See all properties

Cozy Caboose in the city

Top rated by guests
Exterior
Private kitchen
Private kitchen
Exterior
Property grounds
review stars
10.0Outstanding
(99 Ratings)
"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 r..."
Stephanie K.
Don't miss out! Price and availability may change
10.0 / 10.0
Outstanding(99 Ratings)

Apartment in Windham, NY

2 guests · 1 bedroom · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this apartment rental

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 at Cozy Caboose in the city

Family friendly

Map of Windham, NY

city location on map

Nearby attractions

New York State Museum
34.3 mi
Howe Caverns
27.9 mi
Poets' Walk Park
28.3 mi
Rail Explorers: Catskills Division
16 mi

Ratings and reviews

10.0 / 10.0
Outstanding(99 Ratings)
10.0 / 10.0Outstanding·Sep 2025
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.
10.0 / 10.0Outstanding·Aug 2025
Great place. Location was perfect and we didnt need the car all weekend. Windham is a great town in a beautiful location.
10.0 / 10.0Outstanding·Aug 2025
We had a lovely time, the place was great and the whole process was a breeze. Thanks!
10.0 / 10.0Outstanding·Aug 2025
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!
$$$$
vrbo logo

FAQs

Is parking included with this apartment?

Parking is not specified as an available 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 apartment?

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

Is Cozy Caboose in the city pet friendly?

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

What amenities are available at Cozy Caboose in the city?

We found 1 amenities for this rental. This includes , and family friendly.

Explore similar stays in Windham

Explore all stays
10.0 / 10.0
Outstanding(67 Ratings)
Cutest Cabin in Windham close to ski slope and ski town
Cabin
 in Windham
2 guests · 1 bedroom · 1 bath
Free WiFi/internet · Air conditioning · TV

Looking for the perfect place to call home during your trip to Windham? This Cabin offers a comfort and style with top-notch amenities, including Air conditioning, WiFi/Internet and Kitchen, and more.

vrbo logo
View deal
10.0 / 10.0
Outstanding(67 Ratings)
Cutest Cabin in Windham close to ski slope and ski town
Cabin
 in Windham
2 guests · 1 bedroom · 1 bath
Free WiFi/internet · Air conditioning · TV

Looking for a memorable stay in Windham? Our Cabin might just be what you're looking for. Enjoy amenities including Air conditioning, WiFi/Internet and Kitchen, and more during your stay.

expedia logo
View deal
10.0 / 10.0
Outstanding(3 Ratings)
Fantastic 2 family vacation home with EV charger
Chalet
 in Windham
10 guests · 4 bedrooms · 2 baths
Free WiFi/internet · Balcony/Terrace

Indulge in a peaceful retreat at Fantastic 2 family vacation home with EV charger, our elegant Chalet in Windham. Enjoy amenities including Free Parking, Balcony/Terrace and Non-smoking, and more.

booking logo
View deal
Ski, Hike & Golf: Pet-friendly Windham Retreat
Cottage
 in Windham
2 guests
Free WiFi/internet · Kitchen · Microwave

Looking for a memorable stay in Windham? Our Cottage might just be what you're looking for. Enjoy amenities including Non-smoking, Fireplace and WiFi/Internet, and more during your stay.

hotelscom logo
View deal
10.0 / 10.0
Outstanding(1 Rating)
Windham Mountain Vacation Rental ~ 3 Mi to Lifts!
Apartment
 in Windham
8 guests · 4 bedrooms · 2 baths
Free WiFi/internet · TV · Coffee/tea maker

Looking to create some memories in Windham? Look no further than our Apartment, Windham Mountain Vacation Rental ~ 3 Mi to Lifts!. Enjoy top-rated amenities including Pets allowed, Dryer and Mountain view, and more.

evolve logo
View deal
9.0 / 10.0
Outstanding(10 Ratings)
Fantastic 2 family vacation home with EV charger
House
 in Windham
10 guests · 3 bedrooms · 2 baths
WiFi/Internet · TV · Coffee/tea maker

This attractive House in Windham, $203 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
9.6 / 10.0
Outstanding(5 Ratings)
On the Mountain in Windham, New York in the Catskills
House
 in Windham
8 guests · 4 bedrooms · 3 baths
Free WiFi/internet · TV · Coffee/tea maker

