Reviews Travel Deals

Best Travel Deals: Wheatleigh Hotel

Best Travel Deals Wheatleigh
Written by Charlie

Someone asked me recently what was the best travel deal I have ever had. That made me think and I realized I have been the fortunate recipient of many great travel deals. So, I figured I would list some of the best travel deals I have enjoyed over the years and that this will hopefully help you to jump on the great opportunities when they come up. I know for sure that many people have received better travel deals than I have, so please feel free to add your best travel deals as well!

There are two main type of travel deals – actual sales/offers made by the travel provider and mistake fares or deals. My different deals have come from both categories.

Best Travel Deals: Wheatleigh Hotel

I would not be surprised if you have never heard of this hotel. I had never heard of it before I booked a reservation here but I can tell you that it has to be the most luxurious hotel that I have ever had the privilege of staying in. The hotel was built just before 1900 by a rich NY businessman for his daughter who was to marry a Spanish Count. It was built to be there vacation home in the beautiful Berkshire Mountain area. It is situated just outside the little quaint town of Lenox, Massachusetts. To read more about the history, click here.

Best Travel Deals Wheatleigh

Wheatleigh Hotel / Photo Credit: Wheatleigh Hotel

The Travel Deal

In 2008, Leading Hotels of the World (a luxury hotel organization representing many luxury hotels) was celebrating their 80th anniversary of being in existence. To celebrate, they announced that they would be offering rooms at participating hotels from November 1 – December 15 for $19.28 a room (the year they were established). People could sign-up for a maximum of 2 rooms during the promotion and they would release the rooms at a specific time for people to begin the claiming process.

They vastly underestimated the popularity of this promotion and their servers could not handle the onslaught of traffic. The release date ended up being a disaster and they eventually canceled the release and announced they would offer a new method of entering for the rooms in a form of a lottery later in the week. When they released the new system, it was definitely more orderly and it actually gave people a decent shot at getting the rooms (early numbers had said that over 100,000 people had attempted to lock in the just a few hundred available rooms). The new system had people fill out a form and submit it within the short registration window. On the form, you had to select three different participating hotels that you would want to stay at and choose the dates that you would stay at each. Then, based on the time stamp on when they received your submitted form, they went through the forms to assign the rooms to the entrants. I had submitted for the Hay-Adams hotel in Washington DC (right across the street from the White House!), the James Hotel in Chicago, and the Wheatleigh Hotel in Lenox, MA. I chose the two hotels I was really interested in and used my third pick for a place that I figured would not get that many requests. It turned out that was the right approach as there was no room in the first two hotels so I received one night at the Wheatleigh Hotel for $19.28 for the night!

The Hotel

Best Travel Deals Wheatleigh

Photo Credit: Wheatleigh Hotel

The morning of our reservation, we took the 4 hour drive over to Lenox. We arrived there in the early afternoon and found it to be so quiet and beautiful. Someone came out to meet us and insisted on parking our car. We walked in and were met by another employee who took us to our room. Since there are few rooms here (not a traditional hotel – it is a converted mansion), there was no place to “check-in”. The employee just met us and took us up.


Best Travel Deals Wheatleigh

The Small Room – what I was supposed to get

We were showed to our room which was beautiful! Since we were staying here at such a ridiculously low price, I had not even looked at the hotel rooms online. Had I looked before our arrival, I would have realized that our room was actually to be quite small (even though it is apparently the most luxuriously small room in the world). The room was 10′ x 12′. They described it as a ship cabin with a bathroom and double bed. 🙂

Instead of that room, though, we were told that they had moved us to one of their larger rooms since they had no other guests. I have received many upgrades at hotels around the world, but this was the first time that I was upgraded three room types! They moved us to one of their Junior Suites that featured a large balcony looking over the Berkshires, a large bathroom with antique soaking tub (imported from the UK), high ceilings, and a beautiful fireplace. The cost? Our original room was listed at $675 for the night and the upgraded suite was $1,375 per night! Talk about a nice gesture!

Best Travel Deals Wheatleigh

The Junior Suite – what I actually stayed in!

This Junior Suite was absolutely beautiful. Everything in it was very elegantly appointed and decorated. The soaking tub cost over $10,000 and it was really nice! In addition, they had a Borg&Olufsen 42″ TV as well. This TV actually followed the remote around the room – it would rotate on its own to face wherever the remote was so that you could sit wherever you wanted in the room.

Unlike most hotels that I have stayed at, the furniture in this room was very expensive, elegant, and well-built. It felt more like a bed and breakfast than a hotel (though a VERY upscale bed and breakfast). When we entered the room, we found homemade cookies waiting for us on the bed. The lady who walked us to our room asked if we wanted to use the restaurant that night. While we would have loved to, I told her no simply because of the cost. I did not know what the cost of dinner was, but I had found that it was going to cost me $130 if I wanted them to put some roses in the room. With that price, I figured dinner would be out of my budget. Not only that, but it gave us a chance to walk through the very nice town of Lenox. It was early December so they had already started decorating for Christmas time. Very nice area!

All in all, it was a fantastic stay. If I could afford to go back there, I would just because it was that great. However, with the price at almost $1,500 for the room we stayed in for one night, that will not be happening anytime soon. 🙂 One of the best parts about the whole trip was when we went to check out. I received my bill for under $20 for the most luxurious hotel I have stayed at – PRICELESS!

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About the author


Charlie has been an avid traveler and runner for many years. He has run in marathons around the world for less than it would cost to travel to the next town - all as a result of collecting and using miles and points. Over the years, he has flown hundreds of thousands of miles and collected millions of miles and points.
Now he uses this experience and knowledge to help others through Running with Miles.