Condo holiday rentals in Windham

A spacious deck is furnished with a wooden table surrounded by six chairs with soft, plush coverings. Scenic views of rolling green hills and distant mountains are visible under a bright sky with scattered clouds.

4.95 out of 5 average rating, 38 reviews

Panoramic Mountain View Townhome with Hot tub

Just one minute from downtown and sacrificing none of the views of Windham Mountain. With spacious living quarters and panoramic views, the home offers a truly comfortable upstate getaway for those looking to stay close to town but still experience the beauty and tranquility of a natural setting. At night sit on the deck gazing up at the endless stars while listening to the songs of frogs in the nearby pond and the howling of coyotes in the distance or soak your tired muscles in the new hot tub.

A studio condo features a cozy sleeping area with a patchwork quilt covering a spacious bed. A TV is positioned on a wooden dresser, while a red sectional couch is adorned with various patterned pillows. Ambient light enters through a window, creating a welcoming atmosphere.

4.95 out of 5 average rating, 523 reviews

Hunter Mtn. Clean Cozy Close Condo *Great Reviews*

Village of Hunter clean, cozy studio condo featuring vintage decor. Short walk to Ski Slopes, Snowtubing, Scenic Skyride, Dolan's Lake/Beach, Pickle Ball & Basketball Courts, Schoharie Creek, Fly Fishing, Hiking, Disc Golf, Stores, Eateries & Trailways Bus Stop. Murphy bed w/ full size comfy Casper Mattress, sectional couch, kitchen, microwave, electric wood stove, dinette, full bath, WiFi, Smart TV (no cable) w/Netflix, HBOGO, Pandora. No Pets/No Smoking or vaping in or on the property. Thanks

A cozy living room area features a dark leather sofa adorned with decorative pillows. Two lamps light the space, complemented by an ornate side table and a marble coffee table. A large piece of wall art enhances the inviting atmosphere, while a rich area rug covers the wooden floor.

4.96 out of 5 average rating, 253 reviews

Mint*Cozy*Ski In/Out*Hunter Mt Condo w/Fireplace

Best Ski In/Out Location steps to Ski Lifts & Base Lodge! Immaculate, Spacious with Beautiful Views of Hunter Mnt. All Winter Activities Right there: Skiing, Snowboarding, Snow Tubing. ~Enjoy a Private Deck w/2 Lounge Chairs ~Full Kitchen ~Winter Gear Outdoor Closet ~Front Parking Pass Other Nearby Attractions: Zipline, Skyride, Kaatskill Club, Kaaterskills Falls. Top Safety & Cleanliness: -Self Check-in/out -AirFilter Unit w/UV-C Light & Ionizer -Diffuser w/Essential Oil -Deep Sanitizing

4.9 out of 5 average rating, 218 reviews

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.

4.67 out of 5 average rating, 122 reviews

Windham Condo

This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills to enjoy the great outdoors. The complex has a pool, 2 tennis courts and a fire pit. Enjoy the mountain air while working from home with dedicated Wifi. We have a well-stocked kitchen, wood-burning fireplace, and comfy deck. You are in place to enjoy all the skiing, hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.

4.9 out of 5 average rating, 157 reviews

A well-lit bedroom features a spacious bed with white linens and an accent pillow. Bright light streams in through two windows adorned with sheer curtains. A side table with a small lamp adds a touch of warmth to the inviting space.

