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Vacation Rentals in Osterville, MA

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    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 6
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    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    South of Rte. 28 OSTERVILLE Vacation Home! Sleeps Six 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
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    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...
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    5 Bedrooms / 6 Bathrooms / Sleeps 10
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    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
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    1 / 35
    7 Bedrooms / 7 Bathrooms / Sleeps 14
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    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
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    4 Bedrooms / 1 Bathroom / Sleeps 8
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    About this property
    NEW LSITING FOR SUMMER 2015! NEW LISTING FOR SUMMER 2015! Sunny bright Cape (sleeps 8 guests) 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... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Drive to Beach with A/C: Located only 1 mile from Dowses Beach this is a nice 3 bedroom, 2 bath home offering wireless internet, washer/dryer, fully equipped kitchen (with A/C), dining area, living room, garage, patio, sunroom and outside enclosed shower. First Floor: Bedroom #1 – 1 Full (with... View all property information
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    6 Bedrooms / 4 Bathrooms / Sleeps 8
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    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
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    1 / 17
    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    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
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    1 / 19
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    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
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Short walk to Osterville Village and beautiful Dowses Beach(beach pass included)from this 2 bedroom, 2 bath cottage that offers wireless internet, 2 window A/C units and a washer/dryer. This property is all on 1 level and has a kitchen, living room, sun porch and large backyard. Bedroom #1 – 1... View all property information
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    1 / 27
    7 Bedrooms / 7 Bathrooms / Sleeps 14
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    • Hot Tub
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    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
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    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
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    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
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    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
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    5 Bedrooms / 7 Bathrooms / Sleeps 12
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    • Private Outdoor...
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    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
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    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
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    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
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    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
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    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
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    5 Bedrooms / 4 Bathrooms / Sleeps 8
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    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
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    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
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    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
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    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
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    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
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    11 Bedrooms / 7 Bathrooms / Sleeps 12
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    Waterfront directly on Nantucket Sound with private beach and small dock: This is a magnificent home with 11 bedrooms (occupancy 12), 7 bath home with private beach with showers and changing rooms, small dock and incredible views. There is also wireless internet, fully equipped eat in kitchen with... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    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
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    3 Bedrooms / 4 Bathrooms / Sleeps 6
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    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
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    3 Bedrooms / 3 Bathrooms / Sleeps 5
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    Spectacular three bedroom Nantucket style cottage located on a hill over looking Warrens Cove This prestine cottage has been newly renovated with meticulous detail. The property has two decks that overlook the water and a 40 foot dock which is great for boating, fishing, etc. The main level has a... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    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
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    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
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    11 Bedrooms / 8 Bathrooms / Sleeps 20
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    • Balcony
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    • Waterfront
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    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
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    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
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    6 Bedrooms / 6 Bathrooms / Sleeps 12
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    • Air Conditioning
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    • Waterfront
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    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
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
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    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
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
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    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
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    3 Bedrooms / 3 Bathrooms / Sleeps 5
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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
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    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Suitable for children
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    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
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Private Outdoor...
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    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
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Suitable for children
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    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
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Washer
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    • Pets allowed
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    • Suitable for children
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    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
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
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    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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
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    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
    • Balcony
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    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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
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    11 Bedrooms / 6 Bathrooms / Sleeps 12
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    • Air Conditioning
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    • Satellite TV
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    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
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    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
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    4 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Dishwasher
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    • Shared Outdoor Pool...
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    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
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    6 Bedrooms / 5 Bathrooms / Sleeps 11
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    • Air Conditioning
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    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    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
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    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
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    12 Bedrooms / 8 Bathrooms / Sleeps 15
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    • Dishwasher
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    • Grill
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    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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
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