Family-friendly holiday rentals in Osterville, Barnstable

We enjoyed our stay—it was a quick 5-minute car ride to Main Street. We also enjoyed watching wildlife in the river! I wish we had brought our binoculars!

The Penny's House is close to all the beaches, great restaurants and the bike path is accessible via the back of the property which we loved. Her house is beautiful and the kitchen was fully stocked with all cookware you needed to make family dinners together. My family was very comfortable with out stay here! Thanks, Kathleen,Jack and family

Stayed for a weekend with a few friends right before the Cape busy season and had a great time. Check-in was extremely easy, all instructions and rules were clear and reasonable, and check-out was very convenient and straight forward. The house matched all the pictures and was exactly as described, and everything was clean and well stocked. In the future I’ll look to stay at a Del Mar managed location again!

Great stay! Place is in a quiet residential area, yet centrally located and easy to get places. Nice yard and hot tub was a plus (clean and good temp). We didn’t have a chance to use the fire pit, but outdoor furniture and sitting area was nice with space for everyone. House was very clean, beds comfortable. Host was very responsive. Would definitely stay again.

Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.

I had a wonderful experience staying at this Airbnb. The place was exactly as described—clean, cozy, and well-stocked with all the essentials. The host was friendly, responsive, and made check-in and out super easy. The neighborhood was quiet and felt very safe, with great local spots just a short walk or drive away. I’d absolutely stay here again and recommend it to anyone looking for a comfortable and convenient stay!

Resort vibes with a chef's kitchen and stunning views! ***** Our stay at Larry's house was fantastic! The kitchen was absolutely amazing - spacious, modern, and fully equipped with everything we needed. We enjoyed cooking and gathering there. The real highlight was the outdoor space. The view was breathtaking! The pool and hot tub made it feel like we were staying in a private resort. Michael was helpful and responsive, making everything easy from check in to check out. We would love to come back.

It was a beautiful and peaceful place to land after our wedding! We are grateful for the time and would love to come back some day. Sharon, Deb and Rhianna are the most wonderful hosts, very helpful and kind. We will always have lovely memories from here!!

We had a great weekend at Elizabeth's place in Brewster. For us, the location was perfect with a beautiful walking beach <1/2 a mile down a quiet side street as well as being able to ride our bikes a short distance down a dirt road abutting the property to easily access the Cape Cod Rail Trail. The house was warm and cozy, with comfortable beds, and a well-stocked kitchen with everything needed to cook meals throughout our stay. We especially appreciated being about to bring our pup along and she enjoyed running out on the Brewster flats at low tide to chase seagulls and splash around at the edge of the ocean. We would happily come back to enjoy this wonderful spot again hopefully very soon!

Location was great and the neighborhood was quiet and beautiful. Robert was very responsive and accommodating. The ease of finding the home & access with the great directions along with a bottle of wine in the fridge were added bonuses after driving all day/night and a late night arrival.

It was our second time staying at Amanda’s beautiful cottage and we hope not the last! The space is adorable and very spacious for a couple or a couple plus a guest (which was the case on this visit). The garden is a wonderful oasis to hang out and have meals and we appreciated Amanda being flexible to allow us to bring a solo stove. The area is so rich with wildlife and Mashpee Neck and the causeway beach are the best. We had an amazing time and can’t wait to come back.

Fran's house is lovely, everything one needs for a fabulous stay. She is a very good host - responsive and informative. She lives on the prpoerty but we never saw her. We had a really great stay!!!

Great spot with private entrance and cozy setup. Came during winter but can imagine its also a perfect summer getaway. All in all, cute and convenient place!

Sue's place was perfect for our mother-daughter weekend. Sue provided a comprehensive list of restaurants in the area, but we prepared all of our meals in the kitchen, which was well-appointed, very much appreciated. We enjoyed daily walks to the beach. Though it was off-season and overcast, inside it was perfectly cozy. The fireplace was great to return to. Sue was quick to return texts, and very welcoming. The snack basket was well received! Would highly recommend.

The house and property were great! The house was exactly as described, but better. The house was immaculate which is something I really appreciate when I travel. The house was very comfortable and very well stocked. Comfy beds and couch. My husband forgot his toothbrush and was so happy to find a pack of them in the cabinet to avoid a late night run to a local store. The pond was great, we enjoyed fishing and kayaking! Our pup was very comfortable as well. Overall we had a great stay and really enjoyed the house, pond, and amenities. Jennifer was extremely responsive to the few questions we had. Great find!

Perfect location. Host was there to even be sure I got a spot right in front of the cottage because it was busy time around there. Very clean and in tip top shape. Will definitely book there again.

We stayed here for a bachelorette party and the house exceeded our expectations. Sherri was responsive and quick to answer all of our questions before and during the stay.

Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

It is a house that meets all expectations, large and comfortable when spending a few days with the family.. the instructions for the stay were accurate , I loved it !!

This was our family's first visit to the Cape, and the first time that mom had been back in decades. We had a wonderful stay! Mashpee was a great location - there was local access to good beaches and restaurants; but also a great location to access Sandwich and the Canal, Falmouth, Woods Hole and the Islands, all the way to Provincetown and everything in between. And we took advantage of it all over the week we stayed. Ed was a wonderful host! From booking until we checked out, he was very communicative, friendly, and had great information about local attractions and specialties. The property was very comfortable, and big enough for our family to relax and recharge. And our son loved the heated pool! We would definitely rent this or any of Ed's properties again!

We stayed in the tree house suite. It had a lovely deck surrounded by trees and a great view of the sky. Craig and Ginny are as friendly a couple you will ever meet--always quick to answer questions and offer some great suggestions, Craig even offered to drop us off at a few places. They were so kind they felt like old friends. The beach is beautiful and a five minute walk away--which is great because they charge 25 bucks to park. So do the easy walk, and Ginny will provide chairs, towels, and umbrellas. Hyannis itself is a great place to walk around with lots of shops and great restaurants. We also took a ferry to Nantucket which was delightful, as well. I would visit them again without question. Go. You won't be disappointed. Michael and Rebecca

I had a wonderful stay at Eli and Tracy Anne's beautiful home! All instructions were clear, and I appreciated that Eli sent me an information packet with everything I needed to know about the house in advance. Everything was exactly as described and the entire place was sparkling clean (the upstairs bedrooms still had new-carpet smell!) Beds were super comfortable, and the window AC units kept the entire home at a good temperature. I had no problems at all and didn't need to reach out to the hosts once during the entire stay. The location is great, very convenient to Mashpee Commons and other local attractions, but tucked away in a residential area that's extremely quiet and peaceful. I truly didn't want my vacation to end, as I felt so at home during my stay. Thank you to Eli and Tracy Anne for a great experience; I would absolutely stay here again!

Barbara’s condo was roomy and comfortable. We fell in love with the screened in porch. Lovely room for a cup of coffee in the mornings and a glass of wine in the late afternoon. We took a short ride through the woods to the town beach which led us to beautiful views of Tashmoo. We had a great time!

Super responsive, great host. Very friendly, offered us the local newspaper with deals on places to go and everything. incredible space, right along the water. Thank you, Ron!