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Cozy Caboose in the city

Photo gallery for Cozy Caboose in the city

Exterior
Exterior
Bathroom
Bathroom
Room

Reviews

10 out of 10
Exceptional
1 bedroom1 bathroomSleeps 2

Popular amenities

  • Parking available
  • Barbecue grill
  • Kitchen
  • Outdoor space

Explore the area

View map
Windham, NY
  • Place, Windham Mountain Resort
    ‪14 min walk‬
  • Place, Windham Country Club
    ‪2 min drive‬
  • Place, Hunter Mountain
    ‪20 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪63 min drive‬

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!!

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Amenities

Kitchen
Air conditioning
Outdoor space
Parking available
Barbecue

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

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

About the area

Windham

Located in Windham, this apartment is in the mountains. Windham Mountain Resort and Hunter Mountain are worth checking out if an activity is on the agenda. Mountain Top Arboretum and Zoom Flume are also worth visiting.
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Map
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

  • ‪Windham Diner - ‬4 min walk
  • ‪Chicken Run - ‬2 min drive
  • ‪Mountain Express Cafeteria - ‬17 min walk
  • ‪Catskill Mountain Country Store - Windham - ‬9 min walk
  • ‪Higher Grounds Coffee Shop - ‬2 min drive

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.

Reviews

10

Exceptional

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 90 out of 96 reviews
Rating 8 - Good. 6 out of 96 reviews
Rating 6 - Okay. 0 out of 96 reviews
Rating 4 - Poor. 0 out of 96 reviews
Rating 2 - Terrible. 0 out of 96 reviews

Reviews

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

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

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

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

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

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

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

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

10/10 Excellent

Nelson F.

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

Charming and lovely

It’s hella cute and It’s more spacious than you would think from the outside. Should have grabbed another day, as the town is cute and fun with things to do on property and off. Will visit again
Stayed 1 night in Jun 2025

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

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

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

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

10/10 Excellent

Moni O.

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

Fun and excellent location

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.
Stayed 1 night in Jan 2025

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

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

10/10 Excellent

Paul J.

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

Cozy and Convenient

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.
Stayed 2 nights in Feb 2025

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

10/10 Excellent

John T.

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

Cutest

Super cute
Stayed 1 night in Feb 2025

10/10 Excellent

Aimee M.

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

Perfect stay in the caboose

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.
Stayed 2 nights in Feb 2024

10/10 Excellent

Alexandra B.

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

Cozy Caboose Winter Getaway

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!
Stayed 2 nights in Jan 2025

10/10 Excellent

James W K.

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

Amazing location

Everything was perfect. Clean place. Friendly and prompt responses from owner!
Stayed 3 nights in Aug 2024

10/10 Excellent

Lexi K.

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

Absolutely beautiful stay!

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!
Stayed 1 night in Oct 2023

10/10 Excellent

Sarah D.

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

Great little caboose

This little caboose has everything you need and is very clean.
Stayed 3 nights in Jul 2023

10/10 Excellent

Nathan S., Marblehead, MA, USA

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

A unique accomodation

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!)
Stayed 4 nights in Aug 2023

About the host

Hosted by Pat Higgins

Host profile image

Premier Host

They consistently provide great experiences for their guests
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