Condo in Kingston

Cozy & walking distance to town *fall dates!*

Perfect for friends, couples, families, or solo-travelers looking for a comfortable home that’s centrally located and near some of Kingston’s best restaurants and shops! This historic two-unit home is walking distance to the waterfront and a short drive to incredible hikes and farms! *Pet-friendly (no extra fee) *Family-friendly (highchair + Pack n Play for babies, games for kids). Note: Parking onsite or arrive via Metro North to Poughkeepsie, Amtrak to Rhinebeck, or bus to Kingston

4.81 out of 5 average rating, 143 reviews

Studio 3 BEDS-SLEEP 4

Light-filled studio in downtown Windham. Beautiful mountain views from your balcony; at night gaze at the moon & stars If you want solitude, this is the place to be! Daytime, take a walk down to the river & enjoy! Walking distance to restaurants & small grocery. Studio is big, with closet, full bathroom, well-stocked coffee area with microwave and refrigerator. Maximum 3 people; 1 double & 2 twins. Check-in: From 4PM off-street parking, Free Wifi /Basic Cable /Linens/Coffee

A light-filled living area features a tan leather sofa and a glass coffee table, placed atop a patterned rug. A flat-screen television sits on a dark wooden unit. A door leads to additional space, while natural light streams in through a window.

4.57 out of 5 average rating, 54 reviews

2. Beautiful, Cozy Condo with view of Windham Mtn

Get away from the hustle and bustle of city life with a retreat to this 1-bedroom, 1-bath Windham vacation rental! The condo has room for 3 to relax and feel at home with a fully equipped kitchen. Get bundled up for a day skiing the slope of Windham Mountain, take in the views from the Five State Lookout, or plan a trip for warmer weather to hike the nearby Kaaterskill Falls Trail Head. End the day grabbing a bite to eat at a local hotspot like Zack’s Place!

A cozy bedroom features rustic wooden walls with decorative hearts. A spacious bed is dressed in light linens, accompanied by a bedside lamp and a small dresser. A guitar leans against the wall, adding a touch of character to the room.

4.89 out of 5 average rating, 98 reviews

Cozy Gem with Mountain Views

A cozy apartment located less than a mile away from premier skiing and snowboarding at Hunter Mountain. Our place is located in a lovely community that has plenty of space to enjoy some quality time with family and friends. This is our home away from home and you can experience lot of personal touches throughout the apartment such as custom wood work, family photos and seasonal decoration. We can not wait for you to enjoy the beauty of Catskill mountains.

The living area features a pull-out sofa, a woven storage ottoman, and a coffee table on a patterned rug. A kitchen island with seating is visible, alongside a black refrigerator and a wood-burning fireplace. Soft lighting creates a comfortable ambiance.

4.93 out of 5 average rating, 54 reviews

Cozy Slopeside Condo @ Hunter Mountain

Contemporary condo steps away from the slopes at Hunter Mountain! Avoid busy resort parking by staying right on the mountain. Simply walk 350 steps to the end of the road and you will be on Hunter’s Briar Patch trail (rated green for beginners). From there, you can jump on your skis and head down the mountain to access the base lodge, lifts, and everything the resort has to offer. You can even ski back to the condo for mid-day breaks and lunch!

A winding gravel path meanders through a landscape filled with autumn foliage. Tall trees display vibrant orange and yellow leaves, while golden grasses border the trail, creating a serene natural setting. The scene suggests a peaceful retreat into nature.

4.73 out of 5 average rating, 291 reviews

Autumn Retreat w/wood burning fireplace

Leave your worries at home and come relax in cozy, one bedroom condo in the heart of the Catskills. welcome to our end unit,features wood burning fireplace, king size bed, balcony overlooking the grounds and into the woods, includes 2 tennis courts, WiFi and is only minutes away from Windham and Hunter Mountain! Come enjoy all year round with hiking, mountain biking, kayaking, zip lining, snowboarding and skiing!

4.94 out of 5 average rating, 139 reviews

A spacious living area features large windows offering mountain views. A beige couch with textured cushions sits on a plush carpet. A wooden coffee table is positioned in front of the couch, complemented by a decorative wall hanging. A guitar rests on the floor beside a low bench.

