Holiday Homes in Osterville

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Featured Holiday Homes in Osterville and around

"The beach access very nice nice for early morning or evening walks - quiet and private neighborhood. The 2 bedroom unit was comfortable and met our needs."

"The best and the most relaxing stay in Cape Cod. Close to ocean, breathtaking views , beautiful and very comfortable house. "

"We had such an amazing stay! The house was absolutely beautiful and had so much space for our family to relax and enjoy. The pool was incredible — the kids practically lived in it the whole trip! The hot tub was also a wonderful bonus! Everything was clean, comfortable, and even better than expected. The hosts were fantastic — quick to answer any questions and made sure we had everything we needed. We would definitely stay here again and highly recommend it to anyone looking for a perfect...

"Great location, comfortable and perfect for my family of four. "

"We had a great stay. Nice and close to the beach so my mid 80’s mom could even walk back and forth. and the raw bar on property was the perfect place for an easy meal. Would happily stay again."

"Very convenient location, nice location, plenty of room for our group! And being a dog friendly rental was thrilled with the yard. The outside deck was very nice to sit at, very comfortable "

"Perfect spot for a few days away with the kids. The house had everything we needed and was in a great location! Would definitely rent again. "

includes taxes & fees

16 Oct - 17 Oct

Beach nearby, sun-loungers, beach towels

"Great spot, we loved it!"

"My daughters and grandchildren enjoyed our stay. The location was ideal for shopping and restaurants We even invited over other relatives from the area to enjoy a cookout and smores.. I would rent this place again."

"Was a great house!! Clean, comfortable, and inviting. Close to Falmouth to get the ferry, close to Hyannis for dinner. Several great restaurants nearby! "

"This property was as advertised. Right on a private beach, the views here are incredible. Make sure you plan to see a sunrise or sunset! Owner is very easy to work with and responsive. "

includes taxes & fees

11 Oct - 12 Oct

"It a great property, secluded, charming... The beds are very good... Close to the beach, had a wonderful stay!"

"We’d loved our stay. Great house in a great neighborhood. Would love to stay here again!"

includes taxes & fees

7 Oct - 8 Oct

"The most magical place, thank you for the prefect stay."

"Central property with all essentials!"

"Stayed here with 3 friends as we were running the marathon. Better than the photos! So cute, everything was thoughtfully set up, we had anything we needed and having a washer dryer was a huge bonus! Flexible check in as well. Secluded, but easily walkable to many great places to eat and shop. Would 100% stay here again, highly recommend."

"I have stayed in this cottage 3 times, all just by myself, even though it can comfortably accommodate 3 people. It's in Maushop Village, which is a premier location itself, and has fabulous furnishings. I was particularly enchanted by the sleeping porch, where I sat many afternoons, writing in my journal."

"We had a great stay! "

"Awesome, fun place. Has everything you need for a great Vineyard stay!"

"Outstanding location on a quiet cul-de-sac road that backs up to the Cape Trail for biking and walking. Very clean and beautiful home. Nice deck for relaxing and enjoying the morning sun. Definitely recommend!"

View all properties