Vacation Rentals By Owner In Osterville, MA

Showing 20 Of 74 Vacation Rentals

Exceptional(13)

$4238.09

/ Nightly

Private Vacation Home

Expansive Cape Cod Family Retreat

Osterville, Massachusetts, United States

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Bath

Sleeps

$510.83

/ Nightly

Private Vacation Home

Walk to Main St! Osterville Cottage w/ Patio

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(1)

$1917.89

/ Nightly

Private Vacation Home

Elevated Osterville Escape with Heated Pool RPAM128

Osterville, Massachusetts, United States

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Bath

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Exceptional(24)

$915.6

/ Nightly

Private Vacation Home

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

Osterville, Massachusetts, United States

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Bath

Sleeps

$244.35

/ Nightly

Apartment

Private & Serene Stay 2-bedroom studio - Osterville - AC - Free Beach Pass - W/D

Barnstable, Massachusetts, United States

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Bath

Sleeps

Exceptional(10)

$2792.96

/ Nightly

Private Vacation Home

4BR 4BA Osterville home with pool, hot tub, game room-minutes from the beach!

Barnstable, Massachusetts, United States

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Bath

Sleeps

$6287.84

/ Nightly

Private Vacation Home

Welcome to The Barn on Seaview- Cape Cod’s Premier Waterfront Oasis with Pool, Hot Tub & Endless Entertainment

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(48)

$1932.49

/ Nightly

Private Vacation Home

Heated Private Pool, Walk to Beach & Shops, fully renovated house

Osterville, Massachusetts, United States

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Bath

Sleeps

$712.34

/ Nightly

Private Vacation Home

Classic Cape Cod Charm in the heart of Osterville Village.

Barnstable, Massachusetts, United States

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Exceptional(2)

$1217.59

/ Nightly

Private Vacation Home

Impressive Osterville Residence - Ideal Location

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(1)

$467.03

/ Nightly

Private Vacation Home

Cape Cod getaway near Craigville Beach

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(5)

$710.54

/ Nightly

Private Vacation Home

Cozy Cottage: 135-HYP Quintessential Hyannis Port Cottage: Renovated, Putting Green, Walk to Beach

West Hyannisport, Massachusetts, United States

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Bath

Sleeps

Exceptional(1)

$435.89

/ Nightly

Private Vacation Home

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

Osterville, Massachusetts, United States

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Bath

Sleeps

$1006.02

/ Nightly

Private Vacation Home

Cape Cod Escape | Near Beaches | Play Area

Osterville, Massachusetts, United States

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Bath

Sleeps

$368.15

/ Nightly

Apartment

3 Mi to Craigville Beach! Walkable Couple’s Haven

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(14)

$468.1

/ Nightly

Cottage

Walk to Shops & Dining: Cozy Osterville Cottage

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(92)

$1191.43

/ Nightly

Private Vacation Home

BEAUTIFUL and PRIVATE OSTERVILLE HOME, LARGE GAME ROOM, AC,PARKING

Barnstable, Massachusetts, United States

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Bath

Sleeps

$1919.83

/ Nightly

Private Vacation Home

Amazing updated waterfront home located in Osterville with a private dock, elevator and AC.

Osterville, Massachusetts, United States

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Bath

Sleeps

$1573.2

/ Nightly

Private Vacation Home

Seasons by the Sea: Fully Renovated Luxury Cape Cod Home

Barnstable, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$913.89

/ Nightly

Private Vacation Home

Osterville Village - New Pool Large Yard + Outdoor Entertaining Area

Osterville, Massachusetts, United States

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Rent a place that suits your needs

Private vacation home

View 70 Private vacation home

Most popular vacation rentals in Osterville

Exceptional(2)

$587.87

/ Nightly

Private vacation home

Private Pool, Central AC, Dog Friendly!

Barnstable, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$938.50

/ Nightly

Private vacation home

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

Barnstable, Massachusetts, United States

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Bath

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Exceptional(2)

$928.19

/ Nightly

Private vacation home

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

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$915.60

/ Nightly

Private vacation home

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

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$913.89

/ Nightly

Private vacation home

Osterville Village - New Pool Large Yard + Outdoor Entertaining Area

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$829.60

/ Nightly

Private vacation home

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

Truro, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$740.72

/ Nightly

Private vacation home

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

Osterville, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$686.70

/ Nightly

Private vacation home

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

Barnstable, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$435.89

/ Nightly

Private vacation home

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

Osterville, Massachusetts, United States

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Bath

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Exceptional(2)

$451.80

/ Nightly

Private vacation home

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

Osterville, Massachusetts, United States

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Bath

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Vacation Rentals By Owner In Osterville, MA

$4238.09

$510.83

$1917.89

$915.6

$244.35

$2792.96

$6287.84

$1932.49

$712.34

$1217.59

$467.03

$710.54

$435.89

$1006.02

$368.15

$468.1

$1191.43

$1919.83

$1573.2

$913.89

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