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Condo vacation rentals in Woodstock

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Top-rated condo rentals in Woodstock

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Condo in Hunter

4.96 out of 5 average rating, 497 reviews

*Great Reviews* Hunter Mtn. Clean Close Cozy Condo

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

Top guest favorite

A row of Victorian townhouses showcases an elegant architectural style, featuring detailed wooden trims and inviting porches. The image is illuminated by bright daylight, highlighting the well-maintained exteriors with a mix of brick and painted surfaces.

Condo in Poughkeepsie

4.97 out of 5 average rating, 301 reviews

Spacious and stylish entire one bedroom apartment.

Enjoy a stylish experience at this centrally-located one bedroom apartment in Poughkeepsie. Apt is located in a quiet Victorian townhouse on the 3rd floor. Entire rental unit, Parking is included for one vehicle. Located downtown. Walking distance to: Post Office, Courts, County Bldgs, Police Station, City Hall, Nesheiwat Convention Center (fka Civic Center), Poughkeepsie Grand Hotel, Walkway Over The Hudson, Bardavon Opera House, The Academy, train station, waterfront, bus depot, and more.

Top guest favorite

Lush, green mountains stretch under a clear blue sky dotted with white clouds. The scene captures the natural beauty of the surrounding landscape, with rolling hills and dense foliage creating a serene atmosphere.

Condo in Hunter

4.96 out of 5 average rating, 251 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

An icy waterfall cascades down a rocky cliff surrounded by snow-covered trees. The white and blue hues of the ice contrast with the dark rocks, while the icy terrain reflects the frosty environment. Clouds pass overhead, contributing to a serene winter landscape.

Condo in Windham

4.89 out of 5 average rating, 192 reviews

Cozy Mountain hideaway Windham, Hunter

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.

Condo in Kingston

4.92 out of 5 average rating, 143 reviews

Cozy & walking distance to cafés *spring avails*

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

A scenic view showcases rolling mountains adorned with greenery under a cloudy sky. A wooden railing is visible in the foreground, providing a sense of elevation and connection to the surrounding natural landscape, including trees and nearby buildings.

Condo in Windham

4.81 out of 5 average rating, 138 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 serene creek flows gently between lush greenery, with trees lining its banks. The clear water reflects the blue sky and clouds above, creating a sense of tranquility. Pebbles and rocks are visible along the creek bed, enhancing the natural beauty of the scene.

Condo in Windham

4.73 out of 5 average rating, 278 reviews

Summer Retreat w/ Balcony & inground Pool

Leave your worries at home and come relax in our newly renovated, 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! **POOL OPENS MEMORIAL DAY 2023!

A grassy landscape is framed by trees and distant hills under a clear blue sky. A wooden walkway leads from the porch into the open area, enhancing the connection between indoor and outdoor spaces.

Condo in Windham

4.76 out of 5 average rating, 67 reviews

4.Special long term prices - escape the City!

Get away from the hustle and bustle of city life with a retreat to this 2-bedroom, 1-bath Windham vacation rental! The condo has room for 4 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 spacious living area is showcased, featuring a comfortable couch and armchair arranged around a central coffee table. Natural light fills the room through several windows, while a plant adds a touch of greenery. A dining area with wicker chairs is visible in the corner.

Condo in Hensonville

4.88 out of 5 average rating, 72 reviews

Cozy condo in Windham - Near Everything!

Welcome to our cute & cozy condo. Located between Hunter (12 min) and Wyndham Mountain (7 min). Short drive to restaurants/shops and a few walking distance options. This 2 bedroom, 1.5 baths one-level condo is packed with amenities for you to enjoy your stay. Fully equipped kitchen in case you decide to stay in. Several ac units. Enjoy our comfy beds, open concept, board games, easy street parking…. And great hosts :)

A clear blue pool reflects the sky, surrounded by a green landscape. Two individuals are seen diving into the pool, with mountains rising in the background. Lush trees and a fence delineate the pool area, enhancing the serene outdoor setting.

