Condo holiday rentals in Poughkeepsie

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Top-rated condo rentals in Poughkeepsie

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

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Top 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, 545 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
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, 352 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.

Guest favourite
Condo in Windham
4.9 out of 5 average rating, 228 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.

Guest favourite
An outdoor area features a large swimming pool surrounded by a spacious patio, equipped with multiple lounge chairs. Colorful trees with autumn foliage outline the building, which showcases a triangular roof and multiple balconies. The sky is clear, reflecting the vibrant environment.
Condo in Vernon Township
4.97 out of 5 average rating, 269 reviews

Appalachian Mt. View 1 Bdrm Suite 3rd Flr Balcony

This is a premium 3rd floor Mountain View Interior unit #310 with a private balcony. It's a full sized 1 bedroom suite approximately 600 Sq Ft. The master has a King bed, a double window, Hotel style flat screen TV with cable. There is door to the attached huge private bathroom. This unit has slope and pool views and is on the interior of the building away from the street. There is a cozy gas fireplace to warm up to after a day on the slopes or a Spring or Fall day of adventure in the area.

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, 161 reviews

Offseason pricing Cozy & walking distance to town

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

Guest favourite
A spacious bedroom features a large king bed adorned with a patterned quilt and decorative pillows. Soft lighting from a bedside lamp illuminates the area, while the en-suite bathroom is visible through an open door. Neutral tones and artwork add a touch of elegance.
Condo in Vernon Township
4.8 out of 5 average rating, 301 reviews

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

The Appalachian is a true 4 season resort overlooking Mountain Creek Ski Resort/ Waterpark and other activities such as farms, mountain biking, multiple golf courses, horseback riding, and ziplining! NEAR LEGOLAND (25 min drive) Hike the Appalachian Trails, tour the wineries and enjoy Octoberfest/Spas/Pumpkin and Apple picking. This is a true 4 season resort with a heated(in winter) year-round OUTDOOR pool/hot tubs/Suana. Ski-in/out right to the main lift from the building

Top Guest favourite
A spacious living area showcases a large sectional sofa and a coffee table on a patterned rug. Natural light fills the space through expansive glass doors that lead to an outdoor area. A spiral staircase leads to an upper level, while a dining area features a stylish chandelier.
Condo in Vernon Township
4.98 out of 5 average rating, 129 reviews

Skiiis N Tees • Mountain Views, Cozy Vibes

Skiiis N’ Tees is a 3-bedroom, 2-bath, four-season getaway where mountain views and fresh air do wonders for the soul. Just a short drive from NYC, it’s perfect for couples, families, girls weekends, or guys’ golf trips. This stylish end-unit condo sits beside a 9-hole golf course and is just 5 minutes from the slopes. Hike, sip at vineyards, or go apple picking—there’s something for everyone. One dog stays free. Pack & Play available. Come for the views and stay for the vibes!

Top Guest favourite
The kitchen features white cabinetry with glass display doors, showcasing colorful dishware. A Viking range is prominently positioned, with a polished countertop below. A wooden table with two chairs sits on a light yellow floor, illuminated by warm lighting from a nearby lamp.
Condo in Beacon
4.99 out of 5 average rating, 629 reviews

Rustic Spa Retreat

10 minute walk to Main Street (many restaurants, cafes, galleries, etc) 10 minute walk to Mt Beacon TrailHead. (It's not a hotel and not on Main Street: it's in a residential neighborhood) Cozy, small space set up for a couple (or solo traveler) looking for a relaxing short escape from "The Real World". A couple days here really feels likes so much longer (especially if you take a steam and a jacuzzi)!

Guest favourite
Condo in Lanesville
4.89 out of 5 average rating, 149 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.

Top Guest favourite
A cozy bedroom featuring a spacious bed with white bedding and decorative pillows. Two bedside tables with lamps flank the bed, providing soft lighting. A textured wooden accent wall adds warmth to the space, complementing the neutral tones of the room.
Condo in Vernon Township
4.98 out of 5 average rating, 329 reviews

Rustic Chic Stays-Ski-In/Out! Pool, Hot Tub, Sauna

Ski, snowboard, hike, bike, or zip line - then unwind year-round in the Appalachian's heated outdoor pool, 2 hot tubs, and a barrel sauna just steps away. Located in The Appalachian, right next to Mountain Creek Resort, near Vernon Valley farms, golf, the Appalachian Trail, and Warwick, NY. 1BR/1BA • King bed + queen sofa bed • Sleeps 4

Top Guest favourite
A restful bedroom is presented with a wooden bed featuring a quilted navy coverlet. Two bedside sconces provide soft lighting. Windows allow natural light to enter, complemented by neutral walls and dark curtains. A small shelf is mounted beside the bed for convenience.
Condo in Lanesville
4.98 out of 5 average rating, 629 reviews

Ski on/Ski off Trendy Condo Hunter Mountain

Newly renovated modern condo slope-side at Hunter mountain. Come enjoy the beauty of the Catskills & winter events while staying at our cozy and stylish condo. Warm up by the electric fireplace, fix a meal and have a drink in our brand new kitchen, watch a movie, and enjoy a restful sleep in a relaxing bedroom.

Popular amenities for Poughkeepsie condo rentals

Quick stats about condo rentals in Poughkeepsie

  • Nightly prices starting at

    Poughkeepsie holiday rentals start at $199 NZD per night before taxes and fees

  • Verified guest reviews

    Over 350 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Poughkeepsie rentals

  • 5 Average rating

    Poughkeepsie stays are highly rated by guests—averaging 5 out of 5!

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