Condo in East Jewett

MountainViewBrightCondo10MinToColgateLake

Sunny and spacious condo with stunning mountains view, a perfect place to disconnect from busy life . Plush and comfortable decor , fire place , plenty of board games - perfect set up for a group or a family to unwind in the mountains, gather for home cooked dinner and drinks. Spacious deck is a sweet spot to enjoy morning coffee and listen to the birds and frogs .

Popular amenities for Windham condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

A cozy bedroom is highlighted by a plaid bedspread draped over a spacious bed. A wooden nightstand with a lamp stands beside the bed, while large windows allow natural light to fill the room, offering views of the surrounding mountains.

Hunter Mtn 3BR Condo | Ski-In/Ski-Out & Spacious

A well-appointed bedroom features a spacious bed with crisp white linens, flanked by wooden bedside tables with lamps. Natural light streams through two large windows adorned with neutral curtains, offering views of the surrounding greenery.

Hunter Mountain 3BR | Family Condo with Fireplace

A cozy living room features two upholstered sofas with decorative cushions, centered around a wooden coffee table. Natural light fills the space through a large window, illuminating the neutral-toned walls and carpeted flooring. Framed art pieces add character to the inviting atmosphere.

4.44 out of 5 average rating, 9 reviews

Homey Windham Condo: Hike & Ski the Catskill Mtns!

A cozy living area features a tan sofa adorned with a light-colored throw. A small glass table sits in front, positioned on a patterned area rug. A flat-screen TV is mounted on a dark wooden cabinet. A doorway leads to a hallway with additional rooms.

3.33 out of 5 average rating, 3 reviews

Peaceful Catskills Condo w/ Deck + Mountain View!

A cluster of brown wooden condos is set against a backdrop of autumn foliage on a hillside. The buildings feature multiple balconies and large windows. Surrounding greenery includes well-maintained shrubs and trees, complementing the scenic landscape.

4.48 out of 5 average rating, 42 reviews

Hunter Mountain Condo | Walk to Lifts & Town

A spacious two-story condo features a light-colored exterior with dark shutters. Two private balconies are visible on the upper level, framed by lush grass and a clear blue sky, providing an inviting entryway to the property.

Cozy Catskill Condo - 2 Mi to Windham Mountain Ski

An open living space is shown featuring a modern dining table surrounded by four chairs. Natural light enters through skylights, illuminating the area. A wooden staircase leads to a loft, while a kitchenette is visible in the background, enhancing the inviting atmosphere.

4.25 out of 5 average rating, 8 reviews

Outdoor HotTub/Deck, Views! Luxury 2BR Suite, Loft

A welcoming living area features a sectional sofa adorned with various throw pillows, complemented by a decorative wooden coffee table. A flat-screen TV is mounted on a vibrant orange wall, with large windows allowing ample natural light. A wooden staircase leads to the lofted sleeping area.

4.33 out of 5 average rating, 3 reviews

Condo w/ Loft: 2 Mi to Windham Mountain Ski!

Pet-friendly condo rentals

A rustic bedroom features a spacious wooden bed with a patterned blanket, complemented by a decorative bench. Warm wooden paneling adorns the wall, and natural light is let in by a small window, illuminating the inviting space.

4.9 out of 5 average rating, 29 reviews

Catskills Rustic Chic 4 Bdrm w/ Wood Stove

The living area features a pair of patterned armchairs and a comfortable brown sofa, positioned around a wooden coffee table. A television is mounted on the wall, and a doorway leads to a balcony. Natural light enters through large glass doors.

4.92 out of 5 average rating, 12 reviews

Luxury 3-bedroom Condo on Windham mountain

A private outdoor hot tub is prominently featured on a spacious deck, overlooking scenic views of the Catskills. Surrounding greenery and gentle hills can be seen in the background, creating a peaceful natural setting.

4.79 out of 5 average rating, 47 reviews

Brand New Outdoor Hot Tub! 1 Bedroom Luxury Suite

A spacious living area is highlighted by a comfortable sofa adorned with various cushions. A television is mounted on an accent wall, while light wood furnishings add warmth. A loft with a ladder can be seen in the background, enhancing the room's vertical space.

