I've put off this trip for way too long yet finally book my flight from the U.S. to Glasgow, from Mid-Sept to Mid-Oct.
I'll be by myself and currently have no itinerary.
I want to spend a couple of days each, in Glasgow & Edinburgh yet plan to spend the lion's share of my time in the highlands, Skye (and surrounding isles), and hope to make it to both the Orkney & Shetland Isles.
Trying to keep costs down for lodging I hope to find little more than a room with a bed, decent wifi & a place to do laundry every few days. I've had the privilege of being able to working remote for over 13 years & it's allowed me to see parts of the world & still be able to work...so the wifi is necessary.
I have a romantic vision of my trip in that I hope to steer clear of tourist areas, lodge in quiet locations & visit quiet local pubs in the evenings.
I see that a rental car will be quite costly for this length of time yet I'm not into group tours so a car will be necessary.
I am hoping you all might offer feedback, suggestions on how to make my trip most cost-effective, things I must see & places I should probably avoid.
If I had my druthers, I'd go with no scheduled accommodations but for the first few nights, then make them as I go yet I gather that would get expensive.
I plan to post my trip when I go.

Welcome to Fodors.

Unfortunately you are a bit at cross purposes with "I have a romantic vision of my trip in that I hope to steer clear of tourist areas, lodge in quiet locations & visit quiet local pubs in the evenings." then list Skye among other places. Other than Edinburgh, Skye is by far the most popular tourist destination in Scotland. Its insanely popular. But traveling in the Autumn things will be less crowded than in say August.

The possibilities are limitless as to where to travel and for how long. Even with a month you will need to be selective what you can and can't see. I'd suggest you get a couple of guidebooks straight away and if you can find a copy of Peter Irvin's 'Scotland the Best' - ir doesn't have to be the latest version -- there are 14 editions going back decades. This isn't a guidebook as such -- it is well, a list. Of the best of everything Scotland. The best beaches, the best whisky pubs, the best beer, the best hikes, the best hill walks, the best viewpoints, the best islands, the best graveyards, the best scenic drives etc etc etc.

But just for starters -- You might want to devote more than 2 days to Edinburgh.

To give you some ideas, here is a recent Trip Report by another Fodorite Glencoe, Isle of Skye, the Lake District & More!!

and another one: 2023 : A Highland Odyssey

. . . and another good resource https://www.undiscoveredscotland.co.uk

Don't take the 'Undiscovered' part quite literally . . .

Welcome to Fodor's indeed...

You've described a little about where you want to visit and what sort of accommodations you'd prefer, but you really haven't said what in particular interests you or why you've chosen the places you listed. Take Shetland and Orkney for example. Why? The remoteness? Scandinavian associations? Prehistoric monuments? Why the Northern Isles but not the Western Isles?

Castles? Hiking? Music? Whisky? Birding? Genealogical searches? Scotland has so many options, and so many of them world-class, that as Janis says, you're going to have to be quite selective, even with a month. Give us an idea of your wish list, and we can be of more help.

And again, welcome!

Thanks for the feedback so far. The purpose of my post was primarily for ideas on cost-effective places to stay, as well as things to see & places to avoid.
I guess I should have left out things to see as I have researched quiet extensively, the things I want to see.
Going to Orkney & Shetland is about my family heritage...mainly just to see those places.
I'm actually well traveled, having spent much time in England or Ireland yet never having made it to Scotland. It will be the first time I've had a trip of this length where much of the time will be my own yet don't want to spend a lot of it on tour busses or in hoardes of ppl.
For accommodations, i only need something with slightly more privacy that a hostel. 😁
If everything out there mostly goes through AirBnB & VRBO then I will stick with those search options. 😁

Re budget accommodations -- many hostels do have private rooms and in rural areas B&Bs can be inexpensive (of course there are posh/expensive B&Bs too). Rates have risen - hasn't everything?? And new-ish Scottish laws make it harder for B&Bs to manage but when the full (and I mean FULL) Scottish breakfast is factored in a B&B ca be a real bargain.

Mid Sept/mid Oct is low-ish season and many places do reduce their rates. But places like Skye and Orkney you will want to book well in advance. Also anyplace along the NC 500 which has become a very successful marketing campaign attracting more visitors to the far north. But in general rural Scotland is not really a 'hoardes of ppl' sort of place (except for Skye - and even it can absorb them).

On a touring holiday (rather than a week's stay in a rental cottage) I personally would stick with actual B&Bs and hostels in those remote areas -- if a one-off airbnb falls through you'd be pretty much stuck.

Plenty of hostels offer private rooms and bathrooms nowadays. And they offer a laundry very often.
Also consider camp sites, many of which have pods or static caravans to rent.
Much as I dislike booking.com they also offer B&Bs and self catering. The various tourist info site per region also have accommodation.

Consider a trip up through Argyll, a delightful and less visited area after Glasgow. We rented a house on Loch Fyne many years ago and loved the area.
This year we are thinking of visiting East Neuk and the Cairngorms later September. Many places are fully booked though (or silly money) though!

Have you thought of renting a small campervan for the month? Plenty of legal places to stop the night in one for free or not a lot of money, though the Scottish right to wild camp does not apply to them. For some places, like Loch Lomond and Trossachs NP you have to book a place in a car park on their websiite. We did that pre Covid and had a lovely spot right on the Loch.

Oh - just did want to comment re Orkney/Shetland -- you will want a fair bit of flexibility because adverse weather will affect the ferries

Given the weather uncertainties, cost of accessing ferries and the cost of passage on them (especially with a vehicle) I'd actually plan to fly to Shetland from either Edinburgh, Aberdeen or Inverness, get a local car there, then fly to Orkney, ditto, then back to INV, ABZ or EDI, depending on where you plan to go next. Loganair has frequent service to/between all of the above.

While the Scottish government has pledged to expand high speed internet service throughout rural Scotland and the islands, I wouldn't count on having especially fast broadband coverage in more remote places. If you plan to work from the road and if your work needs a lot of bandwidth, I'd definitely check with the accommodation host as to what kind of speed and service they offer.

I agree re flying -- you'll just have to deal with multiple car hires. One for Shetland, one for Orkney, and probably two on the mainland.

I note that you are looking for places to stay at a reasonable price which are less touristy apart from Edinburgh or Glasgow. This might be slightly odd, but you may want to take a look at this website. https://www.dogfriendlycottages.co.uk. Whilst the properties have been selected for dog owners, they have a good range of properties often in quieter locations and the price range includes properties at a reasonable cost. Some of their suggestions are from Laterooms.com but outside the main cities that is not normally the case. You could also look at https://www.welcomecottages.com
Regarding Edinburgh and Glasgow, to keep costs down you could stay somewhere like Bathgate and take the train in to Edinburgh/Glasgow.depending on what you want to do,
Finally I should mention that the school half term holidays fall between October 16 and 27, so places will/may be booked up.

Thank you so much. I'll be checking out those sites. I'll be leaving on the 17th so that would be perfect timing, to avoid the student bookings. Great information!

We bag 4 of the big 5 in Orkney might give you some ideas. Car hire at Orkney airport is limited but fine, you can use a Taxi to get to Kirkwall and there are just a few buses about to the main other towns (by definition very limited) so a car hire makes most sense unless you hire a tour guide.

One of the ferries goes into the centre of Stromness.