Osterville Vacation Rentals

35 Rentals

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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

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

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

This stunning home in the gated community of Oyster Harbors

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

11BR / 6BA - Sleeps 12 - Osterville Home

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

$1,429 / nt

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

5BR / 7BA - Sleeps 12 - Osterville Home

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

$2,143 / nt

Bright and spacious living room

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

4BR / 4BA - Sleeps 8 - Osterville Home

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

$1,215 / nt

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

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

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

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

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

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

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

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

5BR / 5BA - Sleeps 10 - Osterville Home

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

$672 / nt

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 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

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

$643 / 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 / 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

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

OSTERVILLE: Delightful 3 bedrooms, 3 bath homes within a mile of the village and Dowses Beach. This...

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Osterville Home

Short Walk to Osterville Village and just a short drive to the beach: This is a very nice 3 bedroom,...

Osterville Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Osterville Home

Wonderful three bedroom boathouse with a dock and beach. The first level of this house sits above the...

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 / 3BA - Sleeps 6 - Osterville Home

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

Osterville Massachusetts Vacation Rentals - Home

4BR / 4BA - Sleeps 10 - Osterville Home

West Bay Osterville HomeClose to village and not far from the beach. This four bedroom well appointed...

Osterville Massachusetts Vacation Rentals - Home

6BR / 5BA - Sleeps 10 - Osterville Home

Sea View AveThe very best of old + new! 4500+ sq. ft. of vintage Cape charm conscientiously updated...

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