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Osterville: Vacation Rental By Owner

Search result 1 to 18 Of 18
  • Property-1 Image 1
    House Select Dates for Price
    • 5Bed
    • 5Baths
    • (1) Exceptional
    Osterville, MA

    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

  • Property-2 Image 1
    House $674 / Nightly
    • 4Bed
    • 4Baths
    • (11) Wonderful
    Osterville, MA

    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

  • Property-3 Image 1
    House Select Dates for Price
    • 4Bed
    • 4Baths
    • (25) Wonderful
    Osterville, MA

    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

  • Property-4 Image 1
    House $1,065 / Nightly
    • 5Bed
    • 4Baths
    • (18) Exceptional
    Osterville , MA

    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

  • Property-5 Image 1
    House Select Dates for Price
    • 5Bed
    • 4Baths
    • (6) Exceptional
    Osterville , MA

    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

  • Property-6 Image 1
    House Select Dates for Price
    • 5Bed
    • 5Baths
    Osterville, MA

    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

  • Property-7 Image 1
    House $360 / Nightly
    • 3Bed
    • 2Baths
    Osterville, MA

    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

  • Property-8 Image 1
    Cottage $282 / Nightly
    • 2Bed
    • 1Baths
    • (12) Exceptional
    Osterville, MA

    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

  • Property-9 Image 1
    Guest House/pension $111 / Nightly
    • 1Bed
    • 2Baths
    • (2) Exceptional
    Osterville, MA

    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

  • Property-10 Image 1
    House Select Dates for Price
    • 4Bed
    • 6Baths
    • (9) Wonderful
    Osterville, MA

    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

  • Property-11 Image 1
    House $1,716 / Nightly
    • 4Bed
    • 3Baths
    • (9) Wonderful
    Osterville, MA

    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

  • Property-12 Image 1
    Estate $3,161 / Nightly
    • 8Bed
    • 9Baths
    • (2) Exceptional
    Osterville, MA

    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

  • Property-13 Image 1
    House $388 / Nightly
    • 3Bed
    • 3Baths
    Osterville, MA

    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

  • Property-14 Image 1
    House $1,036 / Nightly
    • 4Bed
    • 4Baths
    Osterville, MA

    -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

  • Property-15 Image 1
    Guest House/pension $244 / Nightly
    • 1Bed
    • 1Baths
    • (32)
    Osterville, MA

    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

  • Property-16 Image 1
    House $570 / Nightly
    • 5Bed
    • 5Baths
    • (7) Wonderful
    Osterville, MA

    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

  • Property-17 Image 1
    House $537 / Nightly
    • 4Bed
    • 2Baths
    • (3) Exceptional
    Osterville, MA

    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

  • Property-18 Image 1
    House Select Dates for Price
    • 3Bed
    • 3Baths
    • (4)
    Osterville, MA

    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

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Osterville. Many accommodations in Osterville provide "Non Smoking Only", there are 46, or there are 42 of Vacation Rentals in Osterville with a "Fishing", there are also 40 with "Beach", which is another great reason to visit Osterville.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Osterville. The most expensive month of the next 12 months is in January, where prices hit an average of $0 a night. In , prices will hit an average low of $0 per night.