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Entire apartment

Cozy Caboose in the city

Apartment with kitchenette, near Windham Mountain Resort

Photo gallery for Cozy Caboose in the city

Exterior
Exterior
1 bedroom, WiFi, bed sheets
Shower, hair dryer, towels, soap
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
In downtown Windham, Caboose 1922 offers a one-of-a-kind retreat with its cozy queen-size bed and historic charm. Enjoy easy access to restaurants, bars, shops, and the Windham Ski Mountain within walking distance or half a mile away.

Reviews

10 out of 10
Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 2

Popular amenities

  • Parking available
  • Kitchen
  • Barbecue grill
  • Outdoor space

Add dates for prices

About this property

Entire place

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 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

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

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

Events

No events allowed

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
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

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

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

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Reviews

Cozy Caboose in the city Reviews

10

Exceptional

10

Cleanliness

9.8

Location
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

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

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

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

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

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

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

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

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

John T.

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

Cutest

Super cute
Stayed 1 night in Feb 2025

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

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

Frank C.

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

Perfect.

Cute little place. Perfect for the 2 of us. Zero issues, everything went as smooth as it could have.
Stayed 1 night in Sep 2024

10/10 Excellent

Sheila R.

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

The Caboose that has it all

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!
Stayed 3 nights in Jun 2023

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

8/10 Good

Haley M.

Liked: Cleanliness, communication, location, listing accuracy

Snowboarding + The Caboose

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!
Stayed 2 nights in Jan 2024