Boston is an ideal walking city, with ample public transportation in and out of the city. Many hotels are expensive, but you can find a good hotel for around $120. Sometimes less. I noticed that you have a son. Boston has many things for kids, including the Children's Museum, the New England Aquarium, and the Science Museum. Boston Common has a nice playground and the Frog Pond, where kids can wade. The Public Garden has the swan boats, which you can ride. Outside of Boston, there is Salem, which is focused on the witch trials but is also a longtime maritime city. It is reachable by commuter train from Boston's North Station. Using the same train, you can also go to Gloucester - the famous fishing town - and Rockport, with lots of shops on a wide pier jutting out into the harbor. South of Boston is Plymouth and Cape Cod. It's only 90 minutes to the start of the Cape, or you can take a ferry ride from Boston to Provincetown. West of Boston are the revolutionary war battlefields of Lexington and Concord, along with Walden Pond, made famous by Thoreau. If you decide to come here, feel free to e-mail me for other suggestions. I did a quick search on a few places that are in Boston with reasonable prices. I know these hotels are in decent areas, but otherwise know nothing about them. http://reservations.bostonhotelsandguide.com/cgi-bin/hotelinfo?SID=BTU&Dest=BOS&LKF=BTU&PROD=HOTEL+&DispCurr=USD&ITRK=dbP&qKey=KL181330501151&HtlId=BOS+SHAW&Smk=N - The Shawmut Inn http://reservations.bostonhotelsandguide.com/cgi-bin/hotelinfo?SID=BTU&Dest=BOS&LKF=BTU&PROD=CONDO+&DispCurr=USD&ITRK=dbP&qKey=JU176573200962&HtlId=ZZ+11575&Smk=N - Oasis Guest House http://reservations.bostonhotelsandguide.com/cgi-bin/hotelinfo?SID=BTU&Dest=BOS&LKF=BTU&PROD=HOTEL&HotelId=BOS%20CHAN&HName=CHANDLER+INN&Rating=2.0&Return=Prev - Chandler Inn

You should join great timeshare site that helps with all those timeshare travel questions! My DH and I have been timesharing since 1999, and we love it. I will admit it was a bit mind boggeling in the beginning and parts still are, the website is www.tug2.com and you can join under the basic membership, or pay 15$ and be a ful fledged member. One place you may want to check is Massnutten in Virginia, which would probably work out well. It's a great all season resort, and there would be tons for the whole family. We stayed there and loved it. Good luck!

If you choose to purchase -- I'd probably go with a condo for the ease of maintenance. However, unless you have a spot you ALWAYS go to, and spend quite a bit of time, it is probably best for you to just rent on short term status. If you own it, most relatives/friends will not be helping out with the mortgage and upkeep costs - that will all be on you. If you rent with a group in mind, they are willing to split costs.

Do they plan to use a property manager or will they be managing this themselves? I spent a bundle on sheets for one of our VRBO places. I wanted really wonderful sheets, and felt it would be a selling point as well. It turned out that our property manager for that place uses only their own linens. It saves them housekeeping time, because they show up with the replacement set all ready to go, and leave with the dirty linens. By the time I learned this, I had already washed every thing (sheets and pillowcases for six beds!), and tossed the packaging, so it was really a waste -although occasionally we do use them when we go up. A must have for rentals: plastic coverings for all mattresses, and pillow coverings (that sit between the pillow and the case).