Osterville Vacation Rentals, Homes, & More

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1-50 of 55 Osterville Rentals

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Osterville Massachusetts Vacation Rentals - Cottage
1 / 7

Osterville Cottage
2 Bedrooms / 1 Bathroom / Sleeps 4
Cottage / 2 Bedrooms / Sleeps 4

from

$160

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$160 - $269
Per week:$1,050 - $1,599
Pets allowed:No
Internet:No

Lovely 2 Bedroom home on a quiet street in the desirable Wianno area of Osterville, Cape Cod or Osterville Village. (This is the section nearest to Dowses' Beach! You can't find a rental for this price this close to the beach in Osterville! ! ) The house is bright, clean and...

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1 / 9

Osterville Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$129

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$129 - $258
Per week:$900 - $1,800
Pets allowed:Yes
Internet:Yes

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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 21

Osterville Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$200

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$200 - $258
Per week:$1,400 - $1,800
Pets allowed:No
Internet:Yes

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 ...

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Property 96974
1 / 16

Osterville Home
3 Bedrooms / 4 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$350

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$350 - $700
Per week:$2,450 - $4,900
Pets allowed:No
Internet:Yes

Lovely & bright home on almost three acres in Osterville s coveted "Seapuit" enclave (which fronts North Bay) ~ A gracious & comfortable gem with 3 bedrooms & 3 . 5 baths~each bedroom has it s own private bath. Beautifully furnished and decorated for comfortable living with a NEWLY...

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1 / 12

Osterville Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$100

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$100 - $186
Per week:$700 - $1,300
Pets allowed:No
Internet:Yes

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....

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Osterville Massachusetts Vacation Rentals - Home
1 / 34

Osterville Home
7 Bedrooms / 7 Bathrooms / Sleeps 14
Home / 7 Bedrooms / Sleeps 14

Bedrooms:7
Bathrooms:7
Sleeps:14
Type:Home
Per night:$1,500
Per week:$10,500
Pets allowed:No
Internet:Yes

Heated pool and lovely locationExclusive 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 19

Osterville Home
4 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$643

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$643
Per week:$4,500
Pets allowed:No
Internet:Yes

Waterfront and view OstervilleExclusive 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
5 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

from

$672

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$672
Per week:$4,700
Pets allowed:No
Internet:Yes

Near Village and BeachExclusive 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...

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This wonderful getaway  is sited on .83 acres surrounded by fields of wild flowers & rolling lawns
1 / 11

Osterville Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$472

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$472
Per week:$3,300
Pets allowed:Yes
Internet:Yes

113 Pond StreetExclusive 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 ...

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1 / 22

Osterville Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$500

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$500
Per week:$3,500
Pets allowed:No
Internet:No

138 Bridge StreetCharming 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 ...

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1 / 21

Osterville Home
3 Bedrooms / 4 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$715

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$715
Per week:$5,000
Pets allowed:No
Internet:Yes

64 Bay Street - OstervilleThis 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...

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1 / 33

Osterville Home
11 Bedrooms / 8 Bathrooms / Sleeps 20
Home / 11 Bedrooms / Sleeps 20

Bedrooms:11
Bathrooms:8
Sleeps:20
Type:Home
Per night:$1,786
Per week:$12,500
Pets allowed:No
Internet:Yes

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...

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Cape Cod at its best.
1 / 33

Osterville Home
12 Bedrooms / 8 Bathrooms / Sleeps 15
Home / 12 Bedrooms / Sleeps 15

Bedrooms:12
Bathrooms:8
Sleeps:15
Type:Home
Per night:$1,786
Per week:$12,500
Pets allowed:No
Internet:Yes

The Beacon - 554 Wianno AveExclusive 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 27

Osterville Home
7 Bedrooms / 7 Bathrooms / Sleeps 14
Home / 7 Bedrooms / Sleeps 14

Bedrooms:7
Bathrooms:7
Sleeps:14
Type:Home
Per night:$2,143
Per week:$15,000
Pets allowed:No
Internet:Yes

155 Carriage Lane - Oyster HarborsExclusive 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 22

Osterville Home
5 Bedrooms / 7 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

Bedrooms:5
Bathrooms:7
Sleeps:12
Type:Home
Per night:$2,143
Per week:$15,000
Pets allowed:No
Internet:Yes

Pool OstervilleSpectacular 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 ...

