Monthly Rentals in Middleborough

Peter's place was perfect for my family, place was cozy.

Always clean and very comfortable, we find this a great place to stay. Chris is a great host and very accommodating. We visit the area often and have stayed at both this cottage and his larger rental on the waterfront where he allows water access to his dock and kayaks etc. (Highly recommended for larger families- it has a Beautiful view!) We will be back in the future. Always meets our needs just fine!

What a cool spot! Stayed a couple nights with friends for a "Book Retreat" and had the best time reading in the Hammock, chatting by the fire pit, and cooking together in the kitchen.

Craig’s place on Pelican Bog at Wood Pond was the ideal retreat for our moms’ weekend getaway. Even with a bit of rain, we fully enjoyed the peaceful outdoor space—fishing off the dock, a refreshing dip in the water, and the pond swing, which was such a relaxing and unexpected highlight. The home itself exceeded our expectations. The living room was so much cozier and more spacious than the photos showed—perfect for lounging, laughing, and catching up. The kitchen was impressively well-stocked, making meal prep a breeze. We didn’t find ourselves needing a single thing. Craig was incredibly responsive and took a lot of care to make our stay enjoyable including putting the fishing poles, kayaks, and chairs out for us so enjoy right as we arrived. The air hockey table was also a really great addition. All in all, it was the perfect setting for reconnecting and unwinding. We would absolutely come back!