Like previous posters, I have to say that the staff at the Fairmont Southampton are amazing. They are just genuinely nice people who seem to enjoy their job. The only person who's name I actually caught was Nick, the concierge, but everyone at this property always greeted us with a smile and a hello and was always super helpful.
We booked a deluxe harbour view room and got room 257. This is a corner room that sort of has a partial view of the harbour; if you were in your room you could only see half habour and the other half is (I think) the golf course. If you went to the balcony and faced left you'd see the whole harbour.
I requested for a King sized bed, a crib and a fridge. Crib and fridge were not in our room but a quick call to the front desk had housekeeping bring the items to us in a timely manner. The room is a good size, with double sinks, marble countertops, a separate room for the toilet and bathtub and high end amenities. There is also a flatscreen TV with American cable channels, and desk with two chairs and an armchair/recliner. There is plenty of room, even with our crib, for our son to walk/run around.
We left our room around 12 on most days and by the time we came home (5, 6ish) our room was always cleaned.
I asked to borrow a stroller (which the concierge mentioned they had when I called prior to leaving for my trip) and housekeeping brought that up. It's a somewhat old, metal (re: HEAVY) stroller but still beats us having to lug our own from the States! I also thought this was a great perk and that ALL hotels should have loaner strollers!
There are a few onsite restaurants; Jasmine Lounge has small bites that you can request to take up to your room (no inroom dining charge but 17% gratuity charge). We brought back pizza one night and it's AMAZING but very small! Definitely more a snack and not a meal. We also had dinner one night at the Newport Room; hubby enjoyed the steak very much whereas my mahimahi was only ehhh. Wouldn't recommend the fish but wholeheartedly recommend the steak (and their awesome fries).
There is a bus stop right in front of the hotel and the busdrivers were always very friendly and approachable. We were able to tell them where we needed to go and they would always remind us at that particular stop. Tokens and passes can be bought at the front desk.
The indoor pool can only be used by hotel guests after 6:30pm, which normally wouldn't be an issue but I think during off season this should be a bit more flexible? What if the weather was bad and hotel guests needed to stay indoors? We didn't use the heated outdoor pool since it was just slightly nippy and I wouldn't want my son to catch a cold.
We had free WiFi in our room and the connection was very strong; never had any issues with it.
There is a free ferry that goes to the sister hotel, Fairmont Hamilton that departs at 9:30, 12:30 and 5:30 and returns at 10:30, 1:30 and 6:30. I would've liked a later return (maybe 8, 9?) for those that want to have dinner in Hamilton. It takes about 25 minutes to get to Hamilton on the ferry.
All in all a great experience.