House holiday rentals in Poughkeepsie

4.98 out of 5 average rating, 130 reviews

A modern kitchen features white cabinetry, stainless steel appliances, and a spacious island with seating. Natural light floods the area through a large window, highlighting the light wood flooring and the elegant contrast of dark accents. A green plant adds a touch of nature to the space.

Home in Staatsburg

3BR/3BA Renovated Retreat w/ Firepit By Rhinebeck

Perfect getaway for friends/families in Upstate NY! The newly renovated, spacious 3 bed/3 bath home with BBQ + firepit is just minutes from Rhinebeck + Hyde Park. Nearby attractions include hiking, breweries, kayaking, restaurants, wineries, historical sites, colleges (Marist, Vassar, Bard), golf, farms, skiing + more. 15 min drive to Metro-North & Amtrak for easy travel to/from NYC. 5 min walk to Mills Norrie State Park. 2 hr drive from NYC. 10 min drive to Rhinebeck. 25 min drive to Kingston.

The exterior of the Piersaull House is presented, featuring light beige siding and a welcoming porch with a white railing. Lush greenery surrounds the property, including tall trees and shrubs. A wooden bench is situated nearby, enhancing the outdoor space.

4.98 out of 5 average rating, 131 reviews

Cozy Historic Piersaull House - Charming & Quirky!

Piersaull House, built in 1910 by Charles Piersaull, Hyde Park's fishmonger, photographer, and bicycle repairman, features 630 sqft of quirk and charm, in the heart of the Hudson Valley. This small home lives big with living, dining and kitchen on the first floor, and 2 beds and 1 bath upstairs. Very tall people are destined to bonk their heads in an upstairs room, but will likely grin and relish the charm of this historic property. The privacy of your own house at the price of a hotel room!

4.97 out of 5 average rating, 121 reviews

An open living space features a Foster Leather sectional sofa positioned around a central coffee table. Natural light streams in from a large window, illuminating the wood-burning stove nearby. A cozy area rug adds texture to the floor, creating an inviting atmosphere.

Home in Gardiner

Mindful Escape: Theater, Trails, Wood Stove

Exhale and recharge in this luxurious space at the foot of the Shawangunk Mountains. This gem features an open-concept kitchen and living room, perfect for connecting with nature. Enjoy the high-end Foster Leather Sofa, cozy movie nights on a 120" projector screen, and a wood-burning stove for chilly evenings. Every detail, from fresh linens to a meaningful library, is thoughtfully curated. Discover hidden messages throughout the house, inviting you to explore and unwind in this serene retreat.

4.96 out of 5 average rating, 378 reviews

An open living area features a plush gray couch with decorative pillows, complemented by a cozy armchair. The wooden ceiling and walls create a warm atmosphere, while the tiled kitchen area is visible in the background. A front door offers natural light and exterior access.

Home in Kingston

This New House

Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

A bright living room features a large window inviting natural light. A cozy sofa and a stylish armchair are arranged around a wooden coffee table. A large flat-screen TV is mounted above a decorative fireplace, creating an inviting focal point for relaxation.

4.91 out of 5 average rating, 133 reviews

The Cozy Cape In Historic Hyde Park

Modern amenities meets early 20th century charm our cozy, and totally renovated space situated in the hearth of the historic town of Hyde Park and adjacent to the Hudson River. Built in the 1940s, our Cozy Cape is nestled in a quiet neighborhood off of Route 9 & is central to historic sites, shopping, parks, and dining options. Our home is also minutes by car to the Culinary Institute Of America, Walkway Over The Hudson, wineries, antique shops, Marist and Vassar colleges & Town of Rhinebeck!

4.99 out of 5 average rating, 111 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

The front entry of the house is framed by flower pots and flanked by twin windows with dark shutters. A welcome mat lies outside the dark front door, which features a decorative door handle and is set against a pale yellow exterior. An American flag gently sways in the breeze.

4.84 out of 5 average rating, 239 reviews

Village Cape Getaway

Village Cape on Albany Post Rd in the historic town of Hyde Park. Surrounded by gardens, stone walls, private parking/entry. This 2 story house offers a 1 bdrm apartment that sleeps 3 on the 2nd floor. Close to markets, shops, restaurants. 1 mi to Vanderbilt Mansion, FDR house and library. 2mi to the Culinary Institute of America. 4mi to Marist College. Hiking trails walking distance. Historic drive-in movie in town. Metro north Poughkeepsie sta 6mi south offering taxi and bus service.