This House for $203 in Windham, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

expedia logo
View deal
9.0 / 10.0
Outstanding(2 Ratings)
Ski, Hike & Golf: Pet-Friendly Windham Retreat
House
 in Windham
6 guests · 3 bedrooms · 2 baths
WiFi/Internet · TV · Coffee/tea maker

Enjoy the best of Windham in our House, Ski, Hike & Golf: Pet-Friendly Windham Retreat. A stunning property with amenities including Dryer, Fireplace and WiFi/Internet, and more.

vrbo logo
View deal
You can save with One Key
9.4 / 10.0
Outstanding(10 Ratings)
1/2 Mi to Windham Mtn: Main Street Condo
Apartment
 in Windham
4 guests · 2 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

Discover the beauty of Windham with a stay at 1/2 Mi to Windham Mtn: Main Street Condo, a top rated Apartment with amenities such as Air conditioning, Dryer and WiFi/Internet, and more.

vrbo logo
View deal
Ski, Hike & Golf: Pet-friendly Windham Retreat
Cottage
 in Windham
2 guests
Free WiFi/internet · Kitchen · Microwave

Looking for the perfect place to call home during your trip to Windham? This Cottage offers a comfort and style with top-notch amenities, including Non-smoking, Fireplace and WiFi/Internet, and more.

expedia logo
View deal
You can save with One Key
9.0 / 10.0
Outstanding(58 Ratings)
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
House
 in Windham
7 guests · 2 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

When traveling to Windham, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $192 per night.

vrbo logo
View deal
10.0 / 10.0
Outstanding(6 Ratings)
Mountain view apartment, 5mins to Ski Area!
Apartment
 in Windham
4 guests · 2 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

Enjoy the best of Windham in our Apartment, Mountain view apartment, 5mins to Ski Area!. A stunning property with amenities including Air conditioning, Dryer and Fireplace, and more.

vrbo logo
View deal
8.8 / 10.0
Excellent(58 Ratings)
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
House
 in Windham
7 guests · 2 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

Experience the best of Windham with this House available for $238. This property is equipped with amenities including Air conditioning, Balcony/Terrace and WiFi/Internet, and more.

expedia logo
View deal
Ski, Hike and Golf Pet-Friendly Windham Retreat
House
 in Windham
6 guests · 3 bedrooms · 2 baths
Free WiFi/internet

When traveling to Windham, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $209 per night.

booking logo
View deal
10.0 / 10.0
Outstanding(10 Ratings)
Newly Built 1200sq ft Guest House 4min to Ski & Hiking
Cabin
 in Windham
4 guests · 2 bedrooms · 1 bath
Free WiFi/internet · Air conditioning · TV

Looking to create some memories in Windham? Look no further than our Cabin, Newly Built 1200sq ft Guest House 4min to Ski & Hiking. Enjoy top-rated amenities including Air conditioning, Dryer and Fireplace, and more.

vrbo logo
View deal
9.8 / 10.0
Outstanding(41 Ratings)
Red Fox Townhouse & Alpine hot tub 1 minute to ski slope, bars & ski town
House
 in Windham
6 guests · 3 bedrooms · 2 baths

Indulge in a peaceful retreat at Red Fox Townhouse & Alpine hot tub 1 minute to ski slope, bars & ski town , our elegant House in Windham. Enjoy amenities including Non-smoking, and more.

vrbo logo
View deal
10.0 / 10.0
Outstanding(6 Ratings)
Mountain view apartment, 5mins to Ski Area!
Apartment
 in Windham
4 guests · 2 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

This inviting Apartment in Windham can fit your needs for many types of vacations, at $200 per night.

expedia logo
View deal
10.0 / 10.0
Outstanding(2 Ratings)
Panoramic views four minutes to Windham Mountain skiing.
House
 in Windham
10 guests · 3 bedrooms · 2 baths

Are you ready to indulge in a relaxing getaway? Our House in Windham has everything you need for a rejuvenating stay. Treat yourself to Panoramic views four minutes to Windham Mountain skiing.'s exceptional amenities, such as No pets allowed, Family friendly and Non-smoking.

