Montreal - downtown in the Village just off Ste. Catherine. Few blocks from Berri/UQAM station and 747 bus station. 4 of us stayed there for 100/night. New place, very happy with it. Very nice owner who even shoveled the snow around our rental car for us.
http://www.vrbo.com/199482Shenandoah Valley of Virginia - just off I-81 and US 11, 90 minutes from DC. Have stayed there twice. First time was 10 people (+3 dogs) and $400 total for 2 nights. Second time was 12 people (+3 dogs) and $750 for 3 nights. Attached garage has been turned into game room which is a great place to hangout whether you have kids or a bunch of adults who want a room to hangout in without worrying too much about spilling a drop of beer on carpet or something. Pets cost extra. Very nice place but only 2 true bedrooms that have 1 bed in them. Other rooms have multiple beds or futons.
http://www.vrbo.com/308095near Luray, VA (north of I-64, east of I-81, south of I-66, ~hour from DC) - group of 8 (+2 dogs), decent place with barn that has been converted into cool game room. Cute place but a little smaller overall (better like who you are traveling with!), good living room to hangout in. Cost was $600 total for 3 nights. Pets cost extra.
Dont' forget! Time of year matters!
I've stayed in other VRBO's but I think mentioning that they aren't (as) good would give too much of a negative impression. Even a mediocre rental is still a great weekend with friends and family in my book. The ones above were all very good stays and I couldn't have been happier with the owners as well. Gift baskets upon arrival, replacement of a propane tank in under a half hour, shoveling snow around your car, giving advice about museums and other attractions, clear directions, and other small niceties are the little things that I love so much about renting directly with an owner, as well as what sets apart some owners from others...