Condo vacation rentals in Woodstock

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Top-rated condo rentals in Woodstock

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Guest favorite
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, 531 reviews

Hunter Mtn. Cozy Close Clean 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

Guest favorite
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, 348 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
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.
Condo in Hunter
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

Top guest favorite
Condo in Windham
4.9 out of 5 average rating, 220 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.

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
4.67 out of 5 average rating, 123 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.

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, 160 reviews

Cozy & walking distance to town *superhost!*

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

Superhost
A winter landscape reveals snow-covered trees and a distant ski mountain, with visible slopes and trails. A nearby house is partially obscured by snow, providing a cozy contrast to the white surroundings. Clouds fill the sky, creating a serene atmosphere.
Condo in Windham
4.81 out of 5 average rating, 145 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

Top guest favorite
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, 54 reviews

Gather upstate and walk to trail, restaurant, cafe

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

Superhost
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
4.89 out of 5 average rating, 99 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.

Top guest favorite
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, 99 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.

Top guest favorite
A scenic view of liftside accommodations, set against a backdrop of green hills under a partly cloudy sky. The ski lift is seen overhead, connecting the mountain to the village. The spacious lawn features well-maintained grass, with trees lining the edges.
Condo in Hunter
4.91 out of 5 average rating, 57 reviews

The best of Hunter Mtn. Ski On/Off. 2BR/2BA.

Immaculate liftside location, located in the coveted Liftside Village at the base of Hunter Mountain. This is a family and friends ski and hiking paradise. Experience all the comfort and beauty you could ask for in the very best location. Walk to ski slopes, tubing, hiking trails, base lodge and Van Winkles Restaurant. Cable, Wifi, Xbox, games, fully equipped kitchen with coffee bar and every amenity. Ask about seasonal summer rentals.

Guest favorite
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, 141 reviews

SereneCatskillsMoutainsGetawayMinutesToSkiResorts

A warm, quiet mountain hideaway where the fireplace glows, 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 couples, 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.

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