This restaurant has a nice rustic vibe, with lots of wood and custom accents. The wicker grasshopper, which serves as the hostess counter, is quite unique and memorable. Our meal here was a bit disappointing. Their menu is different from what was posted online. We came wanting to try the brussel sprouts. Online, they were described as crispy, but turned out to be roasted with pancetta. I was also eager to try the soft pretzel. Online, it mentioned it came with a three cheese sauce, but at the restaurant it was served with beer cheese, which I can't eat. The name of the restaurant literally has "cocktails" in it, but they were out of nearly all of their fall cocktails. That being said, we tried to redeem the experience. Our waitress was friendly and kindly let us know that the sulphur in the tap water might be irritating, so we ordered bottled. The house salad was nice and fresh, and I loved the tanginess of the lemon vinaigrette. The mac and cheese was a generous portion size. It was a bit bland and could've used a sharper cheese, but it was very creamy with a nice baked top layer. The broccoli side was tasty and well seasoned with garlic. The onion rings were very crispy and also a good portion. My husband had the New York steak and enjoyed how buttery it was. However, they initially forgot to bring him a steak knife and it was hard to flag down a waitress to get one. Overall, we left full, but our expectations were not quite met. read more

This food is disgusting and not edible. The Caesar salad was soggy, the fish and chips were soggy and the fries were dark like they had been cooked in very old oil, the Sheppards pie was enough to feed a family yet it was just chucks of beef with very little taste. This would be a 0 star! Fast food would be a better option than this restaurant boasting great food at a high price. I had to throw away everything because I couldn't eat it. You need a new chef and live up to your menu! read more

Lily Steaks & Cocktails came highly recommended by locals, so we were excited to give it a try. The interior is stylish and welcoming, and the service throughout our meal was attentive and friendly. We ordered a variety of dishes from the menu, and while most things were enjoyable, the star of the meal--the 42 oz porterhouse--left us a bit underwhelmed. It had decent flavor, but it was served cold, which took away from the overall experience. We also asked for it to be sliced, but it came out only partially cut, which felt a bit odd and made it harder to share. While it's not on par with high-end steakhouses in Manhattan or Long Island, for what it is, Lily holds its own as a decent local spot. I'd definitely consider returning to give it another shot--there's potential here with a few tweaks. read more

Lilly's Steaks & Cocktails - Steakhouses Near Me - Windham, New York

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Overall, an excellent dining experience! The food was delicious, and steaks were cooked perfectly as ordered! The Cowboy Ribeye Steak was tender and flavorful, as was the Filet Mignon. The Double Cut Veal Chop was outstanding! Tender, delicious and cooked perfectly! The sides and drinks were quite good too. We had a variety of servers, as this was an extremely busy night with a packed house, and each one was lovely....efficient, helpful and friendly! In my opinion, it is quite pricey but I cannot deny, everything is these days- and at least their quality matches their prices. Look forward to going back and highly recommend it to others! read more

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My husband and I came here for dinner with our toddler on a Monday night. I started off with a Pumpkin Spice White Russian, which unfortunately was too strong for me. We ordered Lilly's Sprouts as an app, which were nicely roasted but could have used some sort of sauce. For my entree, I ordered the Roasted Free-Range Half Chicken, my husband ordered the Dublin Style Fish and Chips, and we ordered a side of Baked Macaroni and Cheese for our daughter. The chicken and fish were good meals, but I think they were overpriced. For a side dish, the macaroni and cheese was massive - I sampled it and thought it was good, but my daughter didn't end up eating it. Although we were seated right away, the service throughout our stay seemed to be on the slower side. Our food took long to come out and waiting for the check was no different. I had to leave my husband to wait because my daughter was ready to go! read more

