Luxury homes 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

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

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

This updated rental is located in the heart of Osterville walking distance to the village, restaurants, marina, and beaches. There are four bedrooms including a first floor master...

Presented by Jennifer McCartin | 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

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

Welcome to 147 Scudder Road in Osterville! This charming rental offers the perfect blend of convenience and relaxation, just a short stroll away from Main Street and the pristine...

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

Spring, summer, fall rental. Not available as a yearly rental. Just a quick stroll to the village and 1.24 miles to the beach. This pretty Ranch features three bedrooms (two...

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