For the 50+ Traveler

At Christmastime, New York City really dresses up for the season. There’s a sparkling, giant tree at the Rockefeller Center and ice skating in Central Park. The Rockettes dance to live orchestra music, elaborate window displays are everywhere, and the city hosts an enchanting outdoor Christmas market.

For years, a trip to New York City in December was on my bucket list. So last summer, I decided it was time to book it.

Booking With Care

Before choosing an Airbnb, I studied maps of Manhattan. My previous trips to New York City were in the spring and summer, but this trip would entail cold temperatures and possibly snow. I wanted to be near Times Square and the Rockefeller Center to avoid walking too far in the winter weather, but I didn’t want to be too close to the crowds and noise.

After much deliberation, I chose what I thought was the perfect apartment in an area not far from the main sights. The photos were mostly of the living room, and the listing description mentioned that the bedroom was small. I didn’t worry about that, since my family doesn’t require luxury. We’ve stayed in many Airbnbs, and this one promised to be a winner.

My daughter, who has been to New York City on business many times, decided to join us. We were all set for five days of holiday family fun.

The writer with her husband and daughter in New York City.
Sharon Odegaard

Reality Bites

We arrived in New York City at night, with cold rain that would soon become snow. Our Uber driver dropped us off in front of a restaurant that he assured us was our apartment’s address. We found a small door behind a bank of trash cans. Our host’s neighbor met us to unlock the hallway doors. We climbed the stairs covered in threadbare carpet past piles of junk.

Then our host’s neighbor opened the door to our home away from home. A wave of heat greeted us. We started peeling off coats, scarves, gloves, boots, and sweaters. The neighbor explained that it was indeed an unbearable 95 degrees inside, but that the boiler heat from the basement was stuck on, so we’d just have to open a window. California girl that I am, I asked if that would let in snow. The neighbor informed us that it would, but at least we wouldn’t be too hot.

Oh, and there was another slight problem -- the radiator leaked into a large pan of water. We would need to empty this pan every few hours to avoid a flood in the apartment. I worried that this constant flood watch would put a serious dent in our sightseeing plans.

We could live with issues such as the bedroom being so small that there was no floor space around the bed. You had to jump in from the foot of the bed, and all that night I kept kicking the wall right next to my feet. A bigger problem was the noise from the restaurant and street below that drifted through our open windows all night, with people yelling and car horns honking. Sirens pierced the air. This is the city that never sleeps, and neither did we.

The writer's room at the Grand Hyatt.
Sharon Odegaard

The Happy Solution

My daughter arrived at midnight, and we went into conference mode immediately. We had loyalty points with Hyatt and IHG (Ritz-Carltons and Holiday Inns). In no time, we found that our points would get us into the Grand Hyatt in the heart of Manhattan for three nights. It was too late to move there after midnight (the hotel was full), so we suffered through one night in the Airbnb. In the morning, my daughter commented that with the noise and temperature issues and snow drifting through the windows, she felt like she got as much sleep as if she’d spent the night on a plane.

We transferred to the Grand Hyatt the next day, leaving behind the disaster of a place and settling into delightful elegance -- all at no cost to us. We marveled at everything in our new room: The bathroom had no chipped tiles or peeling paint, there were real beds instead of a futon, and there was plenty of room to walk around the beds! We enjoyed a city view out our 34th-floor (closed) window, a block away from the famous Chrysler Building. We didn’t hear a single car horn all night, and we quickly caught up on our sleep in the comfortable room.

I was ready to call it my mistake for booking a hot (and cold), flooding apartment. My daughter was more assertive. When the Airbnb host texted to ask how we were doing, she helped me write a polite but firm response saying we couldn’t stay there and lose so much sleep. To my surprise, he immediately wrote back and offered to refund my payment in full. He just asked that I not leave a negative review. We agreed, and the money was back on my credit card before we flew home. And since we booked the hotel room with points, our lodging situation actually gave us a positive balance in our bank account.

Once that was settled, we had one more night to figure out. It would have been easiest to spend the night at the Grand Hyatt and pay out of pocket. I looked up the cost and was shocked that it would be more than $700. That was definitely not in our travel budget! So, once again, we turned to our stash of points. We found a Holiday Inn around the corner from Madison Square Garden for our last night. We moved from our super-luxurious hotel to a perfectly comfortable hotel in a convenient area. And again, it cost us nothing.

Ice skating in New York City during winter.
Sharon Odegaard

Lessons Learned

Our time in New York City during the holidays far exceeded my expectations. It was charming beyond what I imagined! But we might have spent our time tired and feeling ill from being overheated or cold. And running back to the Airbnb every few hours to empty a pan of water would certainly have disrupted our sightseeing!

Here’s what I learned from this experience.

Collect Hotel Loyalty Points, Even If You Have No Immediate Use For Them

We had points on the back burner, and this meant we could change our plans and move to a place where we could get a good night’s rest. We have points with Marriott and Hilton as well as IHG and Hyatt. It’s not crazy to rack them up -- it can save your trip!

Decide What Issues Are Deal Breakers

We stayed in a different Airbnb in New York City a few years ago that also had a small bedroom. I had to launch myself into the bed, since there wasn’t room to walk around it. We’ve laughed about this many times since. Space is at a premium in New York City, so a cramped apartment wouldn’t be a deal breaker.

I’ve stayed in hotels and Airbnbs with ancient bathrooms and broken tiles and stains. Old floors may slant, and stairs may creak. Entryways may be piled with junk. I can deal with those things, but the heating and flooding issues put me over the edge.

Stand Up For Yourself

I would not have told our host (who was out of town) that we didn’t stay at his apartment. But when I did, at the urging of my daughter, he wrote back right away. The situation was resolved to the satisfaction of both of us. And I’m guessing that when he got home, he fixed the heating and flooding problems ASAP.

Having a backup plan to book hotel rooms for free, knowing our tolerance limits, and being nice but firm with our Airbnb host all paid off. The three of us enjoyed a memorable holiday trip.

Trying to decide between a hotel and an Airbnb for your New York City vacation? Check out our breakdown.