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Vacation Rentals in Osterville, Massachusetts

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about Osterville

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Osterville, Massachusetts vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Osterville are added and updated every week!

Compared to hotels, Osterville vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Osterville, Massachusetts Vacation Rentals and Tourism

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Bedrooms: Min 0, Max 5

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Guest House on Ocean and Beach Front Property
Osterville House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $2,000 - $12,000 /mth
 
 
 
 
 

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Private Family Compound
Osterville Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • sleeps 11
  • baths
  • rates (USD) $700 - $1,000 /nt
    $4,900 - $7,000 /wk
    $16,000 - $25,000 /mth
 
 
 
 
 

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Newly renovated, spacious cottage near Craigville Beach
Osterville Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $250 - $414 /nt
    $1,400 - $2,900 /wk
 
 
 
 
 

9 reviews write a review

Best View in Oyster Harbors with Private Beach and Deep-Water Dock
Osterville House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $428 - $980 /nt
    $2,996 - $6,860 /wk
 
 
 
 
 

5 reviews write a review

Secluded Cape House W/ Dock Close To Craigville Beach And Osterville
Osterville House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $300 - $1,000 /nt
    $1,925 - $6,000 /wk
 
 
 
 
 

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Pleasant Cape Cod-Style Home - One Block from North Bay!
Osterville House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 5
  • rates (USD)
 
 
 
 
 

1 reviews write a review

Immaculate, Renovated Cottage one mile to Craigville Beach
Osterville Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 7
  • baths 1
  • rates (USD) $1,950 - $2,100 /wk
 
 
 
 
 

4 reviews write a review

New Listing! Gorgeous, 2b/2b Home In Picturesque Osterville.
Osterville House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $150 - $228 /nt
    $805 - $1,596 /wk
    $1,950 - $2,550 /mth
 
 
 
 
 

3 reviews write a review

Be Our First Guest Centerville Village, Craigville Beach
Osterville House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,200 - $2,200 /wk
 
 
 
 
 

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Traditional Classic Cape Cod Home Wianno Section of Osterville
Osterville House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $3,500 /wk
 
 
 
 
 

1 reviews write a review

Renovated Wianno Home w/Private Pool, Walk to Dowses Beach & Village
Osterville House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 11
  • baths 2
  • rates (USD) $1,750 - $5,250 /wk
 
 
 
 
 

1 reviews write a review

Interior Designer's Lux-Comfy NearBeach FamilyFriendly Beautiful Home
Osterville House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 11
  • baths
  • rates (USD) $725 - $825 /nt
    $3,750 - $5,500 /wk
 
 
 
 
 

13 reviews write a review

Osterville Village Estate - New Home by award-winning architect
Osterville House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD)
 
 
 
 
 

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