On my Spring 2004 vacation (Boston), I stayed in the Charlesmark, a small hotel that happened to be convenient to a Green Line subway station. The room was actually smaller than that postage-stamp the Chicago W gave me, but it was so efficiently designed, and so free of wasted space (and so free of bovine scat "features" designed to separate guests from their money) that it *felt* bigger than it really was. And the price was very reasonable, and included a free (albeit not as extensive in selection as that of many places I've stayed) continental breakfast, and free internet access in the lobby.
On my Fall 2004 vacation, I stayed at the Pelham in New Orleans (beautiful rooms, convenient to both the Quarter and the St. Charles trolley line; no continental breakfast or free internet access, but nice nonetheless, and very reasonable rates). Then, at WDW, it was the All Star Music. Then, in Williamsburg, I stayed at the cheapest of the CWF hotels, the Governor's Inn (excellent free continental breakfast, its own dedicated shuttle bus, and access to the coin laundry at the Wilderness Lodge), then splurged on my last night for a room in a Colonial House.
In Chicago, I stayed at the Best Western Grant Park Hotel. Not nearly as nice as the Comfort Inn, where I'd stayed the previous year, but much nicer than the W. Then it was back to the Pelham in New Orleans, for one night before catching my flight back home.
This past Spring, in San Francisco, I stayed at my favorite San Francisco hotel, the Columbus Motor Inn. No continental breakfast, internet access, or on-site laundry, but really nice rooms, very conveniently located. Then, in Sacramento, I was at another favorite, the Vagabond, right across the street from the train station on one side, and the Downtown Plaza Shopping Mall on the other, and within walking distance of Old Sac and the RT Metro trolley line. Excellent continental breakfast, and 3 -count 'em- 3 free guest computers in an alcove off the lobby. Then, in Seattle, it was the Best Western Pioneer Square Hotel (originally the historic Hotel Yesler), also with very comfortable rooms, great rates, free internet whenever the conference room is available, and a superb continental breakfast.
On my Alaska cruise (leaving the day I left Seattle), I chose the cheapest passenger billet on the whole ship, and the cruise was just as nice as if I'd spent four times as much on a "verandah suite."
Once I got to Anchorage, I stayed at the Comfort Inn Ship Creek. Nice location (within walking distance of the train station), huge room, excellent continental breakfast, free internet, and a free airport shuttle (which was good, because I was running out of cash, and had walked away from my only Visa card in Seattle!), all for a great rate.
This Fall, in Hawaii, I'm staying at the Ohana Waikiki West in Honolulu, the Maui Beach Hotel (recommended by the local transit authority) in Kahalui, and the Volcano House in Hawaii Volcanoes National Park.
In my experience, I've never found expensive hotels to be cheaper than mid-priced ones, only greedier. And to tie this back to the topic of the thread, I normally actually go for more expensive hotels on vacations than on business trips, at least when I'm picking the hotel. And I think that, unless you're a salesman, and planning to entertain clients in your hotel, that's the way it should be. But we're talking about Disney hotels here, and even the cheapest Disney hotel is going to be closer to, say, a Vagabond, than to a Motel 6 (or to some of the dumps I've stayed in while working video crews). And the rooms at the All Stars certainly aren't as small as the one I had at the Charlesmark, nor are they any shorter on useful space than that postage-stamp room in the Chicago W.