4.94 out of 5 average rating, 268 reviews

A serene stream cascades over smooth rocks, surrounded by a wooded area filled with autumn leaves. A wooden bench sits nearby, offering a tranquil spot to enjoy the peaceful atmosphere. The gentle flow of water reflects the greenery of the trees.

Home in Rhinebeck

3Br Hilltop Ranch on 130acre farm w/ falls & creek

Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

The kitchen features a blend of modern and rustic elements, with white cabinets and a wooden countertop island at the center. A stainless steel refrigerator and gas stove are positioned conveniently, while three pendant lights provide illumination over the work area, enhancing functionality.

4.96 out of 5 average rating, 100 reviews

Walk Across the Hudson + Marist Vassar CIA

Charming restored turn-of-the-century home in historic City of Poughkeepsie offers ideal access to waterfront, green spaces, and biking trails. The famed Walkway Over the Hudson is a short 1/2-block walk, and the area is dotted with restaurants and local shops. The train station is ten minutes on foot, and Marist College, Vassar College, the Culinary Institute and the Medical Center are a quick drive. Explore all the Hudson Valley has to offer (arts, dining, music, outdoor adventure).

4.98 out of 5 average rating, 135 reviews

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

4.95 out of 5 average rating, 124 reviews

The Atala

The Atala is a two story 3BR/2Bath house, nestled in a quiet neighborhood close to the city's excitement and attractions. Warm up by the fireplace in the living room while watching your favorite shows on a 75” flat screen TV, or brew a cup of coffee in our convenient coffee bar. Enjoy three inviting bedrooms with air conditioning/heating and a fully equipped kitchen. Our backyard with furniture, fire pit, and gas grill, is perfect for relaxing with family and friends.

A light-filled living room features a comfortable seating arrangement with beige and blue accents. A decorative fireplace is positioned below a mounted TV, showcasing a scenic view. Large windows allow natural light to brighten the space, complemented by a patterned rug and a round coffee table.

4.96 out of 5 average rating, 342 reviews

4BR|2Bath|King Beds|Walk to Marist|CIA|Pet|Parking

This home is located in the Mid Hudson Valley -just steps away from Marist U, The entrance to Walkway Over the Hudson, MHR Hospital and a 2mi ride to the CIA! Equipped with a full kitchen, king beds, 2 full baths, Roku TV, private parking & spacious backyard- perfect for grilling or cozying up next to the fire pit. Make this cheerful house your home base as you explore all the wonders of the Hudson Valley! We are a small dog friendly! (15 lbs or less)

Popular amenities for house rentals in Poughkeepsie

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 514 reviews

midcentury mod * HOT TUB * walk out trail 2 mohonk

Superhost

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

4.83 out of 5 average rating, 111 reviews

Entire Home (private pool), Event Friendly

The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.

4.94 out of 5 average rating, 140 reviews

Bluestone Escape - Where everyone is at home.

4.96 out of 5 average rating, 172 reviews

A spacious cedar hot tub sits peacefully outdoors, surrounded by a natural setting of trees and open space. Bubbles rise from the water, creating a relaxing atmosphere. Clear blue skies are visible above, enhancing the tranquil environment.

Home in Hudson

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

4.88 out of 5 average rating, 191 reviews

Scenic River View Escape | New Paltz

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

5 out of 5 average rating, 160 reviews

Upstate Modern Scandinavian Barn in the Catskills

The charming home is surrounded by lush greenery and features a welcoming front porch. Its exterior showcases a combination of wood siding and a metal roof, complemented by large windows that invite natural light. A pathway leads to the red front door amidst well-maintained landscaping.

4.92 out of 5 average rating, 110 reviews

Warm & Comfortable Family Stay nr Woodstock

4.96 out of 5 average rating, 291 reviews

A wooden lounge chair is positioned near a serene saltwater pool, surrounded by lush greenery. The pool's clear water reflects the inviting outdoor space, which is complemented by concrete paving and a manicured lawn.

