(Meet me at the Real Estate & Entrepreneurship Conference for Physicians September 26-28, 2024 in Dallas Texas. Send me a message if you are coming so we can meet up. I would love to meet you in person.)
My wife and I just finished a month-long trip visiting areas of New England we have never seen. We booked three weeks of back-to-back timeshares followed by a cruise of the islands south of Cape Cod.
Many people don’t realize how nice the accommodations are and how inexpensive a timeshare can be for those who qualify to own one and learn how to use it. We have owned a single week in New Orleans for more than 30 years. Strategically, we have never stayed in the timeshare we own.
Trading a timeshare is where you gain value. If we stay in the one we own, we could only use it one week a year. Trading it gets us almost limitless weeks. So far this year we have traded our one week of ownership for seven weeks of timeshares in various locations.
The areas in New England we are traveling to this time are the Berkshires in Western Massachusetts, Northern New Hampshire, and Cape Cod, Massachusetts. Here is how it unfolded.
Preparation
I made these timeshare trades in December 2023. I searched for all the available timeshares in the New England area for the first few weeks after school got out. I also looked for cruises off the shoreline in the New England areas that could be combined with the timeshares. Looking at the available dates, I was able to put together three back-to-back weeklong timeshares followed by a seven-day cruise.
We were initially thinking of spending a few days in Boston before or after this trip and therefore had not yet purchased plane tickets when my son asked if we would join him in riding our bicycles across America, starting in early April. Since we didn’t know for sure how long a 3,000 mile bike ride would take, I decided not to buy plane tickets until after returning home from the bike ride.
Since our return was less than two weeks before our New England trip would start, we decided not to spend extra days in Boston. This was the latest I had ever booked airplane tickets for a vacation. With such short notice, we couldn’t get seats together on the flight to Boston, but we could for the trip home. I also reserved a rental car for our four week stay.
I acquired our plane tickets with my credit card air miles, so the airfare was free. The day before the flight, during check in, I was able to switch seats so we could sit together.
Week 1, The Berkshires
We landed in Boston’s Logan airport in the afternoon and picked up our rental car. We then drove 130-miles to our first timeshare, the Berkshire Mountain Lodge in Pittsfield, MA.
Our accommodation was very nice. We had a one-bedroom flat on the third floor with a living room, dining room, kitchen and bathroom. The exercise room was good, and they had a nice indoor swimming pool and outdoor hot tub.
The Berkshires is a very pretty area. All the main streets of towns look beautiful. Seems they don’t have any boarded-up businesses here.
There are many things to do here as it is a destination for vacationers. One of my highlights was visiting the Norman Rockwell Museum. His paintings really speak to the heart.
We attended two live shows this week, West Side Story and A Body of Water.
A beautiful serendipity was the chance to visit Disha Spath, The Frugal Physician. I was a guest on her podcast recently on the topic of real estate investing and when she heard of our trip to Massachusetts we realized we would be very near her home and planned a visit. We enjoyed her hospitality for dinner, met her husband, two boys, and two dogs that looked a lot like small horses. I enjoyed playing a duet with her son, a budding young pianist, on her beautiful baby grand piano.
Week 2, Northern New Hampshire
Saturday morning, we set out for North Conway, New Hampshire, a 227-mile drive. It was a very beautiful drive through the mountains of Western Massachusetts, Southern Vermont, and New Hampshire. Along the way we stopped for lunch and caught a 2pm showing of the musical Jersey Boys. This theater was enroute to our next timeshare and conveniently had a Saturday afternoon show.
After the theater, we finished our drive to the next timeshare and settled into the Eastern Slope Inn. This was a beautiful old New England style building that was remodeled into a timeshare. It had a lot of character and fancy woodwork.
This unit had an upstairs bedroom with two queen sized beds and a bathroom. The main level had a hide-a-bed couch and a murphy bed in the wall of the living room, as well as a kitchen, dining room and a second bathroom. This ability to sleep seven is why timeshares are superb for large families. The gym was very well equipped, and they sported an indoor pool, both indoor and outdoor hot tubs, two clay tennis courts, an on-site fishing pond, as well as a restaurant, and a live theater.
We found ourselves in another very cute mountain town with lots of activities. We did note many families with little children at this site. We saw no young children at the prior resort. This area sports many vacation activities that families love and can do together.
