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

Whether you want to take in those autumnal vibes or go for a vacation on the Atlantic coastline, Massachusetts is a dream destination for digital detoxes and swanky city breaks.

There are so many different types of lodging options that will make your experience unique.

There are some cool Airbnbs in Massachusetts.

Modern Waterfront Getaway

This waterfront property has space for nine people. It’s a great place to take kids or a weekend getaway for girlfriends.

Chatham Cottage

Chatham, Massachusetts

This studio cottage is fitted with a queen bed, a full bath, and a charming kitchen. 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.

Riverfront Getaway

Chester, Massachusetts

This two-bedroom peaceful oasis in Chester overlooks the river. Sit on the deck and soak in the warmth of a hot tub then sleep in bed while listening to the rushing water.

Seaside Haven

New Seabury, Massachusetts

This fashionable beach house has been completely renovated and offers magnificent views of the ocean. It is also steps away from a private beach; it doesn’t get much better than that does it?

Seaside Haven

New Seabury, Massachusetts

This luxurious beach house was 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?

The Writer’s Retreat

Orange, Massachusetts

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

Nature Reserve Tiny House

North Adams, Massachusetts

This is a perfect spot for a romantic getaway. Cook a barbeque and uncork a bottle of wine while you take in the breath-taking view from the top of the Hoosac Range.

Octagonal Glass Treehouse

Otis, Massachusetts

This tree house is truly breathtaking. The jaw-dropping vistas, cozy fireplaces, and chic designer touches make this place amazing.

Eliza Cottage

Nantucket, Massachusetts

Dream about a Nantucket getaway? This quintessential Nantucket home overlooks the harbor. It’s located next door to White Elephant and only a five-minute stroll to Main Street.

Secluded Cabin Next to a Babbling Brook

Monterey, Massachusetts

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

Cottage off Main Street

Nantucket, Massachusetts

This charming cottage sleeps up to six.

You will want to spend hours in the garden, because it has a beautiful patio dining area and a garden full of roses and hydrangeas.

Rustic Berkshire Getaway

Otis, Massachusetts

On the outskirts of Jacobs Pillow, this rustic two-bedroom space has stunning views from the spacious outdoor porch.

High Tide Cottage

Ipswich, Massachusetts

There is a place hidden on an island called Little Neck in Ipswich that is such a dream.

Little Neck is a gated community where you can live in the past. With its private streets and gates, it looks like a small town.

The cottage sleeps up to eight people and includes all modern amenities. It is just a few hundred yards from the ocean. You will have access to a kayak, dock and two kids’ playgrounds along with views of the beach and sand dunes from every room!

Modernized Historic Home

North Adams, Massachusetts

This two-bedroom house 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.

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. Walk to Rockport, which is a village to the north, or spend the day exploring the secluded hiking trails.

Quaint Private Garden Cottage

Uxbridge, Massachusetts

This teeny tiny house will transport you back to the days when you had a secret fort in your backyard.

The Enchanting Tiny Tower at Santarella Gardens

Lee, Massachusetts

This tiny house in the Berkshires looks out of a fairytale. If you are looking to take your knight in shining armor away for the weekend, look no further.

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 and quartzite kitchen and cozy space.

Ocean View Unit with Private Roof Deck

Rockport, Massachusetts

In Rockport you will find a two bedroom apartment with a view of the sea. Kayak in the harbor and taste the ultra-fresh seafood. Back in your apartment, take a break on your roof deck and enjoy the beautiful view.

A really authentic Old-West style home. A real Old West style house.

Marblehead, Massachusetts

This restored nineteenth-century home offers a bedroom for four in Old Town Marblehead. You can barbecue on the back patio, then explore Salem by foot, just outside your door.

Two-Bedroom Cape Cod Cottage

Denis, Massachusetts

Go to the beach and go for a canoe ride. The host will provide you with a canoe and kayaks, so you can paddle around in the bay at your leisure.

Central Boston One-Bedroom

Boston, Massachusetts

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

Quintessential Salem Gothic Home

Salem, Massachusetts

You will feel like you have stepped back in time at this quirky space, which has room for four people.

Pet-Friendly Cottage

Provincetown, Massachusetts

This cozy Victorian cottage is located in the best restaurants and shops in Provincetown. It’s within five minutes driving you can be on some of the most beautiful beaches of Massachusetts.

Charming Lake Cottage

Wrentham, Massachusetts

This lovely cottage is 35 minutes from Boston and 30 minutes from Providence. It was constructed in 1905, so it will have you in the center of all the best options.