A Real Wedding Story: Hotel Babysitting

Natalia Ramos
Jan 28
3 min read

Hotel babysitting is one of those things people don’t really understand until they need it.

This wedding at Pleasantdale Chateau was a perfect example.

The groom reached out because several of his close friends were flying in from the UK; and two of those guests were traveling with babies. Everyone wanted to celebrate fully, but no one wanted to pretend that jet-lagged babies magically sleep on schedule just because there’s a wedding happening.

So we stepped in.

A Venue That Feels Like a Fairytale; and Actually Works

Pleasantdale Chateau is one of those venues that feels like you’ve stepped into a storybook.

It’s a full estate with so many distinct spaces that the day naturally flows:

a castle-like main building
gardens straight out of a fairytale
a grand ballroom for the reception
cozy lounges to step away into
even a tucked-away bar area that becomes the after-party

There’s also an indoor pool and on-site accommodations; which made a huge difference for families traveling with babies.

Some of the parents stayed right on the property, meaning bedtime, feeding, and check-ins stayed close and familiar. Another family stayed at a nearby hotel, where we coordinated hotel babysitting there as well.

Different setups, same goal: keep things easy for parents while the celebration unfolded.

It’s the kind of venue that gives you room to breathe; and when babies are involved, that flexibility matters more than people realize.

First Things First: Getting to Know the Families

Babysitter at hotel service playing with a kid

Once the groom shared the parents’ information with us, we reached out directly via text and email; nothing stiff or overly formal, just real communication.

Each family filled out a short form so we could learn about:

routines
feeding preferences
sleep habits
comfort items

From there, we carefully matched sitters based on experience and temperament. Once sitters were assigned, we sent sitter profiles to each family. Some parents were totally comfortable with that, while others opted for a quick call beforehand.

That one step changes everything. Parents go from “Who’s watching my baby?” to “Okay, I feel good about this.”

Jet Lag + Bedtime = The Real Test

Let’s talk about the hardest part of the night: bedtime.

These babies had just traveled internationally. Their internal clocks were confused. There was crying; and that’s completely normal.

We didn’t rush it. We didn’t force a schedule. We focused on patience and familiarity.

That meant:

white noise
comfort items from home
familiar toys
calm, predictable cues

We always bring age-appropriate toys and materials, but when kids are off routine, the little things that look and feel like home are everything.

Supporting Breastfeeding Moms (Without Making It Awkward)

Another key piece of the night was feeding.

The babies were still young, so breastfeeding was the only option. That meant communication had to be thoughtful and well-timed.

Luckily, feeding aligned naturally with transition moments during cocktail hour. We coordinated closely with the moms so nothing felt rushed or disruptive; and no one felt pulled away from the celebration longer than necessary.

The goal was simple: support the babies and support the parents.

Why We Staffed One Sitter Per Family