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Vacation Rentals in Osterville, MA

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$160
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$214
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4 Bedrooms, 4 Bathrooms, Sleeps 6
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$860
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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4 Bedrooms, 4 Bathrooms, Sleeps 8
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About this property
ID# SPI11 Osterville, magnificently newly redesigned Vacation home with high end features and furnishings, this home is sure to impress! Highlights to point out are a grand, gourmet granite and stainless kitchen with every feature and fully outfitted for entertaining. Along with three spacious en... View all property information
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5 of 5 stars Reviewed June 17, 2014
Our stay at this beautiful home was a feast for the eyes from the moment we stepped into the gourmet kitchen with 14 ft. granite island. Every bedroom had it's own bathroom with...
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$1,250
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1 / 21
3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
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  • Suitable for children
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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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$900
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1 / 5
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
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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$5,000
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1 / 20
6 Bedrooms, 5 Bathrooms, Sleeps 11
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  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair 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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$2,600
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1 / 19
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 / 13
3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Dishwasher
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  • Waterfront
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About this property
Wonderful three bedroom boathouse with a dock and beach. The first level of this house sits above the garage and is a nice open room with kitchen, eating area and living area with wonderful views of West Bay. The next level has a bedroom and a full bath. BR#1 - King, The third level has two... View all property information
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$1,500
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1 / 19
3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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From
$4,500
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1 / 22
4 Bedrooms, 2 Bathrooms, Sleeps 8
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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
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$5,000
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1 / 16
4 Bedrooms, 6 Bathrooms, Sleeps 8
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  • Air Conditioning
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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
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$5,000
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1 / 20
3 Bedrooms, 4 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Dishwasher
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  • Internet Access
  • Satellite TV
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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. For additional... View all property information
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$3,300
Per Week
1 / 11
3 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
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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
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$700
Per Week
1 / 12
2 Bedrooms, 2 Bathrooms, Sleeps 4
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About this property
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 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Air Conditioning
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Suitability
  • Pets allowed
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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
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$2,600
Per Week
1 / 10
2 Bedrooms, 1 Bathroom, Sleeps 4
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  • Internet Access
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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
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$2,500
Per Week
1 / 18
3 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
37 Bates Street - Osterville Close to Dowses Beach and not far from the village. This 1890 Vintage home has been lovingly restore. This three bedroom, 2.5 bath home has central air, beautiful wood floors, updated kitchen. 1st floor bedroom plus 1.5 baths. Living room is perfect for gatherings.2... View all property information
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$2,650
Per Week
1 / 22
3 Bedrooms, 2 Bathrooms, Sleeps 7
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  • Air Conditioning
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  • Dishwasher
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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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$8,500
Per Week
1 / 6
4 Bedrooms, 4 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Heated Pool
  • Hot Tub
  • Internet Access
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About this property
Heated pool Osterville CALL or email for additional details. Amazing views from this Osterville home of the salt water bay with dock. Four bedrooms and 3.5 baths. You have access to Centerville River, Long Beach, and Nantucket Sound. Heated in ground gunite pool. Lovely gardens, 48 deck for... View all property information
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From
$3,000
Per Week
1 / 16
6 Bedrooms, 4 Bathrooms, Sleeps 8
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  • Dishwasher
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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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From
$3,800
Per Week
1 / 13
3 Bedrooms, 3 Bathrooms, Sleeps 5
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  • Air Conditioning
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  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
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About this property
236 Smoke Valley Road 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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$2,500
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1 / 21
3 Bedrooms, 3 Bathrooms, Sleeps 5
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About this property
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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From
$6,750
Per Week
1 / 33
4 Bedrooms, 3 Bathrooms, Sleeps 7
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  • Dishwasher
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  • Internet Access
  • 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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From
$1,100
Per Week
1 / 20
3 Bedrooms, 1 Bathroom, Sleeps 6
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About this property
Osterville Village near Joshua''s Pond! Charm,charm, charm, in this cozy three bedroom with fabulous screened porch for those balmy summer evenings~ this freshly painted home has hardwood floors, tile kitchen with newer appliances, nice sunlit dining room, cozy living area w/HDTV and large private... View all property information
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$15,000
Per Week
1 / 27
7 Bedrooms, 7 Bathrooms, Sleeps 14
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  • Heated Pool
  • Hot Tub
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  • Pets allowed
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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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$2,600
Per Week
1 / 20
3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Housekeeping...
