We’re not the type of family that takes extravagant vacations.
We budget. We plan ahead. We look for places that feel worth it.
Last summer, we decided to spend two weeks in Oak Bluffs, Martha’s Vineyard with our kids — and honestly, it ended up being less about the destination and more about the time together.
The Decision to Stay in a House
At first, we considered a hotel.
But with kids, hotels can feel cramped fast. One bathroom. No kitchen. Everyone on top of each other.
So we rented a house in Oak Bluffs instead.
That changed everything.
We had:
- A kitchen for easy breakfasts
- Space for the kids to play
- A yard for evening tag
- A living room for movie nights
It felt less like a vacation and more like temporarily living somewhere new.
Our Daily Routine (That We Still Talk About)
We didn’t overschedule.
Most days looked like this:
Morning pancakes at the house
Bike ride to the beach
Afternoon sandcastle competitions
Ice cream on Circuit Avenue
Dinner at home or a casual spot near the harbor
We rented bikes for everyone, and that became the highlight of the trip. The kids loved riding along the Oak Bluffs paths. No traffic stress. No big city noise.
Just ocean air and freedom.
The Small Moments Were the Big Ones
The things that stuck with me weren’t the “big attractions.”
It was:
- Watching my son learn to ride farther without help
- Seeing my daughter collect shells at Inkwell Beach
- Walking past the gingerbread cottages at sunset
- Sitting on the porch after the kids fell asleep
Martha’s Vineyard gave us space to slow down.
And that’s something we didn’t realize we needed.
Why Oak Bluffs Worked So Well for Our Family
Oak Bluffs was lively enough that the kids never got bored, but relaxed enough that we never felt overwhelmed.
We could walk to:
- The harbor
- Beaches
- Shops and food
- The Flying Horses Carousel
But we could also retreat back to our rental house when everyone needed downtime.
That balance made the trip easy.
Renting Bikes Was the Best Decision
If I could give one piece of advice for families visiting Martha’s Vineyard, it would be this:
Rent bikes.
It made everything simpler.
Quick beach trips.
Morning coffee runs.
Evening sunset rides.
The kids still talk about riding along State Beach like it was some great adventure — and maybe it was.
Would We Do It Again?
Without hesitation.
Not because it was flashy.
Not because it was extravagant.
But because it felt connected.
Spending time together without rushing from activity to activity was the real luxury.
If You’re Planning a Family Trip to Martha’s Vineyard
Here’s what worked for us:
- Rent a house instead of a hotel
- Reserve bikes early
- Keep your schedule flexible
- Let the kids help plan small activities
- Don’t try to do everything
Martha’s Vineyard isn’t about checking boxes.
It’s about enjoying the in-between moments.