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Browse Select Osterville Vacation Homes

Our top choices for Osterville vacation homes

"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"

CA $476 total

includes taxes & fees

Aug 27 - Aug 28

"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "

CA $953 total

includes taxes & fees

Sep 15 - Sep 16

"Location is very convenient to lake scargo and corporation beach! House was extremely clean. Well appointed. Had games and beach toys and chairs. Great house for family. "

"The property had all the amenities and features to make guests feel right at home. We appreciated all the details in the decor and we appreciated the suggestions for local restaurants. TheTheviewwdrdreadream!amademade"

CA $1,223 total

includes taxes & fees

Sep 2 - Sep 3

1 bedroom, iron/ironing board, internet, bed sheets

"Perfect for one or two people, was great for myself and my dog to stay."

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

"Perfect fall getaway"

"Very warm and comfortable stay with ample space and a massive backyard."

"As always, lovely home. Perfect place."

CA $813 total

includes taxes & fees

Sep 11 - Sep 12

"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 "

"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. "

CA $2,124 total

includes taxes & fees

Sep 21 - Sep 22

"The home was very nice and in a convenient location. Ana was very helpful and quick with communications during our stay. Would highly recommend for anyone traveling to Oak Bluffs! "

Smart TV, fireplace, video games, DVD player

"We had a lovely stay in this home. It modern, beautiful and spacious. The kitchen is well equipped and great for cooking. The bedding is comfortable and views spectacular. We were unable to use the kayaks due to the weather but what a nice treat to have. The town of Wareham is small but if you are willing to take a 30 minutes car ride to Falmouth or 1 hour to Chatham, there are more restaurants and shopping. We enjoyed our stay and would highly recommend. "

"The house was spotless and very well organized. My family and I loved our stay — it’s in a perfect location, close to everything: grocery stores, the beach, restaurants, and more. The owner is very communicative and responds right away to any questions. We would definitely love to come back!"

"A gathering of 16 women stayed at Bride of the Sea for a 5-night long weekend to celebrate a 50th birthday, and we had an incredible time. The home was immaculate when we arrived - and spacious enough to comfortably accommodate everyone with large spaces to gather or escape for some quiet time. The beds were extremely comfortable. Parking was ample, easily accommodating three cars in the garage and the remaining cars in the driveway spaces. Many in our group are hobby "chefs", so we enjoyed...

"This property was even better than expected! Our family of 5 adults all slept comfortably and the kitchen is very well stocked with anything you might need. "

"our family of 7 adults and one baby had a fantastic stay at this house. It is lovely, provisioned with everything you could want in a vacation house, and the owners are very reachable and responsive. This was a perfect house for a week at the Cape!"