Condo holiday rentals in Woodstock

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Top-rated condo rentals in Woodstock

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Guest favourite

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

4.94 out of 5 average rating, 153 reviews

StunningViews•Bright2BR•Pool•NearFarm•Lakes•Farm

A quiet mountain hideaway where the air feels soft and clean, and the view from the deck slows your whole spirit down. This cozy 2BR retreat sits between Windham and Hunter—perfect for families, solo wanderers, and anyone craving calm. Fast WiFi, a full kitchen, and short stays on selected days make it easy to escape, breathe, rest, and reconnect with yourself. Easy drive to charming little towns - Windham, Hunter , Tannersville . Swimming pool with gorgeous views for residents and guests only.

Top Guest favourite

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.

Condo in Windham

4.95 out of 5 average rating, 40 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.

Guest favourite

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.

Condo in Hunter

4.95 out of 5 average rating, 557 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

Top Guest favourite

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

4.96 out of 5 average rating, 76 reviews

Hunter Mountain 2BR Condo - Steps to Ski Slopes!

This 2 BD, 2 level, non-smoking condo is just steps from the slopes at Hunter Mountain. Fully renovated with a full kitchen, new appliances, wash & dryer, oak hardwood floors, and 2.5 bath. 2 bedrooms upstairs and pull-out couch on ground level offer sleeping accommodations for up to 6 people. Private ski on / ski off entrance just steps away. Hunter is part of Vail Resorts and participates in the Epic pass and home to US’s longest and fastest Zipline. Great hikes, fishing, & biking in summer.

Guest favourite

A modern living area features a gray sofa adorned with patterned cushions. Two sleek black tables are positioned on a striped rug, with a small plant on one of the tables. Tall, dark curtains frame the window, allowing natural light to enter the space.

Condo in Poughkeepsie

4.97 out of 5 average rating, 377 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.

Superhost

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

4.89 out of 5 average rating, 174 reviews

walking distance to town and waterfront

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

Top Guest favourite

A spacious living area includes a large green sofa, a wooden coffee table, and a soft rug underfoot. Natural light enters through two windows, illuminating the space. A dog lounges comfortably on the rug, while stylish seating options are arranged around the table.

Condo in Kerhonkson

5 out of 5 average rating, 85 reviews

Hike Minnewaska + Walk to Rail Trail, Food, Drink

Your home base in the Kerhonkson/Accord area - walk to the O&W rail trail, Mill + Main, and Flying Goose or drive 10 mins to Minnewaska, Mohonk, and other great dining options. This sunny 3 BR, 2 BA apartment feels like a full home: private deck, fenced yard, dreamy beds, and loads of local art. You'll find custom Two Queens coffee, great games, a stocked kitchen, and fun design touches throughout. Dog-friendly, fully equipped, and in a perfect spot to explore the best of the Catskills

Guest favourite

A multi-story building features a striking red exterior with a green roof and balconies. Surrounding landscaping includes trees and shrubbery, complementing the natural landscape in the background. The setting is illuminated by soft, natural sunlight under a partly cloudy sky.

Condo in Hunter

4.87 out of 5 average rating, 115 reviews

Cozy Slope Side Retreat

Hunter Mountain Retreat nestled in the Trailside complex is steps from the slopes. During the ski season, you can walk through parking lot & ski down to get your lift ticket. The Kaatskill Mountain Club is on the opposite side of the trails where you can go for dinner or a drink at the bar. Activities include Zipline, Skyride, Disc Golf, Horseback Riding. Trailside is by far the best & most luxurious place to stay in Hunter. Our rates are very reasonable for the luxury & location.

Superhost

Condo in Windham

4.86 out of 5 average rating, 14 reviews

Cozy Mountain Condo w/ Pool

Leave your worries at home and come relax in our cozy, one bedroom condo in the heart of the Catskills. Welcome to our upstate retreat, featuring a wood burning fireplace, king size bed, record player(Bluetooth speakers), balcony overlooking the grounds / woods, tennis courts, 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 or just curl up and relax by the fireplace.

Superhost

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.

Condo in Windham

4.68 out of 5 average rating, 124 reviews

Windham Condo

This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills. The complex has a pool, tennis, pickleball & basketball 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. Your place to enjoy all the hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.

Guest favourite

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.

Condo in Hunter

4.89 out of 5 average rating, 109 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.

Guest favourite

A comfortable living area is presented with a light-colored couch and armchair. A wooden coffee table is situated in front of the seating. A television is mounted on the wall, while natural light enters through the front door and window, enhancing the warm ambiance.

Condo in Hensonville

4.86 out of 5 average rating, 91 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 :)