Alice, what's wrong with flying with a pup?
If it's a domestic flight and not too long I think it'd be better than boarding a 4-month-old pup for two weeks.
Heather's suggestion about renting a personal cottage is excellent. I took a 2-week trip with my GSD pup when he was 4 months old to Prince Edward Island, on a beautiful island in the Canadian maritimes. The owners of the personal cottage we rented were fine with dogs inside.
A definite advantage of renting over staying in a hotel is having a fridge and freezer available. If you're a raw feeder you can certainly appreciate this!!
(My pup was so lucky - being in the maritimes, he got to eat fresh salmon every day during the trip as an addition to his RMB's!)
My pup and I certainly had a great experience travelling by plane (we traveled by Air Canada in August). He wasn't at all nervous, ignored all the loud airport sounds and LOVED all the attention he got from the flight crew. All the flight attendants went over to the cargo hold to make sure he was comfortable before and after each flight.
It was only 2 short flights (26min and 2-3 hours) and I was able to get my pup back between connections.
Usually they don't allow you to access your luggage between connections, but if you have a long wait and you have a pet travelling in the cargo hold, they will make an exception
Trips to the sea are wonderful if you have a pup! Watching them swim for the first time is priceless, especially if they really love it and insist on eagerly swimming after you wherever you go!
A few tips that I picked up from my own experience if you plan to fly with your pup:
1. Fill the crate's water dish & freeze it overnight before you leave. Your pup will have access to water the whole time without it spilling during the flight. Being able to lick the frozen water will also help calm him if he's nervous.
2. Write your pup's name on the outside of the crate so that the workers loading and unloading the luggage from the plane can speak to him and calm him (if he gets nervous). I watched my pup being unloaded from the plane (from inside the airport) and it was the funniest thing to watch all the luggage loaders stop their work and gather around my pup's crate, talking and cooing to him ;o))
3. Before the plane takes off, ask the flight attendant to check with the pilots that the ventilation and temperature control are turned on in the cargo hold.
This probably isn't necessary, but they'll be happy to confirm it for you and it will make you feel much better (especially if you are obsessive over your pup's safety like I am, haha).
Good luck finding a fun vacation for your pup. Travelling is a great socializing opportunity for a pup and having him around will certainly make the whole trip a lot more fun for you