The Hill House

Get in and claim the front deck. The lake view hits immediately. Light the gas fire table, pour something cold, and let the week start. The wood fire pit is out back when you're ready for that later. Check Bristol Mountain's schedule for aerial adventures tomorrow.

Naples Wood Fired Pizza or Naples Hotel Taproom — both are 10 minutes away and perfect for a casual first night. No need to go far.

Bristol Mountain's aerial adventure park is 7 minutes away — zip lines, climbing towers, and aerial courses through the treetops. Best for anyone 7 and up. Go early before it gets busy.

Onanda Park on Canandaigua Lake for a swim and kayak rental — 9 minutes from the house. The lake is beautiful and easily accessible from the park.

Check if CMAC has a show on your dates — 35 minutes away and one of the best outdoor concert venues in the region. Worth going for almost any act.

Hometown Wine Company and Inspire Moore are both in Naples, 10 minutes away. Arbor Hill is 4 minutes and has the added bonus of Brew & Brats right on site. Lunch sorted.

One more cup of coffee on the deck. Pick up a pie from Monica's or Cindy's on the way out — Naples grape pie is a genuine local institution.

The hilltop foliage view in fall is the best version of this property. Get in, open the back deck, and just sit with it for a while. Fire up the fire pit when the sun goes down.

Bob & Ruth's Vineyard Restaurant or Old School Cafe for dinner — both in Naples, both excellent. Warm, easy first night.

Bristol Mountain runs a scenic sky ride in fall — ride the chairlift up for views over the Finger Lakes in peak color. 7 minutes from the house. Go on a clear day.

Harvest season on the wine trail. Arbor Hill and Inspire Moore are both doing fall releases. Hollerhorn Distilling is 15 minutes away — worth adding to the loop.

Fireplace and game room. Open whatever you picked up on the trail.

Grimes Glen Park is 8 minutes away — waterfall hike through a gorge, quick and beautiful. Short enough to fit before checkout if you leave by 9.

Stop at Monica's Pies or Cindy's Pies on the way out. Naples is famous for grape pie — it's a real thing and worth the stop. They sell out on fall weekends.

Get in and light the fireplace. This is the heart of the house in winter. Check the ski report at Bristol Mountain — conditions vary so look the night before you plan to go.

Caruso's Cafe or Naples Hotel Taproom for dinner. Quieter in winter — better service, no wait. Or stay in and use the kitchen with the fireplace going.

Bristol Mountain is 7 minutes away. Good mix of runs for all levels, and not as crowded as the big Vermont resorts. Rent gear there if you need it. Come back early enough to use the game room before dinner.

Fireplace, game room, board games. This is exactly what the house is built for in winter.

Start with the Grimes Glen hike before heading to Canandaigua — the shale gorge is genuinely beautiful in winter, and in January/February the falls freeze over. Easy 2-mile loop, 10 minutes from the house. Stop at Hollerhorn Distilling on the way out for a tasting and warm up before the drive.

Lunch in Canandaigua at Nolan's on the Lake or Lock Stock Bar & Grill, then head home. Easy last morning.

Spring evenings on the hilltop are underrated — cool enough for the fireplace, warm enough to sit on the deck. Do both. The lake view at dusk in May is worth staying in for.

Old School Cafe in Naples for dinner. 10 minutes, consistently excellent, easy first night.

Grimes Glen Park is 8 minutes away. The waterfall is at peak flow after snowmelt in spring — this is the best time of year to go. It's a short hike but beautiful.

The wine trail is waking up with spring releases. Hometown Wine Company and Inspire Moore are right in Naples. Arbor Hill is 4 minutes and has outdoor seating that opens in spring.

Fire pit on the deck. Spring fire pit weather is the best of the year.

Lake View Point Overlook on Naples Road is 10 minutes away — quick stop for the view over Canandaigua Lake on your way out. Worth 20 minutes.

Naples Village for coffee. The whole region is quiet in spring — no crowds, no rush.