We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Osterville, MA

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Price
    per night
    |||
    |||
    $0
    $1,252 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Travellers to Osterville are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $6,265
    / Week
    View Details
    View Details
    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    From
    $4,037
    / Week
    Payment Protection
    View Details
    View Details
    1 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $3,480
    / Week
    View Details
    View Details
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $4,873
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Lovely three bedroom with bonus sleeping area in lower level. This Osterville home is close to Dowses Beach. Spacious and comfortable with a sun room and large backyard for family gatherings. Just minutes to the charming shops and wonderful restaurants lining Osterville s Main Street. Additional... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 1
    4 Bedrooms, 6 Bathrooms, Sleeps 1 | Quick View
    From
    $6,961
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home. Secluded gem features great combination of exquisite home and an ideal location with beach area within walking distance and short distance to Dowses beach. Nestled among woods on a beautiful private road yet right next to village! Extensively remodeled,... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 24
    3 Bedrooms, 6 Bathrooms, Sleeps 1 | Quick View
    From
    $4,037
    / Week
    View Details
    View Details
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Large sunny home in excellent condition available as an academic rental. Located in one of Osterville s established neighborhoods and only a few minutes from the village center, and Craigville and Dowses Beach. Three large bedrooms and 4 1/2 baths. Study could be a 4th bedroom. Formal living room,... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 35
    5 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
    From
    $13,922
    / Week
    View Details
    View Details
    Amenities & Details
    • Parking
    • DVD Player
    • Internet Access
    • Grill
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Osterville Cape Cod Waterfront. Magnificent sun-filled summer home with a private deep water dock on East Bay a short walk from both beautiful Dowses Beach and from Osterville Village for easy access to fine dining and quaint shops. A private retreat that offers panoramic views of the harbor,... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $2,506
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Close to Osterville Village and Joshua's Pond, this charming rental home has four bedrooms including a master suite with full bath on second level and 3 bedrooms and full bath on first floor. Living room and family room and eat-in kitchen. There is a spacious deck off the kitchen and a private back... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 52
    10 Bedrooms, 12 Bathrooms, Sleeps 1 | Quick View
    From
    $20,187
    / Week
    View Details
    View Details
    Amenities & Details
    • Grill
    • Waterfront
    • Satellite TV
    • Parking
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties Rental Seaview Avenue Beachfront Estate. 2005 Custom built home with path to a private beach. This home has glorious ocean views from most all of the rooms and there is a dune path to your own private beach on Nantucket Sound just past the cottage. The main home has... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
    From
    $4,873
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Parking
    • Porch
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Designed by award winning architect, Reed Morrison, this unique and inspirational residence is sited on .83 acres surrounded by fields of wild flowers & rolling lawns. The well equipped kitchen is enhanced with all Viking appliances & limestone counter tops. The master bedroom and two additional... View all property information
    Location Information
    Osterville, Cape Cod
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $2,784
    / Week
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Patio
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This lovely 3 bedroom, 2 bath home is not far from Dowses beach, Osterville Village shops, Restaurants and Kelly Armstrong Park!! Home is tastefully appointed with three bedrooms and 2 baths. Private back yard deck and gas grill. Additional amenities include: coffee maker, washer/dryer, beach -... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 19
    3 Bedrooms, 4 Bathrooms, Sleeps 1 | Quick View
    From
    $6,822
    / Week
    View Details
    View Details
    Amenities & Details
    • Parking
    • DVD Player
    • Internet Access
