Family-friendly holiday rentals in Rhinebeck

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

4.98 out of 5 average rating, 118 reviews

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

5 out of 5 average rating, 102 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

4.91 out of 5 average rating, 570 reviews

A living area features a comfortable sectional sofa adorned with cushions and a low wooden coffee table. Natural light fills the space through two windows, while a floor lamp provides additional illumination. The interior is accented by warm, earthy tones and wooden flooring.

Flat in Stone Ridge

Romantic Apartment in Historic Stone Ridge

Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

A functional kitchen area features gray cabinetry and a white countertop, complemented by a window allowing natural light. A small dining table with chairs is set nearby, adorned with a vase of flowers. A coffee maker and kitchenware are also visible on the counter.

4.82 out of 5 average rating, 103 reviews

Blue Cottage in Rhinebeck

* private and quit with few minutes walk to a lake ( unfortunately not for swimming). * walking trails around the property. * 5 minutes drive to the Dutchess County fairground. * 5 minutes drive to Kingston-Rhinecliff bridge. * Seven minutes drive to the village of Rhinebeck. * twenty to twenty five minutes drive to Woodstock * Twenty minutes drive to the Omega institute. * twenty to twenty five minutes drive to the Culinary Institute of America. * ten minutes drive to Bard College.

4.99 out of 5 average rating, 562 reviews

A charming cottage is framed by trees and illuminated by warm outdoor lights. A winding path with steps leads up to the entrance, showcasing cozy decorations and inviting ambiance as dusk settles over the landscape.

Cabin in Rhinebeck

Acorn Hill Cottage -A mid century farmhouse gem

No list of chores. Just relax! Now accepting dogs on a case by case basis. Must inquire PRIOR TO BOOKING. Minutes to historic Rhinebeck Village, this quaint abode makes for the perfect romantic or mind clearing get away. Located directly off Route 9 tucked in the trees. Enjoy our completely separate art filled cottage. The open 550sq/ft studio floor plan will cheerfully accommodate couples & close friends. 4 persons MAX. Best suited for adult guests as the space is not child proofed.

A wooden deck extends from the cabin, featuring a round table with two transparent chairs. The view includes a forest of bare trees under a setting sun, casting warm light across the space.

4.93 out of 5 average rating, 327 reviews

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, comfortable bedrooms & quiet workspaces- learn more at cascadafarm.com

The exterior of a charming cottage is seen, featuring a front porch with two black chairs and potted plants. Stone steps lead up to the entrance, flanked by shrubs and trees, creating a serene setting within the landscaped grounds.

4.93 out of 5 average rating, 181 reviews

Intimate Cottage on Private Estate

Bulls Head Cottage is a thoughtfully-designed retreat nestled within a 2.5 acre estate 5 minutes from Omega Institute and 10 minutes from the charming Village of Rhinebeck. The 720 square foot guest cottage is a relaxing place for up to 2 guests, offering cozy indoor and outdoor space including an office overlooking the property's pond. Enjoy quick access to hiking, shopping, fine dining and more. Under 2 hours from New York City by car or train. Pets not typically allowed.

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, 178 reviews

15% off, fireplace, workcation spot, private pond

"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.

Superhost

A charming blue house is nestled among lush green trees. A hammock is strung between two trees, while Adirondack chairs are arranged on a stone patio nearby. A small table and a grill are positioned in front of the house, complementing the serene outdoor setting.

4.87 out of 5 average rating, 214 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we use a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

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, 206 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.

4.93 out of 5 average rating, 152 reviews

A spacious studio apartment is highlighted by a large bed adorned with neutral bedding and vibrant throw pillows. A kitchenette with red accents is visible in the background, featuring modern appliances. A work bar with high chairs offers additional seating, while warm wood flooring complements the overall decor.

Flat in Rhinebeck

Hibiscus Suite - Priv. Studio - Rhinebeck Village

This modern studio apartment is ideal for a weekend retreat or remote working base. Just 17 minutes from Omega, we offer a Queen-size bed, free WiFi, and a Smart TV. The fully-equipped kitchenette and work/eating bar make meal prep and productivity easy. The bathroom features a rain shower head and Bluetooth speaker. With its own entrance and ample street parking, it ensures privacy and convenience. Give it a try – you won’t be disappointed!

The architectural design is showcased at dusk, with warm light emanating from large windows. The unique geometric structure stands amidst trees, highlighting its modern features and the surrounding natural landscape.

4.91 out of 5 average rating, 299 reviews

Architectural wonder in the woods

Unique experience, secluded. Enjoy a weekend or a few days eco-friendly retreat in an architectural, geometric masterpiece on 30 preserved acres just minutes from all that Rhinebeck and the Hudson Valley have to offer. The house is an open plan, and though it has zero bedrooms, it can sleep 4! Feel free to send us a message for any requests, we love hearing from people.

Popular amenities for Rhinebeck family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A waterfront home is shown from an elevated view, featuring an expansive deck with outdoor seating and a gazebo. Colorful kayaks are positioned along the water's edge, with lush trees showcasing autumn foliage in the background, contributing to the serene atmosphere.

