Jimmy O’Connor’s Windham Mtn. Inn

Great spot, family run. The best burger around town…old school vibes - in a good way.

This place is the best! We were here for a ski weekend

Absolutely awful experience. Went there for dinner and drinks with my college friends (one of them being a regular). Got told they weren’t serving food at 6:30 pm on a Monday? Numerous other parties were actively being served food/waiting on food and the table next to us ordered 5 minutes prior to us getting there. We left right away, I can also say they lost a regular and none of us are ever going there again.

Popped in for some beers and some dinner after a weekend of work in the area. We immediately fell in love with the cozy, classic charm. Glowing lights, a fireplace, jukebox and piano; all the sweetest touches you don’t find in places anymore these days. The owner stopped by our table and was an absolute gem, just radiating welcoming energy. Beautiful evening, we will return for sure!

Great, atmospheric spot!
The steak was amazing 🥩 — super juicy and cooked perfectly. The whole vibe is cozy, clean, and really welcoming.
I stayed here overnight before riding at Hunter Mountain — perfect place to rest up and head out early in the morning.
Special shoutout to the owner, John — not only a genuinely great guy, but also one of the strongest street snowboarders of his time. ( The latest one according to Denis Bonus 😅)

Highly recommend!

10/10 will never not hit Jimmy's on my way home from a sick day of shredding! Buff chicken salad for dayssss

Very hospitable staff.

Jimmy O'Connor's Windham Mountain Inn is an absolute gem in the Catskills! This is a great welcoming place for a beer and food, with a friendly atmosphere that makes you feel right at home from the moment you walk in.

Best place. Best people. Best atmosphere. Must hit it in Windham!

It’s a great place, with great burgers! Our server/bartender was awesome!

We went to the bar for drinks and dinner on a quiet Monday evening and was met with the most genuine and authentic hospitality by John. This is the Windham experience we have been searching for since having our 2nd home here in 2020. The area changed so much after Covid. But John and Jimmy O’Connor’s reminded us that there are still family run businesses who have been here for a long time and who built the community and culture here. We need to support them more!!!

Good (and affordable) foods and drinks, nice place and really kind people! Worth the visit!

Horrible experience, owner was rude room dirty ,when I asked about it I was neglected next day told no refund or explanation, no response. Would never go to this ace again. Absolutely Horrible experience...........

Great food for a cheap price with amazing service. Overall amazing atmosphere

Not fancy, although super clean motel rooms! And the restaurant is right on property! Perfect ski weekend, the most professional staff ever!