Cozy Caboose in the city

Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

About this condo rental

Located in Windham, this attractive condo for £139 per night is a great choice for your next vacation. 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!!

Amenities

Air conditioner

Kitchen / Kitchenette

Internet / Wifi

Parking

Balcony / Patio

Map of Windham, NY

Nearby attractions

New York State Museum

Rail Explorers: Catskills Division

16.01 miles

Cozy Caboose in the city

5.0

Outstanding(68 Reviews)

Condo in Windham, NY

2 guests · 1 bedroom · 1 bath

Reasons to book

People love it hereGuests give this property a top rating

Includes essentialsKitchen / Kitchenette, Air conditioner, Internet / Wifi and more

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

££££

About this condo rental

Amenities

Air conditioner

Kitchen / Kitchenette

Internet / Wifi

Parking

Balcony / Patio

Map of Windham, NY

Nearby attractions

New York State Museum

Rail Explorers: Catskills Division

16.01 miles

Reviews

5.0/5.0

Outstanding(68 Reviews)

8.0

Jan 2024

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!

5.0

Jan 2024

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.

5.0

Dec 2023

Can’t wait to visit again soon. Great place and guests

5.0

Nov 2023

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

5.0

Oct 2023

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!

5.0

Oct 2023

We had a great stay in the caboose, we were here for a wedding! So cute and comfortable!

5.0

Sep 2023

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!

5.0

Sep 2023

Great little property. Unique and well maintained. Thx!

5.0

Sep 2023

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!

5.0

Sep 2023

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.

5.0

Aug 2023

Fun little place to stay. Restaurants and activities easy to walk to. Would recommend a different cozy getaway.

5.0

Jul 2023

This little caboose has everything you need and is very clean.

5.0

Jun 2023

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!

5.0

Feb 2023

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!

5.0

Oct 2022

I loved my stay in Windham’s historic caboose! The property was amazing and you could tell that the owner spared no expense in restoring the train car to its original grandeur. All the little details like original steel doors and even the steering wheel out front made it a truly unique experience. I especially loved sitting with a glass of wine and enjoying the sunset on the extended back porch. There is a peaceful little creek to look out on - the perfect place to unwind and relax.

5.0

Oct 2022

My 5 year old grandson thought sleeping in this 100 year old caboose was the greatest! It is very clean and creatively designed. We were able to walk to everything in town just by stepping outside onto the main street. Patrick responds quickly to any questions.

5.0

Oct 2022

Everything was as expected. My wife & I were looking for a unique place to celebrate our 46th anniversary. Easy to get to, good food in the immediate area & quiet.

5.0

Sep 2022

Love this property! Cute and clean. Great for a quick getaway. Be aware that if renting in Windham M-W there are limited options for food in the evening if you plan to dine out. The caboose does have a grill on the back deck and a microwave for you to use if you want to bring your own food!!

5.0

Sep 2022

We had a great time staying in the train! It was perfect for 2 guests and had everything we needed for a weekend stay!

5.0

Sep 2022

Of all the places our family has rented for short stays, this was my favorite. It was thoughtfully laid out, impeccably clean, affordably priced, and conveniently located in the center of town. Communication with the host was instantaneous. The hosts are hard-working, welcoming and generous. All of the extra attractions that they own and operate on site make the stay at the caboose even more enjoyable. I wish we lived closer so that we could stay there more often. We cannot say enough positive things about this rental. Thank you for a wonderful retreat. M. Freeman

5.0

Aug 2022

The caboose is exactly as pictured. It is beautifully equipped and maintained, and is absolutely pristine in cleanliness and condition. The host is incredibly responsive, and the location is great for walking to restaurants, easy access to the ski resorts, etc... Everything (that we used) was functional and in good working order, including AC and Wifi. Even the bed was remarkably comfortable. As the description says, it's literally in the parking lot between a fairly major road and the mini-golf place - so there is no privacy when on the deck. That's about the only negative. One thing that some folks might want to know, which I didn't see mentioned in other reviews, is that the toilet is behind a door which doesn't go all the way to the ceiling. There's a pretty industrial strength fan to help out w/ ventilation and we're long married so it wasn't an issue, but it might not be totally comfortable for everyone. We loved our brief stay there and would happily return if we're in the area again.

5.0

Aug 2022

My daughter and I loved staying in this caboose. It has everything we needed plus a huge back deck with grill. Close to amenities. The host is very responsive and straightforward. Would definitely stay again.

5.0

Jul 2022

great location love this place

great location love this place

Patrick is a wonderful host - helpful & responsive. We have family nearby so this was our second stay & my favorite tiny home - thanks so much & we hope to be back again soon!

5.0

Jul 2022

Such a fun stay!

Such a fun stay!

The caboose is my new favorite place that I’ve stayed. It’s cute & utilizes it’s small size so well. There’s all the amenities I need - especially air conditioning and a spacious back porch overlooking a river. And if the putt putt outside got rowdy, I’d close the windows and it was very quiet. Plenty of places to walk to for food and drink as well. 10/10!

