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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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Osterville things to do

 

The Giving Tree Gallery & Sculpture Garden

It's so great to stop in once every few months to view the new collection,. LOVE MarLa Studio designs. Pablo Valencia, phew...Baroni, wow..Lochlan Smith's...read more

 

Hyannis Whale Watcher Cruises

What an amazing day we had on this cruise. We went on an afternoon in the beginning of July and saw over 50 humpback whales. They were right by the boat....read more

 

Willowbend

Granted this was where we were married- so I am completely biased. However, Willowbend CC truly does a great job for their events. Food is excellent....read more

 

Rideaway Kayak- East Sandwich

This place is fabulous! We found them on yelp & loved the $40/3 hour deal they had, so decided to try. While they are located off of 6A, they aren't...read more

 

Lowell Park

I'm hard pressed to think of something more American than Cape Cod Baseball. It's the kind of neighborhood park you envision in Norman Rockwell painted...read more

 

Skydive Barnstable

When I was a kid, my extended family and I took a trip to Toronto. While the rest of my family took the long elevator to the top of the CN Tower, I can...read more

 

Bay Spirit Tours

absolutely loved this tour. we walked around main st in Hyannis and had lunch and shopped a little. We then drove down to the pier around 630pm for the...read more

 

Cape Cod Airfield

Just jump. I have never had this much fun...ever. The experience from arriving to driving off was perfect. Everybody there was very professional and...read more

 

Centerville Yoga

I recently moved down to Cape Cod for the summer on April 1st 2008 and I was very pleased to find this yoga studio and wellness center is right around the...read more

 

Atsakeepa Sportfishing Charters

If you are in Cape Cod, and you want to catch fish, book this guy immediately. We went for a morning, half day trip on a Tuesday, and we were taken out to...read more

 

Cape Cod Melody Tent

The 1st Annual Beer Festival at the Cape Cod Melody Tent was not worth the money. While there was not an overwhelming amount of people at the Sunday...read more

 

The Lanes Bowl and Bistro

7 hour wait to bowl on 4th of July weekend!? I understand that it's a busy weekend on the Cape, and we chose a rainy day.. but 7 hours just seems too...read more

 

Cape Cod Children's Museum

We've been to quite a few children's museums and this is by far my least favorite. It is small and some of the exhibits are pretty lame (the apple garden in...read more

 

Heritage Museums & Gardens

So you say you're a fan of daffodils, hydrangea or rhododendrons? After everything is in bloom, I'm quite positive this is the place to be. They've got...read more

 

Kalmus Beach

Best beach for shells. Actual water is not as good as Nauset beach. Go after 4pm and the parking is free.read more

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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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InteriorDesigner's Lux-Comfy NearBeach FamilyFriendly Beautiful Home
Osterville House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $575 - $850 /nt
    $3,000 - $5,500 /wk
 
 
 
 
 

13 reviews write a review

Beautiful new home, Craigville Beach, Centerville, four seas ice cream
Osterville House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,600 - $2,500 /wk
 
 
 
 
 

1 reviews write a review

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) $500 - $786 /nt
    $2,000 - $3,000 /wk
    $4,000 - $20,000 /mth
 
 
 
 
 

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) $200 - $275 /nt
 
 
 
 
 

4 reviews write a review

Newly renovated, spacious cottage near Craigville Beach
Osterville Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $300 - $600 /nt
    $1,500 /wk
 
 
 
 
 

9 reviews write a review

Private Family Compound - Craigville Beach - Heated Pool (and a Pond!)
Osterville Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • sleeps 11
  • baths
  • rates (USD) $700 - $1,100 /nt
    $4,900 - $7,700 /wk
    $16,000 - $30,000 /mth
 
 
 
 
 

3 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 - $995 /nt
    $2,996 - $6,965 /wk
 
 
 
 
 

5 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

Private Spacious Lakefront 4 Bdrm with Dock, Steps Away from Ocean Beaches
Osterville House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $5,000 /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

5 Bed/3 BA Renovated Wianno Home W/ NEW Private Heated Pool, Walk to Village
Osterville House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 15
  • baths 3
  • rates (USD) $1,750 - $6,500 /wk
 
 
 
 
 

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PRIVATE OSTERVILLE ESTATE
Osterville House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $2,900 - $3,900 /wk
 
 
 
 
 

4 reviews write a review

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

3 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 - $857 /nt
    $1,925 - $6,000 /wk
 
 
 
 
 

1 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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