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.
mm/dd/yyyy mm/dd/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 range
    ($729 Average)
    $0per night $1,000+
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    loading...
    From
    $160
    / Night
    Payment Protection
    View Details
    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    From
    $2,450
    / Week
    Payment Protection
    View Details
    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8
    other traveler has booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    From
    $850
    / Night
    Payment Protection
    View Details
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    From
    $4,000
    / Week
    View Details
    1 / 28
    6 Bedrooms, 4 Bathrooms, Sleeps 13
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Fireplace
    • Waterfront
    • Internet Access
    • Dryer
    • Washer
    • Air Conditioning
    • Deck
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ivy Woods - Osterville This wonderful Osterville rental 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 bedrooms and... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $15,000
    / Week
    View Details
    1 / 36
    5 Bedrooms, 6 Bathrooms, Sleeps 15
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Fireplace
    • Air Conditioning
    • Deck
    • Internet Access
    • Washer
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Heated pool family home Exclusive Robert Paul Properties rental home. This family home has it all! Heated pool, large yard, well appointed, game room, movie room and all located in Oyster Harbors. There are 5 bedrooms and plenty of room. For more information about this rental email... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $2,000
    / Week
    View Details
    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 5
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Fireplace
    • DVD Player
    • Deck
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Close to village Close to town and not far from Dowes beach. This two bedroom home makes a great rental home. For more information about this rental, please email Michelle Sylvia at michelle@robertpaul.com or call 508-648-2967. Additional amenities include: coffee maker, utilities included in... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,500
    / Week
    View Details
    1 / 15
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Washer
    • Deck
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Fireplace
    • Dryer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $2,600
    / Week
    View Details
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    • Balcony
    • Dryer
    • Washer
    • Refrigerator
    • DVD Player
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $2,500
    / Week
    View Details
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stove
    • Refrigerator
    • Fireplace
    • TV
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Osterville rental home BRAND NEW RENTAL 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 sunroom overlooking a fully fenced yard. The two... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $4,500
    / Week
    View Details
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    • Dryer
    • Refrigerator
    • Satellite TV
    • Grill
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Oyster Harbors - Grand Island NEW RENTAL HOME. Exclusive Oyster Harbors vacation rental. Enjoy the privacy of a gated community in Osterville. This 3 bedrooms 2 bath home has a private yard and is not from all Osterville Village has to offer. For more information about this rental please email... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $3,800
    / Week
    View Details
    1 / 13
    3 Bedrooms, 3 Bathrooms, Sleeps 5
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Fireplace
    • Deck
    • Satellite TV
    • Washer
    • Waterfront
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $5,000
    / Week
    View Details
    1 / 31
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Deck
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Fireplace
    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02622
    From
    $3,000
    / Week
    View Details
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Refrigerator
    • Fireplace
    • Internet Access
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,250
    / Week
    View Details
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Fireplace
    • Washer
    • Dryer
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Grill
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    JULY 4th - JULY 11th STILL 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... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02649
    5 of 5 stars Reviewed March 23, 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
    $2,450
    / Week
    View Details
    1 / 16
    3 Bedrooms, 4 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Fireplace
    • Air Conditioning
    • Satellite TV
    • Deck
    • Washer
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    END OF SUMMER SPECIA RATE! WEEKS STILL AVAILABLE! 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... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $4,000
    / Week
    View Details
    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Washer
    • Internet Access
    • Garage
    • Satellite TV
    • Dryer
    • Deck
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pool BRAND NEW RENTAL HOME. 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,... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $2,500
    / Week
    View Details
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Deck
    • Internet Access
    • Washer
    • Dryer
    • Grill
    • Air Conditioning
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $5,000
    / Week
    View Details
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Washer
    • Fireplace
    • Deck
    • Satellite TV
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $10,500
    / Week
    View Details
    1 / 35
    7 Bedrooms, 7 Bathrooms, Sleeps 14
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Gym
    • Washer
    • Deck
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $8,500
    / Week
    View Details
    1 / 6
    3 Bedrooms, 4 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Fireplace
    • Private Outdoor...
    • Waterfront
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    Get the List
    From
    $5,000
    / Week
    View Details
    1 / 16
    4 Bedrooms, 6 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Dryer
    • Refrigerator
    • Washer
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Stove
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,800
    / Week
    View Details
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Deck
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Refrigerator
    • Satellite TV
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,200
    / Week
    View Details
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Washer
    • Fireplace
    • Dryer
    • Deck
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,500
    / Week
    View Details
    1 / 21
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Grill
    • Air Conditioning
    • Waterfront
    • Dryer
    • TV
    • Patio
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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! Unique four bedroom with 2 full baths, hard wood floors and 4 window air units. Words are difficult to describe this well maintained home. Call to view and... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $15,000
    / Week
    View Details
    1 / 22
    5 Bedrooms, 7 Bathrooms, Sleeps 12
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Deck
    • TV
    • DVD Player
    • Internet Access
    • Private Outdoor...
