Woodside Retreat

02/15/2026

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Liv Golf Season Finale is back in Westfield for 2026 and we have the spot for you and up to 14 of your friends!

01/25/2026

Basketball Season is Upon Us. Let Woodside Retreat be your home base for the Big Dance!

01/23/2026

This view coming this weekend….

01/23/2026

With possible snow coming, just a reminder that Woodside Retreat is magical blanketed in snow. Warm up by the wood burning fireplace, watch movies on the big screen, and enjoy the hot tub while snow falls around you. Sounds like a great way to spend a snowy weekend. Unlimited firewood for cozy moments❤️

Here are the latest projected snow totals for the weekend winter storm — which will be accompanied by bitter cold temperatures.

FULL FORECAST: https://www.wthr.com/article/weather/weather-blog/weather-indiana-snow-storm-snowfall-accumulation-chance-weekend-saturday-sunday-cold-january-indianapolis-when-expect-2026/531-5c0dc7b5-1a6a-4310-b636-16b663d402e1?utm_medium=social&utm_source=facebook_WTHR-TV

01/13/2026

📣📣Announcement📣📣

Many of you have been patiently awaiting the release of our 2026 dates. We are so grateful for those that have been gracious as we analyzed making changes to how we do things at Woodside Retreat. Many repeat guests and new guests have been lovely to wait while we considered changing directions.

As we conclude our 5th year of hosting at Woodside Retreat and 15 years in the business, we look ahead to our 2026 season with a shift on how we handle bookings. Due to changes within the Airbnb and VRBO platforms (all of which we believe to be moving in the wrong direction for guests and hosts), we will primarily be accepting reservations through direct bookings. You can anticipate the same hospitality, memorable spaces, attentiveness and protections offered through booking platforms like Airbnb and VRBO. However, a direct booking option offers more direct access and control for the guests and the hosts than the booking platforms can provide. Additionally, fees have recently increased dramatically on those platforms while customer service for host and guest has decreased. Guests are now paying nearly 20 percent of the total booking in Airbnb/VRBO fees.

We look forward to filling the calendar with many of the wonderful people like you that have made Woodside the top short-term rental in our area. We couldn't be more grateful that our space is part of the memories you make as family and friends. You will find our property on Airbnb eventually, but peak dates will be first opened to those that have reached out requesting a 2026 stay. We understand some guests may only feel comfortable booking on the booking platforms, and for now, that option will be available in some form. Peak dates will eventually be released once all known direct guests have finalized their bookings.

Thank you for entrusting your Indiana visits to us. We are excited to see how this new chapter works for us and for guests. There may be a transition period before a website is available, but 2026 dates will be immediately available this week through manual direct bookings. Thank you also for your patience while we implement some new systems. You can reach me directly with any booking requests through social media messaging and email at [email protected]. Future websites will be posted at a later time.

01/13/2026

12/20/2025

Our community showing off on Today Show yesterday! There are still a few days left to experience the Christmas magic. Christmas dates are still open at Woodside Retreat to continue the magic at the market in your very own holiday home. Special pricing and direct booking options available. Happy Holidays everyone!

10/03/2025

09/08/2023

2024 is going to be a big one in our area…we have Taylor Swift for 3 nights and the path of totality for the solar eclipse of 2024 will be here. We still get the biggest spectacle in racing and a lot of Big 10 tourneys this year. We look forward to welcoming new guests and friends and the return of so many of our wonderful past guests. We typically book the majority of the next year’s calendar within a few weeks.

08/16/2023

We stayed in a couple of hotels, but most of our lodging was in apartment rentals. As a family of 5, apartments were usually the better and cheaper option compared to hotels.

As hosts, we view rentals differently than most guests. It is very hard to remove the "host hat" as it is what we live and breathe every day. We notice the things no one else notices, we definitely notice the "weird stuff" (there were a few examples), we understand the challenges a host might face and are often understanding of issues that might arise because we understand stuff happens, and we are some of the cleanest guests. If we think of something that is a constructive comment, something they might not be aware of, or a way to improve, we will share it privately with the host. I almost never address is publicly unless it is really egregious and other guests should be made aware. The tendency is also very strong to clean or organize more than we should, but then I remember this is our vacation!

Although, I completely geek out on noticing the details in rentals. Every property I stay in makes me want to analyze, compare, think of solutions, consider owning in the area, and so on. I could definitely see myself launching a career in vacation rental consulting/analysis...staying in people's properties before they launch, after they see a lull in booking, or after bad reviews. Maybe my third career:)

Nevertheless, we had some great places to stay. We enjoyed feeling a bit more "local" thanks to several beautiful and functional places. We hope you enjoyed a little glimpse into our turn as guests. We don't get to leave town too often as a family with rental properties, so this dream trip was at treat that was worth the saving and planning!