Cabin holiday rentals in Windham

5 out of 5 average rating, 206 reviews

The A-frame cabin is surrounded by vibrant autumn foliage, showcasing hues of gold and orange. A welcoming red door stands out against the green exterior. A wooden deck extends from the cabin, providing an inviting entry point amidst the natural landscape.

Cabin in Margaretville

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

4.94 out of 5 average rating, 248 reviews

A warm living area is featured, showcasing wooden walls and a vaulted ceiling. Comfortable seating is arranged around a coffee table with an assortment of plants. Large windows reveal a snowy landscape, while shelves display books and decorative items.

Cabin in Maplecrest

The Cabin - Ski House near Windham

The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

4.99 out of 5 average rating, 182 reviews

The cozy cabin exterior is lit softly by string lights as dusk sets in. A fire pit surrounded by adirondack chairs occupies the grassy area in front, while large windows offer glimpses of the warm interior and the surrounding forest.

Cabin in Prattsville

Alpine Ridge - Mtn. Views, Fire Pit, Pizza Oven

Alpine Ridge is set on 3 acres of land, high up on a private road. From the house, you'll see the Bearpen Mountain Range across the valley. We designed and curated our home to be a perfect escape. Though remote, we are close to town for all the essentials: 5 mins to Prattsville, 15 mins from Windham and 25 mins from Hunter. The Catskills are abundant with hiking trails, ski slopes, quaint towns, local events, wedding venues, and farm-to-table restaurants. Follow us on IG: @alpineridgeny

A charming log cabin is viewed from above, surrounded by trees and set against a twilight sky. A wooden pathway, illuminated by string lights, leads to the cabin's entrance. A fire pit, accompanied by seating, is positioned on the lawn, enhancing the idyllic setting.

4.94 out of 5 average rating, 108 reviews

Kashmir on the lake Catskills Hunter, NY

Why Kashmir on the lake? in 2004 the house was built by a local husband and wife who were dedicated to having their grandchildren enjoy this special place in the Catskills. The family decided to move south and listed the home to rent occasionally - especially for the music festival Mountain Jam in Hunter . Robert Plant stayed in the house while performing at Mountain Jam! Enjoy Kashmir on the lake only 1 mile from the mountain and close to restaurants/shopping. *Photos by Chris & Pam Daniele*

An aerial view captures the chalet, surrounded by a lush, open green lawn. Trees line the property, providing a natural border. The distant mountains and hills are visible, with a gentle gradient of colors as sunset approaches, suggesting a serene rural setting.

4.95 out of 5 average rating, 464 reviews

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

4.97 out of 5 average rating, 128 reviews

Casa Magda - Designer Home near Hiking + Swimming

Relax and recharge at Casa Magda—a design-inspiring home on 9 acres in Windham, NY—just 2.5 hrs north of NYC! For design lovers and nature seekers, this 1980s gem has been redesigned with modern flair and offers serene solitude. Relax by the hot tub, cozy up by the fireplace with a record and lounge around the campfire to view stellar constellations and the Milky Way. Explore nearby eateries and hikes. Ski the Windham slopes within a 7 min drive, or head to Hunter in 15 mins.

4.95 out of 5 average rating, 189 reviews

The log cabin features a sloped metal roof and large windows, surrounded by trees. A spacious wooden deck with a railing offers outdoor seating options. The area is adorned with fallen leaves, enhancing the natural setting.

Cabin in Margaretville

Catskills log cabin in the sky with mountain views

Welcome to Cabin in the Sky! At 1,671 ft elevation, Cabin in the Sky is a newly renovated log cabin nestled in the mountainside with tranquil views. The home offers the perfect combination of seclusion and convenience. In the mornings/evenings, enjoy a cup of coffee or glass of wine from the private deck which overlooks pure nature (not a car, street or building in sight). During the day, take advantage of the local hiking, skiing, farmer's markets, restaurants and shopping.

4.88 out of 5 average rating, 273 reviews

An outdoor seating area is presented alongside a hot tub and a fire pit. The seating features a sectional sofa with light-colored cushions. Dividing panels with a leaf design create a sense of privacy, while surrounding trees provide a natural backdrop.

Cabin in Prattsville

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

The cabin is set in a lush green landscape, surrounded by trees. A spacious deck features outdoor seating, while a fire pit is situated within a circle of chairs, inviting gatherings. The facade displays large windows, enhancing the connection to nature.

4.95 out of 5 average rating, 157 reviews

The Creekside Cabin - 5 mins to Windham Mt!

Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

An outdoor deck area features a hot tub surrounded by a wooden railing. Two comfortable chairs and a wooden table provide a relaxing spot to enjoy the scenery. Large windows reflect a serene natural setting, enhancing the peaceful atmosphere of the cabin.

