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Towns for a 'Ladies Night Out' in New England/B+B Searches?

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Hey all, my very dear friend is marrying her childhood sweetheart this May and I'm beginning to plan our all-lady pre-wedding celebrations for the weekend before, and I'm hoping for some inspiration.

So far we are planning to whisk her away after the official bridal shower the Mothers are throwing in Western Massachusetts, go to the spa a friend has an in at for some hot tubbing or maybe a massage, somewhere along the way we need to have a cheese/wine "tasting" (we may very well just hit up a Whole Foods and put this one on ourselves somewhere), and end up somewhere fun and new for a decent sit down dinner and then night out drinking and dancing before crashing at some kind of Bed and Breakfast/Inn/whathaveyou followed up with a really great breakfast/brunch somewhere- the lady is a HUGE morning food enthusiast.

So far we're thinking possibly Newburyport, MA or possibly Providence RI? Would love to stay out of the immediate Boston area- friend now lives there and we all grew up not far and have "been there done that"- it just wouldn't be as special of an occasion. Basic requirements would somewhat affordable with good food and some nightlife, best brunches get brownie points, we'll be swooping in and out pretty quick so daytime activities are less exciting, and we're trying to stay within a few hours of either Northampton or Boston MA.

My search method at the moment is a lot of throwing darts at the google map, and I could certainly use some direction! Ideally we're looking for an Inn/BnB or something on the smaller side with lots of character. On the one hand we're only crashing for an evening and wont be spending a lot of time in the room(s) (wine/cheese tasting most likely, sleeping, and little else), but on the other hand this is a special occasion and we want more than JUST a place to sleep. Ideal location would be within walking distance or easy cab distance to dinner/bars/etc. Oh, and to top it all off! There's eight of us and adjoining rooms/suites/something would be ideal. Are there any great search engines that cater more this direction than say something like Kayak?

Thanks guys!

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