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 Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 60 Rentals in Osterville
    loading...
    Sort by
    From
    $3,011
    / Week
    Payment Protection
    View Details
    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    From
    $197
    / Night
    Payment Protection
    View Details
    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    From
    $1,044
    / Night
    Payment Protection
    View Details
    1 / 18
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    From
    $1,057
    / Night
    Payment Protection
    View Details
    1 / 15
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Fishing...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Single family, 4 bedroom 4 full baths, 8 rooms total, 2100 square feet Best town on the Cape, Osterville! High cathedral ceilings in queen bedroom and king master bedroom. Newly renovated, bright, cheerful, updated décor, comfortable living space. House is conveniently located on beautiful ½... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,536
    / Week
    View Details
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    STILL SOME SUMMER WEEKS AVAILABLE!! OSTERVILLE !! Come enjoy this bright & sunny south of rte. 28 vacation home on a quiet street in lovely Osterville Woods! Quick access to beautiful Dowses Beach on Nantucket Sound (BEACH PASS PROVIDED ) Joshua s 'cystal clear' Pond & the charming quaint village... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02649
    5 of 5 stars Reviewed 23 March 2015
    We have rented different properties on Cape Cod in different locations. This is one of the best. It is close to Boston, very nice neighborhood, 5 minutes from the town beach...
    See all reviews
    From
    $4,301
    / Week
    View Details
    1 / 22
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    138 Bridge Street Charming 1900 period home with many updates for todays comfort! This waterfront home is part of the Nauticus Marina compound! Enjoy privacy off season and busy harbor life in season! What fun! Boat dockage available upon request. 4 unique bedrooms with 'nooks and crannies', hard... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,072
    / Week
    View Details
    1 / 17
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Close to Village and Beaches. Main house with 3 bedrooms, 1 1/12 baths. Cottage on on fully fenced property with LR, BR, K, and bath w/shower stall. Enclosed outside shower. Main house with central a.c.; separate window a.c. units in cottage. Screened porch in main house. Bedroom in cottage now has... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,011
    / Week
    View Details
    1 / 16
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Lovely & bright home on almost three acres in Osterville s coveted 'Seapuit' enclave (which fronts North Bay) ~ A gracious & comfortable gem with 3 bedrooms & 3 .5 baths~each bedroom has it s own private bath.Beautifully furnished and decorated for comfortable living with a NEWLY REMODELED KITCHEN... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $4,055
    / Week
    View Details
    1 / 11
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    113 Pond Street Exclusive Robert Paul Properties Rental. 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 &... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,994
    / Week
    View Details
    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Osterville near village Not far from Village and Beaches. Main house with 3 bedrooms, 1 1/12 baths. Cottage on on fully fenced property with living area, full bath bedroom , fridge and microwave with seating. Enclosed outside shower. Main house with central a.c.; separate window a.c. units in... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $3,932
    / Week
    View Details
    1 / 16
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    79 Gunstock Road Lovely Osterville home. Four bedrooms, 2 full baths with central air. First floor master bedroom and second bedroom plus full bath. Not far from Dowses beach with a beach pass provided. For more information about this rental, contact Michelle Sylvia at 508-648-2967 or email... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $2,212
    / Week
    View Details
    1 / 22
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Charming Osterville home Exclusive Robert Paul Properties rental home. 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... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $12,902
    / Week
    View Details
    1 / 35
    7 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Heated pool and lovely location Exclusive Robert Paul Properties rental home. Stunning 7 bedroom home with a heated pool. Two kitchens, screened in patio, dance studio and large yard complete with basket ball hoop. Central air and lovely location. For additional information please call Michelle... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,072
    / Week
    View Details
    1 / 26
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    24 South Street Lovely four bedroom rental home in the heart of Osterville. Short walk to village and not far from Dowes Beach. For more information about this listing contact Michelle Sylvia at 508-648-2967 or email michelle@robertpaul.com Additional amenities include: coffee maker, utilities... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,195
    / Week
    View Details
    1 / 10
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    165 Wianno Circle Wonderful location! Close to Dowes 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.... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,932
    / Week
    View Details
    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    48 Pine Avenue Exclusive Robert Paul Properties RentalClose to Main Street in Osterville and Dowes Beach. 3 bedrooms and a bonus sleeping area with bunk bed, couch and flat screen. This well appointed home is the perfect vacation home. For additional information please call Michelle Sylvia at... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $12,288
    / Week
    View Details
    1 / 24
    5 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    14 Indian Trail - Oyster Harbors Private gated community surrounded by water in prestigious Osterville. This Shingle Cottage style home was built in 2004 and comes with a sandy beach area. Amazing attention to details. Over 3100 square feet with grand entry and open floor plan, every room in the... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $6,144