vrbo logo
View deal
10.0 / 10.0
Outstanding(10 Ratings)
Newly Built 1200sq ft Guest House 4min to Ski & Hiking
Cabin
 in Windham
4 guests · 2 bedrooms · 1 bath
Free WiFi/internet · Air conditioning · TV

Business stays, family stays, couples stay, getaway vacation, and rental in Windham at Newly Built 1200sq ft Guest House 4min to Ski & Hiking for $281 for your next trip.

expedia logo
View deal
You can save with One Key
9.8 / 10.0
Outstanding(12 Ratings)
Stunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna
House
 in Windham
10 guests · 5 bedrooms · 3 baths
Free WiFi/internet · Air conditioning · Pool

Soak up the beauty of Windham in our House, Stunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna. With a range of amenities such as Air conditioning, Balcony/Terrace and Dryer, you'll feel right at home.

vrbo logo
View deal
10.0 / 10.0
Outstanding(1 Rating)
Stunning Chalet style home with 8 Person Hot Tub, Fire pit & Sauna & steam rm.
House
 in Windham
10 guests · 5 bedrooms · 3 baths

Looking for a House in Windham, this House for $807 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

vrbo logo
View deal
10.0 / 10.0
Outstanding(41 Ratings)
Red Fox Townhouse & Alpine hot tub 1 minute to ski slope, bars & ski town
House
 in Windham
6 guests · 3 bedrooms · 2 baths

Looking to create some memories in Windham? Look no further than our House, Red Fox Townhouse & Alpine hot tub 1 minute to ski slope, bars & ski town . Enjoy top-rated amenities including Non-smoking, and more.

expedia logo
View deal
10.0 / 10.0
Outstanding(8 Ratings)
Beautiful Windham Chalet 2 minutes to the Mountain
Chalet
 in Windham
11 guests · 4 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · Balcony/Terrace

Discover the beauty of Windham with a stay at Beautiful Windham Chalet 2 minutes to the Mountain, a top rated Chalet with amenities such as Free Parking, Pets allowed and Golf course (within 2 mi), and more.

booking logo
View deal
You can save with One Key
9.0 / 10.0
Outstanding(2 Ratings)
In the Heart of Windham - Best Location
House
 in Windham
13 guests · 5 bedrooms · 3 baths

This House in Windham, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

vrbo logo
View deal
9.9 / 10.0
Outstanding(77 Ratings)
Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too.
House
 in Windham
10 guests · 3 bedrooms · 2 baths
WiFi/Internet · TV · Coffee/tea maker

Looking for the perfect place to call home during your trip to Windham? This House offers a comfort and style with top-notch amenities, including Dryer, Fireplace and WiFi/Internet, and more.

vrbo logo
View deal
9.0 / 10.0
Outstanding(10 Ratings)
Fantastic 2 family vacation home with EV charger
House
 in Windham
10 guests · 3 bedrooms · 2 baths
WiFi/Internet · TV · Coffee/tea maker

Looking for a House in Windham, this House for $254 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

expedia logo
View deal
10.0 / 10.0
Outstanding(28 Ratings)
Windham Private heated indoor pool.
House
 in Windham
12 guests · 5 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · Pool

This attractive House in Windham, $1,281 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
10.0 / 10.0
Outstanding(3 Ratings)
Beautiful Windham Chalet 2 minutes to Town and the Mountain
Chalet
 in Windham
11 guests · 4 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

Chalet in Windham, for $436 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

vrbo logo
View deal
10.0 / 10.0
Outstanding(3 Ratings)
Beautiful Windham Chalet 2 minutes to Town and the Mountain
Chalet
 in Windham
11 guests · 4 bedrooms · 2 baths
Free WiFi/internet · Air conditioning · TV

This attractive Chalet in Windham, $436 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

expedia logo
View deal
You can save with One Key
9.6 / 10.0
Outstanding(5 Ratings)
On the Mountain in Windham, New York in the Catskills
House
 in Windham
8 guests · 4 bedrooms · 3 baths
Free WiFi/internet · TV · Coffee/tea maker

The best choice in Windham for House, for $156 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal