We had a weeks stay at Chestnuts in September, myself and partner and my 85 year old father. Dad had a single garden room (12) and we were in a front facing double on the first floor (10). I must admit to being a bit taken aback when we were shown Dads room as it's through the hotel and out the back door. It's a small single room but has a lovely small shower room/toilet and ample storage space, freeview telly, basin, bedside table and light along with supplementary heater and blanket. Dad was very comfortable there.
Our room was a comfortable double on the first floor with again small shower room/toilet, ample storage etc. Excellent shower with good pressure although Dads had to be run for a while to get the hot through.
The whole hotel was beautifully decorated in a light modern style with lots of prints and pictures on the walls. There's a small TV lounge and the dining room is open plan with the bar area and forms a nice communal space so you can chat with other guests easily if you wish.
Chris and her son Luke run the place and are so friendly and helpful. Lukes breakfasts are the best. There is such a choice and it's all very well cooked and presented. You can eat there in the evenings if you book ahead and the dinner menu has a large choice. We didn't but lots of the others did and the food looked and smelt lovely.
The hotel is located within easy walking distance of the seafront (if you're fit as it's a steep walk back up), there is a cliff lift which operates between 10am and 6pm. It's also handy for the town although again there are hills involved but the whole island is quite hilly. When booking this holiday I was torn between Shanklin and Ventnor and am so glad I picked Shanklin as Ventnor must have some of the steepest hills on the island.
All in all we loved the Chestnuts and Chris and Luke and would not hesitate to return there or recommend them to others. I would have rated it perfect but for the hill down to the beach.
Chris recommended a couple of eating places which we loved. The Pointer pub for Sunday lunch (booking recommended), Black Cat Thai restaurant in the old town, and the Chinese just 50 yds from the hotel (I've forgotten its name unfortunately). All had lovely food, reasonable prices and good friendly service.
Visit Waltzing Waters if you can for a fascinating show with a difference.

We recently stayed at the Chestnut for a week, with my husband, two children aged 6 and 15 and my mother in law. The Hotel is in an excellent location for the beach and its only s short walk into the beautiful village of Shanklin. We walked on the sea front into Sandown which took about 45 minutes but the view was gorgeous so it didnt matter. Chris was very helpful with ideas for our visit. We had an excellent meal at Legends, booking advised. The breakfast was lovely and nothing was too much trouble, the waitress was a very pleasant young girl. We spent alot of time away from the hotel as we had a packed holiday but on our return it was always clean and tidy. The games for the children were brill on a quiet afternoon me and my children had fun with the scrabble and jacks house. A lovely hotel and a beautiful island well worth a visit.:)

We have just enjoyed a lovely week here with friends and other friendly guests. Chris and son Luke provided excellent food and service . The bedrooms were small doubles but extremely clean. There is good off road parking and the Chestnuts is so well situated only minutes away from the beach one way and old Shanklin the other way. A place we would return to.

We stayed in 2 rooms my mum with one son and myself with my other son. I stayed in a lovely double bedroom on the 1st floor with ensuite and mum had a twin room at the back overlooking the garden. Both rooms spotless, the bathrooms too.
Fantastic breakfast - not greasy! Lovely atmosphere especially when having a little drink before bed!
Location wise - only down side is a very steep walk down to the esplanade but not the end of the world. Parking was handy and as we drove all around the island we found that it was very easy to navigate onto the main roads.
To sum up we would thoroughly recommend this hotel to anyone wanting a comfortable Cosy hotel during their short break.
We will be coming back :-)