4.98 out of 5 average rating, 136 reviews

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing pond and a deck offering panoramic resort views, it's a perfect outdoor retreat. Inside, enjoy a pool table, Pac-Man arcade, and shuffleboard for endless fun. A 2-minute drive to town makes dining and shopping convenient. The cabin's modern amenities, cozy fireplace, outdoor firepit, and hot tub guarantee a comfortable and relaxing stay.

4.98 out of 5 average rating, 104 reviews

A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.

Cabin in Round Top

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. Ready to escape the ordinary? Book your stay today.

4.98 out of 5 average rating, 246 reviews

The deck features a hot tub and a seating area with comfortable wicker furniture. A grill is visible nearby. In the background, serene rolling hills are bathed in soft hues of sunset, while warm outdoor lights create a welcoming ambiance.

Cabin in Prattsville

Private Catskill Getaway | HotTub w/ Mountain View

Your perfect leaf peeping getaway to the Catskills!!! Escape the busyness of life and unwind at The Catskills Mountain House — a cozy, private cabin getaway on 8 wooded acres with breathtaking mountain views from the hot tub. Come relax, reconnect, and return home renewed! Perfect for birthdays, proposals, anniversaries, honeymoons, or just quality time together. Follow us @ thecatskillsmountainhouse for local recs

Popular amenities for cabin rentals in Windham

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cabin rentals with a hot tub

4.91 out of 5 average rating, 111 reviews

A peaceful outdoor scene features red Adirondack chairs positioned on lush green grass. The morning sun casts long shadows, illuminating the surrounding trees and the misty mountain view in the background.

Cabin in Arkville

Mountain View Hideaway

4.89 out of 5 average rating, 187 reviews

A cozy cabin is illuminated at night, surrounded by string lights that outline its exterior. A fire pit is situated in the foreground, with guests gathered around. The expansive deck is partially visible, enhancing the inviting atmosphere of the outdoor space.

Cabin in Gilboa

Catskills Retreat - hot tub, views, and dog run!

4.87 out of 5 average rating, 304 reviews

A cabin nestled among tall trees is gently illuminated at dusk. Soft light streams through the open sliding door, revealing a cozy sleeping area with a person resting on a bed. The surrounding forest is lush with greenery, enhancing the serene atmosphere.

Cabin in Saugerties

40-Foot Container Cabin in the Catskills

4.98 out of 5 average rating, 135 reviews

The log cabin features a welcoming front porch with rocking chairs and a green door. Flanking the porch are neatly trimmed evergreen shrubs. A hot tub is visible on the side, surrounded by a grassy area and stone pathways that lead to the entrance.

Cabin in Arkville

Little Log Cabin with Hot Tub

A spacious living area features a large sectional couch paired with two accent chairs, inviting relaxation. The room is illuminated by natural light filtering through multiple large windows, showcasing a serene winter landscape covered in snow. A coffee table sits at the center.

4.97 out of 5 average rating, 118 reviews

Cozy Catskill Mountain House with Pond & Hot Tub

4.95 out of 5 average rating, 173 reviews

An A-frame cabin is nestled among trees, with a metal roof and wooden deck. An outdoor fire pit, surrounded by stone, features several dark chairs arranged invitingly. The natural setting is enhanced by vibrant autumn foliage, providing a tranquil retreat atmosphere.

Cabin in Stamford

The A-Frame on Pudding Hill

A cozy outdoor fire pit area is highlighted with wooden chairs arranged in a circle around a central fire. The cabin is illuminated in the background, surrounded by lush greenery and twinkling string lights, offering an inviting atmosphere for relaxation.

4.91 out of 5 average rating, 205 reviews

QUINN HOLLOW - Hunter Mountain Cabin in the Woods | Hot Tub

4.98 out of 5 average rating, 136 reviews

A fire pit is surrounded by seating on a deck, with a sunset casting a warm glow over the landscape. A glass of red wine and a can of beverage are placed beside a plate of sliced fruit, creating an inviting atmosphere for outdoor relaxation.

Cabin in Margaretville

Retreat in the sky - Hot Tub with Panoramic Views

Pet-friendly cabin rentals

4.96 out of 5 average rating, 582 reviews

A charming cabin stands surrounded by trees, illuminated by soft string lights. A fire pit with glowing embers is positioned in front, with a charcoal grill nearby. The cabin features large windows, allowing for views of the serene wooded landscape.

Cabin in Kerhonkson

Cozy Cabin - pet friendly + near hiking

4.98 out of 5 average rating, 536 reviews

The interior features exposed wooden beams and walls, with a warm wooden floor. A cozy living area accommodates a dark sofa and a fireplace. A dining table with four chairs is positioned nearby, and large glass doors provide access to outdoor views.

