You'll have the entire apartment to yourself and will only share it with other guests in your party.
Cozy Caboose in the city
Cozy, restored 1922 Caboose for rent in the center of downtown Windham...walking distance to restaurants, bars, shops, bus station...1/2 mile to Windham Ski Mountain...located on property of Triplex Movie theatre, Subway & Carvel shops, Game Room, Laundromat..caboose has queen size bed, TV, Wifi, Microwave, refrigerator, air conditioning, ample parking...A unique, historical overnight experience!!
Property manager
Pat Higgins
Add dates for prices
Property amenities
Internet
Available in the apartment: WiFi
Parking and transport
Parking on site
Kitchenette
Coffee/tea maker
Cookware, dishware, and utensils
Microwave
Paper towels
Refrigerator
Bedrooms
Bedroom
Bedsheets provided
Bathroom
1 bathroom
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Entertainment
TV with cable/satellite channels
Outdoor areas
Barbecue grill
Outdoor furniture
Patio
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
Smoke-free property
Location highlights
In the mountains
Things to do
Arcade/game room
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
Similar properties
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
You will receive an email from the host with check-in and check-out instructions
Pets
Pets not allowed
Children and extra beds
Children are welcome
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property is also known as
Vrbo Property
Cozy Caboose in Town Windham
Cozy Caboose in Town Private vacation home
Cozy Caboose in Town Private vacation home Windham
About the area
Windham, NY
What's nearby
Windham Mountain Resort - 14 min walk - 1.3 km
Windham Country Club - 2 min drive - 1.9 km
Windham Vineyards and Winery - 12 min drive - 11.8 km
Hunter Mountain - 20 min drive - 19.6 km
Zoom Flume - 25 min drive - 20.6 km
Getting around
Hudson, NY (HCC-Columbia County) - 53 min drive
Restaurants
Chicken Run - 2 min drive
Catskill Mountain Country Store - 9 min walk
Waffle Cabin - 3 min drive
Higher Grounds Coffee Co. - 2 min drive
Windham Diner - 4 min walk
Frequently asked questions
Is Cozy Caboose in the city pet-friendly?
No, pets are not allowed at this property.
What time is check-in at Cozy Caboose in the city?
Check-in begins at 4:00 PM.
What time is check-out at Cozy Caboose in the city?
Checkout is at 11:00 AM.
Where is Cozy Caboose in the city located?
Situated in the mountains, this apartment building is within 1 mi (2 km) of Catskill State Park and Windham Mountain Resort. Windham Country Club is 1.2 mi (2 km) away.
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Cozy Caboose in the city Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.More informationOpens in a new window
Rating 10 - Excellent. 82 out of 88 reviews
10 - Excellent
82
Rating 8 - Good. 6 out of 88 reviews
8 - Good
6
Rating 6 - Okay. 0 out of 88 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 88 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 88 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10
Super cute, clean and in the perfect location.
Dennis C.
Stayed 1 night in Feb 2025
10/10
Great visit, thank you!
kelli o.
Stayed 2 nights in Feb 2025
10/10
Super cute and clean.
Douglas S.
Stayed 1 night in Oct 2024
10/10
Clean , comfortable , convenient , very nice stay
Flynn O.
Stayed 3 nights in Jul 2024
10/10
This place was amazing, clean, and had the perfect location! Absolutely loved staying here!
David B.
Stayed 1 night in Oct 2024
10/10
We stay in Windham often, and this is centrally located to food and entertainment. Super cute, well maintained, and spectacularly clean. Patrick is nice and available nearby.
Moni O.
Stayed 1 night in Jan 2025
10/10
My girlfriend and I went to Windham to ski for the weekend. The caboose is very close to the mountain, and a short walk to all the downtown shops and restaurants. The caboose was very clean and cozy as described. Would recommend for two people.
Paul J.
Stayed 2 nights in Feb 2025
10/10
Super cute
John T.