One highlight of the stay was our drive to the top of Mount Washington, the tallest mountain in New England. What a great view from the top. There was also a cog wheel train running to the top and many multi-day hikers stopping for lunch.
While in the area we saw two more plays: Camelot and Harvey.
On the final day at this site, my wife did laundry in the free guest laundry room. Anytime we travel for more than two weeks, we plan on doing laundry. We pack light and do not bring enough clothing to last a month without doing laundry.
Week 3, Cape Cod Massachusetts
Saturday morning, we set out for our third stop, the Courtyard Resort in Hyannis, MA. This drive was 207 miles and took us back through Boston. Upon reaching Boston, we took a several hour break to visit the John F. Kennedy Presidential Library and Museum. I find presidential libraries fascinating.
We then completed the drive to Cape Cod and checked in. This resort was not one of the finest RCI has to offer. It was a motel, converted into a timeshare. The room was better than a standard motel though. Our studio unit included a bed, living room furniture with the TV on the dresser, a kitchen table with four chairs, a small kitchen, bathroom, and a large balcony. It did not have a gym but it did have an indoor pool.
The reason we chose a less than stellar place was because it fit into our schedule and was in a great location. We sometimes sacrifice staying at a 4-5 star rated timeshare for a specific time or location that we especially want.
We were located right on Main Street in a great beach tourist town. This is the location of the Kennedy summer compound. It is also centrally located in Cape Cod. We are within walking distance of dozens of restaurants, museums and the beach. There are lots of things to do in this area that are very different from the other two mountain retreats we just visited.
Two highlights were visiting the Pilgrims landing in Plymouth and the Cape Cod National Sea Shore. This is a very long stretch of nice beaches with two great visitor’s centers. It was also the first time I had ever seen a shark warning sign on a beach.
This week we took in three live theater productions: Satellites, The Drowsy Chaperone, and Trish LaRose’s Come on-a My House.
At the end of the week, we drove to Fall River, MA, to catch The American Star. This ship in the American Cruise Line Fleet is a 100-passenger coastal vessel, that’s touring the islands of Martha’s Vinyard and Nantucket as well as some additional New England Costal Towns.
We then drove back to Boston to catch our flight home.
Cost of using our timeshare
Many people who don’t know how to get the most from their timeshare complain about the cost. The cost is very reasonable though, as you will see from this breakdown of our cost for the three weeks we used in New England.
We bought our timeshare long ago for $16,000. We didn’t know better back then and paid the full retail price. If we were to buy one today, we would pay between $0 and $2,000 for a timeshare week on the secondary market. This year marks our 91st week of use. Dividing the purchase price by the weeks of use, we are currently averaging $176 per week and dropping.
Our yearly maintenance fee was $733. Since we have traded for seven weeks this year, that maintenance fee comes to $105 per week.
We pay an RCI membership fee enabling us to trade the timeshare week that we own for other timeshares all over the world. We buy that membership in five-year allotments for $399. That comes to $80 a year. This $80 fee divided by the seven trades we booked this year comes to $12 a week.
In addition to the membership fee, we pay RCI for each trade we make to the toon of $299.
Totaling those costs for each week comes to $176 + $105 + $12 + $299 = $592 per week. That is less than $85 a day and would be even less if I had known to buy my timeshare on the secondary market. It’s not easy to find a decent motel for $85 a night, let alone one with a kitchen that will sleep a family of seven like the second place did. The Econo Lodge down the road from our third week’s stay is advertised at $270 a night.
You can see the cost of having and using a timeshare is not the high figure people gripe about. Interestingly, I have never met someone at a timeshare who was complaining about the cost. However, I can see why those who don’t use it, but are required to pay the annual maintenance fee, might be unhappy with owning a timeshare. But instead of complaining about the cost of their timeshare they should learn to use it efficiently.
Pick up a copy of my book A Guide to Loving Your Timeshare and start experiencing great and inexpensive vacations using timeshares.
Thank you for explaining how to buy and use a timeshare strategically . I had not considered it before.
I am a lifelong New Englander – glad you enjoyed yourself in my neck of the woods . I was not aware that the Eastern Slope Inn was now a timeshare. We used to be frequent visitors to the North Conway area many years ago , mainly in winter but sometimes in summer . Great memories.