    • Washer
    • Fireplace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $4,900
    / Week
    View Details
    1 / 20
    3 Bedrooms, 4 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • DVD Player
    • Internet Access
    • Deck
    • Washer
    • Satellite TV
    • Dryer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $4,500
    / Week
    View Details
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    • Washer
    • Stereo System
    • Deck
    • Fireplace
    • Boat Available
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $4,700
    / Week
    View Details
    1 / 17
    5 Bedrooms, 5 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Deck
    • Washer
    • Dryer
    • Internet Access
    • Satellite TV
    • DVD Player
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $12,500
    / Week
    View Details
    1 / 34
    3 of 5 stars (1) Average
    11 Bedrooms, 8 Bathrooms, Sleeps 20
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Stereo System
    • Satellite TV
    • DVD Player
    • Washer
    • Dryer
    • Waterfront
    • Deck
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    3 of 5 stars Reviewed June 25, 2015
    First the good news. The house is big, the rooms are, for the most part, a decent size. It has a huge lot with beach access. We had twelve adults and two children and it...
    See all reviews
    From
    $20,000
    / Night
    View Details
    1 / 26
    5 Bedrooms, 5 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Boat Available
    • Air Conditioning
    • Internet Access
    • Deck
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Waterfront with pool Exclusive Robert Paul Properties rental home. This home is located in prestige s Oyster Harbors. Heated pool, dock, small beach area and privacy. First level master suite and four other bedrooms. For more information about this rental email Michelle Sylvia at... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $15,000
    / Week
    View Details
    1 / 27
    7 Bedrooms, 7 Bathrooms, Sleeps 14
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Deck
    • DVD Player
    • Hot Tub
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,400
    / Week
    View Details
    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Fireplace
    • Internet Access
    • Dryer
    • Satellite TV
    • DVD Player
    • Deck
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wianno Area Four Bedroom ! Seaview Avenue area of Osterville! Open concept Cape/ close to the small but beautiful Seaview Ave beach, Dowses Beach, or go to all of the many town of Barnstable public beaches, as Barnstable beach pass is included. WEEK OF AUGUST 2 -9 STILL AVAILABLE!! (linens... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $12,500
    / Week
    View Details
    1 / 33
    12 Bedrooms, 8 Bathrooms, Sleeps 15
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Dryer
    • Stereo System
    • DVD Player
    • Internet Access
    • Satellite TV
    • Deck
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,300
    / Week
    View Details
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Deck
    • Satellite TV
    • Washer
    • Dryer
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,250
    / Week
    View Details
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • DVD Player
    • Dryer
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $2,800
    / Week
    View Details
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Washer
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • DVD Player
    • Deck
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,000
    / Week
    View Details
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Dryer
    • Air Conditioning
    • Deck
    • Fireplace
    • Washer
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $10,500
    / Week
    View Details
    1 / 36
    5 of 5 stars (1) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Deck
    • Dryer
    • Satellite TV
    • Waterfront
    • Washer
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    5 of 5 stars Reviewed August 17, 2015
    Last year my husband and I toured the cape and after much research and viewing of properties selected 405 Seaview for our family reunion of 20 people. We rented two homes at 405...
    See all reviews
    From
    $2,650
    / Week
    View Details
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Patio
    • Air Conditioning
    • Washer
    • Dryer
    • DVD Player
    • Deck
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,650
    / Week
    View Details
    1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    • Grill
    • Deck
    • Washer
    • Dryer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $2,500
    / Week
    View Details
    1 / 25
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Deck
    • Satellite TV
    • Dryer
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,400
    / Week
    View Details
    1 / 21
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Washer
    • Deck
    • DVD Player
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ENJOY the charm of Osterville Village! Lovely 4 bedroom 2 bath Cape Located in Osterville Village, near to EVERYTHING that suits your vacation needs! ~ shops,bistros,the newly built library,boating, & less than 1 mile to beautiful Dowses Beach. BEACH PASS PROVIDED. Home sleeps 8 guests & has a... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,200
    / Week
    View Details
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Dryer
    • Washer
    • Air Conditioning
    • Deck
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $10,000
    / Week
    View Details
    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Waterfront
    • Washer
    • Deck
    • TV
    • Fireplace
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $25,000
    / Week
    View Details
    1 / 34
    7 Bedrooms, 7 Bathrooms, Sleeps 12
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    • DVD Player
    • Waterfront
    • Deck
    • Satellite TV
    • Hot Tub
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $3,300
    / Week
    View Details
    1 / 11
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Deck
    • Air Conditioning
    • DVD Player
    • Dryer
    • Satellite TV
    • Washer
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $12,500
    / Week
    View Details
    1 / 34
    11 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Washer
    • Deck
    • Internet Access
    • Refrigerator
    • Waterfront
    • Air Conditioning
    • Dryer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Private beach & dock Large waterfront home with private beach on Nantucket Sound. This great home has 11 bedrooms and 7 baths. There are incredible views and a large yard. For additional information call Michelle Sylvia at 508-648-2967 or email michelle@robertpaul.com Additional amenities... View all property information
    Make Inquiry
    Location Information
    Osterville, Cape Cod 02655
    From
    $1,300
    / Week
    View Details
    1 / 17
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Dryer
    • Air Conditioning
    • Deck
    • Internet Access
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655
    Inquire for rates
    1 / 23
    9 Bedrooms, 9 Bathrooms, Sleeps 15
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Waterfront
    • Patio
    • Washer
    • TV
    • Dryer
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Inquiry
    Location Information
    Osterville, Cape Cod 02655