Stayed 1 night in Feb 2025
10/10
We thoroughly enjoyed our stay in Windham. Such a unique experience staying in the caboose! Right in the heart of town walkable to restaurants, bars, and less than 5 min drive to the mountain. The caboose was plenty warm and cozy. Had everything we needed.Pat the owner was fantastic- super responsive and accommodating. Highly recommend booking!
Alexandra B.
Stayed 2 nights in Jan 2025
10/10
This was my second time staying here and every time I wish I never had to leave. Can't wait to hopefully visit again sometime in the next couple ski seasons.
Leah N.
Stayed 3 nights in Jan 2024
10/10
We had a great stay in the caboose, we were here for a wedding! So cute and comfortable!
Allyson T.
Stayed 1 night in Oct 2023
10/10
Fun little place to stay. Restaurants and activities easy to walk to. Would recommend a different cozy getaway.
John r.
Stayed 3 nights in Aug 2023
10/10
The location of this rental could not be any better - center of downtown with many restaurants with in walking distance. Rental was clean and provided all essentials for a weekend stay.
Aimee M.
Stayed 2 nights in Feb 2024
10/10
Everything was perfect. Clean place. Friendly and prompt responses from owner!
James W K.
Stayed 3 nights in Aug 2024
10/10
I would highly recommend this stay! It is one of a kind, very clean, everything was as described. I couldn’t have been happier! Host was very kind!
Lexi K.
Stayed 1 night in Oct 2023
10/10
This little caboose has everything you need and is very clean.
Sarah D.
Stayed 3 nights in Jul 2023
10/10
Cute little place. Perfect for the 2 of us. Zero issues, everything went as smooth as it could have.
Frank C.
Stayed 1 night in Sep 2024
10/10
Another enjoyable stay in the Catskills. The caboose is a great place to stay, complete with a private deck. Windham has some great eateries, and there's plenty to do in the area (not just hiking!)
Nathan S.
Stayed 4 nights in Aug 2023
10/10
Great little property. Unique and well maintained. Thx!
Jared S.
Stayed 1 night in Sep 2023
10/10
Everything was perfect and host super easy to contact! Place was spotless and plenty of space. Everyone should stay in a train caboose - so fun!
Matthew Q.
Stayed 2 nights in Feb 2023
10/10
Welcoming and unique experience. Owner could not be more accommodating. The townspeople were the nicest and the restaurants (of which there were many) were amazing. There is something for everyone at this getaway. Just plain relaxing fun!
Sheila R.
Stayed 3 nights in Jun 2023
8/10
Stay was great! Super clean and the place was very warm in the cold weather. Walking distance to stores and bars. Short drive to both Windham and Hunter Mountain. Only negative was a very tourist-y sign in front of the caboose. Loved it though!
Haley M.
Stayed 2 nights in Jan 2024
10/10
Staying here for the night was amazing! I was obsessed with Thomas the Tank Engine as a kid so this listing made me super giddy!
The bed was comfortable, a lot of thought was put into the design, and we had everything we needed!
If you're looking for a unique place to rest, this is the place to do it!
Eric D.
Stayed 1 night in Feb 2024
10/10
Do not pass up this opportunity to stay at possibly the coolest Vrbo ever. I mean, it’s a train! Inside it’s meticulously finished and incredibly cozy. Heat and cooling worked flawlessly. Only regret is not staying long enough!
Xusheng Y.
Stayed 1 night in Sep 2023
10/10
They did a great job making this old train caboose into a very nice lodging option. Nice finishes. Owners were super welcoming and helpful. Bed was nice and firm with nice bedding. The two of us could’ve stayed a whole week and been totally comfortable. The pictures in the listing are very accurate. The bath and shower are small, as to be expected, but we are pretty tall and we were fine. You can walk to about every restaurant in town. Windham is very quaint. We saw a new release movie at the theater on property and it was great. Overall, it was a neat experience. We’d recommend it.