House holiday rentals in Rhinebeck

4.98 out of 5 average rating, 126 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.

4.94 out of 5 average rating, 363 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

4.95 out of 5 average rating, 454 reviews

A spacious interior features exposed wooden beams and light-colored flooring. Large windows allow natural light to illuminate the room, highlighting comfortable seating areas and a dining table. A staircase is visible, leading to the upper level, enhancing the open and airy design.

Home in Germantown

Rustic Swedish Barn/Featured in Airbnb Magazine

Enjoy expansive views of the Catskill Mountains from this stunningly renovated Scandanavian barn. Featured in more than 10 magazines and catalogues, including AirBnB Magazine! Walk the property, with its big open fields, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

4.99 out of 5 average rating, 106 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.

A wooden bridge spans a gently flowing creek, surrounded by vibrant foliage in various autumn hues. The lush, wooded area features scattered rocks and a grassy bank, inviting exploration and relaxation in a serene natural setting.

4.92 out of 5 average rating, 253 reviews

3Br Creekside Cottage on 130 acre forest w/ trails

Creekside Cottage is an extraordinary private escape nestled against a winding creek running through the rocky gorge of an 130 acre magical historic farm. Explore miles of hiking trails through old forests, trout creeks, and a 90ft waterfall or simply relax by the fire pit while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplaces, great wifi and comfortable bedrooms with quiet workspaces- learn more on our site cascadafarm

4.97 out of 5 average rating, 103 reviews

A wooden house is set against a wooded backdrop, featuring a dark facade with large windows. An outdoor fire pit is surrounded by seating arrangements on either side. The grassy area offers a natural and open invitation to enjoy the surrounding landscape.

Home in Catskill

Modern High-end 2BR2BATH in the woods of Catskills

Modern and spacious house located in the woods, surrounded by nature will make a perfect getaway. Wide open layout with a large living room/kitchen area in the center of the house, 2 Massive suites, one on each side overlooking the woods, both with comfy king bed and private bathroom - perfect for 2 couples, and suitable for a family as well. Beautifully designed with high end finishes, white oak flooring, custom made kitchen and toll ceilings, as well as cozy fireplace for warm nights.

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.

4.98 out of 5 average rating, 129 reviews

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!

4.96 out of 5 average rating, 143 reviews

A spacious living area showcases light-colored sofas arranged around a wooden coffee table. Large windows provide views of the lush outdoors, while a patterned rug anchors the space. A chair and stylish lamps enhance the inviting atmosphere.

Home in Staatsburg

Serene Retreat with Outdoor Firepit and Pond Views

Nestled among the trees, this bright and serene home is off a quiet road just minutes outside the village of Rhinebeck. The house features lots of light, direct pond view, indoor fireplace, and renovated kitchen. We offer a great value while providing high-end amenities like luxury linens and towels, hybrid memory foam beds, and down pillows and comforters. This home sleeps eight (and up to ten with the two rollaway beds) and is the perfect getaway for a group trip or family stay.

A spacious living area is highlighted by a cozy sectional couch and a contemporary coffee table. Natural light floods in through a skylight and large windows, illuminating the brick fireplace and wooden beams on the ceiling. A wall-mounted TV is positioned for entertainment.

4.89 out of 5 average rating, 170 reviews

15% off, workcation spot, private pond, fireplace

"Pictures understate this well-appointed home. The beds were so comfortable and the pond is so tranquil!" -Kate, May '24 Newly renovated, perfect for groups of friends, couples, and families. Large (1,700+ sq. feet), quiet, 3-bedroom home 4 min to the Village and a 7-min Uber to Rhinecliff train station (2h to Penn Station). Close to hiking, skiing, grocery stores, shops and restaurants. Back yard features a tear-drop pond, BBQ, firepit, and large dining area.

4.96 out of 5 average rating, 363 reviews

A bright living space features a white sofa with light striped cushions, complemented by a wooden coffee table. A dining area with a light wood table and chairs is present. Large glass doors open to a scenic outdoor view, enhancing the open and airy ambiance.

Home in Germantown

Private Cottage/Mountain Views/Trails/Fire pit

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!

An airy room is highlighted by wooden beams and large windows that overlook greenery. A spacious bed with a patterned duvet is positioned beside a cozy bed. A round table and chairs are situated in one corner, complemented by a woven rug and a decorative basket.

4.97 out of 5 average rating, 201 reviews

Honeybug Snug near Omega Institute!

Welcome to the Honeybug Snug! Now with AIR CONDITIONING : ) The Snug is perfect for a family of 4 or 4 close friends. : ) We still have a little work to do on her and you get to watch her grow. Your comments will be taken to heart, as your comfort is our priority! We live right next door if you need anything : ) We are .9 miles for The World Renowned Omega Institute -Center for Holistic Studies. Less than 15 Minutes to Downtown Rhinebeck.

The exterior of Long Pond Cottage is featured, showcasing a charming Victorian design surrounded by lush greenery. A welcoming porch with seating invites relaxation, while vibrant flowers add a touch of color to the landscape. The tranquil setting is enhanced by the surrounding trees.

4.98 out of 5 average rating, 173 reviews

Long Pond Cottage, Country Retreat in Rhinebeck

Nestled down a quiet, country road, you’ll find this charming, idyllic retreat. Less than 15 minutes from the village of Rhinebeck, Long Pond Cottage captures the best of the Hudson Valley. This two bedroom, one bathroom Victorian sits on just under an acre of land, offering ample outdoor space to enjoy the warmer months, and is the perfect cozy spot when the weather turns colder. Self check-in at 4pm and check-out 11am. Pet friendly.

