1. Captain's Inn Point Lookout

1. Captain's Inn Point Lookout

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Windham, NY

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Captain's Inn Point Lookout

4.7 (3 reviews)
Closed 4:30 pm - 8:00 PM

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Hotel Vienna

Hotel Vienna

(66 reviews)

$$

Loved it here! I'm so glad I stayed here. I chose this hotel for it's pool…read more The location is great. It's very close to the mountain and a couple blocks from the main street in Windham with restaurants, coffee shops, and more. The rooms were updated and nicely decorate. The front desk employee informed me that they're shutting down for a month in a few weeks to complete more renovations. I can't wait to stay here again! They had a great breakfast, movie room, fire pit, pool, sauna, and more! Highly recommend!

We were running late and were met and checked in by Jacob. He was very welcoming and gracious. He…read moreloved our little puppy and gave him a treat which he loved. We were hungry and with most of the restaurants closed or closing soon, Jacob offered to make us some chicken tenders. They were absolutely delicious and really hit the spot. You have a variety of choices for breakfast - warm muffins, croissants and chocolate croissants, fruit, oatmeal, cereals, granola and your choice of teas as well as coffee, cappuccino, and macchiatos from a machine I wish I had at home. Starbucks watch out...lol. The warm croissants are made each and every morning by Jacob. Our Mountain View room had a king size bed, which was so comfortable and oversized pillows that felt like clouds. Everything was so luxurious and very clean. Coming back to our room on Valentine's Day, we found a box of chocolates and a Rose left on our bed. What a pleasant surprise! You can tell that Jacob, his family and staff really love what they do. It's this small family feel that you will not find at any hotel chain. Downstairs there's a lounge area with board games, a foosball table and lots of places to sit, eat, read, talk and just relax. There's a separate building with a heated pool and a sauna right outside. We didn't get a chance to use this, but look forward to it the next time. You have access to the Windham Path right from the property as well. Lots of restaurants in town and our favorite breakfast place, Clutch and Throttle is a must go to. And make sure you visit the Gem Mercantile for your clothing needs or gifts to take back home. We are looking forward to another visit to Hotel Vienna in the future.

Wylder Hotel Windham - Evergreen room

Wylder Hotel Windham

(19 reviews)

This is a quaint resort in the heart of the Catskills. We stayed for two nights…read more They have several buildings to choose from for accommodations depending on whether you want a view of the mountains or the surrounding grounds. We opted for a mountain view in the Evergreen building, which was stunning. Our room had a porch with wooden chairs that overlooked the golf course. The entrance also offered a peek of the creek on the other side of the building. Many of the guests were families with kids. The resort charges a fee, which gives you access to their plethora of activities on site including oak barrel saunas, pickle ball, e-bikes, hammocks, a wooden swing, and more. They also offer various classes and guided workshops such as tye dying, book folding, and cocktail making. They had a magic show and live music as well. S'mores kits could be purchased for $15 for two people. Our room was clean, with a modern bathroom. The shower got very, very hot. The thermostat worked well. They have a restaurant on site. The bakery served pastries, hot breakfast, and drinks in the morning. Reservations were recommended for dinner. Overall, it was perfect for a quiet weekend getaway.

Came back again this year because last year was so magical... amazing yet again and we cannot wait…read moreto come back again. I have to give a special shout out Rebecca ! This woman runs a tight ship behind the bar and is a great person. She deserves a raise. Also the GM was also great ! We love this place.

East Wind Hotel & Bar

East Wind Hotel & Bar

(38 reviews)

There is so much good to mention from our stay at East Wind in Windham. There was also a few little…read moresurprises that were mostly because we didn't read the website description or dig thoroughly enough, so I will try to make this as helpful as possible! For reference, we stayed in one of the Lushna cabins that are best described as the size of a big teepee tent with one beautiful window wall. First surprise, I don't think were were fully expecting how small it was and that there is basically just a bed and then room for a bag or two. Yes, the bathrooms are detached and you have to go outside to get to them but they are a few feet away, private, and they keep them so incredibly warm that it was actually really nice in there. They are very spacious, have plenty of shelves and the shower is huge and luxurious. My bathroom at home honestly pales in comparison. There are two saunas on property but the one right outside of our cabin was not working, most likely because of how cold it was outside. It was a bummer, especially because we didn't want to trek to the other farther away one. We ate at Dandies, their on site restaurant, our first night and everything was incredible. Their staff was super friendly and lovely to chat with. We went back for the mulled wines more than once and stopped by in the AM for coffees before leaving for the day. It was great to have so close by. Our first morning we tried the breakfast basket and loved that it just appeared at our door. For $30 we got a Stanley thermos of coffee, hard boiled eggs, yogurt parfaits, OJ, and croissants. Nothing too crazy but I loved having a slow start to the day with breakfast in bed. Windham is filled with great places to eat, cute antique shops, a movie theater, bars, and is not far at all from other great towns. This wasn't a ski trip for us, but we never ran out of things to do. Yes, it was expensive and might not have fully felt like it was worth the price with all of the surprises, but we had an amazing time and we also got engaged over this weekend in this teeny tiny little teepee tent so my heart is full of love and 5 stars for everyone.