Condo in Hunter

4.94 out of 5 average rating, 33 reviews

Cozy Mt. Getaway/community pool!

Fully remodeled in 2022! Conveniently located to the villages of Hunter and Tannersville, skiing, dining, shops, hiking, golf and more. The view from the community pool is positively amazing! This quiet condo is just a short walk from Scribner's Catskill Lodge, where you can savor fine dining and craft cocktails at the stylish Prospect restaurant. Enjoy the best of the Catskills from this centrally-located oasis!

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

4.97 out of 5 average rating, 122 reviews

MountainViewSunnyNearFarmLakesTrails

Sunny and spacious condo with stunning mountains view, cozy and warm 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 frog songs.

Aerial view of a snow-covered landscape showcases the slopes of Hunter Mountain in the background. A cluster of residential buildings and roads can be seen, nestled among patches of trees and snow, creating a serene winter scene.

Condo in Lanesville

4.92 out of 5 average rating, 102 reviews

Cozy Downtown Hunter Mountain Getaway

Keep it simple at my peaceful and centrally-located loft. You are at the footsteps of Hunter Mountain, right beside Dolan's Lake and a very short drive to all of Village of Hunter restaurants, bars, cafes, hikes and conveniences. You can easily walk to Hunter Mountain and the Trailways Bus line. The condo has its own wifi and 2 roku TV’s.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Woodstock condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

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.

Condo in Windham

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.

Condo in Windham

3.33 out of 5 average rating, 3 reviews

Peaceful Catskills Condo w/ Deck + Mountain View!

An inviting living area features a pool table ready for play and a cozy seating arrangement near a stone fireplace. Light fixtures with a rustic style hang from the ceiling, creating a warm ambiance. A large TV is mounted on the wall, enhancing the entertainment options.

Condo in Hunter

New place to stay

Hunter Condo Practically Ski on Ski Off

An open living area features a marble dining table surrounded by four chairs, with a modern kitchen visible in the background. A spiral staircase leads to an upper loft, while large windows and skylights illuminate the space with natural light.

Condo in Windham

4.33 out of 5 average rating, 6 reviews

Outdoor Hot Tub! Luxury 2 Bedroom Suite + Loft

A private outdoor hot tub is situated on a wooden deck, offering scenic views of rolling hills and trees. The landscape features a mix of greenery and autumn-colored foliage under a clear sky, creating a serene atmosphere.

Condo in Windham

4.68 out of 5 average rating, 41 reviews

Brand New Outdoor Hot Tub - 1 Bedroom Luxury Suite

A spacious living area features a comfortable sectional sofa and wooden coffee table, illuminated by natural light from large windows. A loft area is visible above, accessed by a sturdy staircase. A flat-screen TV is mounted on the wall, enhancing the room's functionality.

Condo in Windham

4.33 out of 5 average rating, 3 reviews

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

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.

Condo in Windham

4.51 out of 5 average rating, 45 reviews

2. Beautiful, Cozy Condo with view of Windham Mtn

A serene lake reflects the surrounding trees and sky, with gentle ripples on the water's surface. A small platform is visible in the center of the lake, framed by vibrant autumn foliage. The sun shines brightly overhead, enhancing the tranquil scene.

Condo in Hunter

4.82 out of 5 average rating, 39 reviews

Hunter Mountain Ski Retreat - Steps to Lift!

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.

Condo in Lanesville

4.89 out of 5 average rating, 28 reviews

Catskills Rustic Chic 4 Bdrm w/ Wood Stove

A inviting living area showcases a stone fireplace and wooden furniture. A rectangular dining table with chairs occupies the space, complemented by a comfortable seating arrangement. Natural light filters through large windows, highlighting a patterned area rug that adds warmth to the room.

Condo in Hunter

4.93 out of 5 average rating, 14 reviews

Condo on Hunter Mt.

A cozy living area features a leather sofa with decorative pillows and a round coffee table. Natural light enters through a window covered with sheer curtains. A flat-screen TV is positioned near an electric fireplace, while a dining table with high chairs is set against a tastefully adorned wall.

Condo in Lanesville

4.68 out of 5 average rating, 19 reviews

First-Floor Hunter Condo < 1 Mi to Slopes!

A cozy bedroom setting features a spacious bed with a patterned coverlet. A television is positioned across from a comfortable seating area with cushions. A writing desk with a lamp is placed near a window adorned with patterned curtains, allowing soft natural light to enter the room.

Private room in Saugerties

4.88 out of 5 average rating, 177 reviews

Hudson Valley Hiker’s Loft-Private Room Queen Bed

Top guest favorite

The living area features a spacious green sofa facing a wooden coffee table, surrounded by two armchairs. Natural light enters through the windows, illuminating a cozy atmosphere. A dog rests on a warm-toned area rug, while decorative elements include candles and a plant.

Condo in Kerhonkson

5 out of 5 average rating, 20 reviews

Bright & Cozy | Walk to Rail Trail

A private outdoor hot tub is prominently featured on a wooden deck, surrounded by lush greenery and a scenic mountain view. The bubbling water invites relaxation, and two wicker chairs sit nearby, offering a serene space to enjoy the natural surroundings.

Condo in Windham

4.75 out of 5 average rating, 4 reviews

*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.

Condo in Windham

4.84 out of 5 average rating, 83 reviews

3.Special long term prices - escape the CITY

Top guest favorite

The exterior of the condo is showcased, featuring a two-story structure with a combination of red siding and stone accents. Balconies with wooden railings extend from the upper levels, and a prominent stone chimney rises against a cloudy sky.

Condo in Hunter

4.95 out of 5 average rating, 60 reviews

Hunter Mountain 2BR Condo - Steps to Slopes!

Condo rentals with a pool

An outdoor swimming pool is surrounded by a chain-link fence, featuring clear blue water and several white lounge chairs positioned beside the pool. Lush green grass and trees frame the area, with a view of a red building in the background.

Condo in Hunter

4.87 out of 5 average rating, 86 reviews

Cozy Gem with Mountain Views

An outdoor heated pool is surrounded by a spacious patio, with two hot tubs nearby. Lush greenery and vibrant autumn foliage create a scenic backdrop. Multiple lounge chairs are positioned along the poolside, inviting relaxation in a serene setting.

Condo in Windham

5 out of 5 average rating, 21 reviews

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

An outdoor swimming pool is surrounded by a secure fence and shaded by tall trees. Several lounge chairs are positioned around the pool area, and blue umbrellas provide shade. Clear blue water reflects the sky above, inviting relaxation.

Condo in Windham

4.67 out of 5 average rating, 117 reviews

Windham Condo

A spacious balcony offers a view of a well-maintained pool surrounded by greenery. The landscape features a variety of trees displaying autumn colors and mountains in the distance, with clear blue skies above.

Condo in Windham

5 out of 5 average rating, 8 reviews

Luxury 3-bedroom Condo on Windham mountain

A welcoming living area features large glass doors offering views of the outdoors, with natural light enhancing the space. A comfortable seating arrangement includes a dark blue chair and a sectional sofa, while a stylish large area rug adds warmth. Decorative elements include wall art and a blooming floral arrangement.

Condo in East Jewett

4.97 out of 5 average rating, 29 reviews

Hunter & Windham: Hikes, Lakes, 2BR

An indoor pool area is showcased, featuring a large swimming pool with clear blue water. Sunlight filters through multiple windows, illuminating the space. Wooden beams and a high ceiling create a spacious atmosphere, complemented by seating options along the poolside.

Condo in Windham

4.92 out of 5 average rating, 60 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

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.

Condo in Windham

5 out of 5 average rating, 5 reviews

Luxury Ski in Ski out Condo + Amenities

Destinations to explore