Massachusetts Vacation Rentals New England cottages and homes available to rent for your next vacation. All of MassachusettsCape Cod Area Cotuit Dennisport Eastham Falmouth Mashpee Sandwich Welfleet Yarmouth People 1+ 2+ 3+ 4+ 5+ 6+ 7+ 8+ 9+ 10+ 11+ 12+ USA > Massachusetts 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 Massachusetts Destinations Dennis, MACape Cod, MAYarmouth, MAFalmouth, MA Find Your Massachusetts Rental 17 Liberty Street Sandwich, MA 8 Guests 2 Bdrms 1 Bath From $498/night incl. feesnext avail May 14–19, 2027 · 5-night min New Property 88 Ashumet Road East Falmouth, MA 7 Guests 4 Bdrms 2 Baths From $968/night incl. feesnext avail Oct 8–9 New Property 87 Regis Road East Falmouth, MA 7 Guests 4 Bdrms 1 Bath From $751/night incl. feesnext avail Oct 8–9 New Property 56 Baxter Ave West Yarmouth, MA 4 Guests 2 Bdrms 1 Bath From $564/night incl. feesnext avail Oct 17–18 New Property 55 Pawkannawkut Drive South Yarmouth, MA 6 Guests 3 Bdrms 1 Bath From $585/night incl. feesnext avail Oct 11–12 The Shore House Falmouth, MA 6 Guests 3 Bdrms 1 Bath From $751/night incl. feesnext avail Oct 8–9 New Property 65A Boreen Eastham, MA 6 Guests 2 Bdrms 0 Baths From $625/night incl. feesnext avail Oct 8–9 New Property 65 Boreen Eastham, MA 6 Guests 2 Bdrms 0 Baths From $635/night incl. feesnext avail Oct 8–9 Featured Property 146 Telegraph Dennis Port, MA 7 Guests 3 Bdrms 2 Baths From $497/night incl. feesnext avail Oct 27–30 · 3-night min 12 Paola Drive East Falmouth, MA 6 Guests 3 Bdrms 1 Bath From $641/night incl. feesnext avail Oct 8–9 Wellfeet Retreat Wellfleet, MA 6 Guests 3 Bdrms 1 Bath From $445/night incl. feesnext avail Oct 11–13 · 2-night min New Property 65 & 65A & 85 Boreen Eastham, MA 12 Guests 6 Bdrms 0 Baths From $807/night incl. feesnext avail Oct 8–9 Search while moving Featured Massachusetts Vacation Rentals Featured Property 146 Telegraph Dennis Port, MA 7 Guests 3 Bdrms 2 Baths From $497/night incl. feesnext avail Oct 27–30 · 3-night min Featured Property 430 Davisville Road East Falmouth, MA 4 Guests 2 Bdrms 1 Bath From $570/night incl. feesnext avail Oct 8–9 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. Learn More 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 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 Sign up for emails Trip inspiration, special offers, and vacation planning tips. Name(Required) First Last Email By submitting this form, I agree to SkyRun’s Privacy Policy Δ