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Osterville Massachusetts Vacation Rentals - Home
1 / 35

Osterville Home
6 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:6
Sleeps:12
Type:Home
Per night:$1,500
Per week:$10,500
Pets allowed:No
Internet:Yes

405 Sea View AveExclusive 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,...

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Osterville Massachusetts Vacation Rentals - Home
1 / 34

Osterville Home
11 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 11 Bedrooms / Sleeps 12

Bedrooms:11
Bathrooms:6
Sleeps:12
Type:Home
Per night:$1,786
Per week:$12,500
Pets allowed:No
Internet:Yes

Private beach & dockLarge 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 michelle@robertpaul....

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This stunning home in the gated community of Oyster Harbors
1 / 34

Osterville Home
7 Bedrooms / 7 Bathrooms / Sleeps 12
Home / 7 Bedrooms / Sleeps 12

Bedrooms:7
Bathrooms:7
Sleeps:12
Type:Home
Per night:$3,572
Per week:$25,000
Pets allowed:No
Internet:Yes

77 Pirates Cove - Oyster HarborsLuxury 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 ...

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Osterville Massachusetts Vacation Rentals - Home
1 / 20

Osterville Home
6 Bedrooms / 5 Bathrooms / Sleeps 11
Home / 6 Bedrooms / Sleeps 11

from

$715

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:11
Type:Home
Per night:$715
Per week:$5,000
Pets allowed:No
Internet:Yes

8 East Bay Road - OstervilleExclusive 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,...

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
4 Bedrooms / 6 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$715

/ night

Email Owner
Bedrooms:4
Bathrooms:6
Sleeps:8
Type:Home
Per night:$715
Per week:$5,000
Pets allowed:No
Internet:Yes

Osterville near villageExclusive 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 6

Osterville Home
3 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
Per night:$1,215
Per week:$8,500
Pets allowed:No
Internet:Yes

Heated pool in OstervilleContact 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 22

Osterville Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$258

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$258
Per week:$1,800
Pets allowed:No
Internet:Yes

Charming Osterville homeExclusive 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 22

Osterville Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$465

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$465
Per week:$3,250
Pets allowed:No
Internet:Yes

Osterville near villageNot 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$472

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$472
Per week:$3,300
Pets allowed:No
Internet:Yes

Close to Dowes beachLovely 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 31

Osterville Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$715

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$715
Per week:$5,000
Pets allowed:No
Internet:Yes

71 Bumps River RoadFieldstone 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$429

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$429
Per week:$3,000
Pets allowed:No
Internet:Yes

44 Sunset LaneExclusive 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. comAdditional...

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Osterville Massachusetts Vacation Rentals - Home
1 / 17

Osterville Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$429

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$429
Per week:$3,000
Pets allowed:No
Internet:Yes

33 Waterfield RoadExclusive 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$358

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

225 Wianno CircleExclusive 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. comAdditional amenities include: coffee...

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Osterville Massachusetts Vacation Rentals - Home
1 / 17

Osterville Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$400
Per week:$2,800
Pets allowed:No
Internet:Yes

Osterville rental not far from Dowes and VillageThis 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....

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Osterville Massachusetts Vacation Rentals - Home
1 / 13

Osterville Home
3 Bedrooms / 3 Bathrooms / Sleeps 5
Home / 3 Bedrooms / Sleeps 5

from

$543

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:5
Type:Home
Per night:$543
Per week:$3,800
Pets allowed:No
Internet:Yes

On the water with dockThis 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 ...

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Osterville Massachusetts Vacation Rentals - Home
1 / 10

Osterville Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$372

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$372
Per week:$2,600
Pets allowed:No
Internet:Yes

165 Wianno CircleWonderful 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 15

Osterville Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$215

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$215
Per week:$1,500
Pets allowed:No
Internet:Yes

Walk to villageThis 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 1

Osterville Home
9 Bedrooms / 9 Bathrooms / Sleeps 15
Home / 9 Bedrooms / Sleeps 15

Bedrooms:9
Bathrooms:9
Sleeps:15
Type:Home
Per night:$3,572
Per week:$25,000
Pets allowed:No
Internet:Yes

Mellon Estate in Oyster HarborsQuiet 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 ...

