Osterville: Vacation Rental By Owner

Beautifully decorated 5 Bedroom 4.5 Bathroom home in the Wianno section of Osterville. This 3400 square-foot home is laid-out beautifully for your next family... ...more

Large contemporary home on private waterfront 2 1/2 acres. Located on North Pond and just a mile from Craigville Beach. Additional $200,000 in upgrades just... ...more

A five minute walk to the Wianno Club on Seaview Ave and Dowse's Beach, this four bedroom, four bath home is being renovated this winter (2018) with all new,... ...more

Beautifully presented summer home on an acre of land, featuring a brand new gunite 18 x 36 ft heated pool, is perfect for family gatherings. Four bedrooms plus... ...more

Exclusive Robert Paul Properties rental home less than a mile to heart of downtown Osterville and 1 mile to Dowses Beach this location is perfect! This lovely,... ...more

Enjoy the water views and the boats as they go by from this grand and classic Cape Cod summer house with fabulous views and sea breezes. This lovely home has a... ...more

Located on a quiet street mere blocks to Osterville Village and Dowses Beach, this lovely 3 bedroom, 1.5 bath year round ranch home affords plenty of room for... ...more

Our quaint cottage is located just a minute's walk from Osterville's village center, with its upscale shopping, dining and charming ambiance. It's a quick bike... ...more

Welcome to Primrose Cottage, a perfect getaway or seasonal rental. This beautiful, custom designed Cape Cod style home offers an amazing open floor plan with... ...more

Newly renovated 3,000 sq ft Osterville Cape, located on a private setting. Enjoy entertaining in the gourmet kitchen with 10ft granite island or outside on... ...more

Newly renovated 3,000 sq ft Osterville home that boasts the detail of a traditional Cape as well as the luxury of a newly renovated addition. Enjoy entertaining... ...more

Anchor to Windward consists of a main house with 5 bedrooms and 5.5 baths and a boathouse directly on a private beach with 3 bedrooms and 2 baths. The property is... ...more

Imagine getting home from one of the beaches the complimentary beach pass allows you to visit, then washing off the sand in your enclosed outdoor shower. Relax in... ...more

-Location! Location! Location! Perfect for two families (4 bedrooms double occupancy (8) with two of the bedrooms with an extra twin bed each for 2 additional... ...more

Designer's property: Separate entry to guest house with one gueen bedroom, vaulted ceilings, 3/4 bath , plus the lovely 'summer living room' (screened... ...more

Osterville on Cape Cod. Pleasant Cape Cod-style home one block from North Bay just off Bay Street. Walk to village and shops. This house was renovated in 2009... ...more

Traditional Osterville Cape Cod home located on the second fairway of Wianno Country Club. Enjoy all the town of Osterville has to offer with a short walk to the... ...more

Enjoy life on the Cape in this relaxing cape cod home with a pool. 3 bedrooms, 2 baths. 1/4 mile walk to the village of Osterville, restaurants, local shops and a... ...more