Our Airbnb Road Trip Through New England and Canada

From time to time I will be sharing the lost posts of Dream Depart Explore. This is one such post as we took this trip in July and August of 2016. We did then enjoy time away in Scotland as mentioned and it went just as well.  Stay tuned for lost Scotland posts as well. Now, without further ado, our thoughts on a road trip that relied heavily on Airbnb to provide places to lay our heads as we dreamed happy vacation dreams.


We ADORE our immediate family, our extended family, and our friends who live in the Northeast and that is why we travel there so often.  This past summer though we decided to get our munchkin (I need a new nickname, she and I literally see eye-to-eye these days) to the parts of the Northeast she hadn’t seen yet.  Until this year she had been to New York, Connecticut, and Massachusetts many times but that was it. So off we went.

This was the longest family vacation we have taken to date and we brought the dog. (Yes, some of my animal issues have subsided, who couldn’t love this face?)

We were gone for 16 days and drove over 3500 miles. My hubby is a champ!!

Our itinerary was a bit strange in that it wasn’t all that efficient. Though one of the main goals of this trip was to give small-fry (nope, that’s not better) a chance to explore the New England states she had yet to visit, we also wanted to be respectful of our family members. We stayed with each of my brothers for 3 nights and wanted those to be mostly on the weekends. We may have been on vacation but they weren’t and still had jobs to get to as did the rest of our friends and family we were hoping to see.

In 15 nights on the road, we stayed in 9 different places.  Two were siblings’ homes, 1 hotel, 1 traditional bed & breakfast, and 5 Airbnbs.  Before this trip we had stayed in just one Airbnb in Wisconsin.  Did I mention I LOVE Door County?  We had such a great experience and saved so much money, we decided to really test our luck on this trip.  It was an excellent decision!

We were able to stay much closer to the action than we could have in traditional hotels so we saved a lot of time. We also saved quite a bit of money even with paying for parking in Boston.  It is tricky to find hotels that will allow dogs, even house trained, crate trained, non-shedding, hypoallergenic, 12 pound cutie pies. When you do find them, there is usually a $35-ish charge per night and there is not much in the way of a safe place to walk the puppy.  By staying in Airbnbs (use that pet filter well my friends) we had lots of options, nearly all of them cheaper than hotels in the same area. We had neighborhoods and parks to explore and we got to meet lots of nice neighbors walking their own dogs.

During this trip we stayed in entire homes or apartments. When we travel with kiddo (yes!) we tend to do this.  It is much easier to have our own space. However, when my husband and I travel by ourselves or as a couple we are just as likely to stay in private rooms within family homes.

So, where did we stay?

Let me open my handy app and check it out!

  • In Boston we stayed in a fun and funky lofted apartment in a brownstone in Beacon Hill not far from Boston Public Gardens and Boston Common.  We parked our car and forgot about it for 3 days as we walked everywhere.  Thanks to our apartment in Back Bay, we were close enough to everything to do so.  This all went so well that my daughter now has her eyes on Boston/Cambridge for college. She’s thinking MIT.  We’ll see!
  • In Portland, Maine we stayed in a house that I’d guess was about 100 years old and had been converted to apartments. It was right down the street from a large park and a donut shop. Apparently they are the best donuts in Maine so we dutifully checked them out. They did NOT disappoint! We also visited the Portland Museum of Art and enjoyed time in the cafe and gift shop. Not far away was the Spring Point Ledge Light.  Before we left the state we did make sure to stop at the LLBean outlets in Freeport.  We spent nearly all day there, actually.  It did my New England heart good!
  • In Vermont we stayed on a farm that came with goats and chickens and my daughter saw more stars than she has ever seen growing up in suburbia. (On our upcoming trip out west she insists that we camp a few nights so she can see more!) We were within a mile of the Ben & Jerry’s Factory.  Bonus: Our host pointed us to The Reservoir restaurant in town.  We enjoyed the wine at dinner so much that the next day we took off for the vineyard.
  • In Montreal we stayed in a converted cigarette factory that had the most gorgeous pool and patio on the roof.  Once again it was walking distance to what we needed.  There is a very eclectic set of restaurants and shops about 2 blocks away. Three blocks or so away and we found the Metro which we used well.  Among other places, we hopped a ride as we headed to the Musée des beaux-arts de Montréal. They had the coolest Pompeii exhibit while we were there.  The permanent collection is well worth the trip too.
  • In London, Ontario we stayed in the most spectacular basement apartment I’ve ever seen. It was so clean and modern, and extremely well appointed. This was a stopover point for us but the hosts (who live upstairs) were extremely kind and hospitable. There wasn’t anything we needed that they didn’t provide for us.

The best part? We had our own local guides to ask for activity and restaurant suggestions. We even had people who located dog parks for us and drove us over to them!

We met the nicest people and have memories to last a lifetime. We did so well that when hubby and I head over the pond to Scotland in May we will be staying exclusively in Airbnbs.  Some are entire homes and some are private rooms, one even has a dog.  Wish us luck!  Check back here to see how it went.

If you are interested in trying Airbnb for yourself, feel free to use my link here to get $40 off your first home booking of $75 or more.

**This is not a paid post, I am simply an enthusiastic Airbnb community member who loves to share my experiences with others.

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