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I had to get a take-out order because I couldn't bring my dog to dine in with me which I understand that. The con part of taking out was the food won't be good as you eat at the restaurant. If something wrong with the food and you don't have any access or cooking wear to fix it yourself, you will have to accept it or just throw it away. My husband and I were blessed enough to be able to bring it to our place and eat at the hotel cafe. We ordered..... - Porterhouse: looked good from outside. we told the restaurant to make it medium but the steak still more rare so the rest of rare part, we gave it to our dog, and he loved it. 7/10 - Lilly's Beef Wellington: Prime 8oz Filet Mignon with wild mushroom in red wine glaze. I rarely see mushroom inside the wrap. Beef was good and perfectly cooked. I just didn't like the dish, so I gave it to my husband that was still hungry from giving half of his steak that wasn't cooked enough to our dog. 7/10 Overall, food was ok, I wish I could eat that the restaurant. read more

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Try to make reservations before you go especially on the weekends as it gets very busy! We didn't have to wait too long for a table of 2 At around 7pm and were able to have a drink at the bar. For our appetizer we had the fried Brie and the French onion soup. Both were extremely delicious! For our entree we had the filet and seafood linguini pasta. Our food was flavorful! The only downside is that they were so busy our server forgot about us. The host was super friendly though and brought our icecream on the house to celebrate my Fiancés birthday which was nice! I'll definitely be coming back the next time I'm in town! read more

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Had reservations sat down right away ordered apps & drinks. After an hour of waiting (we only had bread the whole time we were waiting) dinner came and our apps never showed up. I asked to speak to the manager and turns out our server was our manager ( ok!) Apps forgotten! No apologies for waiting an hour! They had a take out order I guess that took precedence over the seated guests. For the price we were charged service aaa not up tot par nor was the food. You guys have to do better. Not planning on coming back read more

The owner of the Airbnb we were staying recommended this place and we are glad they did. It's on Main Street and easy to get to. Staff were friendly and the ambiance was nice inside. It was packed on a Sunday night. My husband and me shared a steak with sides and had the octopus for an app and all was delicious! Steak isn't always the first thing I order but wanted to taste it here. Was very pleased! From flavor to texture! I recommend this steakhouse! read more

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Food was good. Service was lovely. It was a quiet night. a r is super dark so make sure you ask for a table light that works. And order bottled water as tap water smelled like sulfur. But our food was great. There were 5 of of us. We ordered Chicken Fracese, Filet Mignon Hero, would you?18oz Rib Eye, ahi crusted tuba, and crab stuffed shrimp. All was good. Not excellent but good. read more

If you would have told me that the most delicious sole would be found in upstate NY, I would have been surprised -- However, the baked sole is absolutely melt-in-your mouth delicious -- and the portion is enormous! The lovely waitress shared that the portions were massive and she wasn't kidding us. We also had a tomato appetizer, cooked spinach (really amazing), broccoli, baked potatoes, and salmon. I was stuffed -- in a good way. read more

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Went to lilys lastnight with my fiance. I'd like to start off by saying that I have been stuck on the toilet all morning after dining there lastnight. Our server was nice and attentive! The food was mediocre and very over priced! I ordered a Pepsi which was diet at first and then when I was given a regular Pepsi I was appalled to taste sulfur mixed into the drink. The server mentioned the water they have which has sulfur in it mixes into the soda. Yikes! We started with a Caesar salad that had very small cut pieces of romaine almost like it came from a bag. We then had a French onion soup which came out so piping hot that we couldn't enjoy it let alone eat the cheese which curdled into a ball and fell to the bottom of the soup due to its temperature. My wife had the penne ala vodka a 38$ meal and she said she liked it but she is also regretting that on the toilet this morning. I had the chicken Parmesan chicken a 38$ meal was barely beaten and held a lot of moisture almost watery. The pasta was over cooked and very soft. And the red sauce was also not salty almost bland and had a watered down taste to it. I didn't enjoy it much and like I said before I'm currently fighting for my life in my bathroom . The check was 140$ which I thought was alittle over priced but I still tipped 20%. I probably will not be going back here! read more

Lilly's Steaks & Cocktails - Steakhouses Near Me - Windham, New York

Went here o 5/17/25 . The food was delicious, friendly service & a nice ambiance. Had the potato & leek soup, watermelon, goat cheese, arugula salad with a citrus dressing. Also had oysters + a calamari, shrimp over pasta in the most DELICIOUS red sauce I will be back. Cathy Mechow read more

Service was great. The food was delicious. I had the ribs they were the special that evening. The sauce on the ribs were delicious and their macaroni and cheese is one of the best I've ever had. The atmosphere is warm inviting. read more

Such a cozy, great cocktail and delicious food spot! The staff is lovely and had spot in recommendations! Will be back!

