Vacation Rentals By Owner In Osterville, MA

Showing 74 Of 74 Vacation Rentals

Exceptional(2)

$541.84

/ Nightly

Cottage

Charming cottage near Osterville Village and Dowses beach RPMS094

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$1644.81

/ Nightly

Private Vacation Home

BRAND NEW LISTING-Amazing Waterfront 5BD Private Setting-Pool & Hot Tub-Sleeps 10-Osterville-Beach Permit Included

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$1524.76

/ Nightly

Private Vacation Home

Beautiful designed, newly constructed home- all the amenities, close to beaches

Barnstable, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(15)

$1550.8

/ Nightly

Private Vacation Home

The Half Shell Cottage in Osterville Village

Barnstable, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$587.87

/ Nightly

Private Vacation Home

Private Pool, Central AC, Dog Friendly!

Barnstable, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$686.7

/ Nightly

Private Vacation Home

Osterville - close to town & beach, AC, beach pass

Barnstable, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(15)

$326.76

/ Nightly

Private Vacation Home

THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$298.33

/ Nightly

Private Vacation Home

Perfect Vacation Getaway!

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(24)

$406.3

/ Nightly

Private Vacation Home

Osterville Escape to our Spacious Family Getaway. Barnstable Beach pass included

Ostervillle, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(12)

$631.77

/ Nightly

Private Vacation Home

Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(14)

$503.58

/ Nightly

Private Vacation Home

Pristine Osterville Cottage

Barnstable, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

Select Dates for Price

Private Vacation Home

In the Heart of Osterville Village, Newly renovated, Pets considered RPMS087

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(20)

$928.19

/ Nightly

Private Vacation Home

Osterville 4BD on Wianno 2nd Fairway! Walk to village/marina or bike to beach.

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$2131.06

/ Nightly

Private Vacation Home

Lovely Osterville Home With New Gunite Pool and Beach Pass.

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 70 Private vacation home

Most popular vacation rentals in Osterville

Exceptional(31)

$587.87

/ Nightly

Private vacation home

Private Pool, Central AC, Dog Friendly!

Barnstable, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$938.50

/ Nightly

Private vacation home

5 minutes to beach, newly redone house w hot tub/screening room in osterville

Barnstable, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$928.19

/ Nightly

Private vacation home

Osterville 4BD on Wianno 2nd Fairway! Walk to village/marina or bike to beach.

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$915.60

/ Nightly

Private vacation home

Beach pass included • Modern 3BR Osterville retreat, walkable to village center

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$913.89

/ Nightly

Private vacation home

Osterville Village - New Pool Large Yard + Outdoor Entertaining Area

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$829.60

/ Nightly

Private vacation home

Private, dead-end on National Seashore, 3 bed/1.5 bath

Truro, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$740.72

/ Nightly

Private vacation home

Osterville Retreat – A/C, WiFi & Pet-Friendly

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$686.70

/ Nightly

Private vacation home

Osterville - close to town & beach, AC, beach pass

Barnstable, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$435.89

/ Nightly

Private vacation home

Enchanting 2 Bedroom Cottage - 1 block to Village Center-BEACH PASS-Weekly only

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(31)

$451.80

/ Nightly

Private vacation home

Charming home with open layout, deck, grill, AC, W/D, & yard

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

Vacation Rentals By Owner In Osterville, MA

$541.84

$1644.81

$1524.76

$1550.8

$587.87

$686.7

$326.76

$298.33

$406.3

$631.77

$503.58

$928.19

$2131.06

Rent a place that suits your needs

Most popular vacation rentals in Osterville

$587.87

$938.50

$928.19

$915.60

$913.89

$829.60

$740.72

$686.70

$435.89

$451.80

Most Popular Cities in Massachusetts