Location

Dates

Guests

Vacation rentals in Windham, New York, United States

Bedroom - 1 full bed

AC, TV, basic cable, wifi

Catskill Getaway - Ski Windham

Desk, Dining area / kitchenette view from the bedroom

Catskill Getaway - Ski Windham

Catskill Getaway - Ski Windham

1 bedroom·1 bath

Windham • New York

5(52 reviews)

$260.82 USD total for 3 nights

Sep 7 – 10, 2026

Birch ladder to loft, star skylight, moon window, bedroom behind the birch wall

Table and chairs, retro fridge and microwave, bay window, love seat, birch sink

Retro Fridge, microwave, coffee maker, electric water boiling kettle

Retro fridge and microwave, custom built birch sink, coffee maker, kettle

View of the custom built sink, love seat, barn style door, two stars skylights

Domeo - Romantic Magical Dome

1 bedroom·1 bath

Windham • New York

4.89(161 reviews)

$438.88 USD total for 3 nights

Sep 7 – 10, 2026

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

4 bedrooms·3 baths

Windham • New York

4.94(18 reviews)

$1,570.00 USD total for 3 nights

Sep 7 – 10, 2026

Hilltop Horizons

Hilltop Horizons

Hilltop Horizons

Hilltop Horizons

Hilltop Horizons

Hilltop Horizons

6 bedrooms·5 baths

Cornwallville • New York

$1,785.40 USD total for 3 nights

Sep 7 – 10, 2026

Enjoy the cozy living room decorated for the holidays.

open dining room

Dog friendly/Generator/ Level 2 EV charger image 3

Fire pit in the backyard

Second bedroom on the second floor with king bed.

Dog friendly/Generator/ Level 2 EV charger

3 bedrooms·2 baths

Lanesville • New York

4.93(94 reviews)

$1,227.84 USD total for 3 nights

Sep 7 – 10, 2026

Villa Gran Sasso

Villa Gran Sasso

Villa Gran Sasso

Villa Gran Sasso

Villa Gran Sasso

Villa Gran Sasso

4 bedrooms·3 baths

Hunter • New York

5(106 reviews)

$1,140.00 USD total for 3 nights

Sep 7 – 10, 2026

Enjoy a private, secluded spot away from the hustle and bustle, tucked amongst the trees and mountains. Experience the country life!

Enjoy a nice cup of coffee on the balcony after a peaceful slumber while you listen to the sounds of nature (no sirens or constant construction here!).

Picture yourself spending a perfect evening in the backyard—relaxing in the barrel sauna, sharing a meal with friends at the dining table (seats 8) under charming bistro lights, and unwinding by the firepit as the stars come out. Perfect night!

Sink into your leather couch after a day of exploring the beauty of the Catkills. Your open concept living and dining space is perfect for relaxing with friends and family, connecting and making memories.

How lovely to enjoy a hot tub soak as a family - perfect when the weather starts to turn a bit brisk on fall days. Kids will want to get off the slopes and return to their private hot tub after a busy day of skiing!

Scandi A-Frame w/Hot Tub & Sauna

3 bedrooms·2 baths

Prattsville • New York

5(103 reviews)

$1,356.00 USD total for 3 nights

Sep 13 – 16, 2026

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

1 bedroom·1 bath

Prattsville • New York

5(34 reviews)

$260.82 USD total for 3 nights

Sep 7 – 10, 2026

Dining and kitchen area, view to bedroom 1

View to the dining and living room area from bedroom 1

Bedroom 1(included when renting for up to 3 guests). Queen and single bed

Bedroom 1 (queen bed)

Catskill Cottage - 2 bedroom by Windham and Hunter

2 bedrooms·1 bath

Prattsville • New York

4.9(30 reviews)

$289.80 USD total for 3 nights

Sep 7 – 10, 2026

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

3 bedrooms·3 baths

Greene County • New York

$258 – $740/ night(excl. fees & taxes)

The view from the south field. Many deer cross this field into the forest. They also like to eat from the apples that fall from the nearby trees.

The view of cabin in the surrounding field. Taken from the dirt road. The water tank is where the rain is stored for the eco-bath tub.

The most fascinating mountain valley view from our secluded dirt road. Tiny home sits 1600 feet above sea level.

As you walk in the front door. Queen bed to the right, wall of windows to the left. Back of the house find bath tub, eating nook area, counter top with sink. All while inhaling the sweet smell of cedar wood walls.

