Osterville: Vacation Rental By Owner

Showing 17 Of 17 Vacation Rentals
  • Property-1 Image 1
    Guest House $111 / Nightly
    • 1 Bed
    • 2 Baths
    • (5) 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-2 Image 1
    House Select Dates for Price
    • 4 Bed
    • 4 Baths
    • (32) Wonderful
    Osterville, MA

    A five minute walk to Osterville's Wianno Club on Seaview Ave and to Dowse's Beach, this four bedroom, four bath home was completely renovated this past... ...more

  • Property-3 Image 1
    House $674 / Nightly
    • 4 Bed
    • 4 Baths
    • (13) 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-4 Image 1
    House Select Dates for Price
    • 5 Bed
    • 5 Baths
    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-5 Image 1
    House Select Dates for Price
    • 4 Bed
    • 6 Baths
    • (13)
    Osterville, MA

    Fully 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-6 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    Osterville, MA

    Set in a lovely neighborhood by the beach, this 3 bedroom Osterville cottage is the perfect home to make family memories on Cape Cod. Enjoy shopping and eateries... ...more

  • Property-7 Image 1
    House $360 / Nightly
    • 3 Bed
    • 2 Baths
    • (1) Exceptional
    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
    Estate $3,161 / Nightly
    • 8 Bed
    • 9 Baths
    • (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-9 Image 1
    House Select Dates for Price
    • 5 Bed
    • 5 Baths
    • (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-10 Image 1
    House $1,065 / Nightly
    • 5 Bed
    • 4 Baths
    • (24) 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-11 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (12)
    Osterville, MA

    Originally built as a whaling captain's home, the Captain Alexander Bacon house combines old world charm with modern living. The home is located on a private acre... ...more

  • Property-12 Image 1
    House Select Dates for Price
    • 5 Bed
    • 4 Baths
    • (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-13 Image 1
    Cottage $282 / Nightly
    • 2 Bed
    • 1 Baths
    • (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-14 Image 1
    House $1,036 / Nightly
    • 4 Bed
    • 4 Baths
    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
    • 1 Bed
    • 1 Baths
    • (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
    • 5 Bed
    • 5 Baths
    • (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
    • 4 Bed
    • 2 Baths
    • (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

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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 June, where prices hit an average of $765 a night. In July, prices will hit an average low of $157 per night.