Osterville Vacation Rentals

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Osterville Massachusetts Vacation Rentals - Home

11BR / 7BA - Sleeps 12 - Osterville Home

Waterfront directly on Nantucket Sound with private beach and small dock: This is a magnificent home...

$1,250 - $1,786 / nt

Osterville Massachusetts Vacation Rentals - Home

5BR / 4BA - Sleeps 8 - Osterville Home

14 Indian Trail - Oyster HarborsPrivate gated community surrounded by water in prestigious Osterville....

$1,429 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Osterville Home

420 Starboard LaneLovely Colonial with seasonal views of Bumps River. 4 bedrooms, 2. 5 baths. Centra...

$543 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Osterville Home

33 Waterfield RoadExclusive Robert Paul Properties Rental Wonderful Osterville vacation rental. Walk...

$429 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 4BA - Sleeps 6 - Osterville Home

Gracious Seapuit area estate over 2. 5 acres with lovely 3 bedroom 3 . 5 bath renovated ranch style home...

$315 / nt

Osterville Massachusetts Vacation Rentals - Home

2BR / 1BA - Sleeps 4 - Osterville Home

Walk to villageThis is the most charming and updated cottage in the "Village" that you will find! Just...

$215 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 6 - Osterville Home

South of Rte. 28 OSTERVILLE Vacation Home! Sleeps SixCome enjoy this bright & sunny south of rte. 28...

$179 - $214 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Osterville Home

Wianno Area Four Bedroom ! Seaview Avenue area of Osterville! Open concept Cape/ close to the small...

$200 - $258 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Osterville Home

ENJOY the charm of Osterville Village! Lovely 4 bedroom 2 bath Cape Located in Osterville Village,...

$258 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 1BA - Sleeps 6 - Osterville Home

Osterville Village near Joshua''s Pond! Charm, charm, charm, in this cozy three bedroom with fabulous...

$158 - $200 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 5 - Osterville Home

Spectacular three bedroom Nantucket style cottage located on a hill over looking Warrens Cove This prestine...

$358 - $565 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 7 - Osterville Home

Private Pool, Tennis Court and home with Central A/C: This is a gorgeous 4 bedroom (includes room over...

$965 - $1,072 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Osterville Home

Oyster HillsLocated in the convenient and sought- after neighborhood of Oyster Hills, this ranch style...

$372 / nt

Osterville Massachusetts Vacation Rentals - Home

7BR / 7BA - Sleeps 12 - Osterville Home

77 Pirates Cove - Oyster HarborsLuxury at it s best! This stunning home in the gated community of Oyster...

$3,572 / nt

Osterville Massachusetts Vacation Rentals - Home

11BR / 6BA - Sleeps 12 - Osterville Home

Private beach & dockCharming waterfront home with private beach and small dock on Nantucket Sound. This...

$1,429 / nt

Osterville Massachusetts Vacation Rentals - Home

5BR / 7BA - Sleeps 12 - Osterville Home

Pool OstervilleSpectacular and spacious home in the Seapuit area of Osterville. Gorgeous landscaping...

$2,143 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 8 - Osterville Home

113 Pond StreetExclusive Robert Paul Properties Rental. Designed by award winning architect, Reed Morrison,...

$472 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Osterville Home

Close to Dowes beachLovely three bedroom with bonus sleeping area in lower level. This Osterville home...

$472 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 6 - Osterville Home

71 Bumps River RoadFieldstone Estates. Beautiful home, private setting with estate- like grounds and...

$715 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 5 - Osterville Home

236 Smoke Valley RoadThis stunning waterfront home is a one of a kind with breathtaking views from every...

$543 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Osterville Home

138 Bridge StreetCharming 1900 period home with many updates for todays comfort! This waterfront home...

$643 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 4BA - Sleeps 8 - Osterville Home

Heated pool OstervilleCALL or email for additional details. Amazing views from this Osterville home of...

$1,215 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 6BA - Sleeps 8 - Osterville Home

Osterville near villageExclusive Robert Paul Properties Rental Secluded gem features great combination...

