Why We Bet on a Second Ski Chalet in Maine

When we sold our lake house vacation rental in Wisconsin, we were faced with an exciting decision: how to reposition our equity and what type of property to invest in next. After looking at several options, we finally decided to purchase a brand-new home on the same street as our ski chalet in the Sunday River area of Maine.

Here's why we chose to go down this path:

1. Market Knowledge

We already knew the Sunday River area well—seasonality, local hotspots, and activities—so launching a second rental here meant less guesswork and a smoother start. 

2. Reliable Local Team

Over time, we’ve built a trusted team: a cleaning crew, handyman, and house manager who treats our homes like their own. Since the new chalet is just 2 minutes away from the first one, we can count on the same awesome team to keep everything running smoothly.

3. New Construction

We chose a spec house from a reputable local builder, which meant we could customize a few details like flooring and cabinets. Plus, we planned ahead by wiring for amenities like a hot tub and sauna, and adding a power backup generator—saving both time and money.

4. Creating a Unique Experience

We wanted to design a property that offers more than just a place to stay—something with luxury amenities throughout the property, stunning mountain views, and a cozy yet stylish atmosphere that makes guests feel at home, whether they’re here for outdoor adventures or relaxing indoors.

5. Avoiding Self-Competition

While our first chalet is a great mid-tier option, we wanted the new one to be a luxury property. This way, we’re offering a higher-end experience without competing with ourselves.

How We Made It Happen

After months of careful planning, we were able to move quickly once we closed on the property. Here’s a sneak peek at the timeline of how we pulled it all together:

Prior to Closing:

• 8 weeks before closing: We brought in a professional short-term rental (STR) designer to help us create the perfect vibe for the interior and exterior space.
• 4 weeks before closing: Design finalized, and we kicked off product merchandising to start preparing the space for guests. This involved countless hours of shopping on Amazon, Etsy, Wayfair, Home Depot, and a few other spots to find the perfect pieces. Let’s just say our carts were very full!

After Closing:

• Day 1: Our local install team moved hundreds of boxes from a 40’ storage container to the house.

• Days 2–11: The team worked around the clock to furnish and set up the property. Major amenities like the hot tub and barrel sauna were delivered, while contractors spent days building the custom bunk bed, fire pit and children's playground. It was truly all hands on deck!

• Day 12: I flew in to oversee the final touches, ensure everything was perfect, and familiarize myself with the house so I’d be fully prepared to host our guests.
• Day 14: Staging and photography were done.

• Day 22: We received gorgeous photos from our photographer (they really captured the magic of the place!).

• Day 23: The listing went live on Airbnb, followed by VRBO.

• Days 24–27: 3 bookings came in.
• Day 28: Our first guests arrived for their Thanksgiving stay, and we were thrilled to hear their feedback: “Truly amazing experience and spotless clean!”

In the end, it was all about creating a space that offers both luxury and comfort—one where guests can make lasting, joyful vacation memories. We’re beyond excited to share this new chapter with our guests and can’t wait to see where this journey takes us!

*****

Interested in getting started with Short-Term Rental (STR) investing or elevating your existing rental? Book a free 30-minute discovery call today. 📞✨

*****