Skip to main content
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 grill

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 transportation

  • 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

  • Smoking not allowed

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

Dining
2 Min Walk to Windham Town | Hot Tub | Fire Pit
  • Hot tub
  • Washer
  • Dryer
  • Air conditioning
10.0 out of 10, Exceptional, 1 review
The price is ￥30,833
￥84,701 total
includes taxes & fees
Jan 21 - Jan 22
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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 neighborhood

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.
Visit our Windham travel guideOpens in a new window
View more Apartments in WindhamOpens in a new window
Map
NY, Windham

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
  • ‪Catskill Mountain Country Store - Windham - ‬9 min walk
  • ‪Babblers - ‬2 min drive
  • ‪Windham Diner - ‬4 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?

Onsite 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?

Check-out 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.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Cozy Caboose in the city Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers 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. 96 out of 103 reviews
Rating 8 - Good. 7 out of 103 reviews
Rating 6 - Okay. 0 out of 103 reviews
Rating 4 - Poor. 0 out of 103 reviews
Rating 2 - Terrible. 0 out of 103 reviews

10

Cleanliness

9.8

Location

Reviews

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

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

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

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

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

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

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

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

kenneth f.

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

Weekend getaway

The caboose was absolutely adorable, comfortable and perfectly secluded. I wish I stayed longer. I will rent again and again. Process was simple and easy. Love the decor and the vibe. Perfect little retreat
Stayed 1 night in Oct 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

10/10 Excellent

Eric D.

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

Fulfilled a lifelong dream I didnt know I had!

Staying here for the night was amazing! I was obsessed with Thomas the Tank Engine as a kid so this listing made me super giddy! The bed was comfortable, a lot of thought was put into the design, and we had everything we needed! If you're looking for a unique place to rest, this is the place to do it!
Stayed 1 night in Feb 2024

10/10 Excellent

Norris E., South Portland,ME

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

Pleasant and Unique

Unique and different, not your standard hotel room. It looked like a noisy setting, but quiet inside.Bed was comfortable and firm, just the way I prefer it. Walking distance to attractions and restaurants. Came stocked/ supplied with everything we needed.
Stayed 2 nights in Sep 2023

10/10 Excellent

Melissa J.

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

Quirky & Cute!!!

Perfect little spot for a romantic getaway. Surprised my boyfriend with this stay and just gave him the address. He loved how unique and different this was. The interior is clean and tidy, the ac worked great and we loved sitting on the rocking chairs at night. I had brought a citronella candle to keep the bugs away bc this is situated right on the creek. Even though it’s next to the manifold, it was still so quiet inside! Thank you for a great stay!
Stayed 1 night in Jul 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

10/10 Excellent

Amber g.

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

Hidden gem, perfect getaway!

This was my first time staying in a Vrbo and it was a memorable experience. First, the property is amazing. There were many things on the property, and shops walking distance from the caboose. Everyone was very friendly, even offering to help bring our bags inside. Pat was incredibly attentive and even allowed a special request. The river running behind the caboose is stunning. The caboose itself was beautiful. The interior is so cozy and truly gorgeous. It feels like you're in your own little world! There's a cute couch where you can sit and watch TV. Overall, an incredible experience, I can't wait to go back. Thank you!
Stayed 1 night in Sep 2023

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

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