Holiday rentals with a pool in Hillsborough County

This place is simply incredible. A vintage mid century modern gem overlooking a lovely farm with mountains on the horizon. The pictures don't do it justice. The kitchen is incredibly well stocked with everything you could desire to host large family get togethers. Philip was extremely responsive and friendly throughout. My only regret is not knowing how to play the piano. We can't wait to come back in the warmer months to see the farm and garden in full effect. 10/10 recommend.

100 stars! Holy smokes - we just loved our experience here!! The house was incredible - so well thought out with anything we could ever need and SO many entertainment items! Rooms were spacious and beds were very comfy. The house smelled so clean upon arrival and not an item was out of place. You can’t beat the scenery at this gorgeous house. It was so peaceful and exactly what we were looking for. Tons of games (foosball, ping pong, darts, basketball, punching bag, air hockey, baseball, and more), ATV’s, the cutest chicken coop, a hot tub - the list goes on!! James was so kind and so responsive throughout our trip! We could not recommend this place, and James as a host, enough! 100% perfect

Our family getaway of 3 generations enjoyed the beautiful outdoors- between the magnificient pool, peaceful lake and the expansive yard where we were able to have fun playing the bocce set and cornhole game we brought. The outdoor seating kitchen area was perfect for gathering and so inviting for conversation and just relaxing. Ashley was easy to reach and responded to any questions.

Daniel and Monica were great hosts that responded to any questions or needs. They live right next to this guest house so we’re quick to respond. This house is a bit small but has enough space for up to three or maybe one more on the sun porch if using an available air mattress. It is comfortable and homey. The bedroom in the basement is fine but the rest of the basement is mostly unfinished. The pool would be a nice feature but it was too early in the season for a dip in the cold water. Plenty of stores and restaurants are within 5-10 minutes of here including a Market Basket, Whole Foods, Trader Joe’s, and big REI store among many others.

Friends and I had a great time at the Airbnb and we all felt at home. It was very spacious and decluttered, making it easy for us to fit ourselves in and get organized. Robert was very responsive and did his absolute best to make sure we had everything we needed, he even came by to clean the pool after a rainy day. Our only issue was the grill was actually a griddle and unfortunately the previous guests didn’t respect and clean it so it wasn’t usable. There’s a good chance we will come back if we plan another trip to MA or NH

we had a lovely stay in this beautiful lakeside home. the location was stunning and it was the perfect way to relax in the stunning location after a busy few weeks of travel. Thanks for hosting us

Great stay! House was clean and spacious for our party of 8. We had everything we needed for our weekend stay in January. We traveled with our twin 18 month olds and had access to playpens and a high chair for which I was very grateful! They even had some books and legos for the kids to play with!

Stepping Stones is a treasure of a home. It’s an authentic colonial era homestead with a lot of amazing history. The grounds and setting are bucolic. We loved feeding the chickens our scraps and collecting fresh eggs. The pool was a delight. There’s so much space for a large gathering of friends and family to feel at home and still each have our own personal space. Be prepared for normal old home quirks like uneven floors and basic bathrooms. But the plumbing works just fine, the kitchen is well equipped, there are ac’s in all the bedrooms to keep things comfortable on hot nights. We didn’t need them most of the time, though. The WiFi is great. Boo is the most welcoming host. 100% would recommend!!!