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Bright, lovely secluded home on almost 3 acres in prestigious Seapuit enclave of large estate homes. Main house has 3 BR (each w/private bath). Meticulously maintained, with beautiful landscaping, serenity, and privacy. Royal Barry Wills inspired home is walking distance to bayfronts, Joshua’s Pond... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 31
    11 Bedrooms, 7 Bathrooms, Sleeps 1 | Quick View
    From
    $17,402
    / Week
    View Details
    View Details
    Amenities & Details
    • Parking
    • Satellite TV
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Large family home waterfront home on Sea View Ave in Osterville with 140' +/- of soft sandy beach on the shores of Nantucket Sound, this quintessential Osterville estate is set on 2.23 acres of rolling green lawns, beautiful gardens, mature vegetation and stone walls. Situated down a long driveway,... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 53
    6 Bedrooms, 4 Bathrooms, Sleeps 1 | Quick View
    From
    $6,961
    / Week
    View Details
    View Details
    Amenities & Details
    • Parking
    • Grill
    • Porch
    • Internet Access
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home. This wonderful Osterville home overlooking Neck Pond is a great private get-away. Located across from the Wianno Golf Club, this is an ideal location. Not far from the village and Dowses beach. The house, set on a private acre, has a lovely porch, six... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 15
    5 Bedrooms, 7 Bathrooms, Sleeps 1 | Quick View
    From
    $20,883
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Patio
    • Internet Access
    • Parking
    • DVD Player
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Spectacular and spacious home in the Seapuit area of Osterville. Gorgeous landscaping abounds with water garden, heated pool with pool house and veranda designed for dining. 5 bedrooms and 6 and 1/2 baths. Close to Main St in Osterville. Additional amenities include: coffee maker, outside shower -... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $3,689
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Desirable Wianno Circle rental home. Close to Dowses beach and village. Three bedrooms and two full baths. This rental has window air units in the bedrooms and provides a town beach pass. Additional amenities include: coffee maker, outside shower - enclosed, washer/dryer, beach - town, pillows,... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 20
    7 Bedrooms, 8 Bathrooms, Sleeps 1 | Quick View
    From
    $20,883
    / Week
    View Details
    View Details
    Amenities & Details
    • Patio
    • Grill
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties Rental Stunning home in the gated Community of Oyster Harbors. Walk into a tastefully decorated, bright, kitchen with gleaming dark hardwood floors. Top of the line appliances in the kitchen make it easy to entertain a large group. The living room has an over sized... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 26
    5 Bedrooms, 5 Bathrooms, Sleeps 1 | Quick View
    From
    $27,844
    / Week
    View Details
    View Details
    Amenities & Details
    • Grill
    • Patio
    • Waterfront
    • DVD Player
    • Satellite TV
    • Parking
    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home. This home is located in prestigious Oyster Harbors. The home boosts a heated pool, dock, small beach area. There is privacy and luxury in this newer updated home. The first level has a large master suite with full bath. There are four bedrooms and two... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 24
    12 Bedrooms, 8 Bathrooms, Sleeps 1 | Quick View
    From
    $17,402
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Parking
    • Porch
    • Waterfront
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties Rental home. Cape Cod charm at its best and most elegant. An exquisite home for your family's ideal vacation. Private beach, tennis court. This grand house boasts 12 bedrooms, 7 full baths, 2 living rooms, a pool table, wrap around porch, and an expansive yard... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 1 | Quick View
    From
    $6,961
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Porch
    • Grill
    • Parking
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This home was designed by a Well Known Architect. Walk to Main Street in Osterville and 1.5 miles from Dowses Beach. This home has a well-appointed kitchen with an open floor plan. There is a deck with automatic screens, central air and WIFI. This is an allergen free home. House is supplied with... View all property information
    Location Information
    Osterville, Cape Cod
    Get the List
    1 / 36
    4 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
    From
    $7,657
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Parking
    • Grill
    • Private Outdoor...