    / Week
    View Details
    1 / 16
    4 Bedrooms / 6 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Osterville near village Exclusive Robert Paul Properties Rental Secluded gem features great combination of exquisite home and an ideal location with beach and water rights! Nestled amongst woods on a beautiful private road yet right next to village! Extensively remodeled, shingled Cape is like new... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $18,432
    / Week
    View Details
    1 / 22
    5 Bedrooms / 7 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Pool Osterville 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. For additional information please call... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $2,458
    / Week
    View Details
    1 / 10
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Short Walk to Osterville Village and just a short drive to the beach: This is a very nice 3 bedroom, 2 bath home with garage, central A/C, fully equipped kitchen with dishwasher, dining area, family room with television and porch extending off the back of the house; along with a comfortable living... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 03655
    Get the List
    From
    $5,530
    / Week
    View Details
    1 / 19
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Waterfront and view Osterville Exclusive Robert Paul Properties rental home. 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... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,106
    / Week
    View Details
    1 / 9
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    New to the market! Nice clean 4 bedroom, 2 bath home located a couple of miles from Osterville Village and the beach. The property is tastefully decorated and has air conditioning. Beds Level One - BR#1 - Queen, Level Two BR#2 - 2 Twin, BR#3 - 2 Twin, BR#4 - 2 Twin *****Saturday to Saturday -NO... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,072
    / Week
    View Details
    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    225 Wianno Circle Exclusive Robert Paul Properties rental. Desirable Wianno Circle home. Close to Dowes beach and village. 3 bedrooms 2 full baths. For additional information call Michelle Sylvia at 508-648-2967 or email michelle@robertpaul.com Additional amenities include: coffee maker,... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,597
    / Week
    View Details
    1 / 17
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    NEW LSITING FOR SUMMER 2015! NEW LISTING FOR SUMMER 2015! Sunny bright Cape with large deck for BBQ s and an enclosed outdoor shower for days back from nearby Dowse s Beach on Nantucket Sound (BEACH PASS INCLUDED) OR Joshua s (crystal clear) Pond ! Explore the charming village of Osterville for... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,256
    / Week
    View Details
    1 / 22
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    154 Tower Hill Road This adorable house is close to the best of Osterville - Main Street and Dowes Beach. It has three bedrooms, 2 full baths, a lovely fenced in yeard, and a great patio. $2650 week. Cleaning fee and secuirty deposit required. For more information please call Michelle Sylvia at... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,686
    / Week
    View Details
    1 / 17
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    44 Sunset Lane Exclusive Robert Paul Properties Rental Walk to village from this lovely 3 bedroom 3 bath home. Central air, screened deck and not far from Dowes Beach. For additional information please call Michelle Sylvia at 508-648-2967 or email michelle@robertpaul.com Additional amenities... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,686
    / Week
    View Details
    1 / 16
    6 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    OSTERVILLE: Spotless and spacious 6 bedrooms, 4 bath home with central a/c, internet and washer/dryer located between Village and Dowses Beach. This home is tastefully decorated with the first floor offering a large formal dining room, well equipped kitchen with a casual eating area, comfortable... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $30,720
    / Week
    View Details
    1 / 23
    9 Bedrooms / 9 Bathrooms / Sleeps 15
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Mellon Estate in Oyster Harbors 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... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $2,028
    / Week
    View Details
    1 / 26
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Osterville rental Charming 3 bedroom in quiet Osterville neighborhood. Short Drive to Dowses Beach and village, not far to Mashpee Commons shops, restaurants and more. Beach pass provided. For more information about this rental please contact Michelle Sylvia at 508-648-2967 or email... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $10,445
    / Week
    View Details
    1 / 6
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Heated pool in Osterville 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,... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $9,216
    / Week
    View Details
    1 / 19
    5 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Lovely larger home located on the 8th hole of Oyster Harbors Golf Course. The first level has a large living room, dining room, den, kitchen and first floor bedroom. The second level has four large bedrooms and 4 full baths and 2 half baths four. The backyard is on the golf course is is very... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $15,360
    / Week
    View Details
    1 / 34
    11 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Private beach & dock Large waterfront home with private beach and small dock on Nantucket Sound. This great home has 11 bedrooms and 7 baths. There are incredible views and a large yard as well as a dock. For additional information call Michelle Sylvia at 508-648-2967 or email... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $6,144
    / Week
    View Details
    1 / 20
    6 Bedrooms / 5 Bathrooms / Sleeps 11