This place was absolutely horrible. The crab in the crab stuffed shrimp tasted like cardboard. Our steak, ordered medium, came out hardly cooked and still dark red. They cut our double cut pork chop into two, and it was extremely dry and hard to eat. Cutting a double cut pork chop into two and taking out the bone destroys the whole point of a double cut pork chop. So basically, they will either not cook your food or extremely overcook it. The service was horrible as well. Our server hardly ever came. We ordered wine and she left it closed and didn't pour it. The price was also extremely high for the horrible food. There was four of us, and it costed 300 dollars! The ambiance was also horrible. There was a cardboard cut out of Harry Styles standing right next to us. There were tons and tons of exposed wires next to me too. The wallpaper was different everywhere. Never, ever, ever, ever come here! read more

Here we are in Windham. NY. Just another work day and I really don't want to be here. A client, and not a good one asks if we'll do this property for them. My answer, NO. That's right, a big fat NO. But Mrs. Says Oh but we get away for the weekend and see the changing of the leaves. Not a thrill for me but you know what they say about a wife. Blah blah blah. Okay so my rant is over. For now. So Yelp suggests this restaurant for dinner. Good ratings so let's do it. Municipal parking a couple of doors away. Actually a dirt parking lot but whatever. I guess the ranting isn't over yet. So we walk in because they don't take reservations. It's very crowded, a good sign, but they seat us pretty quickly. Our waitress is a lovely women offering the specials for the day. I just want a good steak and they have them here. I think I'm driving home, 4 hour drive, so no alcohol for me just sparkling water. Mrs., the lush that she is, is drinking beer. Can you imagine? I have the Jack Daniels Peppercorn Steak, and Mrs. E, in between her beers has a rib eye. Both come with sides, rice for me and potatoes for her.we also get a side of creamed spinach to share. So all steaks are a minimum of 12 oz. and go up to 48 oz. We both go with 12. Food comes pretty quickly and they're both very good. Cooked perfectly and very tender. So it's getting late and we decide probably a good idea to stay over in a hotel. Problem, no availability anywhere. Remember our lovely waitress? I ask for suggestions and she tells me about a new hotel just a short distance from the restaurant. They have availability. I love our waitress, at least for now. We pay the bill, but as we are leaving there's a long wait list for seating. People are at the hostess station and outside waiting for tables. It's worth the wait. Service very good, food excellent, ambiance nice. If I'm ever in this god forsaken town again in my life I will definitely eat here. And just because I'm not happy today don't let that be an influence. I know you'll love this restaurant. Remember the hotel our waitress recommended? That review will follow shortly. If you think I'm ranting here. It's nothing compared to what's coming. read more

Sue from the closed Messina's is behind the bar. The food is great if not a tad pricey for the area. Think Manhattan steak house prices. We had a superb seafood pasta, they gave us bread and butter to go. But they asked us what we wanted for veggies and potatoes and they we not there when we got home. read more

Avoid this restaurant like the plague. Service was slow. Meal was just ok. Prices are extremely high for the area. That is not the reason for this review. They charge a 5% surcharge for using a credit card. Nowhere on the menu, door, etc. do they mention this exhorbitant charge. When I questioned the waiter, he got beligerant. He claimed it was a discount for paying cash. I'm calling bs on that. read more

Lilly's Steaks & Cocktails - Service charge - Steakhouses Near Me - Windham, New York

Great steakhouse in the heart of Windham. Friendly service. Decor is what you would expect of a steakhouse in ski town windham. Highly recommend. read more