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Set down a quiet lane in a prime Osterville village location sits this spacious four bedroom Ranch. Enjoy deeded beach and water rights on North Bay with access to Nantucket Sound, only a short walk from the home. The light filled home features an updated kitchen and an ideal floor plan with the... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
    From
    $6,961
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Parking
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Fieldstone Estates. Beautiful home, private setting with estate-like grounds and refreshing built-in heated pool. Home has central air conditioning, hardwood floors, first floor master bedroom, additional two second floor bedrooms, laundry room, three bathrooms and an open floor plan. Fully... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 48
    11 Bedrooms, 8 Bathrooms, Sleeps 1 | Quick View
    From
    $17,402
    / Week
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Waterfront
    • Satellite TV
    • Parking
    • Internet Access
    • Porch
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Wonderful old world charm! This 11 bedroom home with a private beach is perfect for a large family gathering. Offering a tennis court and Basketball hoop, a beach house on the sand with an enclosed outdoor shower, a deck for watching the magnificent Cape Cod sunsets or simply relaxing during or... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
    From
    $4,177
    / Week
    View Details
    View Details
    Amenities & Details
    • Grill
    • Satellite TV
    • DVD Player
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home. Walk to the village from this lovely Three bedroom, three full bath home. There is central air for your comfort as well as a screened in deck for relaxing. This home is not far from Dowses beach and a beach pass is provided. Additional amenities... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 5
    3 Bedrooms, 4 Bathrooms, Sleeps 1 | Quick View
    From
    $11,834
    / Week
    View Details
    View Details
    Amenities & Details
    • Parking
    • Patio
    • Internet Access
    • Grill
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Contact us for additional photos and details. Amazing views from this Osterville home of the salt water bay with dock. Three bedrooms and 3.5 baths. Bonus room in lower level walk out can be turned into a fourth bedroom, if needed. You have access to Centerville River, Long Beach, and Nantucket... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 4
    4 Bedrooms, 4 Bathrooms, Sleeps 1 | Quick View
    From
    $7,379
    / Week
    View Details
    View Details
    Amenities & Details
    • Grill
    • Patio
    • DVD Player
    • Internet Access
    • Porch
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home. This home has been totally renovated from top to bottom for the 2016 rental season. There are four bedrooms. A master suite on the first level and three bedrooms upstairs. Three full baths and TV room in lower level. Sun porch with flat screen and... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 1 | Quick View
    From
    $3,898
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • Patio
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Wonderful location! Close to Dowses and not far from Main Street, also close to Wianno Golf Course and Crystal Lake! This lovely 2 bedroom, 1 bath home sits on a quiet village lane. Enjoy casual elegance and an open floor plan with wood floors, living room and separate den area. Fully equipped... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $4,177
    / Week
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties Rental Wonderful Osterville vacation rental. Walk to village and Joshua s Pond. Not far from Dowses beach. Well appointed three bedroom, two full bath home, with central air, new kitchen with granite, stainless and a large dining area for entertaining. Open floor... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $4,455
    / Week
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Parking
    • Satellite TV
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home close to Main Street in Osterville and not far from Dowses Beach. Three bedrooms and a bonus sleeping area with bunk bed, couch and flat screen TV. Private deck, outdoor shower. Lovely setting in Osterville. Additional amenities include: coffee maker,... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    From
    $223
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Outdoor Dining Area
    • Washer
    • Parking
    • DVD Player
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Lovely 2 Bedroom home on a quiet street in the desirable Wianno area of Osterville, Cape Cod or Osterville Village. (This is the section nearest to Dowses' Beach! You can't find a rental for this price this close to the beach in Osterville!!) The house is bright, clean and newly painted with 2... View all property information
    Location Information
    Osterville, Cape Cod 46032
    5 of 5 stars Reviewed 5 October 2014
    This cute cottage was everything we wanted/needed. The owners were terrific and answered all our many questions. The cottage was clean, neat and decorated very tastefully...
    See all reviews
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $2,506
    / Week
    View Details
    View Details
    Amenities & Details
    • Patio
    • Internet Access
    • Grill
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Comfortable four bedroom rental home in Centerville. There is a first level master suite with a full bath as well as another bedroom and full bath in the hall. Upstairs has two large size bedrooms. Great outdoor space with gas grill and seating. This home has a den, sun porch and lower level TV... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 32
    9 Bedrooms, 9 Bathrooms, Sleeps 1 | Quick View
    From
    $34,804
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Waterfront
    • Porch
    • Satellite TV
    • Patio
    • Grill
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Quiet luxury on the water’s edge. Feel at one with the sand, surf, and sun while luxuriating on your own beach surrounded by a private and lush 26 acres in the exclusive gated paradise that is Oyster Harbors. Complete with a tennis court, beach house, artist’s studio, and dock, this property... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 12
    5 Bedrooms, 6 Bathrooms, Sleeps 1 | Quick View
    From
    $11,137
    / Week
    View Details
    View Details
    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • Grill
    • Waterfront
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home situated at the end of a long and winding driveway this expansive Cape style home offers over 3,900 square feet of living space. Fronting Bog Pond and with views also of North Bay in the distance the home offers not only privacy, but a heated in ground... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 2
    6 Bedrooms, 5 Bathrooms, Sleeps 1 | Quick View
    From
    $16,010
    / Week
    View Details
    View Details
    Amenities & Details
    • Private Outdoor...
