Here's a compilation of the coziest, most unique places I've ever laid my head to rest:

HOSTEL
Hosteling International in Husey, Iceland
Price: $20/night (private room), horse back riding additional This one farm 'town' is barely a dot on the map. It's enveloped in fog and feels like the end of the world, but I think this is precisely why the seal-hunting, hostel-running family has made it their home. The accommodations are cozy, there is plenty of home-made food available and the other visitors are like-minded. The highlight are the beautiful Icelandic horses that go out twice a day for a trot through the area, teasing the seals that also make Husey's beaches their homes.
Fondest memory: Sharing shots of bourbon with new friends in the large solarium front room.

CAMPGROUND:
Cape Breton National Park, Canada
Price: $25/night (one night); $14/night (7 nights) When staying in nature the comforts of home are probably least important (although the park offers all the basics). What you're really after is scenery and wildlife. The southern most site in the park (near Cheticamp) seemed to be frequented by families of moose (or at least it was during our stay, they even nibbled at our smelly socks drying on the line). And if you choose a spot on the cliff's edge, secure your tent well, night time winds can be of gale strength, but the views are definitely worth it. The camp sites in the north of the park offer close proximity to towns with excellent whale-watching tours. A must see, as is a trek along the Sky Walk hiking trail.
Fondest memory: A sleepless night spent duck-taping our tent rods together to prevent the tent from blowing away with us in it.

APARTMENT:
Papilani in Hana, Maui
Price: $110/night (apartment sleeps 6) We've stayed in many apartments along the way, in fact it's our favourite way to travel. It's comfortable, affordable and quickly it changes your mindset from tourist to local, when you find yourself shopping for toilet paper or dish soap. Papilani stands out for a few reasons: the breathtaking garden, full of palms, flowers and off-the tree mangoes which surround the property; the outdoor rain shower you share with tropical critters like frogs and tiny lizards; the wonderful hosts Sybil & Dave and of course, the location. Papilani is situated on the outskirts of Hana town, at the end of one of the world's best ocean-side drives, it's a short drive/hike from natural pools, a bamboo forest, and yes, some fantastic surfing beaches.
Fondest memory: Waking up with the sun every morning (it seems they don't believe in curtains over there).

B&B:
Brockwell Chambers in Sault St. Marie, Canada
Price: Under $85/night (for two) While Sault St. Marie may not be a traveler's dream, the Brockwell B&B certainly is. It was the highlight of our stay (other than the wedding we were there to attend). In a slightly grim, blue-collar town this charming historical property is an oasis. The hosts were lovely, rooms spotless and elaborately decorated (like staying at a fancy grandma's house) and the breakfast decadent.
Fondest memory: The fruit salad in the morning, served in crystal glasses.

HOTEL:
Hotel Chelsea in New York* 
Price: $160/night (for two) There is not too much to be said for the room we stayed in, it was clean, had bathroom and kitchen facilities. For New York, it was affordable and the staff super helpful. But the Chelsea, is legendary for other reasons: it's been the home or temporary refuge for the coolest characters imaginable: from Jimi Hendix to Patty Smith, from William Burroughs to Bob Dylan. It's also the place where Dylan Thomas died of alcohol poisoning and Sid Vicious killed his girlfriend Nancy. Perhaps a little morbid, but you can't help but be charmed by the history which is still palpable as you walk down each unique hallway filled with art, curiosities and mementos of its famous patrons.
Fondest memory: Chilling on the fire escape, wondering about the hotel's ghost residents.

* Update: Since my stay at the Chelsea in mid-July, the hotel was sold and closed to visitors for year-long renovations. Concerned residents speculate about the hotel's future and their own. We'll have to watch and see the story unfold. But I sincerely hope that the hotel will remain open & affordable so that people can continue to enjoy it and celebrate it's rich past.