Jimmy O’Connor’s Windham Mtn. Inn - Restaurant in Windham - 141 South St, USA

Room was clean and smelled clean, and appeared “rustic”, if a little outdated, but more than functional. Bed was immaculate and super comfy. Shower had plenty of hot water and good pressure. Fridge and microwave worked very well and were CLEAN. Staff was excellent, efficient and pleasant attitude. Bar/restaurant is very convenient, just a short walk across parking area. Couldn’t be closer to Windham Mountain, 3 minute drive! No complaints at all, we’ll definitely see you all again. Thank you…

The host is extremely welcoming and friendly. Nice family business with lots of history. We had a great time at the bar, and the room was above my expectations. Thanks for taking such a good care of us. Definitely coming back

This place is really incredible and the bar has such a cool, pub/family style atmosphere that can be felt as soon as you walk in and greeted by the friendly staff. My girlfriend and I enjoyed a few drinks at the bar and the next day, we went to the “Mash and Bash”, which is a community event hosted by the owner of the Inn, Johnny. Not only is he a generational talent on a snowboard, but someone who really cares about his community and the youth. This place deserves all the business it can get because of someone who gives back like that. My friend Matt recommended to come here, and I would also recommend any friends or family to come as well!

Stayed from 1/13/24 to 1/15/24. Don't judge the book by it's cover. At first look, the inn is just your typical budget friendly motel/pub. However, it exceeded our expectation at every level. We stayed in Room 6 (double bed with an additional cot), and for the three of us, it was plenty of room. The official website's photos are accurate. Mostly importantly, if you are traveling with family with multiple devices, they have enough plugs to help charging everything. The room has a good-sized flatscreen tv, small fridge (or you can just leave your cans in the car lol), and a microwave. We ended up using them to make instant cup-noodles and other snacks. Hot water comes out fast so we didn't wait long at all. Oh, the only item that was missing (or we didn't see it) in our room was a blowdryer. But then again, we didn't bother asking management about it. Plently of pillows and blankets so in case you are the type who needs extra. The only thing is when you first check in, you need to turn up the thermostat so the room heats up. That initially took about 10 mintues. The Wifi works great and we had fast internet for all 6 of our devices. Oh, they also do room service while we were out skiing. What really won us over, however, is the staff at this place. From checking in to dining, they were super friendly and welcoming. The place got crowded fast on early Saturday evening (standing seat only by the time we walked over from our room). It was a friendly crowd, and we had no trouble getting our orders in and later getting seats. We absolutely loved the steak and burger. It is as good as other reviews have stated. We ended up eating dinner there both nights (first night we brought food back to our room). Overall the experience was great, and I definitely see us going back again later this season now that we've discover this cozy establishment!

The nicest staff you can find. For me the location is good. I booked and rebooked a few times. Food / bar on premises is a very nice option to have. Food was good, not fancy, but I liked the flexibility and welcoming. The rooms are not up to date but are clean. If you travel in the area, it's a very good choice.

This wonderful family-owned establishment offers a warm and inviting ambiance, complete with friendly proprietors. It boasts a kids' playground and an onsite bar/restaurant. I relished watching the sunset while sipping beer beside the fire pit. The place exudes a local charm and a laid-back atmosphere, complemented by delightful individuals who brighten your day. Recommended for families with kids and couples as well as single people who looking for a quiet weekend vacation after a busy NYC. The rooms are quiet and clean, a bit old but well-maintained. Huge outdoor space to play with kids, playground for little ones. Great food and drinks on the bar, made of high-quality ingredients. Lots of places to eat and drink around, breakfast place right after the corner. Trails, bike trails, skiing, tubing, golf, farmer markets. Amazing views and fresh air. I've already made reservations to return during the fall foliage season.

The place was convenient enough to get to all ski activities easily. You have to check in at the restaurant but they were very kind and courteous. Had no hassles getting or finding the room. A good place to go if you just need a place to stay for the night. When I came back to just settle in after the first night they cleaned the room while we were gone and nothing was taken (which is usually NOT the case with other motels I've been to) so that was a def plus! Would definitely use it again for my next trip. Just wished the room was a little bigger for the price but overall very pleasant stay.

Headed out to Jimmy O'Connor's for NYE weekend and had nothing short of a great time. The bar serves terrific burgers/fingers/chicken sando's/fries, and the drinks were nothing short of great. As a multi-time visitor, I find that the staff and owners are wonderful people who always take great care of their clientele. The room was super clean, cozy, and the beds were very comfortable. If you're looking for a great affordable place in the Windham area, then this is a great place to stay!