Massachusetts Vacation Rentals

New England cottages and homes available to rent for your next vacation.

USA > Massachussetts

Plan your Massachusetts vacation

Steeped in American history and touched by natural beauty, Massachusetts offers many options to travelers. Stroll along historic cobblestone streets, savor delectable seafood along the scenic coastline, and experience the vibrant museums, art galleries, and cultural events across the cities and towns that call Massachusetts home. Whether you plan to explore the nearly 200 miles of picturesque coastline or walk in the footsteps of our forefathers, a stay at one of our vacation rentals is sure to help you discover what makes this state revolutionary in more ways than one!

Favorite Massachussetts Destinations

Property Management You Can Trust

Owning a vacation rental shouldn’t be stressful. Let SkyRun ease your worries and increase your revenue with our vacation rental management solutions.

Why choose SkyRun? As locally owned businesses, our homeowners are not just a number to us, they’re our neighbors. But as a franchise, we have access to tools and tech that help you stay ahead of the game. That’s why thousands of second homeowners trust us with their properties.

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If you are looking for the best full service vacation rental property management, stop searching and call SkyRun. They have systems and processes in place to ensure the highest possible short term rental revenue and guests love them! We couldn’t be happier with their management of our homes.

TheodoreScottsdale, Arizona

“My property’s income has doubled in the last year! SkyRun is a great business partner to me and their willingness to listen and grow revenue has been stellar.”


Kay JohnsonDestin, FL

With SkyRun, we immediately felt respected as homeowners. We’ve owned in Ridgepoint for over 25 years. This is not our first rodeo, but it is our best one.

Ken & DianaBeaver Creek, CO

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