Because I am cheap, I find staying at expensive hotels stressful. If I am spending $500 a night for a room, I feel I should stay in it as much as I can so that I get the maximum value. When I was asked to visit all-inclusive resorts near New York City, I wondered: what would it be like to be in a hotel without hoping that my wife stays away from the minibar?

The Point is a five-hour drive from New York City and is on Saranac Lake. The resort used to be the summer camp for the Rockefellers and is aggressively camplike. The buildings—there are only 11 rooms—are rustic. There are stuffed animals on the walls. Every room appears to have a fireplace. When I pulled into the resort’s driveway, my old Toyota was taken from me, and I was led inside the main building for lunch. The Point has a renowned chef—and for once, the chef appears to have earned his renown. The halibut on shredded brussels sprouts was excellent. For me, because of my cheapness, the most noticeable part of the meal was that the wineglass kept being refilled without my asking. I suddenly realized that not calculating the cost of every additional item ordered was a wonderful, worry-free sensation.

The Point has several boats available to guests to explore beautiful Saranac Lake. There are also hiking trails, and nearby is the town of Lake Placid, where the U.S. Winter Olympic team trains. Because the Point is expensive, though, I found myself staying on the resort’s grounds. My wife and I went for walks. We had a picnic. In some ways, not going out and doing all that I could forced me to calm down.

Twin Farms, the other of the all-­inclusive resorts I went to, was owned by Nobel Prize–winning author Sinclair Lewis. Located in Vermont and also about a five-hour drive from New York, the hotel has 20 rooms and cottages, which are looked after by a staff of 38. The grounds include hiking trails, private ski runs, and, in January, a meadow that is flooded to create an ice-skating rink. The cottages are all of different designs, from a glass-walled structure to a cozy one-bedroom house that overlooks a stream.

Again, not having to think about the cost of things, I felt the deep satisfaction that I had experienced at the Point. But because Twin Farms is so expensive, I found myself not wanting to leave the resort to explore the region. There are naturalists on staff who can take guests around and identify animal tracks and different birds, so this time I had a better excuse to stay within the grounds.

The third resort I visited, the Ocean House in Westerly, Rhode Island, opened in 1868 and was one of the grand ocean-facing hotels of its period. For 135 years, it was open to guests. When it shut down, a new owner bought it and spent tens of millions of dollars rebuilding a hotel that exactly replicated the exterior of the old building. As the name suggests, the place faces the ocean and has a private beach. Partially because this hotel was less expensive than the other two, I did not feel compelled to stay on the property. My wife and I went into Westerly and walked around—the hotel was beautiful enough, though, that we did want to hurry back and wander its gardens.

The Ocean House is not all-inclusive in that one has to pay for food and drinks. One does not have to pay tips, however. When the valet parked my car and when my luggage was delivered, I took out my wallet and both times was told that tips were included. It was at this time that I first thought that in the same way that I am comforted by not having to think about how much something costs, the staff must also be comforted in not having to think about whether they will receive a fair tip.