$715 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Osterville Home

48 Pine AvenueExclusive Robert Paul Properties RentalClose to Main Street in Osterville and Dowes Beach....

$458 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 7 - Osterville Home

154 Tower Hill RoadThis adorable house is close to the best of Osterville - Main Street and Dowes Beach....

$379 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 4BA - Sleeps 6 - Osterville Home

64 Bay Street - OstervilleThis home was designed by a Well Known Architect. Walk to Main Street in Osterville...

$715 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 6 - Osterville Home

37 Bates Street - OstervilleClose to Dowses Beach and not far from the village. This 1890 Vintage home...

$358 / nt

Osterville Massachusetts Vacation Rentals - Home

2BR / 1BA - Sleeps 4 - Osterville Home

165 Wianno CircleWonderful location! Close to Dowes and not far from Main Street, also close to Wianno...

$372 / nt

Osterville Massachusetts Vacation Rentals - Home

5BR / 5BA - Sleeps 12 - Osterville Home

Oyster HarborsExclusive Robert Paul Properties Rental Stunning home in the gated Community of Oyster...

$2,143 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Osterville Home

Osterville rental not far from Dowes and VillageThis lovely 3 bedroom, 2 bath home is not far from Dowes...

$400 / nt

Osterville Massachusetts Vacation Rentals - Home

2BR / 1BA - Sleeps 4 - Osterville Home

Short Walk to Osterville Village: This is a newly renovated 2 bedroom, 1 bath cottage with wireless...

$143 - $200 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Osterville Home

Charming Osterville homeClose to Osterville Village and Joshua s Pond, this charming rental home has...

$258 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 6 - Osterville Home

44 Sunset LaneExclusive Robert Paul Properties Rental Walk to village from this lovely 3 bedroom 3 bath...

$429 / nt

Osterville Massachusetts Vacation Rentals - Home

5BR / 6BA - Sleeps 10 - Osterville Home

Lovely larger home located on the 8th hole of Oyster Harbors Golf Course. The first level has a large...

$372 - $500 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Osterville Home

Short Drive to Beach with Central A/C: This is a wonderful 4 bedroom, 3 bath home with central a/c,...

$215 / nt

Osterville Massachusetts Vacation Rentals - Home

11BR / 8BA - Sleeps 20 - Osterville Home

Sea views at its best! Exclusive Robert Paul Properties Rental Wonderful old world charm! 11 bedroom...

$1,786 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Osterville Home

New to the market! Nice clean 4 bedroom, 2 bath home located a couple of miles from Osterville Village...

$129 - $258 / nt

Osterville Massachusetts Vacation Rentals - Home

6BR / 6BA - Sleeps 12 - Osterville Home

405 Sea View AveExclusive Robert Paul Properties Rental Seaview Avenue Beachfront Estate. 2005 Custom...

$1,500 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Osterville Home

225 Wianno CircleExclusive Robert Paul Properties rental. Desirable Wianno Circle home. Close to Dowes...

$358 / nt

Osterville Massachusetts Vacation Rentals - Home

5BR / 5BA - Sleeps 10 - Osterville Home

Near Village and BeachExclusive Robert Paul Properties rental. This magnificent, renovated home is set...

$672 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 4BA - Sleeps 10 - Osterville Home

Waterfront view OstervilleEnjoy sunsets from this charming Cape Cod rental overlooking West Bay. A deeded...

$643 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Osterville Home

Osterville near villageNot far from Village and Beaches. Main house with 3 bedrooms, 1 1/12 baths. Cottage...

$465 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Osterville Home

Central air conditioned cape - First floor: Entry to bright formal living room/dining area. To the right...

$215 - $315 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 4BA - Sleeps 8 - Osterville Home

ID# SPI11 Osterville, magnificently newly redesigned Vacation home with high end features and furnishings,...

$500 / nt

Osterville Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Osterville Home

154 Scudder RoadExclusive Robert Paul Properties Rental A perfectly situated Osterville home - close...

$643 / nt

Osterville Massachusetts Vacation Rentals - Home

6BR / 5BA - Sleeps 11 - Osterville Home

8 East Bay Road - OstervilleExclusive Robert Paul Properties rental home located in the heart of Osterville,...

$715 / nt

Osterville Massachusetts Vacation Rentals - Home

12BR / 8BA - Sleeps 15 - Osterville Home

The Beacon - 554 Wianno AveExclusive Robert Paul Properties Rental Cape Cod at its best and most elegant....

$1,786 / nt

Osterville Massachusetts Vacation Rentals - Home

6BR / 4BA - Sleeps 8 - Osterville Home

OSTERVILLE: Spotless and spacious 6 bedrooms, 4 bath home with central a/c, internet and washer/dryer...

$429 - $572 / nt

Osterville Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 6 - Osterville Home

Stunning Osterville Home With New Heated Pool! Beautiful Osterville Pool Home With Desirable Open Floor...

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