Home in Cottekill

Peace & Privacy - High Falls (hot tub & salt pool)

Weekly house rentals

The exterior of the retro-chic house is illuminated at night, highlighting its warm wooden facade and angular architectural lines. The outdoor patio features a stone pathway, dining area, and two blue chairs, creating a welcoming space surrounded by trees.

4.97 out of 5 average rating, 254 reviews

Retro-Chic Cabin in Woodstock - Sauna

An outdoor area features a wooden hot tub and a grill, set against the background of a dark gray cabin and a blue house. Decking surrounds the hot tub, and a patio provides additional relaxation space. Tree branches are visible along the perimeter.

4.94 out of 5 average rating, 119 reviews

New Paltz Zen Wellness Cabin + Hot Tub /Fireplace

Superhost

The airy living space features a comfortable gray sofa paired with a leather lounge chair, complemented by a soft white pouf. Large windows provide natural light and a view of the surrounding greenery. A sleek wood stove adds a modern touch to the relaxed atmosphere.

Home in High Falls

4.9 out of 5 average rating, 115 reviews

Mossy Moody Cabin in High Falls, NY

4.76 out of 5 average rating, 188 reviews

A spacious living area features a light-colored couch alongside a round coffee table. Sliding doors provide separation from the sleeping area, which contains a large bed dressed in light linens. Natural light filters through the nearby windows, illuminating the warm wooden floor.

Home in Milton

Historic 1 BR Family Home Near Buttermilk Falls

4.92 out of 5 average rating, 104 reviews

Beautiful, Fun, Spacious 5 Acre Family Retreat

The farmhouse exterior features a spacious porch with steps leading down to a grassy area. The surrounding landscape includes trees, providing a natural setting. Large windows allow for plenty of natural light, enhancing the home's open feel.

4.92 out of 5 average rating, 281 reviews

Beautiful farmhouse with Mountain View- HITS- AC

The living room features large windows offering views of the river and surrounding trees. A blue sofa and a beige tufted couch are positioned around a wooden coffee table, while a colorful area rug adds warmth to the space. Bright yellow walls enhance the inviting atmosphere.

4.94 out of 5 average rating, 334 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

4.94 out of 5 average rating, 192 reviews

A modern, single-story home is situated among tall trees, featuring a welcoming front porch with two blue chairs. A charcoal grill is positioned nearby on a gravel path, and ample greenery surrounds the property, creating a serene outdoor environment.

Home in Kerhonkson

Shawangunk House

Private house rentals

4.98 out of 5 average rating, 54 reviews

Private retreat on 12 acres w hot tub and bbq

5 out of 5 average rating, 12 reviews

The exterior of a modern Scandinavian cabin is showcased, featuring dark wood siding and large windows framed by green foliage. A concrete path leads to the entrance, inviting guests to explore the serene surroundings.

Home in Ulster Park

Old Post Cabin

A modern kitchen is presented, featuring dark cabinetry, stainless steel appliances, and light countertops. A wooden dining table with black chairs is situated in the center, while a comfortable living space is visible on the right, highlighted by a leather sofa and a stylish lamp.

5 out of 5 average rating, 19 reviews

Hudson Valley Retreat I Foliage + Orchards

4.84 out of 5 average rating, 77 reviews

An entertainment area is displayed with a wall-mounted television above a sleek console. A decorative lamp and a wooden sculpture add warmth. A serving tray with glasses and an ice bucket is positioned nearby, along with a board game for casual gatherings.

Home in Highland

Hudson Valley Boutique Airb&b

4.93 out of 5 average rating, 59 reviews

3000 sq ft Poughkeepsie home with chef's kitchen

4.84 out of 5 average rating, 25 reviews

A cozy seating area features two plush armchairs facing large glass doors that open to a private deck. Scenic views of the Hudson River and a nearby bridge are visible beyond the deck, framed by a light curtain drape.

Home in Highland

Hudson Escape W/ Hot Tub + Bridge View

Home in Mount Carmel Historic District

4.88 out of 5 average rating, 49 reviews

Charming Townhouse in Historic District

Superhost

A serene outdoor space features a gravel patio with a circular fire pit surrounded by four comfortable chairs. A pink-striped umbrella shades a nearby seating area, adding a pop of color. Lush greenery and mature trees frame the yard, providing a secluded feel.