The food was great! Pork chops, stuffed sole, Brussels sprouts and octopus app. Warm bread was tasty. There was an unbearable noise coming from the AC unit that my sensitive ears could not take. Our waitress did turn it off when we mentioned it then we could hear the soothing jazz. Great place with great ambiance and actually really really good food. read more

Lilly's Steaks & Cocktails - Lilly's pork chops - Steakhouses Near Me - Windham, New York

In town for a ski trip. Stopped by Lilly's for a steakhouse. Up and down. Overall, not bad but could be better. Pro: steak were solid. No compliant. Brussels sprout is very good. Pasta is also quiet decent for a steakhouse. Drinks were great as well. Sounds like kitchen have no issue at all Cons: There is a heavy egg smell/taste in tap water. We mention to the waiter about it and they got us bottle water without us finishing the sentence. 1. We didn't know they got us bottle water, 2. we found out is 8 bucks for water in the end. I can see potential folks to be upset by this. It is bit weird, maybe communication could have been better. I just wish bus boy would stop coming over and asking if I'm done with food and attempting to take my plate away 3 times. I mean, the steak/salad is still visibly on there. First time I'll assume is a mistake, but when the 3rd time comes around I just assume your trying to take my plate away asap or get me out the restaurant. (7pm seating so not like they were closing soon) TL DR; Solid food, great drinks. Service/water can be weird. Skip the water, order beer/drinks. Don't mind the waiter. Here for a good time not a long time. read more

My food was great but my parents food was overcooked and took long for our food I literally saw people got here later than us get food before read more

Was in Wyndham for a bachelor weekend and came here to eat one of the evenings. This is a great steakhouse in the Catskills! A very impressive NYC style steakhouse menu with quite a variety of protein choices. I had the Cowboy Ribeye with an assortment of sides. The steak was cooked a perfect medium rare and was delicious! Also, the prices are extremely reasonable, in NYC you'd probably pay $30 more per steak. read more

Lilly's Steaks & Cocktails - Cowboy Ribeye Steak - Steakhouses Near Me - Windham, New York

Great ambiance, drinks, food and service. My favorite Windham restaurant this year. I recommend the mussels, steak, fish and my fave veal ossobucco. read more

We enjoyed our brunch at Lilly's. We got there a little before they were scheduled to open, but our waitress very kindly seated us anyways. We weren't super hungry, but what we did have was good! I ordered the parfait, and while I wish there were more berries mixed throughout, it was a good parfait. My fiancé had an omelet, and the breakfast potatoes that came with it were delicious! It was interesting they charge $1 per omelet topping- without toppings I'm pretty sure it's just eggs?- but that was fine. I also ordered a mimosa which was fine but not great, I think the orange juice may not have been very high quality. My fiancé tried the lily's Irish coffee and the pumpkin spice martini, which were both very good and I'd recommend those to anyone who visits! The service was also a bright spot to our experience! Our waitress was very nice, made friendly conversation, and the meal was well timed. As other reviews state, there was a credit card fee, which I was not aware of until I reviewed our check. I usually read menus thoroughly, but if it was mentioned on the menu I must have missed it. read more

We were greeted by a very friendly hostess who sat us right when we walked in. The ambience was cozy and inviting. They had a good list of wines. Our waitress was nice and attentive. The steak that we ordered was delicious. Will come again! read more

Very nice steak restaurant and one of our favorites in Windham. Good beer on tap and the best steak in the county (imho). Cocktails are made properly. Very few drawbacks, though some of the bar stools are either too high, too low, or need firmer upholstery. It would be nice to see another vegetarian offering for my vegetarian friends, but they can usually find something - and it's usually good. read more

Been here many times, but never wrote a review. I love this place. Food is always spot on, appetizers are great. Where else can you get fresh oysters on the half shell, on the mountain top?! I always get the Beef Wellington which is absolutely delicious. Very very friendly and accommodating staff. read more

Lilly's Steaks & Cocktails - Dining room - Steakhouses Near Me - Windham, New York