Popular amenities for Rhinebeck house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 223 reviews

An inviting living room features a spacious sectional couch adorned with patterned cushions. Natural light filters through large windows, highlighting the exposed beams and brick details. A cozy fireplace serves as a focal point, with a hanging chair positioned nearby for relaxation.

Home in Woodstock

Cozy Woodstock Retreat—Near Village & Fireplace

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

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, 139 reviews

Bluestone Escape - Where everyone is at home.

A spacious living area features a hand-built stone fireplace adorned with decorative elements. Large windows allow natural light to fill the room, which includes a dining space with a long table set for guests. Comfortable seating is positioned around the fireplace on a well-defined area rug.

4.95 out of 5 average rating, 109 reviews

MODERN FARMHOUSE in the WOODS

An aerial view captures The Evergreen retreat set on three acres, showcasing a spacious yard surrounded by trees. A heated pool is visible beside a patio area with a dining table, while a fire pit is centrally located, enhancing the outdoor experience.

4.99 out of 5 average rating, 107 reviews

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

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, 159 reviews

Upstate Modern Scandinavian Barn in the Catskills

5 out of 5 average rating, 106 reviews

A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.

Home in Taghkanic

Sunbeam Lodge: Sauna+Hot Tub, 50 Acres, ‘70s Oasis

Superhost

The exterior of the house showcases a combination of stone and brick, framed by well-kept landscaping. A mature tree offers shade in the front yard, while a pathway leads to the entrance. The roof features a peak with multiple gables.

4.8 out of 5 average rating, 114 reviews

Hudson River views with pool and hot tub

Weekly house rentals

A wooden dock extends into the calm waters of the Esopus Creek, surrounded by lush greenery. The tranquil surface of the water reflects the surrounding trees, creating a serene atmosphere. Smooth stone steps lead down to the water's edge, enhancing accessibility.

4.96 out of 5 average rating, 313 reviews

Creekside Cottage

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, 274 reviews

Beautiful farmhouse with Mountain View- HITS- AC

4.94 out of 5 average rating, 53 reviews

A modern living area features a large stone fireplace, surrounded by two coral-colored sofas and a circular wooden coffee table. Expansive windows allow natural light to fill the space, while shelves line the walls filled with books. A soft area rug enhances the cozy setting.

Home in Port Ewen

Hudson Waterfront Mid-Century Modern Home

4.94 out of 5 average rating, 231 reviews

A spacious living area features a comfortable gray sofa alongside a wooden coffee table. Shelves adorned with books and decor create an inviting atmosphere. Floor-to-ceiling windows allow natural light to illuminate the space, while a unique patterned area rug adds texture beneath.

Home in Hurley

Hot tub with stunning views, 5 min to Woodstock

A wooden dock extends over the calm water, surrounded by lush greenery. Adirondack chairs offer a relaxed seating area, providing a view of the serene reflections in the water. Ferns frame the scene, enhancing the natural setting.

4.97 out of 5 average rating, 296 reviews

Cottage on the Creek

4.92 out of 5 average rating, 130 reviews

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.

Home in Hyde Park

The Cozy Cape In Historic Hyde Park

A spacious living room features large windows allowing natural light to fill the area. A grand piano is positioned near a comfortable seating arrangement, which includes a sofa and chairs. A decorative area rug adds warmth, while framed artworks adorn the walls.

4.97 out of 5 average rating, 110 reviews

Large 2-BR apartment in historic waterfront home

4.99 out of 5 average rating, 138 reviews

An aerial view showcases a three-story chalet-style home surrounded by lush greenery. The extensive decks feature ample seating, while the structured landscaping blends seamlessly into the natural surroundings. The driveway leads to the main entrance, providing a welcoming approach.

Home in Port Ewen

River View outside Kingston w/ Hot Tub & Sauna

Private house rentals

The historic colonial farmhouse is flanked by lush greenery and flowering plants. A stone pathway leads to the inviting covered porch, where deep green columns support the upper deck. The metal roof glistens under the bright blue sky scattered with fluffy clouds, creating a peaceful country scene.

5 out of 5 average rating, 24 reviews

All-Season Rhinebeck Modernized Colonial Retreat

4.97 out of 5 average rating, 62 reviews

An open-plan living area features original wooden beams in a minimalist design. A modern fireplace is centered against a grey wall. A sectional sofa and a dining table are positioned, with ample natural light flooding through large glass windows on two sides.

Home in Hyde Park

Modern Barn w/Hot Tub, Games Room & Kid's Playset

5 out of 5 average rating, 14 reviews

An open kitchen features a large antique wood island adorned with a colorful rug and fresh produce. Natural light floods in through mullioned windows, highlighting the patterned tile floor and stylish bar stools. Vintage pendant lights add a touch of charm above the island.

Home in Pine Plains

Stunningly Designed Historical Icon w/ Hot Tub

4.98 out of 5 average rating, 83 reviews

A newly built cabin features a charming wooden exterior with warm lights illuminating the porch. The stone walkway leads to a grassy area beside the cabin, surrounded by trees. An outdoor pizza oven is visible on the patio, enhancing the inviting ambiance.

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

The living room features warm wooden floors and exposed beams, creating a cozy atmosphere. A spacious sofa is paired with a modern armchair and side table. A fireplace is flanked by shelves displaying books and decor, while a guitar rests against a wall.

4.96 out of 5 average rating, 45 reviews

Luxe Historical Style - 2 FP’s & Soaking Tub

Superhost

Home in Mount Tremper

5 out of 5 average rating, 4 reviews

Catskill Mountains Forest Nest for 2 +

5 out of 5 average rating, 82 reviews

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

Home in Accord

Accord River House

A modern house is set amidst natural surroundings, featuring large windows that offer abundant natural light. The structure is surrounded by landscaped greenery, and a stone patio extends from the home's exterior, providing potential outdoor seating areas.