If your long lost Aunt Agnes doesn't live a 3-mile bike ride away in Swampscott, you might consider staying in town.
Most folks book at a lovely B&B right around the corner from Judith's, where the majority of our time is spent:

Darci's Parkside Inn Bed and Breakfast (circa 1910)

4 Wyman Road, Marblehead, MA 01945
http://www.dpinn.com 1-888-273-7704

This Victorian bed and breakfast features three lovely guestrooms and two suites, all individually designed, furnished and decorated; three of the rooms has a built-in double Jacuzzi.and fireplacees. All of the guestrooms offer private baths and pillow top mattresses, and a generous Continental breakfast, as well as the daily newspaper, is included.

If you are looking for something a little upscale with folks that are passionate about the arts try:

Tuscanino

http://www.tuscanino.com.

My friend Greg and his wife run it and they have many an arts based activity there.

Other Bed & Breakfasts in Marblehead

There is a comprehensive list of local B&B's on the Marblehead web site:

http://www.marbleheadchamber.org/catDir.asp?action=getCategory&category=Accommodations