Family-friendly vacation 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, 130 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.

KitchenIndoor spacesBathroom

4.99 out of 5 average rating, 152 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!

Indoor spacesKitchenWalkability

4.98 out of 5 average rating, 130 reviews

The modern cabin is illuminated by string lights, creating a warm ambiance against the dark backdrop of surrounding trees at night. The deck extends outward, providing a welcoming entrance, while large windows hint at the interior’s cozy atmosphere.

Cabin in Red Hook

Design-Forward Riverfront Cabin on 120 Acres

Far from the road, a tranquil modern cabin sits directly above a state-stocked fly-fishing and tubing river - an intimate, private escape under two hours from NYC. Set on a 120-acre property, with access to trails, river swimming, and a private cabin beach, you’ll feel completely secluded while still being 10–30 minutes from Red Hook, Rhinebeck, Hudson, and Kingston. Radiant floors, a Swedish composting toilet, Tesla Powered, w/ 500 Mbps fiber internet make it easy to unplug without sacrificing.

FamilyIndoor spacesDecor

4.99 out of 5 average rating, 134 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 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee 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 an exciting, romantic, unique experience but can accommodate a 3rd person.

FamilyIndoor spacesBathroom

An open-concept space features wooden beams and large windows, filling the area with natural light. A dining table with six chairs is positioned centrally. A cozy seating area includes a sofa and armchair, while a staircase leads to the loft bedroom above.

4.99 out of 5 average rating, 181 reviews

Fabulous Lemon Cottage in Rhinebeck, NY

This cozy, clean, and light-filled cottage with its bedroom loft provides a perfect getaway anytime of the year. When you do venture out, you're in the heart of it all; only a few miles from Rhinebeck village, but also close to Red Hook, Bard, Kingston, Woodstock, Hudson, etc. Use our guidebook to explore the area, or choose to stay in at this quiet, private cottage with views of the woods. LGBTQIA+ friendly. All people from all cultures and backgrounds, without exception, are welcome.

Indoor spacesFamilyCleanliness

4.99 out of 5 average rating, 148 reviews

A bright living area is designed with a gray sectional sofa and a coffee table. A vase of fresh flowers is placed at the center. Decorative oars and a scenic image adorn the walls, while natural light streams in through the front door.

Guesthouse in Rhinebeck

Country Suite Near Omega Institute & Rhinebeck

We designed our guesthouse with the comfort seeking guest in mind. Enjoy our comfy plush beds, soft bed linens, luxurious towels, and complimentary bath amenities for your ultimate getaway. Complimentary snack and beverage selections are also provided in our efficient kitchenette (no stove) which can accommodate light meals. Our 2nd floor guesthouse offers ductless HVAC to provide the ultimate comfort AC or heating as needed. Many guests comment on our relentless pursuit of cleanliness.

FamilyKitchenWalkability

The exterior of the guest house displays a blue wooden façade with multiple windows. A wooden deck, equipped with a couple of white chairs, extends from the house. Surrounding greenery and a grassy area complement the inviting outdoor space.

4.98 out of 5 average rating, 110 reviews

Rhinebeck Guest House, 5 min. from town, King Bed!

Lovely Rhinebeck Guest House features large bedroom with king-size memory foam bed, large living/dining room with piano, full bath and kitchen. Lots of windows and light, plus a perfect deck for drinks overlooking the pond at sunset, or enjoying coffee/tea in the AM. Property adjoins beautiful 75-acre Burger Hill Park, all 5 minutes to Rhinebeck Village! 20 minutes to Kingston, 30 minutes to Millbrook, and 40 minutes to Hudson. Kitchen has full cooking pot/pans/knives etc. supplies

Indoor spacesKitchenParks

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.

4.95 out of 5 average rating, 300 reviews

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

FamilyKitchenHiking

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, 193 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.

FamilyIndoor spacesAmenities

4.98 out of 5 average rating, 745 reviews

Cottage in Red Hook

bright serene + spacious barn @barn and bike

a bright serene space built by us on the property we live on. we are in - what we think - is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes all around. 6 quaint towns are within 10-25 minutes drive. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking (no cats) • we look forward to having you here!

KitchenIndoor spacesSolo travel

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.

4.96 out of 5 average rating, 216 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.

KitchenIndoor spacesCondition

4.94 out of 5 average rating, 178 reviews

Apartment 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!

KitchenFamilyValue

Popular amenities for Rhinebeck family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

A cabin nestled among tall trees is gently illuminated at dusk. Soft light streams through the open sliding door, revealing a cozy sleeping area with a person resting on a bed. The surrounding forest is lush with greenery, enhancing the serene atmosphere.