Bath tub closes Sept 18.

The grill in a small stone patio area with picnic table and chairs.

Cozy, mountain top off-grid glamp

1 bedroom·1 bath

Preston-Potter Hollow • New York

4.92(84 reviews)

$300.00 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

The A-frame nestled in our thick forest.

The back deck with 2 zero gravity lounge chairs.

Entrance to the A-frame. Sink station on the left.

Cooking and hang out area under the deck. Stays dry and provides shade. Coleman mini propane stove.

Make your way from the top deck to the cooking and hang out area below.

A-frame sleeps 3 - Queen + single foam mattress

1 bedroom·1 bath

Preston-Potter Hollow • New York

5(2 reviews)

$300.00 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

A room with a VIEW!

Main building is on the left, the smaller building to right is going to be a bath house, but this part is not yet complete.

The tinted glass area is the outdoor tub (CLOSED FOR WINTER) , and picnic table and chairs to the right.

A look from above. The blue cabin at the bottom is where you will stay.

The bigger white house on the right is where owners live. The buildings are separated by 150 feet.

View from your tiny deck with tiny lounge chairs.

Stargazer Glamp, Wi-Fi, Heat, Outdoor Eco Bath Tub

1 bedroom·0 baths

Preston-Potter Hollow • New York

4.97(68 reviews)

$339.00 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

The rustic and charmingly simple Sun Barn.

A view above the Sun Barn and the great view you have from the many windows.

Real photo taken at night by a previous guest.

Wood stove (we supply all the firewood), eating table and chairs.

The Sun Barn Glamp High in the Catskill Mountains

The Sun Barn Glamp High in the Catskill Mountains

1 bedroom·1 bath

Preston-Potter Hollow • New York

4.94(155 reviews)

$363.00 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

Geodesic Dome Glamping in the Catskills

Geodesic Dome Glamping in the Catskills

Geodesic Dome Glamping in the Catskills

Geodesic Dome Glamping in the Catskills

Geodesic Dome Glamping in the Catskills

Geodesic Dome Glamping in the Catskills

1 bedroom·1 bath

Gilboa • New York

$501.20 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

Glamp Under Stars in the Heart of the Catskills

Glamp Under Stars in the Heart of the Catskills

Glamp Under Stars in the Heart of the Catskills

Glamp Under Stars in the Heart of the Catskills

Glamp Under Stars in the Heart of the Catskills

Glamp Under Stars in the Heart of the Catskills

1 bedroom·1 bath

Gilboa • New York

5(2 reviews)

$501.20 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

1 bedroom·1 bath

Gilboa • New York

$501.20 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

Luxury Dome Glamping in the Heart of the Catskills

1 bedroom·1 bath

Gilboa • New York

$501.20 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

1st Floor Kitchen/Dining/Living Room

3BR Mountain Getaway in the Heart of the Catskills

3BR Mountain Getaway in the Heart of the Catskills

3BR Mountain Getaway in the Heart of the Catskills

3BR Mountain Getaway in the Heart of the Catskills

3 bedrooms·2 baths

Shandaken • New York

$930.00 USD total for 3 nights

Sep 7 – 10, 2026

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

3 bedrooms·2 baths

Catskill • New York

5(14 reviews)

$1,400.00 USD total for 3 nights

Sep 7 – 10, 2026

Modern Mountain Retreat

Front View of house, Photo by: Bertrand Cavalier

Living Room, Photo by: Bertrand Cavalier

Living room, vie of back deck, Photo by: Bertrand Cavalier

Dining table Photo by: Bertrand Cavalier

Modern Mountain Retreat

3 bedrooms·2 baths

Mount Tremper • New York

5(32 reviews)

$10,600.00 USD total for 30 nights

Sep 7 – Oct 7, 2026

Free cancellation

Woodstock Manor

Woodstock Manor

Woodstock Manor

Woodstock Manor

Woodstock Manor

Woodstock Manor

3 bedrooms·1 bath

Woodstock • New York

5(2 reviews)

$925.60 USD total for 3 nights

Sep 7 – 10, 2026

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

4 bedrooms·2 baths

Fleischmanns • New York

4.91(79 reviews)

$1,210.00 USD total for 3 nights

Sep 7 – 10, 2026

Dining area with a wood burning stove

Living room with Smart TV and a fireplace

Treetops Mountain House - 5 Mins to Belleayre

3 bedrooms·2 baths

Arkville • New York

5(2 reviews)

$930.00 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation