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I'm glad that you'll be paying us a visit! Here's what I see as the lodging "lay of the land".
McMenamins Old St. Francis School is downtown - great location. It is a former Catholic School which makes it quite unique. Because McMenamins is also a brewery, it has a pub-type restaurant as well as a bar. They also have a few small houses on their property that can be rented. The one downside that I have heard is that people in some of the hotel rooms can hear the noise from the bar.
Also downtown is the Phoenix Inn. It's been undergoing remodeling for a long time, and it looks like half of the hotel is still being worked on. They're in a good location for walking around downtown.
The Ameritel Inn overlooks the Old Mill District It's a very nice place. Walking distance to a martini bar and some nice restaurants and close to the Deschutes River. Several block walking distance to downtown.
Pine Ridge Inn - beautiful, romantic, boutique hotel. Close to downtown and the Old Mill District, but you still have to drive to get there. Probably the best hotel in Bend.
The Riverhouse Resort and the Shilo Inn are right next door to each other. They are next to the Deschutes River. Unless you get a river view room (which cost more), you have a view of the parking lot. Both hotels are pretty nice. Right on highway 20, making it easy to get places. The Riverhouse has a golf course, which makes it a resort.
There are a couple of other resorts in and close to Bend. The one in town is Mt. Bachelor. Most if not all of the condos are privately owned so they will vary in decor. They have some houses for rent too. Convenient location, but you need a car to get to where you're going. Seventh Mountain Resort is on the way to Mt. Bachelor, so it is out of town a bit. They have a nice restaurant, but some of their rental units are in need of refurbishment while others have been recently redone. Close to Widgi Creek Golf and you can whitewater raft. You need to drive to get anywhere in Bend from there.
We also have some nice Bed & Breakfasts; the nicest is probably Lara House. It's beautiful and very expensive. A two block walk to Drake Park and close to downtown. Chef-prepared breakfast. The Mill Inn is a few blocks from downtown and the Old Mill District. Known for its breakfast. The rooms are nice, the owner a fun but kind of quirky New Yorker. Sather House is another highly recommended B&B but I have not visited it.
Almost every main brand of chain hotel/motel is here. Most of them are along Highway 97 (Third Street), which is the main route through Bend that gets a lot of traffic. Also along the highway are a number of independently owned motels. They will be your least expensive lodging option. Some of them are not desirable, and some of them are pretty nice, so if you are interested, I can give you a couple of places.
If I could afford it, I'd stay at Lara House. Next on my list would be Ameritel Inn. Third choice McMenamins. If you are going to be here for several days, there are also several people who rent little cottages, so that could be an option for you too.
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