4.85 out of 5 average rating, 91 reviews

3.Special long term prices - escape the CITY

A spacious sectional couch, upholstered in dark fabric, is arranged around a glass coffee table. The wall is decorated with three art pieces featuring deer antler silhouettes. Light cream curtains frame a window, and a lamp provides additional lighting in the cozy seating area.

4.8 out of 5 average rating, 15 reviews

Ski Windham Mountain ( Catskills, NY)

The two-level condo features a combination of wood and stone accents, with a prominent chimney and multiple balconies. Lush greenery surrounds the property, and mountain views are visible in the background under a clear blue sky. A pathway leads to the entrance.

4.96 out of 5 average rating, 69 reviews

Hunter Mountain 2BR Condo - Steps to Mtn /Zip line

A bright dining area features a large wooden table surrounded by six chairs. Light-colored cabinets and countertops create an inviting kitchen space. Various kitchen appliances and decorative items are displayed on shelves, contributing to the functional and spacious environment.

4.77 out of 5 average rating, 316 reviews

Hiking, fishing,mountain view condo

The living area features a cozy seating arrangement with a black sofa and a coffee table. A TV is positioned above a fireplace, while large sliding doors provide access to the deck. Decor includes ski equipment mounted on a wall and a dining table set for four.

4.83 out of 5 average rating, 29 reviews

Cozy Getaway Gem for 2 at Windham Quads.

Condo rentals with a pool

A spacious living area is illuminated by large windows showcasing mountain views. A comfortable sofa and two plaid chairs are arranged around a wooden coffee table. Warm light is provided by a standing lamp, and a flat-screen TV sits on a brick fireplace console.

Hunter Mountain 2BR Penthouse | Vaulted Ceilings

A spacious living area is furnished with a plaid armchair, a wooden coffee table, and a comfortable sofa. A dining table with four chairs faces a kitchen equipped with modern appliances. Natural light enters through the window, and light-colored walls create an open atmosphere.

Hunter Mountain 1BR Suite | Jacuzzi & Fireplace

A modern kitchen area is presented, featuring stainless steel appliances, including a refrigerator and microwave. A bar counter with three dark wooden stools provides seating. Soft lighting is emitted from pendant fixtures above, illuminating the warm wood cabinetry and granite countertops.

4.92 out of 5 average rating, 61 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

A comfortable living area showcases a sectional sofa and two armchairs arranged around a round coffee table. Natural light floods in through large windows, highlighting a TV mounted on the wall and a gas fireplace. Neutral tones and a ceiling fan create a serene ambiance.

5 out of 5 average rating, 33 reviews

5-Star Lux Condo: Ski-In/Out, Heated Pool, Hot Tub

A spacious living area is highlighted by large windows that provide views of the surrounding landscape. A modern fireplace is set against a stone feature wall, while comfortable seating options include a sectional sofa and accent chairs. A flat-screen TV is mounted above a stylish entertainment unit.

5 out of 5 average rating, 4 reviews

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

An aerial view captures the Whisper Creek condo set against a snowy mountain backdrop, with ski slopes winding down the hillside. The landscape features a mix of pine trees and winter terrain, while the luxury building connects to the scenic outdoors.

5 out of 5 average rating, 6 reviews

Luxury Ski in Ski out Condo + Amenities

A cluster of two-story condos is set against a backdrop of lush greenery. The modern structures exhibit a combination of dark and light materials, with large windows that reflect the sunny sky. Neatly trimmed landscaping enhances the welcoming exterior.

Entire condo in Hunter NY, Gorgeous area- sleeps 6

A cozy bedroom features a wooden bed and a fireplace. Natural light filters through two windows, adorned with elegant drapes. A dresser adds functionality, complemented by a mirror. A black chair provides extra seating, while soft carpet enhances comfort.