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7604 State Route 23, Windham, NY 12439-5153
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Prices above are provided by partners for one room, with variable occupancy rules as provided by the property, and do not include all taxes and fees. Please see our partners for full details.
Traveler (49)
Room & Suite (20)
Dining (4)


#1 of 2 Specialty lodging in Windham
Captain's Inn Point Lookout is historically located 2000 feet high in the Catskill Mountains. It has an unprecedented Five State, 180 mile view into Vermont, New Hampshire, Massachusetts, Connecticut, & New York. It is in close proximity to Windham Mountain, Hunter Mountain, and offers a huge variety of year round activities,Fishing, Hiking, Mountain Biking, ZIP LINING, Boating Kayaking, snow-shoeing, Snow skiing, snow boarding, Leaf peeping, sight-seeing, scenic drives, Golfing, hunting, discovering, The Great Northern Catskills. The Restaurant has received accolades for its performance and vows to continue to be better. A wonderful place to come for a getaway, a delicious meal, or a quick bite to eat in the lounge. Family friendly with a great children menu.
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Free breakfast
Bar / lounge
Non-smoking hotel
Room features
Flatscreen TV
Room types
Non-smoking rooms
Family rooms
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Good to know
Great View
127Reviews1Q+A23Room tips
Traveler rating
  • 88
  • 25
  • 2
  • 6
  • 6
Traveler safety
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Popular mentions
MATTYJ1320 wrote a review Nov 2019
Little Neck, New York15 contributions7 helpful votes
This was a great place, as seen by my previous reviews- However, we won't go back for a few reasons- 1- The owner is inappropriate with Ladies- and cannot handle alcohol very well 2- how the owner treats his staff- it is very disrespectful 3- The rooms were dirty- Puke stains on the bed- that had not been cleaned- ever 4- the food made us ALL very ill one evening- 5 of us were ill the next morning and could not hit the mountain- instead we hit the bathroom 5- Booking- We had friends call to book, only to be turned away because was booked... we were one of 2 couples that stayed there It is sad- it started off as a great relationship- but considering the above... it broke us. It was when he was inappropriate and "touchy" with the ladies in our party, that was the last straw.
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Date of stay: December 2018
Room Tip: Don't go here with Ladies
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1 Helpful vote
S N wrote a review Oct 2019
2 contributions1 helpful vote
Serious safety incident
I'll preface this by saying the staff and food are great and the only reason we have frequently visited. The owner, "Captain Wayne" however is the reason we will never return. His constant inappropriate comments and sexual innuendo are barely tolerable when he's not intoxicated. Which is a rare occasion. It has been an issue several times. Our last visit found him drunken and slurring at the bar and ended with us exiting quickly as his attempts to touch my wife were leading to an altercation. I would avoid this establishment like the plague unless your party doesn't include any females. Nor would I ever consider sleeping there in the hotel. My sympathies to the hard working staff as they have to deal with this regularly. I challenge ownership to call me a liar.
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Date of stay: October 2019Trip type: Traveled with friends
2 Helpful votes
William R wrote a review Oct 2019
Stamford, Connecticut10 contributions
If you are looking for a weekend getaway from the NYC area. Just two hours north is Windham mountain peaking at 3,150 ft (1,000 meters). This is my second time staying at Captain's Inn. I definitely recommend the valley view rooms if available. The morning sunrises are spectacular. See photos. Owned and operated by a real sea captain. The cap is friendly and knows every guests first name. This is the kind of of friendly service you'll experience here. If you are here during the warmer months, I'd recommend a patio lunch or dinner at 2,000 feet with a view. See Shrimp scampi photo. Overall, it is a great spot to relax and disconnect from NYC's rat race.
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Date of stay: October 2019
Sleep Quality
Room Tip: Choose Valley View Rooms - see photo
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Jim w White Corvette wrote a review Sep 2019
2 contributions
I stopped at this place for lunch today for the first time. The food was outstanding and the bill was reasonable. I paid the bill and left to get I to my car and the owner came running out and said "excuse me you seemed to have dropped this under your chair" and was holding 2 $100 bills! I checked my money clip and apparently the bills had fallen out as I put my change from the tab back into it. I would have never known this until I went to pay for something else MUCH later in my day!! THANK YOU for HONEST people in this day and age!! Jim with the White Corvette
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Date of stay: September 2019Trip type: Traveled solo
MJB638 wrote a review Jun 2019
Greenport, New York7 contributions3 helpful votes
On Monday June 10, 2019 my wife and I - together with another couple patronized this outstanding restaurant for their "Prime Rib" night. It was the second time we visited and it is my habit to not rate a restaurant unless we experience the food, service and dining room at least two times. Consistent with our last visit the food and prices were both beyond acceptable but this time we got to watch the team exhibit their problem solving skills. Shortly after we were seated a storm blew into the area as we looked out the the enormous windows peering north. Suddenly the electric power went out as the late spring windy, cloudy and rainy sunset approached. The staff never missed a beat - they continued to serve the mostly filled dining room and had no problem checking out checks manually. We enjoyed the food and the candle lit dining and were impressed with our waitress' calm and reassuring approach to service. This is a great place that all in the northern Catskill area should experience!
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Date of stay: June 2019
Trip type: Traveled as a couple
Room Tip: Best view from the north side consistent with the dining area
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$95 - $140 (Based on Average Rates for a Standard Room)
point lookout mountain hotel windham
Point Lookout Mountain Inn
United StatesNew YorkCatskill RegionWindham
Payments made by partners impact the order of prices displayed and, for featured or sponsored sort orders, partners’ payments may also influence the order of the accommodations listed.
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Frequently Asked Questions about Captains Inn Point Lookout
Which popular attractions are close to Captains Inn Point Lookout?
Nearby attractions include The Windham Path (4.5 miles), Zoom Flume (2.8 miles), and Our Lady of Knock Shrine (4.2 miles).
What are some of the property amenities at Captains Inn Point Lookout?
Some of the more popular amenities offered include free wifi, free breakfast, and an on-site restaurant.
What food & drink options are available at Captains Inn Point Lookout?
Guests can enjoy free breakfast, an on-site restaurant, and a lounge during their stay.
Is parking available at Captains Inn Point Lookout?
Yes, free parking is available to guests.
What are some restaurants close to Captains Inn Point Lookout?
Conveniently located restaurants include Vesuvio Restaurant, Nana Gail's Cafe, and The Yellow Deli.
Does Captains Inn Point Lookout have any great views?
Yes, guests often enjoy the mountain view available here.