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Apartment

Cozy Caboose in the city

Photo gallery for Cozy Caboose in the city

Exterior
Exterior
Bathroom
Bathroom
Room

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
1 bedroom1 bathroomSleeps 2

Popular amenities

  • Onsite parking available
  • Kitchenette
  • Air-conditioning
  • Barbecue grill
  • Deck or patio
  • Internet access

Rooms & beds

1 bedroom (sleeps 2)

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchenette

About this property

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!!
Our prices include all fees. No hidden fees.

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About the area

Windham

Located in Windham, this apartment is in the mountains. Hunter Mountain and Windham Mountain Resort are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Catskill State Park and Bearpen Mountain State Forest. Mountain Top Arboretum and Zoom Flume are also worth visiting.
View more Apartments in WindhamOpens in a new window
Map
Windham, NY

What's nearby

  • Catskill State Park - 2 min walk - 0.2 km
  • Windham Mountain Resort - 14 min walk - 1.3 km
  • Windham Country Club - 2 min drive - 1.9 km
  • Hunter Mountain - 17 min drive - 19.9 km
  • Kaaterskill Falls - 37 min drive - 38.1 km

Getting around

  • Hudson, NY (HCC-Columbia County) - 53 min drive

Restaurants

  • ‪Higher Grounds Coffee Shop - ‬2 min drive
  • ‪Mountain Express Cafeteria - ‬17 min walk
  • ‪Chicken Run - ‬2 min drive
  • ‪Catskill Mountain Country Store - Windham - ‬9 min walk
  • ‪Waffle Cabin - ‬3 min drive

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 99 out of 107 reviews
Rating 8 - Good. 8 out of 107 reviews
Rating 6 - Okay. 0 out of 107 reviews
Rating 4 - Poor. 0 out of 107 reviews
Rating 2 - Terrible. 0 out of 107 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Austin L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute unique stay, right in town and walkable to many restaurants and bars
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Mark D R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Name says it all super cozy, perfect location and Patrick was more than accommodating. We are sure to go back!
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Jorge V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was absolutely attentive and friendly. The Caboose was definitely a great unique staying experience that I recommend to all.
Bed was comfy and clean.
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Jen G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The caboose was modern, clean, and spacious. It had everything we needed and because it’s in town, there are lots of places within walking distance. Would definitely stay here again!
Stayed 1 night in Nov 2025
Verified

8/10 Good

John T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect set up after skiing all day
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Flynn O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is our second stay here and it was excellent again , clean , convenient to where we were going , very quiet at night for sleeping .
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Dia F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was very accommodating and attentive. The caboose was an awesome experience. Super clean and cozy.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

James S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
So conveniently located, great amenities, cozy touches. Unique tiny house-in-a-train-car experience. Very communicative host.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Jeffrey I.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Place was exactly as advertised! Would definitely recommend!
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Tim D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place. Location was perfect and we didnt need the car all weekend. Windham is a great town in a beautiful location.
Stayed 1 night in Aug 2025
Verified

10/10 Excellent

Dennis C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Super cute, clean and in the perfect location.
Stayed 1 night in Feb 2025
Verified

10/10 Excellent

Flynn O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay for a local bluegrass music festival

Clean , comfortable , convenient , very nice stay
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Douglas S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay.

Super cute and clean.
Stayed 1 night in Oct 2024
Verified

8/10 Good

Angela L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Right in town, lots of things to do within walking distance. Nice and quiet too. Only thing was the shower and toilet areas were kinda tight.. although it's completely understandable it being in a caboose.We enjoyed our stay and hope to be back.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Seth T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing experience
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Alexandra P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very fun place to spend a few days and surprisingly comfortable! Short walk to shops and restaurants in town and the front porch is perfect to enjoy in the evening. I would highly recommend this special experience!
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

David B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent

This place was amazing, clean, and had the perfect location! Absolutely loved staying here!
Stayed 1 night in Oct 2024
Verified

10/10 Excellent

Stephanie K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The caboose was a one of a kind stay that we hope to come back to one day! It had everything we needed for our weekend in Windham. Highly recommend! Location is in close distance to coffee shops and restaurants and other fun activities.
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

David B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is the second time we’ve come here. It is always a great time!
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

kelli o.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy & charming caboose

Great visit, thank you!
Stayed 2 nights in Feb 2025
Verified

10/10 Excellent

Allyson T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun Stay!

We had a great stay in the caboose, we were here for a wedding! So cute and comfortable!
Stayed 1 night in Oct 2023
Verified

10/10 Excellent

Bob W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely time, the place was great and the whole process was a breeze. Thanks!
Stayed 1 night in Aug 2025
Verified

10/10 Excellent

John r.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great little getaway!

Fun little place to stay. Restaurants and activities easy to walk to. Would recommend a different cozy getaway.
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Michael K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Pat was very easy to work with and very flexible
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Leah N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love staying at this cozy caboose!

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.
Stayed 3 nights in Jan 2024
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