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Cozy Caboose in the city

Apartment with kitchenette, near Windham Mountain Resort

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
    ‪16 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪51 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!!

Add dates for prices

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.
View more Apartments in WindhamOpens in a new window
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 - 9 min drive - 11.8 km
  • Hunter Mountain - 16 min drive - 19.9 km
  • Zoom Flume - 21 min drive - 20.6 km

Getting around

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

Restaurants

  • ‪Chicken Run - ‬2 min drive
  • ‪Windham Diner - ‬4 min walk
  • ‪Catskill Mountain Country Store - Windham - ‬9 min walk
  • ‪Babblers - ‬2 min drive
  • ‪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.

How much does it cost to stay at Cozy Caboose in the city?

As of 9 Nov 2025, prices found for a 1-night stay for 2 adults at Cozy Caboose in the city on 10 Nov 2025 start from AU$348.85, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

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. 92 out of 99 reviews
Rating 8 - Good. 7 out of 99 reviews
Rating 6 - Okay. 0 out of 99 reviews
Rating 4 - Poor. 0 out of 99 reviews
Rating 2 - Terrible. 0 out of 99 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

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

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

Jared S.

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

Great Windham getaway

Great little property. Unique and well maintained. Thx!
Stayed 1 night in Sep 2023

10/10 Excellent

Matthew Q.

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

Great ski weekend in Caboose!

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!
Stayed 2 nights in Feb 2023

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

Xusheng Y.

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

The stay of a lifetime.

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!
Stayed 1 night in Sep 2023

10/10 Excellent

Seth T.

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

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

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

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

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

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

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

Frank C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot! Loved it!
Stayed 1 night in Jun 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

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

John T.

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

Cutest

Super cute
Stayed 1 night in Feb 2025

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

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

Keri S.

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

They thought of everything at this charming caboose stay

While on a motorcycle ride through the Catskills we saw this cute caboose and I knew I’d have to book a night to check it out. This may have been the most adorable place I’ve stayed and I try to check out unique places to stay. The owners thought of everything here, the bed was really comfortable, the place was spotless and very well maintained. The kitchen area had plenty of room, the deck off the back was great listening to the birds in the evening by the creek. Got a bit chilly at night and the heater worked great. All of the furnishings were gorgeous and inviting and the bedding itself was cozy as well. I can’t rate this place any higher! Food was in walking distance, the town here is charming as well. I’d say do yourself a favor and stay here.
Stayed 1 night in Oct 2024

About the host

Hosted by Pat Higgins

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Premier Host

They consistently provide great experiences for their guests
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