4.94 out of 5 average rating, 199 reviews

Waterfront Three bedroom in Saugerties w/ Hot Tub

A modern house is surrounded by trees with colorful autumn leaves. The exterior features a wraparound deck, and snow lightly covers the ground and plants. Clear blue skies enhance the peaceful outdoor setting, creating a serene atmosphere.

4.92 out of 5 average rating, 252 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

4.92 out of 5 average rating, 338 reviews

A large, serene pool reflects the surrounding greenery and the stone facade of a historic guesthouse. Sun loungers are positioned beside the water, and well-maintained gardens and patios are visible in the backyard, inviting relaxation and outdoor enjoyment.

Guest house in Kingston

The Antique Stone House

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, 142 reviews

Bluestone Escape - Where everyone is at home.

4.96 out of 5 average rating, 837 reviews

The Treehouse is nestled among trees, elevated above a tranquil pond. Its wooden structure features large windows that provide views into the surrounding greenery, while the natural landscape is reflected in the pond's surface. The setting offers a secluded feel contrasting with the nearby wooded area.

Treehouse in Willow

Willow Treehouse - secluded, unique, romantic

4.98 out of 5 average rating, 134 reviews

The exterior of a modern cabin is showcased, featuring dark wood siding and large windows that invite natural light. A pair of black rocking chairs sits on the deck, complemented by a small metal table and logs stacked nearby. Lush green grass and scattered yellow wildflowers enhance the outdoor setting.

Cabin in Saugerties

Modern Cabin in the Woods with Hot Tub

4.99 out of 5 average rating, 197 reviews

Guest suite in Woodstock

Woodstock retreat with hot tub and deck with view

4.98 out of 5 average rating, 101 reviews

A warm and inviting living space is seen, featuring a round wooden dining table surrounded by four rustic chairs. An adobe wood-burning fireplace is visible in the background, with seating arranged nearby for relaxation. Natural light flows in through a window, enhancing the cozy atmosphere.

Home in East Jewett

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

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 117 reviews

Cabin in Elka Park

The Paradise Cabin w/ Sauna - 10 min to Hunter Mnt

4.97 out of 5 average rating, 144 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

A bright dining area features a long white table surrounded by wooden chairs. Large glass doors open to a deck with river views. Sunlight fills the space, highlighting the clean lines of the cabinetry and décor in soft, neutral tones.

4.93 out of 5 average rating, 180 reviews

Upstate Waterfront Saugerties Retreat-Near HITS

4.93 out of 5 average rating, 107 reviews

A spacious living area features a neutral-tone sectional sofa and an armchair, complemented by a wooden coffee table. A television is positioned on a white dresser. Light from a nearby window illuminates the room, which includes a decorative screen and a ceiling fan.

Guest suite in Rhinebeck

The Rhinebeck Hideaway

4.85 out of 5 average rating, 197 reviews

The exterior of a rustic cottage is presented, featuring large windows that allow natural light to fill the interior. A wooden deck leads to a glass-paned door, framed by light-colored siding and contrasting trim. Trees and greenery are visible in the background.

Flat in Salt Point

Arcady - Modern, 1br cottage

4.99 out of 5 average rating, 352 reviews

A modern tiny house is framed by lush greenery, featuring a wooden exterior and large windows that invite natural light. A spacious deck with a full-size dining table is visible, surrounded by a well-maintained landscape of plants and grass.

Tiny home in Saugerties

Modern Catskills Cabin

4.96 out of 5 average rating, 408 reviews

A spacious bedroom features a queen bed adorned with simple linens. A large wooden barn door provides entry to the adjoining room. Two comfortable chairs sit beside a sleek television stand, with natural light filtering through large windows framed by greenery.

Flat in Kingston

Dog Friendly Uptown Apt Near Stockade + Backyard

4.99 out of 5 average rating, 168 reviews

The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.

Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 227 reviews

Apartment in Windham

Hideaway Windham/Hunter Fireplace, Snow & Skiing

4.97 out of 5 average rating, 150 reviews

A modern cabin stands against a backdrop of lush greenery and mountains. Large windows invite natural light, while a deck with seating is visible in the foreground. Surrounding landscaping includes trees and shrubs, creating a serene and private outdoor space.

Cabin in Arkville

Ski & Sauna! Modern Mountain Escape

4.82 out of 5 average rating, 198 reviews

Cottage in Kingston

Cottage with Private Deck on 8 acres of Woods

4.96 out of 5 average rating, 174 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

4.95 out of 5 average rating, 157 reviews

A small red cabin is framed by lush greenery, with a welcoming porch featuring two wooden rocking chairs. Natural stone path leads to the entrance, surrounded by a forest of tall trees and soft moss-covered ground.

Cabin in New Paltz

The Little Shelter at Gunks EcoLodge

Guest house in Stanfordville

A bright living room features a sofa facing large glass doors that open to a view of the forest. A cozy armchair is situated nearby, along with a simple coffee table. A bookshelf contains various items, and a wood stove is positioned in the corner.

4.93 out of 5 average rating, 190 reviews

Eco Cottage in the Woods

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, 162 reviews

Upstate Modern Scandinavian Barn in the Catskills