A hotel for myself, husband, 9 month old and my 2 parents?
We want to do a long weekend away and are totally open to suggestions- Maine, VT, NH, the Cape, the Berkshires. . . Basically we'd like to find a hotel or B&B with a pool and that has hotels/shops within walking distance. But not looking for a big city (like Portland, ME). Would love to find a quieter/quaint town.
Chatham (on the Cape) is my quintessential New England happy place. The Chatham Bars Inn is amazing and has a great oceanfront pool and is walking distance to town, but it is quite expensive during the season. Most of the other places that I can think of with pools are oceanfront and not necessarily within walking distance of many shops. You can stay just about anywhere on the Cape and drive elsewhere, though. Harwich Port is cute but small. Dennis Port has several affordable oceanfront properties with pools. Provincetown is beautiful but not quiet.
In the Berkshires, I can't think of many hotels in town that have pools. But we've stayed at the Seven Hills Inn in Lenox which does have a pool and is just a quick drive to the town center and Tanglewood.
Portsmouth Inn in NH. Pretty basic but we've always enjoyed it there. The Lane Hotel in Keene NH is right in town. No pool but all the other things are there. Holbrook House in Bar Harbor
North Conway is great. Lots of good little restaurants, all kinds of hiking (light to challenging), covered bridges to explore, a little outlet shopping, drive up Mt. Washington, etc.
I've only stayed at one B&B there and it had the most AMAZING breakfast, but no pool so I can't help with lodgings.
A little late to this post, but we stayed in the newer building at The Nonantum Resort in Kennebunkport and had a great time. We walked to the shops/restaurants but you could also drive there. It's on the water and has an outdoor pool.