From the desk of someone who always plans ahead.....

This is right up my alley. I manage a coastal hotel in california where we allow people to bring hteir pets. At first I thought the hotelowners must be crazy to do so but after being here 6 years I can say that we have only had about 2 incidents with the dogs and that was just them chewing furniture.
Since you are going to be crating him that is obviously not going to be a issue of him chewing but the crying factor might be a issue if you think he would be horribly loud and bother the other guests. We have a 10 minute barking rule, if the dog barks without provocation then we call the owners on their cell phone to inform them of the disturbance. If the dog is barking in reply to outside noises we give le-way. 3-4 hours is NOT to long but you may want to put one of your dirty shirts in the kennel to comfort your baby. Customers who dont feel comfertable leaving the dogs alone finda local babysitter to just sit with the dog while they are gone. Any teeneager who loves dogs wouldnt mind making a couple extra bucks to just sit for a couple of hours and any good hotel will have refferals for nearby sitters. Plus you wont have to worry as long as you tell them to not take the dog anywhere, just pop ina movie or do some homework! That way your baby wont have a whole weekend without you and can explore the destination with you and your partner!

We've taken Marley everywhere since he was four months old. He seriously is fine for a few hours in his crate in a hotel room! He just lays there. As long as Ben is crate trained...I'm sure he will be fine. []

I think it should be fine too - as long as he is crate trained, and maybe try to tire him out a little bit beforehand...  3 or even 4 or 5 hours is totally fine!  Have fun!!

Thank you - I will be so much more relaxed knowing he is OK and near me, rather than worrying about him (which I would, no matter how nice the kennel).  When I am relaxed I take better photographs lol.
 
And sheprano - that is a great idea.  I'll see if the hotel can give me any leads on that.
 
Kate

Stupid Question: Whats a SO?
 
But anyway, as long as you have someone to take him out or play if the need arises, take him with! I couldnt dream of going anywhere without Lizzie

Stupid Question: Whats a SO?

 
No question is stupid its stupid to not ask if you don't know something.[8D]
Anytime I have seen it used it means significant(sp) other.

Ben is going to love it! I agree as long as he is crate train he should be fine. Just make sure to pack toys with him to keep him busy, too.
 
I took Blue to his first hotel a year ago and loved it. He gots lots of attention from the staff.

I participate in dog sport.  My dogs have been traveling to major specialty shows and staying with me in hotels very early in their lives.  Think of it as an ultimate socialization opportunity.  The one issue you need to be working on now, is reinforcing quiet behavior.  Some dogs will develop the habit of barking associated with getting out of the crate.  That can easily develop into barking while in the crate.  You need to develop a very strict plan for the people in Bens life, so that will not happen.  The easiest way to do this is set up training times where you will leave him in the crate while you are around in the same vacinity and when you leave and come back.  Load up really really really good TINY pieces of food for treats (Boil chicken breast in water full of garlic powder or prepair liver, PM if you would like the recipe, or you can order Great Bait over the Net).
Set up the training so the initial check ins, pop in your head, feed if quiet (1-2 pieces) then leave.  Come back, leave etc.  Vary this with your trips to the grocery etc.  Make sure his body is calm and there is no noise before you offer the treat.  If he is being a goof, calmly and quietly turn your body so your shoulder is to the great but you can still monitor the activity and noise.  DO NOT GIVE any eye contact or verbal interaction while he is moving or "talking"  When he is quiet, mark that with a clicker or a "Yes" then hand him one or two treats.
If you really want to make this training work effectively, print out a monthly calendar.  Write the times and locations you are going to use for training (try for 3-4 a day).  Use a stop watch or watch with second hand to keep track of how quickly he settles when he sees you.  When he maintains a time for 8 of 10 training sessions on 4 of 5 days, increase the amount of time he has to wait before he gets the treat.  At his age, work in 5 second intervals.  I know it seems like it will take forever,  it wont.  The behavior starts building on itself.  If you record the times on the calendar, you will be able to track it very easily.

Respectfully.  When he is a bit older, start looking for a kennel.  Start having him stay a partial day, a full day and over night while he is a puppy.  That way if there is ever an emergency it is one less stress for you and him.  I did not board my first dobe bitch until she was seven, it was quite hard on her.  Used this approach for the rest of the dogs, they look at it as doggy camp now.

mrv - that is all excellent advice, thank you, I really appreciate it.  I will start working on that with him, he already loves being in his crate and goes in there to chill out by himself so I think we have a good building block to start from.  I am going to copy and save what you wrote about training him to be quiet, if that's ok with you.
 
I was certainly planning on finding a good kennel and getting him used to it gradually, because I know there may be times that I do have to kennel him overnight.  For example, I am going to the Maldives on my honeymoon next year and I think taking a dog on a 10 hour flight to endure 15 days of minimum 90 degree heat is not the nicest thing I could do for him.  My dad and sister in law will be looking after him while we are away, but there may be 1 or 2 nights when they will need to kennel him - so I had already planned on preparing him for that. 
 
In this case, though, since he would be welcome and my partner would be able to attend to him while I work, I was thinking it would be nice for all of us to go.  If, closer to the time, I think he won't be able to handle it I will rearrange my plans, but I am hoping that by that point in his development and our training, he will be ok.
 
Thanks again for the great advice.  []
 
Kate

Absolutely, feel free to PM with questions any time.