    • Parking
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The very best of old + new! 4500+ sq. ft. of vintage Cape charm conscientiously updated for today’s lifestyles. 1930’s family summer home on Nantucket Sound. Private beach with ocean views from every room. Modern amenities include heated pool, full A/C, updated eat-in kitchen and baths, flat screen... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 15
    4 Bedrooms, 4 Bathrooms, Sleeps 1 | Quick View
    From
    $6,265
    / Week
    View Details
    View Details
    Amenities & Details
    • Grill
    • Satellite TV
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Enjoy sunsets from this charming Cape Cod rental overlooking West Bay. A deeded path meanders down to the bay for easy access to the water. This 4-bedroom, 3.5-bath home is perfectly located in the heart of Wianno and within walking distance to Osterville village with convenient shopping,... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 1 | Quick View
    From
    $5,569
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Grill
    • Parking
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This spacious four bedroom with pond views and gorgeous in ground pool is located in the sought after area of Wianno Circle in Osterville village; Just a short distance to the beach, village, restaurants, shopping, post office and more; Boasting a large, updated, eat-in kitchen, living room with... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 41
    7 Bedrooms, 7 Bathrooms, Sleeps 1 | Quick View
    From
    $15,314
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Parking
    • DVD Player
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home with heated pool and private large yard. Stunning 7 bedroom home with main kitchen and caterers kitchen. There is a sunroom and large deck overlooking the back yard, dance studio in lower level and basketball hoop in driveway. Central air and lovely... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
    From
    $3,898
    / Week
    View Details
    View Details
    Amenities & Details
    • Parking
    • Satellite TV
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home. Charming home in Osterville with an open floor plan. 3 bedrooms. First floor master with an en-suite bath , spacious dining room, Three season glassed sun room overlooking a fully fenced yard. The two additional large bedrooms share the upstairs... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 42
    5 Bedrooms, 7 Bathrooms, Sleeps 1 | Quick View
    From
    $20,883
    / Week
    View Details
    View Details
    Amenities & Details
    • Parking
    • Private Outdoor...
    • Satellite TV
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Exclusive Robert Paul Properties rental home in prestigious Oyster Harbors gated community. This family home has it all! Heated pool, large yard, game room with pool table and foze ball. There is a theater/media room and a wonderfully well-appointed kitchen as well as other living areas. Five full... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 1 | Quick View
    From
    $5,847
    / Week
    View Details
    View Details
    Amenities & Details
    • Parking
    • Patio
    • Waterfront
    • Satellite TV
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This stunning waterfront home is a one of a kind with breathtaking views from every angle. There is a 40 pier (5.5 draw) that’s ideal for boating and fishing. This three bedroom home is perfectly appointed and comes with a private tennis court, large patio with a fire pit, and incredible views... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
    From
    $2,784
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Robert Paul Properties rental. Walk to the village from this two bedroom, two full bath first floor condo unit on Parker Road. Garage for use while renting and not far from Dowes beach. There are two screened porches and a great large floor plan. One queen master and a second bedroom with two twin... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 19
    5 Bedrooms, 5 Bathrooms, Sleeps 1 | Quick View
    From
    $14,618
    / Week
    View Details
    View Details
    Amenities & Details
    • Porch
    • Grill
    • Parking
    • Waterfront
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Private gated community rental home surrounded by water in prestigious Oyster Harbors. This Shingle Cottage style home was built in 2004 and comes with a sandy beach area as well as amazing attention to details. Over 3100 square feet with grand entry and open floor plan, every room in the house is... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 1 | Quick View
    From
    $2,088
    / Week
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Parking
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This is the most charming and updated cottage in the 'Village' that you will find! Just 1 block to all Osterville Shops and Restaurants. This stunning little 2 bedroom gem is totally turn key with custom and designer details throughout! The pictures say it all! Central air, gas fireplace, hard wood... View all property information
    Location Information
    Osterville, Cape Cod