Cabin in Boiceville

Winston's Place - Woodland Cozy Catskills Cabin

4.98 out of 5 average rating, 130 reviews

A modern cabin is nestled among lush greenery, showcasing a covered porch that extends from its large glass windows. A neatly manicured lawn, bordered by wood chip landscaping, leads to the wooden steps of the porch, emphasizing the tranquility of the natural surroundings.

Cabin in Saugerties

Cozy Catskills Cabin

4.97 out of 5 average rating, 140 reviews

A warm living area features a stone fireplace and a wooden ceiling with exposed beams. Large windows allow for natural light, while a cozy seating arrangement includes a leather sofa and wooden chairs. A flat-screen TV is positioned near a stacked log pile.

Cabin in West Kill

Mtn Views • Firepit • 5 Min to Hiking + Brewery

4.97 out of 5 average rating, 149 reviews

A spacious living area features a wood-paneled ceiling with four skylights, allowing natural light to brighten the room. A cozy sectional sofa offers a comfortable seating option. A stone fireplace is positioned next to a wall-mounted television, with large glass doors leading to the outdoor deck.

Cabin in Shandaken

Catskills Cedar House | cozy retreat in the woods

4.9 out of 5 average rating, 131 reviews

A modern living area features a leather sofa paired with a wooden coffee table, accented by a ceramic vase. A cozy patterned wall hanging adds texture. A dining space is visible in the background, complemented by natural light from the windows.

Cabin in Big Indian

Birch Creek House - Private & Cozy Creekside Cabin

4.88 out of 5 average rating, 402 reviews

A gentle waterfall cascades over rocky terrain, surrounded by autumn foliage in varying shades. The water flows into a clear pool, with smooth stones lining the edges. Tall trees in the background create a lush, green canopy, while fallen leaves blanket the ground.

Cabin in Rhinebeck

Sunset Bungalow-Mt views on 130acre forest & falls

4.98 out of 5 average rating, 245 reviews

A cozy living area is highlighted by wooden walls and multiple windows allowing natural light. A stone fireplace is framed by greenery and festive decor. A dining table with chairs is positioned centrally, complemented by a textured area rug that adds warmth to the space.

Cabin in Chichester

Cozy Creekside Cabin in the Catskills

Private cabin rentals

A modern living space is highlighted by large windows allowing ample natural light. A cozy sofa is positioned next to a round dining table, with colorful accents and greenery present. Exposed wooden beams add warmth to the open layout, creating a welcoming atmosphere.

4.97 out of 5 average rating, 37 reviews

Moritz -Cozy Modern with a Nice View of the Slopes

4.93 out of 5 average rating, 165 reviews

A charming cabin, constructed with dark wood, sits surrounded by lush greenery. A stone pathway leads to the front entrance, where steps are flanked by ornamental plants. The backdrop features rolling hills, showcasing a blend of nature and tranquility.

Cabin in Arkville

Dry Brook Cabin

5 out of 5 average rating, 48 reviews

The modern cabin exterior is characterized by dark wood-like siding and ample windows, allowing natural light to fill the interior. A spacious outdoor deck is fitted with lounge seating and decorative string lights, providing a welcoming space for relaxation in a wooded setting.

Cabin in Jewett

Everwylde | Stunning Retreat in the Mountains

5 out of 5 average rating, 285 reviews

A wooden porch with two rustic chairs provides a view of the expansive landscape. The sunset casts warm colors across the sky, while the horizon stretches over a wooded valley. Logs are stacked along the edge, enhancing the serene atmosphere of the setting.

Cabin in Palenville

Big Medicine Ranch-Rustic Sunrise Cabin-Catskills

5 out of 5 average rating, 15 reviews

The living area features a cozy arrangement with a gray sectional sofa and an orange armchair, inviting relaxation. A modern television is mounted above a black fireplace, which is framed by natural wood accents. Large windows allow natural light to fill the space, showcasing rustic wall textures.

Cabin in Ashland

Luxury Cabin Retreat - 7 Mins to Windham

4.99 out of 5 average rating, 380 reviews

A charming country cottage is surrounded by lush greenery and features a wooden exterior. A set of steps leads to the entryway, adorned with seasonal flowers. A sun porch is visible on the side, inviting relaxation in a natural setting.

Cabin in Kingston

How to Stay in "The Shoe"

4.97 out of 5 average rating, 653 reviews

The cottage exterior is illuminated in the evening, highlighting its wooden facade and glass double French doors. A small deck features a table with two chairs and candles, surrounded by greenery, creating a welcoming outdoor space.

Cabin in Phoenicia

Cozy Catskills Cottage on the Esopus Creek