Places to stay are graded on a 0-100 scale. The higher the grade, the easier it is for travellers to find restaurants and things to do within walking distance.
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!
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Date of stay: January 2023
Value
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Service
Trip type: Travelled with friends
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
I stayed at Jimmy O'conners Windham Mountain Inn for three nights. We had a blast. The room was comfy and cozy. It is also just minutes from Windham mountain and a breakfast spot. We had dinner at the bar on site one night- I loved all the old photos and memorabilia. When you stay here you are supporting a family owned business.
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Date of stay: February 2023
Value
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Service
Trip type: Travelled with friends
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
My son and I stayed one night after a day of skiing at Wyndham. The room was warm and comfortable. The room is a nostalgic throwback to the heyday of the Catskills and is well kept and clean. Not even dusty. Really.. Nice tiled shower in pink of course! But it has been rebuilt one can ascertain (I just had a shower stall renovated so..) . The beds were very comfortable. To be real I will say towels could be plusher. The TV seemed disconnected from service. The Bar/Restaurant was closed. We asked our host and she said it will be open later for takeout. The restaurant photos looked similarly period and I was disappointed but these days there is lots of that with restaurants due to restrictions.
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Date of stay: January 2021
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Service
Sleep Quality
Room Tip:Clean and Well Kept near ski slope
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Dirty, outdated and sad. Should have realized and cancelled when I had to “check in” at a bar full of locals. Definitely not family friendly. I cancelled my second night as soon as I saw the place. I don’t know where the other reviewers stayed but it was not the same place.
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Date of stay: August 2021Trip type: Travelled with family
Room Tip:Avoid staying here.
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Jimmy O'Connors is a combination neighborhood bar, 8 motel units, and rooming house with 10 bedrooms. Each building is separated from each other by 300 feet. I stayed in the boarding house. As you entered the rooming house, there is a downstairs sitting area with T.V. and several couches, and if I recall, some board games and books for your enjoyment. In the back of the room is a small dorm refridgerator that I am told works fine, and a small turntable microwave, that if it stops rotating, needs a gentle slap on the right side to work again, according to my inside source. Climbing the stairs, you turn left or right, according to your room number. Left was closed due to renovations. My room was well lit by windows, a overhead covered light, and two small lamps on the bed stands on either side of a full bed. Bed comfort was a little too soft for me, but I have the same problem in " Name Brand " properties for a lot more money. Bed mattress and sheets were clean. Every thing in the room appeared clean and in working order. Television was the older cathrode ray tube, which I would expect in a property in this price range. Bathroom was clean, well kept and stocked with supplies. Maid service was daily with fresh supplies, clean linen and a freshly turned bed. If I recall the bathroom floor had a slight tilt to one side. Shower water was hot and plentiful, a delight after a day on the slopes or snowshoeing in the back country. If your back acts up, as my quirky back did a day after arrival, be sure to schedule an appointment with Windham Chiropratic. Dr. Laura had me in fine shape in a day. The room was quiet, but I was the only one staying here for seven days, and one other person I saw was there for a night or two. This may change due to circumstances. I did not stay or see the motel units, so I cannot comment, but it may be worth checking into for your group or significant other. The tavern is a few feet away with a few beers on tap and bottled beer. And, no, they don't offer single malt scotch. A patron did ask. Menu items were hamburger, cheeseburger, fried chicken, fried fish, with or without freedom fries ( George Bush's translation of the English Language ) . I believe steak may have been offered in the $20.00 dollar range. Other menu items ranged from $ 8:00 to 10:00 dollars. I had a cheese Burger ( no fried onions, only raw, ) and fried chicken another night, and both were good. The tavern is more of a friendly local's meet skiers kind of place when the mountain closes. Windham mountain is a half mile. Town center is a half mile. Cinema with pizza and popcorn and candy ! Library next door in the back of Church with computers with free internet ! Center of downtown starts here with a brewery, and restaurants in every price range. Take a stroll and find your spot. Is this property for you ? It's not a budget chain, ( though it does have budget rates ), it's not a bed and breakfast, ( no pancakes with strawberries and whip cream here ). I think it would appeal to a solo traveler or group of friends with an adventurous spirit who are not freaked out by the little things, and maybe get a kick out of it. Think Hostels of our youth. When you enter the Tavern and order a beer, ( and I know you will, I just know these things ) and maybe a shot of Old Grand Dad Bourbon, tell Jimmy you came recommended by me. Ask him to save my room for July.
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Date of stay: February 2013
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Trip type: Travelled solo
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
I am unable to tell you anything about the actual hotel. We had a reservation here and because of some error writing down my credit card number and unable to reach me (though I am not sure how hard they tried), they gave our room away to someone else that was going to stay an extra night. I am glad that I found this out prior to showing up at the hotel, I am not sure what we would have done at that point. See, it was the Mountain Bike World Cup and all the local hotels were booked. I have never heard of a hotel giving up reservations. One, a deposit was not required so that wasn't it. Two, I was out of town all week and never received the message on my home phone, no message was left on my cell phone. So the only thing that makes any sense, if you can call it that, is they just wanted more money from the extra night and had no problems giving up our reservation. This is NOT what I call smart business.
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Date of stay: August 2015
Value
Service
Trip type: Travelled with family
Room Tip:Don't stay here!
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Stayed here with a group of friends. Nice spot. close to the slopes. The rooms I saw were clean and well appointed. Don't know what the "Dont Expect a receipt" review is about but I got one without an issue. Friendly staff good place to stay skiing or for one of the many local sporting events.
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Date of stay: October 2014
Value
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Location
Cleanliness
Service
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Trip type: Travelled with friends
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Jimmy's is a wonderful country motel. It is quint, clean and has all you need to relax abd enjoy the view. The rooms have a mico, refridg and coffee pot. Rooms are nice and beds are comfortable. The bar and restruant is cozy and though the menu is small the food is great. Had a steak and fries and it was tender and cooked as I ordered. While its nothing fancy; it is well worth the price. I will be back..
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Date of stay: October 2018Trip type: Travelled on business
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Do not stay at this place! the owner is rude to customers and was not able to provide me a receipt after we stayed there. The place is run down and does not look like it has been cleaned in a few months. Most of the bedding looks like it has been on the beds for years!
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Date of stay: June 2014
Cleanliness
Service
Sleep Quality
Trip type: Travelled on business
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
It was great to get back to jimmy o connors, we stayed Friday and Saturday night and as usual we had a great time, we got a lovely greeting from the staff, we skied Sunday and had a great day, jimmy o connors is still the best deal on the mountain, and still has the best burger
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Date of stay: December 2014
Value
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Location
Cleanliness
Service
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Yes by all means. Though there are many places in the Catskills that are "cash only", Jimmy O'Connor's is not one of them, they take all credit cards that I can think of, good luck, and have fun!
There are more places to choose from in the Windham area.
PRICE RANGE
S$217 - S$268 (Based on Average Rates for a Standard Room)
LOCATION
United StatesNew YorkCatskill RegionWindham
NUMBER OF ROOMS
18
Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
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