plan ahead.  Stay tuned for Day 6 for apple picking, cider donuts, and the cutest family-friendly lodge in Vermont! •••••••••••••••••••••••••••••••••••••••••••• Have you been to Woodstock, Vermont?

@vermonttourism @visitnew_england
#vermont #newenglandroadtrip #woodstockvermont