I stayed at the Red Lion (in Medford) last year and it was OK - the restaurant was pretty good.
There are a couple of suites and connecting rooms that might suit your needs at the Bard's Inn, in Ashland. I am pretty sure they allow 17-year olds, not sure about the Harvanese? ;) I have stayed there several times over the last several years, and it's a "good" hotel, close to downtown.
In February you will not see much action as far as Shakespeare is concerned. It looks like maybe only two or three of the plays will have just started. Keep in mind there are never plays on Mondays.
Dress warmly and enjoy!
We have stayed at the La Quinta property when it was another hotel chain. Keep in mind that the location is not walking distance to anything, you will have to drive into town to retsaurants, theaters, shops, etc.
The Bard's is in a great location, it is right across the street from the Plaza Inns & Suites where we have stayed several times. Since you're staying so long, I think it would be nice to be able to walk to restaurants, shops, etc. Chateaulin is very nice there in downtown Ashland for a good meal. Also check out the Peerless at the Peerless Hotel for a really nice dinner. Enjoy Ashland! :)
I've stayed at the Windmill Inn-that was pretty nice. They had a shuttle to Ashland since it is located on the other side of the freeway from downtown Ashland(about 3-4miles away), not sure if they still offer this service.
La Quinta does not charge for dogs, even if they are 8lb Havanese..but they really do vary in quality.
We stayed in all LQ hotels in a cross country drive with our large dog.
I have not stayed in these hotels but thought I would mention the no charge for dogs policy :)
I've done the LaQuinta thing (at the north end of town) and it was fine. I think their pool is open late, which might be good for the teens. I believe I had waffles at their breakfast bar.
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