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Osterville Massachusetts Vacation Rentals - Home
1 / 11

Osterville Home
4 Bedrooms / 2 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$458

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
Per night:$458
Per week:$3,200
Pets allowed:No
Internet:Yes

79 Gunstock RoadLovely 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- ...

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Osterville Massachusetts Vacation Rentals - Home
1 / 21

Osterville Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$236

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$236
Per week:$1,650
Pets allowed:No
Internet:Yes

Osterville rentalCharming 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 ...

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Osterville Massachusetts Vacation Rentals - Home
1 / 2

Osterville Home
3 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$700

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
Per night:$700
Per week:$4,900
Pets allowed:No
Internet:Yes

Private & Serene Osterville EstateBright, 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$458

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$458
Per week:$3,200
Pets allowed:No
Internet:Yes

48 Pine AvenueExclusive 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 2

Osterville Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

24 South StreetLovely 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. comAdditional amenities include: coffee maker,...

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Osterville Massachusetts Vacation Rentals - Home
1 / 24

Osterville Home
5 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 5 Bedrooms / Sleeps 8

Bedrooms:5
Bathrooms:4
Sleeps:8
Type:Home
Per night:$1,429
Per week:$10,000
Pets allowed:No
Internet:Yes

14 Indian Trail - Oyster HarborsPrivate 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 22

Osterville Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$379

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$379
Per week:$2,650
Pets allowed:No
Internet:Yes

154 Tower Hill RoadThis 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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 17

Osterville Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$179

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$179 - $214
Per week:$1,250 - $1,495
Pets allowed:No
Internet:Yes

STILL SOME SUMMER WEEKS AVAILABLE! ! OSTERVILLE ! ! Come enjoy this bright & sunny south of rte. 28 vacation home on a quiet street in lovely Osterville Woods! Quick access to beautiful Dowses Beach on Nantucket Sound (BEACH PASS PROVIDED ) Joshua s "cystal clear" Pond & the charming...

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$200

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$200 - $258
Per week:$1,400 - $1,800
Pets allowed:No
Internet:Yes

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!...

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Osterville Massachusetts Vacation Rentals - Home
1 / 5

Osterville Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$129

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$129 - $186
Per week:$900 - $1,300
Pets allowed:No
Internet:Yes

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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 8

Osterville Home
3 Bedrooms / 1 Bathroom / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$186

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:6
Type:Home
Per night:$186
Per week:$1,300
Pets allowed:No
Internet:Yes

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 ...

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
4 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

West Bay Osterville HomeClose to village and not far from the beach. This four bedroom well appointed home has it all. For more information about this rental contact Michelle Sylvia at 508- 648- 2967 or email michelle@robertpaul. comAdditional amenities include: coffee maker, 2 queen...

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Osterville Massachusetts Vacation Rentals - Home
1 / 2

Osterville Home
6 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 6 Bedrooms / Sleeps 10

Bedrooms:6
Bathrooms:5
Sleeps:10
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Sea View AveThe very best of old + new! 4500+ sq. ft. of vintage Cape charm conscientiously updated for today’s lifestyles. 1930’s family summer home on Nantucket Sound. Private beach with ocean views from every room. Modern amenities include heated pool, full A/C, updated...

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1 / 18

Osterville Home
5 Bedrooms / 6 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

Bedrooms:5
Bathrooms:6
Sleeps:10
Type:Home
Per night:$1,072
Per week:$7,500
Pets allowed:No
Internet:Yes

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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 33

Osterville Home
4 Bedrooms / 3 Bathrooms / Sleeps 7
Home / 4 Bedrooms / Sleeps 7

from

$965

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:7
Type:Home
Per night:$965 - $1,072
Per week:$6,750 - $7,500
Pets allowed:No
Internet:Yes

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, ...

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Osterville Massachusetts Vacation Rentals - Home
1 / 19

Osterville Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$215

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$215 - $315
Per week:$1,500 - $2,200
Pets allowed:Yes
Internet:Yes

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...

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Osterville Massachusetts Vacation Rentals - Home
1 / 10

Osterville Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$286

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$286
Per week:$2,000
Pets allowed:Yes
Internet:Yes

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...

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