When we had to drive from MA to be in CT & NYC for a few family gatherings, this was the perfect spot to stay in, especially if you're not crazy about staying in the city or in a cookie cutter hotel. More like a B&B with world class charm and half the price of a similarly located non-chain small hotel a few miles south in Greenwich. Close to 95 so NYC very accessible. We love old homes, and this one is exquisitely re-done, beautifully clean and well-maintained. Lovely original art on the walls. It's in a neighborhood of charming old homes, although you do have to drive a short distance through a not so beautiful neighborhood to get there. Once there, not a problem. Short-medium walks to two beaches (one sandy, one rocky) with incredible views of the sound and Long Island's north shore. Only a few rooms have a view, however. Our room was on the 3rd floor (no elevator) and had a side view of a beautiful garden. Decor wonderful, bed extremely comfortable. Great TV, husband quite happy watching important games while I visited with friends. Bathroom large, altho ours did not have a tub, but the shower was perfect. Towels lush, and very, very quiet all night for 3 nights in a row. There's no restaurant on site, but there is a small kitchen and staff brings you every thing you need if you have food delivered. Wonderful seafood restaurants around. Staff extremely responsive in every way. We'd stay there again, for sure.

A nice spot. You need a car if you are going to stay here. Will make going out to dinner much easier!

The Hotel Chesterfield is THE best hotel/ B&B my girlfriend and I ever stayed in. The Gillespie room was extremely comfortable, modernly decorated and chic, romantic, elegant, cozy and charming. We could have stayed in our room all weekend and still would have had a great time. The King-size bed was like sleeping on a cloud of feathers. The staff was very accommodating, helpful, sincerely genuine, and overall friendly. They catered to all our needs and made sure our stay was more than enjoyable. The continental breakfast had a variety of items to choose from. Just don't forget to spray the waffle iron with non-stick spray before placing the batter in (thanks unknown lady who ruined a possible delicious waffle breakfast that morning!) The Chesterfield also offers a free shuttle to practically anywhere within reasonable distance (i.e. downtown or one of the beaches). They pick you up in a Porsche Cayenne (we were expecting a 12 seater van or something) and drop you off wherever you'd like. We took this shuttle our first night there for dinner downtown and took a short cab ride back to the Chesterfield later that night (the one way cab trip was roughly $10 the most) The downtown Stamford area offered many distinct restaurants with several ethnic flavors to choose from (try Barcelona!) and had several nightclubs/lounges that were very lively and fun overall (try Park and Mojitos!) There are also a few beaches nearby that you can visit. The closest one is walking distance; a small private beach that the Hotel Chesterfield shares with some of the community in the neighborhood. The Cove Park Beach is the next closest. The free shuttle transported us there (about 10 minute drive) and although it was a chilly Labor Day weekend we were still able to sun bathe. All in all our time at the Chesterfield Inn was incredible and memorable. I wish I could return there every weekend

I kidnapped my husband from the train station- drove straight to The Hotel Chesterfield in Shippan Point, east of Stamford, CT. He had no clue what to expect (except he figured out quickly his tennis game was a rouse to keep from working late at the office.) I had planned this for two months- kids, dogs taken care of.
We were warmly greeted, bags ensconced upstairs, to be greeted with wine on the lovely wrap around porch of this 19th century meticulously restored mansion. (this was hard to decide where the glass of wine would be consumed, each room inside was calling us...but wrap around porches are a weak spot for me!)
Every inch of this beautiful inn has been touched by loving hands, the amazing artwork, the finishing and the details. Each room is named, we stayed in the Gilespie on second floor; I want a bathroom like this one!
Continental breakfast and a newspaper greeted us each morning in the sun room over looking the lovely gardens.
It simply was an amazing oasis that was only 7 miles from our New Canaan home- but far enough away that you felt removed- without the hassle of long drives, airplane rides. We most definitely will return. Nearby are great restaurants recommended by the hotel and if you like shopping the Stamford Town enter Mall has everything you need. This Inn rivals Relais and Chateaux I have stayed at world wide. Quiet, elegant and a gem...I would not bring the kids...it is our secret now.