Cabin in Saugerties

4.86 out of 5 average rating, 349 reviews

40-Foot Container Cabin in the Catskills

Indoor spacesKitchenLocation

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.

4.91 out of 5 average rating, 265 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

KitchenFamilyLocation

4.98 out of 5 average rating, 545 reviews

Home in New Paltz

midcentury mod * POOL * walk out trail R2R/Mohonk

Indoor spacesKitchenLong stay

4.99 out of 5 average rating, 122 reviews

Guesthouse in Hurley

Cozy Hillside Hideaway with Hot Tub

FamilyKitchenOutdoor spaces

5 out of 5 average rating, 115 reviews

A spacious living area is framed by rustic wooden pillars, featuring a large tan sofa and two green armchairs. A wooden coffee table rests on a light rug, with natural light streaming through a wide window adorned with sheer curtains.

Farm stay in Germantown

Nordic modern getaway on an Alpaca Farm

FamilyKitchenHospitality

Superhost

Home in Hurley

4.93 out of 5 average rating, 275 reviews

Hot tub with stunning views, 5 min to Woodstock

FamilyIndoor spacesOutdoor spaces

4.99 out of 5 average rating, 103 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

KitchenFamilyBathroom

4.93 out of 5 average rating, 106 reviews

The cabin's exterior is framed by lush greenery, featuring large windows that invite natural light. A deck extends from the side, offering a seamless connection to the surrounding woods. The dark wooden siding complements the serene outdoor environment.

Cabin in Red Hook

Secluded Cabin in Woods With Hot Tub

FamilyIndoor spacesAir conditioning

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 394 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

Scandinavian Cottage/Mountain Views/Fire pit

FamilyKitchenGrill

4.95 out of 5 average rating, 366 reviews

A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.

Home in Kingston

Hudson Valley Hygge House~ comfort in the country!

KitchenIndoor spacesDecor

4.99 out of 5 average rating, 371 reviews

A cozy living area is highlighted by two wooden chairs positioned around a central rug. A gas fireplace provides warmth, with shelves filled with books flanking the fireplace. Soft light filters in through large windows, illuminating the space.

Home in Germantown

Private Hudson Valley Loft on 200 Acre Horse Farm

FamilyKitchenCheck-in

4.96 out of 5 average rating, 391 reviews

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

Indoor spacesKitchenValue

4.96 out of 5 average rating, 155 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

Nature Retreat with Pond Views and Fire Pit

FamilyKitchenDecor

4.98 out of 5 average rating, 115 reviews

A cozy living space features a modern gas fireplace centrally placed against a white brick wall. Two stylish chairs with black woven seats are positioned beside the fireplace, while a natural wood table adds warmth. A patterned rug enhances the inviting atmosphere of the room.

Cottage in Red Hook

Creekside Cottage | The Fitz House Red Hook NY

FamilyIndoor spacesBathroom

4.97 out of 5 average rating, 166 reviews

An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.

Cabin in Saugerties

Luxury A-Frame Cabin in the Woods with Sauna

KitchenFamilyLocation

4.95 out of 5 average rating, 495 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

Indoor spacesFamilyOutdoor spaces

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 115 reviews

A spacious living room features a large flat-screen TV mounted on a light-colored media console. Comfortable seating includes two armchairs and a sectional sofa. Natural light fills the room through sliding glass doors, leading to a balcony overlooking the backyard, complemented by soft drapes.

Cabin in Kingston

Modern Fall Getaway in Kingston - 1.5hr from NYC

KitchenFamilyAccuracy

4.91 out of 5 average rating, 166 reviews

A serene meadow unfolds beneath a cloudy sky, with lush green grass leading into a gentle expanse of golden fields. Towering trees line the horizon, creating a natural boundary between the open landscape and the dense wooded area beyond.

Farm stay in Ulster Park

Lovely country house; stunning view

Indoor spacesFamilyHiking

4.99 out of 5 average rating, 111 reviews

A serene pool area is surrounded by lounging chairs and umbrellas, offering picturesque views of the lush landscape. The pool is framed by stone paving and overlooks rolling hills under a clear blue sky. A detached structure is visible in the background.

Guest suite in Red Hook

Panoramic Mountain Views!

KitchenIndoor spacesTV

4.92 out of 5 average rating, 111 reviews

Home in Hudson

Hudson River Sunset Getaway

KitchenIndoor spacesNearby

4.98 out of 5 average rating, 174 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

KitchenFamilySleep quality

Guesthouse 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, 201 reviews

Eco Cottage in the Woods

Indoor spacesFamilyHeating

4.96 out of 5 average rating, 306 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)

KitchenFamilyWifi

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.