5.0

Jun 2022

cozy & Unique

cozy & Unique

We stayed for a long weekend and enjoyed the unique accommodation. It's a great location for catskills hikes.

5.0

May 2022

All aboard!

All aboard!

Cute, kitchy place to stay! Very well kept!

5.0

May 2022

Amazing time. Everything was perfect. Back porch morning coffee was the vibe, right on the creek!?!?! Pssshhhhh!!!!! Would stay again!!!

5.0

May 2022

Caboose is Loose

Caboose is Loose

Amazing time. Everything was perfect. Back porch morning coffee was the vibe, right on the creek!?!?! Pssshhhhh!!!!! Would stay again!!!

5.0

Mar 2022

Anniversary Getaway

Anniversary Getaway

Such a cute place. Right in town. Walking distance to everything in town. Location is basically at the end of a parking lot, and I think it backs up to a creek. Very close to Windham mountain for skiing. Modern and clean inside, but keep in mind, it’s a caboose, so it will be neat and memorable and unique, but it isn’t huge inside. It does, however, have everything you could need.

5.0

Mar 2022

Cozy Caboose

Cozy Caboose

My husband and I stayed here for an overnight ski trip. Did not disappoint. Super cute decor and conveniently located to both restaurants and the mountain. Would 100% recommend!

4.0

Mar 2022

All Aboard!

All Aboard!

Rented this immaculate kitschy caboose for my train enthusiast husband. Caboose is exactly as pictured. Smart move by owner to put in a queen mattress...very firm and comfortable. For those more rubenesque, the shower is tight yet serviceable. Patrick was very responsive to my queries.

5.0

Feb 2022

Perfect Caboose Ski Getaway!!

Perfect Caboose Ski Getaway!!

A perfectly restored genuine iron caboose, intimate and inviting, granite kitchenette with farm sink, tiled shower, real “train” bathroom, tiny and terrific, a firm bed for a great sleep, and views of the mountains and river. Added plus, right in Windham and a short drive to the ski slopes.

5.0

Jan 2022

Such a unique and fun home. It was perfect for my husband and I to spend our first weekend getaway without our daughter. The caboose was clean and super comfortable for us. I loved the beautiful decor and the most efficient use of space in this home. It was conveniently located to restaurants and Windham Mountain. Would definitely come again!

5.0

Jan 2022

Cozy Caboose!

Cozy Caboose!

5.0

Jan 2022

Spent one night with my girlfriend

Spent one night with my girlfriend

The caboose is a cool little spot. Perfect for a couple. Easy access to the mountains, and walking distance to many of the bars and restaurants in the area. Highly recommend for a quick winter getaway.

5.0

Jan 2022

The listing is very accurate so I can’t add much. Charming and comfortable. We only stayed one night and don’t need to use the shower. It’s just a shower stall but looks like it would serve its purpose well. There’s also a Keurig with coffee pods, which we appreciated. Only glitch was the heat, which at first was getting the room into what must’ve been the 80s even though it was sad in the low 70s. Pat, the owner, who was very responsive, told us to set it significantly lower. We finally set it to the lowest setting, 60°, and that worked!! It looks like when it’s super cold out the thermostat on the heater reads lower than the room because it’s picking up cold from the outside. We greatly enjoyed our stay!

5.0

Jan 2022

Great find right near Windham Mountain.

Great find right near Windham Mountain.

5.0

Jan 2022

Super close to skiing, coffee shops and dining. Can’t wait to return!

5.0

Dec 2021

Love it!

Love it!

Super close to skiing, coffee shops and dining. Can’t wait to return!

5.0

Dec 2021

Cozy

Cozy

Perfect for 1 person getting away for the day of hitting the slopes. Comfortably fits 2, but I was alone. Restaurants are all walking distance and so is the convenience store.

FAQs

How much does this condo cost compared to others in Windham?

The average price for a rental in Windham is £343 per night. This rental is £204 less expensive than the average.

Is parking included with this condo?

Yes, parking is listed as an amenity at Cozy Caboose in the city. For more information, we encourage you to contact the property about where to park.

Is there a pool at this condo?

We didn’t find pool listed as an amenity for this condo. It may be worth double checking if a pool is important for your stay.

Is Cozy Caboose in the city pet friendly?

Unfortunately, this condo is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Cozy Caboose in the city?

We found 6 amenities for this rental. This includes air conditioner, kitchen / kitchenette, internet / wifi, parking, and balcony / patio.

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4.1

Excellent(128 Reviews)

Cozy Caboose in the city

About this condo rental

Amenities

Map of Windham, NY

Nearby attractions

Cozy Caboose in the city

Condo in Windham, NY

Reasons to book

About this condo rental

Amenities

Map of Windham, NY

Nearby attractions

Reviews

FAQs

How much does this condo cost compared to others in Windham?

Is parking included with this condo?

Is there a pool at this condo?

Is Cozy Caboose in the city pet friendly?

What amenities are available at Cozy Caboose in the city?

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