No reservations required, just walk in. The wings were SO good! And the steak was cooked just right. Long story short, the food was great, the staff was friendly, the vibe was very chill with calm soft yellow lighting. Definitely recommend you pay a visit here. read more

Lilly's Steaks & Cocktails - Lilly's 16 oz steak. - Steakhouses Near Me - Windham, New York

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My partner and I ate here while visiting Windham and we were very pleasantly surprised. Food was excellent as was the service. I highly recommend this place if you are looking for a good steakhouse. read more

Walk-ins only, no reservations. We stopped in on a Friday night and sat at the bar. Kitchen open late with late night bar menu. Burger I had requested no onions, but was served them anyways. They also won't substitute the fries for another side, you have to buy a salad or something if you don't want the fries. Shepherds pie was good, large portion. Moscow mule was also very refreshing on a hot summer night. Located in the center of town on rt23. Parking on street or municipal lots a short walk away. Overall a good option in town, one of the larger restaurants that can accommodate big groups. read more

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To Danille: We always enjoy the dinner at your location. Excellent service, food, and Sue does make a fine Martini !!!!... Five Stars aren't enough to give, but this is all they allow on Yelp. See you all soon, and enjoy the Summer. Our very Best: Dante, June & Nicole read more

The food was goood! The water glasses smelled like sewage. I wasn't familiar with the sulfur issues upstate. We spent 400+ dollars at our table and they charged 8 dollars for CORE room-temperature water in a plastic bottle.. I thought this was a bad call on management. I suggested a few things and they snub me. I've been in Food Service high-end for 15+ years! I think the restaurant charging for basic water is a bad call if the tap you offer smells like sewage..... read more

Overall the experience at Lilly's was really good. We were seated really fast and our server was great. She brought us water while we looked at the drink menu and had great drink recommendations. The specials all sounded delicious but we wanted to try the steaks. In general the food is decently priced for what you'd expect at the kind of restaurant in the area that it is. The steaks were both cooked to perfection and they tasted great, we ordered the New York strip and the porterhouse. The let down came with the sides. Each dish comes with mash potatoes which you could sub for rice or fries but it didn't come with a vegetable or other sort of side, you had to pay extra. Both sides (we got broccoli and mash and broccoli and rice) were mediocre and didn't match the quality of the steak. The only dessert they had was cake which was a little disappointing. read more

Very sub-par. The bartender is a nice kid, but very much a kid who has not been properly trained on being a bartender. He made a dirty martini which tasted like water. So I returned it and ordered a French martini, which was better. He charged me for the French martini. then they charged us to share a plate without us telling them we wanted to split the plate. Further, they never even told us they was an additional charge. The vibe and energy in the place was deflated too. Probably because of the bartender who no one seemed to care terribly for. Very disappointing, especially on New Year's Eve. read more

Excellent restaurant! Menu is good for everyone, food is great, bar is on point. Great staff and all around service which can be hard to find in town. Get there! read more

My new favorite restaurant in Windham! The steak was cooked to perfection, and the service was lovely. Not pictured here but also very delicious was the beet salad, espresso martini, and the peach tea lemonade with vodka. Also a huge shoutout to the 10 year year old hostess in training! (I believe the owners daughter). She came by to make sure our dinner was going well and followed our waitress around while taking notes. Will definitely be back! read more

Lilly's Steaks & Cocktails - 28oz Steak - Steakhouses Near Me - Windham, New York

I knew this was going to be an exceptional meal from the moment I ordered my drink. Suffice to say the meal was delicious. I chose the pear salad with some steak (a special for the evening) and the portion was very generous and it was more than fulfilling for an entre. The pears were fresh and roasted (a lost art) and everything was done to perfection. This was easily the best pear salad with steak I have ever had. The apple pie a la mode was phenomenal too. Can't wait to come back. read more

Lilly's Steaks & Cocktails - Roasted pear salad with steak. - Steakhouses Near Me - Windham, New York

Nice ambience, food usually good but last time the mussels were awful. Half of them closed. It is however overpriced-I feel like I am back in the city when going here due to the expense. Will go here 4 times a year maybe. read more