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About this property
Oyster Hills Located in the convenient and sought-after neighborhood of Oyster Hills, this ranch style home has all the essentials! Professionally decorated & fully furnished in upscale comfort, this sunny home offers first floor living at its best!!! Pack your personal belongings and nothing more!... View all property information
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From
$1,800
Per Week
1 / 21
4 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Air Conditioning
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  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
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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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$5,000
Per Week
1 / 31
3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Outdoor Pool
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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
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1 / 12
3 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
OSTERVILLE: Delightful 3 bedrooms, 3 bath homes within a mile of the village and Dowses Beach. This home offers central a/c, washer dryer and a nice deck. This is a 2 story home that is spacious, bright, open floor plan and beautifully maintained. The first floor of the home offers a kitchen with... View all property information
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From
$1,400
Per Week
1 / 16
4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
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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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From
$3,250
Per Week
1 / 22
4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
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  • Internet Access
  • Satellite TV
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  • Pets allowed
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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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$4,500
Per Week
1 / 32
4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
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  • Internet Access
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About this property
154 Scudder Road Exclusive Robert Paul Properties Rental A perfectly situated Osterville home - close to both town and beach. This wonderfully appointed 4 bedroom home features a sunroom off the kitchen, a spacious first floor master bedroom with en suite bathroom, 3 bedrooms on the second level,... View all property information
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From
$10,500
Per Week
1 / 36
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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From
$3,200
Per Week
1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
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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
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From
$15,000
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1 / 22
5 Bedrooms, 7 Bathrooms, Sleeps 12
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Heated Pool
  • Internet Access
Suitability
  • Pets allowed
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  • Suitable for children
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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
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From
$2,500
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1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Dryer
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  • Internet Access
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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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$900
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1 / 9
4 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Dishwasher
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  • Internet Access
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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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
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$3,000
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1 / 17
3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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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
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$4,500
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1 / 19
4 Bedrooms, 4 Bathrooms, Sleeps 10
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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 view Osterville Enjoy sunsets from this charming Cape Cod rental overlooking West Bay. A deeded path meanders down to the bay for easy access to the water. This 4-bedroom, 3.5-bath home is perfectly located in the heart of Wianno and within walking distance to Osterville village with... View all property information
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$12,500
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1 / 34
11 Bedrooms, 8 Bathrooms, Sleeps 20
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  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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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
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$4,700
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1 / 16
5 Bedrooms, 5 Bathrooms, Sleeps 10
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  • 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
  • ?
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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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From
$1,500
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1 / 11
4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Dishwasher
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Short Drive to Beach with Central A/C: This is a wonderful 4 bedroom, 3 bath home with central a/c, garage, washer/dryer, fully equipped kitchen with dishwasher, dining area, large living room, outside shower (not enclosed). You enter from the garage into a three season TV room with sofa and... View all property information
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$2,800
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1 / 17
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
  • ?
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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
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$12,500
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1 / 33
12 Bedrooms, 8 Bathrooms, Sleeps 15
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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
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$1,800
Per Week
1 / 22
4 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
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  • Wheelchair access
  • Elder access
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About this property
Charming Osterville 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 eat-in kitchen. There is a spacious deck off the... View all property information
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$25,000
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1 / 34
7 Bedrooms, 7 Bathrooms, Sleeps 12
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Outdoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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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
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From
$15,000
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1 / 25
5 Bedrooms, 5 Bathrooms, Sleeps 12
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Outdoor Pool
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Oyster Harbors Exclusive Robert Paul Properties Rental Stunning home in the gated Community of Oyster Harbors. Tastefully decorated, bright, kitchen with gleaming hardwood floors. Top of the line appliances in the kitchen make it easy to entertain a large group. The living room has comfortable... View all property information
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$1,000
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1 / 10
2 Bedrooms, 1 Bathroom, Sleeps 4
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  • Dishwasher
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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
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$3,000
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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