Luxury Properties for rent in Osterville, Massachusetts

Spend your Cape Cod vacation in this magnificent property located on Garrison Lane in Osterville. Enjoy your days relaxing by the private pool surrounded by professionally...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Prepare to indulge in the Osterville lifestyle with this sophisticated Cape house with deeded beach rights to picturesque North Bay. As you enter the front door, experience the...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Welcome to your ideal summer retreat at 360 Main St, Osterville. This exceptional property offers everything you need for a luxurious and relaxing stay. Enjoy the stunning outdoor...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

This home is located in the heart of Wianno, only minutes to Dowses Beach and the village of Osterville. The first floor offers an open floorplan including living room, dining,...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Osterville Village! Leave your car at home! You'll fall in love with this updated ranch set in the heart of Osterville that offers a modern and stylish coastal living experience...

Presented by Colleen Riley | Sotheby's International Realty - Osterville Brokerage

Off the beaten path, this long driveway leads to a magnificent waterfront property. Enjoy the breathtaking views and gorgeous sunsets overlooking West Bay. This home features five...

Presented by Jan Macallister | Sotheby's International Realty - Osterville Brokerage

Osterville Village! Discover the true feeling of coastal living in this newly remodeled home with detached cottage, just a short stroll to Joshua's Pond. The main house sleeps 4,...

Presented by Colleen Riley | Sotheby's International Realty - Osterville Brokerage

Perfectly located between Dowses Beach and the Village on a quiet side street, this updated four bedroom, three bath home will be a perfect vacation spot. This bright kitchen has...

Presented by Jennifer McCartin | Sotheby's International Realty - Osterville Brokerage

Majestically sited high on a hill is this dramatic Nantucket Style one of a kind Cottage. All newly renovated to perfection with every detail throughout. A world unto itself with...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Cape Cod summertime magic awaits at this classic shingled charmer in the heart of Wianno. Just moments from Osterville Village and Dowses beach, and superbly appointed, everything...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Welcome to Seasons by the Sea! This fully remodeled Osterville home offers four bedrooms, three and a half baths and all the outdoor living space for a perfect beach vacation....

Presented by Jan Macallister | Sotheby's International Realty - Osterville Brokerage

This charming three-bedroom, two bath home is located in the heart of Wianno. Dowses Beach and the village center are just a short distance away. After a relaxing day at the...

Presented by Jan Macallister | Sotheby's International Realty - Osterville Brokerage

Coastal charm at its best. This home is a short stroll to Osterville Village and Dowses Beach, sits on an expansive lot with plenty of room for backyard play. A sizeable...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Spring, summer, fall rental. Not available as a yearly rental. In the heart of Osterville - this pretty Ranch features two bedrooms (a master with private bath and full bed), a...

Presented by Joanne Murphy | Sotheby's International Realty - Osterville Brokerage

Spring, summer, fall rental Elegant two-bedroom, one-bath cottage. All living spaces are on ground level. Located on a quiet cul-de-sac, just two minutes to Osterville Center....

Presented by Bonnie Zappala Britt | Sotheby's International Realty - Osterville Brokerage