AI · alternatives · 2026

24 alternatives to Vacation Buddy

Plan holidays smarter

Below are 24 products that do a similar job, ranked by how close each is in meaning and then by launch-day votes. Prices are shown for the 1 we have checked on their own sites, 1 of them free or with a free tier.

1
Stretch My Time Off – An Algorithm to Optimize Your Vacation Daysfree▲358
Hey HN! I built StretchMyTimeOff as a quick experiment using Cursor (Anysphere's AI code editor) and GPT-4o to see how far AI could go in building a simple, functional site. What it does: The site helps you get the most out of your vacation by suggesting optimal days to take off around national holidays, maximizing long breaks with minimal vacation days, anywhere in the world and for any calendar year. It's an idea I've had for a while, and building the algorithm with GPT was a fun challenge. Any feedback or ideas I'm all ears :)
2024 · stretchmytimeoff.com · its alternatives →
2
Vacation Tracker▲137
The easiest way to track your team’s vacations and days off.
2019 · vacationtracker.io · its alternatives →
3
VacayWiser▲216
Find the best days for vacation
2024 · vacaywiser.com · its alternatives →
4
Calendar Buddy▲77
Plan your time and achieve your goals
2021 · apps.apple.com · its alternatives →
5
Buddy Trip Planner▲108
Plan trips with your buddies, no matter the distance
2023 · hitina.gumroad.com · its alternatives →
6
Breaktime Buddy▲257
Smarter breaks. Sharper mind. Escape the doomscroll.
2025 · terspective.com · its alternatives →
7
Stretch Your Annual Leave▲75
Tool to help workers get the longest possible vacations
2018 · stretchyourannualleave.com · its alternatives →
8
Slack Holiday Mode by Spoke.ai▲262
Your AI assistant for your first day back
2024 · spoke.ai · its alternatives →
9
Stretch My Time Off▲10
Optimize your vacation days with AI-powered planning
2024 · stretchmytimeoff.com · its alternatives →
10
koalalu▲68
Slack bot that tells you when someone is on vacation
2022 · its alternatives →
11
Vacation Genius▲1
Find the best vacation time and preferences for your group!
2025 · its alternatives →
12
PlanMoreTrips▲124
Github for travel planning - no more spreadsheets!
2020 · planmoretrips.com · its alternatives →
13
Hoku▲87
The best way to organize your group travel plans
2021 · hoku.travel · its alternatives →
14
Holidaying▲79
Plan and book offbeat trips by travel influencers and locals
2021 · its alternatives →
15NF
Nowcation - find spontaneous travel deals▲50
2013 · nowcation.com · its alternatives →
16
Welcome▲113
A smart travel companion
2019 · dorsia.com · its alternatives →
17
Public Holiday app for Slack▲86
Change user status during public holidays in their country
2024 · blixtdunder.com · its alternatives →
18
VacationCounts▲6
Track your Vacation Days to Take More Time Off to Travel
2019 · its alternatives →
19
TravelPal▲116
Effortless vacation organization w/ personalized suggestions
2024 · travelpal.ai · its alternatives →
20
Lodgify App▲61
Manage your vacation rental from your smartphone
2022 · lodgify.com · its alternatives →
21
Trippers▲63
The best way to plan your next friends' weekend getaway
2021 · its alternatives →
22
Off Day App▲5
Maximize time off with minimum leave days
2025 · offday.app · its alternatives →
23
Vacation Inbox▲56
All your vacation research and ideas in one place
2021 · vacationinbox.com · its alternatives →
24
Vacation Tracker for Microsoft Teams▲82
Remote-friendly leave tracking solution for Microsoft Teams.
2021 · vacationtracker.io · its alternatives →

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Ranked by how close each launch is in meaning, then by votes. Prices were read from each product’s own site when checked and can change. Refine with your own description →