My son and I recently spent a few days at Eastwind, and it was one of the best one-on-one trips…read morewe've taken together. We stayed in a Lushna Suite, which was fantastic. It was clean, comfortable, unique, and a lot of fun, offering the perfect mix of adventure and relaxation. What I loved most was that it felt like camping, but without sacrificing comfort. The Lushna Suite gave us that outdoorsy experience and connection to nature while still having a real bed. My back was extremely thankful that I was sleeping on a comfortable mattress instead of the ground. I was also a little concerned that being so immersed in the woods would mean dealing with bugs, but we had absolutely zero issues during our stay. The property itself is beautiful, with plenty of fun things to do on-site, but we spent most of our days exploring the surrounding area. We hiked, kayaked, and fished, then returned each evening to relax and enjoy the atmosphere at Eastwind. A special shoutout to the food. The BBQ was outstanding, honestly some of the best I've had in a very long time. It far exceeded expectations and ended up being one of the highlights of the trip. Specialty drinks were delicious too and my son said it was the best Shirley Temple he's ever had! The combination of unique accommodations, great food, a beautiful setting, and easy access to outdoor activities made this a truly memorable getaway. Most importantly, it gave me the opportunity to spend quality time with my son and create memories we'll both cherish for years to come. I would highly recommend Eastwind to anyone looking for a relaxing escape, an outdoor adventure, or simply a chance to reconnect with family while enjoying all the comforts of home. We will absolutely be back.

Beds on Clouds

Beds on Clouds

(25 reviews)

Amazing historical inn and art gallery !! Amazing stay and art gallery!! Rebecca is an amazing…read moreresource of information!! If you visit Rebecca say Egor and Rachel Astakhov have recommended you to stay!! Rebecca is a lovely art manager!! It is a beautiful bed and breakfast to stay!! Please enjoy your time here - windhan and Hunter are 5 and 20 minutes away respectfully. Thank you again Rebecca!!

So it is super cute and clean and the beds are very comfortable. It is no longer a bed and…read morebreakfast though, it's just a bed. They blamed it on Covid, but it became clear that they just can no longer get it together. Unfortunately, the owner is quite ill, and admittedly on "very heavy drugs," which she asked us to forgive her for while she took a half hour to find our reservation and room. She is also very cranky. I received a 10 minute condescending lecture on how to lock the door and was told repeatedly that "bad boys" break in and wander the halls. There was a helper in the parking lot who was not very helpful. He accused me over and over again of hitting another guest's car, which I did not, as I was the only one in the lot for 2 days. Clearly the other guest hit me when she arrived. I felt harassed. Let's just say they care nothing for customer service. It was very expensive for no breakfast. I can totally see that it had it's day, and many good reviews from the beginning of the year, but must have been a rapid decline. Time to sell.

Cave Mountain Motel - The Cave Mountain Motel Rooms

Cave Mountain Motel

(8 reviews)

$

It's a classic motel and you park in front of your room. The interior is cozy warm, design like a…read morelodge in a winter mountain. I stayed at room #3 with two double beds, and there was a 32" TV and good size refrigerator. Free WiFi. Bright enough and very clean. Plenty towels, I'm not a fan of scented detergent but they were soft and comfy. I spoke with the owner? when I checked in about pathways to go to Hunter Mt. for next morning. Later that night the snow started, and he knocked on my door to suggest me to take another way to avoid hills for my safety. What a wonderful and respectful attentiveness for their guests!! Hard to find such a lodge these days. I highly recommend this place. They have a nice cat in the lobby area too.

For our visit to Hunter Mountain (15 min drive away, Windham is even closer), we decided to stay…read morehere since it was close and affordable. Building/Room: It was a small room with two beds, cable TV, dresser, and night stand. The bathroom had a standing shower. It had the basics of everything we needed. The walls are thin, so we can hear the cars going by on the road, and the wind was strong and you can hear the building squeaking at night... You could hear the neighbors mumbling, couldn't make out the words (though we didn't really try either...) Breakfast is included, it is "light continental" meaning there are pastries (coffee cake, muffin), coffee, hot water and tea bags, and yogurt available in the little dining/kitchen area. Check in/out: It was super easy. We drove up and she looked up our reservation and then gave us the keys. Check out is at 11 AM and you just leave the keys on the dresser.

Captain's Inn Point Lookout - hotels - Updated July 2026

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