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    8 East Bay Road - Osterville Exclusive Robert Paul Properties rental home located in the heart of Osterville, close to shops, restaurants, Dowses Beach, and tennis. This exquisite professionally designed vacation home offers a fabulous gourmet kitchen with granite, sub- zero, and Viking appliances,... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $5,775
    / Week
    View Details
    1 / 17
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Near Village and Beach Exclusive Robert Paul Properties rental. This magnificent, renovated home is set on 1.46 acres just off the Village center. This charming five bedroom home is well appointed with a first floor master with a luxurious master bath, there is an open kitchen with dining area. TV... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,441
    / Week
    View Details
    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Osterville rental not far from Dowes and Village This lovely 3 bedroom, 2 bath home is not far from Dowes 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. For additional... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,686
    / Week
    View Details
    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    33 Waterfield Road Exclusive Robert Paul Properties Rental Wonderful Osterville vacation rental. Walk to village and Joshua s Pond. Not far from Dowes beach. Well appointed three bedroom, two full bath home, with central air, new kitchen with granite, stainless and a large dining area for... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $18,432
    / Week
    View Details
    1 / 27
    7 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    155 Carriage Lane - Oyster Harbors 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... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $12,902
    / Week
    View Details
    1 / 36
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    405 Sea View Ave 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 all rooms and there is a dune path to your own private beach on Nantucket Sound. 6 elegant bedrooms, most with... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $15,360
    / Week
    View Details
    1 / 33
    12 Bedrooms / 8 Bathrooms / Sleeps 15
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The Beacon - 554 Wianno Ave Exclusive Robert Paul Properties Rental Cape Cod at its best and most elegant. An exquisite home for your familys 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... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $4,055
    / Week
    View Details
    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Close to Dowes beach Lovely three bedroom with bonus sleeping area in lower level. This Osterville home is close to Dowes Beach. Spacious and comfortable with a sunroom and large backyard for family gatherings. Just minutes to the charming shops and wonderful restaurants lining Osterville s Main... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $4,669
    / Week
    View Details
    1 / 13
    3 Bedrooms / 3 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    On the water with dock 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 firepit,... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $30,720
    / Week
    View Details
    1 / 34
    7 Bedrooms / 7 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    77 Pirates Cove - Oyster Harbors Luxury at it s best! This stunning home in the gated community of Oyster Harbors has a main home with 4 plus bedrooms, media room, formal dining room, living room, gourmet kitchen, den/library, and a deck overlooking the back yard. There is a pool and a Cabana pool... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,843
    / Week
    View Details
    1 / 15
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Walk to village 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... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $6,144
    / Week
    View Details
    1 / 31
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    71 Bumps River Road 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... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02622
    From
    $6,021
    / Week
    View Details
    1 / 20
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Private & Serene Osterville Estate 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... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $6,144
    / Week
    View Details
    1 / 21
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    64 Bay Street - Osterville 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... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $15,360
    / Week
    View Details
    1 / 34
    11 Bedrooms / 8 Bathrooms / Sleeps 20
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Sea views at its best! Exclusive Robert Paul Properties Rental Wonderful old world charm! 11 bedroom home on a private beach, tennis court, beach house on the beach with outdoor shower and deck for watching the sunset or relaxing for dinner. There are 11 bedrooms and plenty of room for large... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $8,294
    / Week
    View Details
    1 / 33
    4 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Private Pool, Tennis Court and home with Central A/C: This is a gorgeous 4 bedroom (includes room over pool house), 3 ½ bath home with garage, private pool, central a/c, wireless internet, washer/dryer, fully equipped kitchen with dishwasher, informal dining room, bar, informal living room, formal... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,843
    / Week
    View Details
    1 / 19
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Central air conditioned cape - First floor: Entry to bright formal living room/dining area. To the right of the entry is a nice family room with a fireplace and a new kitchen with granite and stainless. Island eating for 4 to 6. Full bath off of the back hall. Glass sun porch with a new sofa, large... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02556
    From
    $1,229
    / Week
    View Details
    1 / 10
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Short Walk to Osterville Village: This is a newly renovated 2 bedroom, 1 bath cottage with wireless internet, washer/dryer, hardwood floors, fully equipped granite kitchen with stainless appliances and dishwasher, dining area, living room, deck with gas grill enclosed outdoor shower.. Bedroom #1 -... View all property information
    Make Enquiry
    Location Information
    Osterville, Cape Cod 02655