Luxury Properties for rent in Osterville, Massachusetts

236B Smoke Valley is serene and surrounded by nature, offering peaceful mornings, beautiful sunsets, and water access right outside your door. A deep-water pier and float can...

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

Pretty Osterville ranch in the heart of Wianno. This home is just moments to Main Street's fine restaurants, shops, library and beautiful Dowses Beach. Features include three...

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

Osterville Summer Rental! $2500/week or minimum of three-night stay; please call for nightly and off-season rates! This Osterville home is uniquely styled with fine furnishings...

Presented by Marina Davalos | 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

Escape to one of Cape Cod’s most coveted neighborhoods with this beautifully renovated 5-bedroom, 5-bath home in Wianno. Perfect for family gatherings or a relaxing getaway, this...

Presented by Gene Orloff | 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