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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 - Cozy Caboose in the city (Windham)
Exterior - Cozy Caboose in the city (Windham)
1 bedroom, WiFi, bed sheets - Cozy Caboose in the city (Windham)
Shower, hair dryer, towels, soap - Cozy Caboose in the city (Windham)
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils - Cozy Caboose in the city (Windham)
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

  • Kitchen
  • Outdoor space
  • Parking available
  • Barbecue

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

Similar properties

Outdoor spa tub
2 Min Walk to Windham Town | Hot Tub | Fire Pit
  • Spa pool
  • Washing machine
  • Dryer
  • Air-conditioning
10.0 out of 10, Exceptional, 1 review
The price is AU$793
includes taxes & fees
5 Jan - 6 Jan 2026
2 Min Walk to Windham Town | Hot Tub | Fire Pit

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
Information provided by the property may be translated using automated translation tools

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

  • 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 - 15 min drive - 19.6 km
  • Belleayre Mountain Ski Center - 42 min drive - 60.2 km

Getting around

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

Restaurants

  • ‪Chicken Run - ‬2 min drive
  • ‪Windham Diner - ‬4 min walk
  • ‪Babblers - ‬2 min drive
  • ‪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.

How much is parking at Cozy Caboose in the city?

On-site parking is available at the 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

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. 93 out of 100 reviews
Rating 8 - Good. 7 out of 100 reviews
Rating 6 - Okay. 0 out of 100 reviews
Rating 4 - Poor. 0 out of 100 reviews
Rating 2 - Terrible. 0 out of 100 reviews

10

Cleanliness

9.8

Location

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

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

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

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

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

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

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

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

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

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

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

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

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

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

reg j.

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

Sleeping in the Caboose

Can’t wait to visit again soon. Great place and guests
Stayed 1 night in Dec 2023

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

Angela D.

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

Birthday adventure

Very unique property with a lovely host! Was the perfect getaway for one night to celebrate my daughters birthday
Stayed 1 night in Aug 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

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