I am heading to Boston towards the end of October and would love recommendations of either bed and breakfast establishments ( (in a private home) or accomodation in the 2/3 star category. I have been horrified at the dearth of affordable accommodation in Chicago so would love some personal recommendations. I would want to pay around $200 US per night - am I being unreasonable?

You might try priceline for accomodations and www.hotels.com for more suggestions.

If you will have a car, I just did a trip to Boston and stayed in Waltham at the Extended Stay Boston-Waltham, and got the room (with full kitchen) on priceline for $50 a night. There is a commuter rail line close by, but staying there you would need a car.

Have a great time.

Please be aware that the Head of the Charles Regatta (an American Henley with the possibility of horrible weather) is the weekend of October 22 and accomodation will be in very short supply as rowers and their supporters from all over the world will be here. On the other hand, the weather may be great and you should be able to find a room at that price in a private home or the like. Have yout tried Craigslist?

Try the Newbury Guest House.

I enjoyed Encore B&B near Copley Square - very sleek modern rooms in a brownstone walk-up. Hospitable german hosts. My stay was short, but I would definitely stay there again. If I recall the rates were $175ish?

newbury guest house is great

Thanks for some great suggestions. Am checking out availability right now!

Don't want to sound negative...but why did you wait so long.. Aikislander is right.. the Head of the Charles Regatta on the Charles and the "leaf peepers" not to mention cruisers makes Boston a wonderful and exciting spot..but good luck with the B&B... Newbury Street is great location if you can get in.. also check for places in the South End..close to Tremont Street..