Hotel recommendation in Jerusalem

Some related questions on my planned visit to Tel Aviv, Jerusalem, Petra, and Dubai. I'm planning to fly to Tel Aviv, spend a couple of days, then take bus to Jerusalem, spend a few days, then travel from Jerusalem to Amman then to Petra. Or should I get back to Tel Aviv and take a flight to Eilat? Is the border crossing much easier at Eilat? In that case maybe I should visit Jerusalem first and then Tel Aviv since from TLV airport it's about the same distance.

We've only stayed at one hotel in Jerusalem, Hotel Gloria, in several attempts to visit Jerusalem in the past 15 years. We absolutely loved the location of the hotel, right in the walled city just past Jaffa Gate. There are other modern, tourist/business class hotels near the walled city but this is the real deal in the heart of old Jerusalem. I see online that it has undergone a recent renovation but not a change of ownership. It looks like it has kept much of its charm.

I'm planning to fly to Tel Aviv, spend a couple of days, then take bus to Jerusalem, spend a few days, then travel from Jerusalem to Amman then to Petra. Or should I get back to Tel Aviv and take a flight to Eilat? Is the border crossing much easier at Eilat? In that case maybe I should visit Jerusalem first and then Tel Aviv since from TLV airport it's about the same distance.

The border crossing at Eilat/Aqaba is mainly for tourists. The border crossing nearest Jerusalem (Allenby) is not. It is much easier and faster to cross in Eilat. In Aqaba, you get your visa on entry. If you should choose the Allenby crossing, you must obtain a Jordanian visa in advance. There is an exit fee when you leave. In fact, there is usually an exit fee when you leave most countries, but since you fly and the fee is included in the price of the ticket, you aren't aware of it. Start your Jordanian trip in Aqaba, then Petra, then other sights on the way to Amman.

It's about a 5-hour bus ride to Eilat from Tel Aviv or Jerusalem. Buses often fill up so you'd need to reserve a place at few days in advance. It's much easier to fly from Tel Aviv's Sde Dov airport. Both Arkia and Israir have several daily flights and you can buy tickets through their websites. The Tel Aviv airport is a short taxi ride from about any Tel Aviv hotel.

I would plan to start in Jerusalem, then Tel Aviv, then fly to Eilat and cross the border to Aqaba.

For hotel recommendations in Jerusalem, a major consideration is your budget. Another is the dates of your trip.

Years have passed but we stayed at the Hotel Jerusalem on Nablus Road, near the Damascus Gate. Loved it, just loved it. It is beautiful inside and out. Breakfast in the garden is one of my memories. Bus to West Jerusalem stops just outside, which we took to reach our conference location there, but we loved getting back to our East Jerusalem hotel every evening.

Jamie:
In Jerusalem try the Dan Boutique Hotel outside the city walls and facing Mount Zion. I stayed there with a group in May. For inside the city walls, look into the Austrian Hostel. Didn't stay there but stopped for coffee and dessert. The Austrian Hostel was on the Via De La Rosa.
Judy

Thank you everyone for the suggestion. I'll be visiting during x'mas holiday in December this year, still trying to finalize the trip plan, will definitely look into these hotels, budget wise hope to keep under $300/night.

I would stay outside the Old City walls. After the shops close, the streets can be pretty deserted and there's virtually no public transportation in the Old City. It may not be pleasant walking back late at night, though if you stay very close to Jaffa Gate, you should be okay.

The Dan Boutique is too far from the center and good transportation for my taste. I stayed there 2-3 times before the Dan chain bought it. Nothing particular to recommend it. A lot of people have told me the Harmony Hotel is great, in the center of town. It's location is excellent. Another option is the Notre Dame Guest House, which is across the street from the New Gate to the Old City, though this one may be pushing your budget to the limit. Friends of mine stayed there and loved it. Gorgeous view from the roof-top bar/cafe. It is walking distance to the center. The Three Arches is also well within your budget and well-located. It is in a great Ottoman style building, across the street from the King David Hotel. I'm not sure, though, if they've finished the latest cycle of renovations (that were needed a few years ago).

I stayed at the Olive Tree hotel twice. I enjoyed it, the location was great!