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.

Indoor spacesFamilyAir conditioning

4.87 out of 5 average rating, 109 reviews

A spacious living area features large picture windows offering natural light, with a brick fireplace as a central focal point. Two chairs and a small table sit on a green rug, complemented by wooden flooring. Colorful artwork adorns the walls, enhancing the modern design.

Home in Staatsburg

Contemporary Hudson Valley home

Our home is a 1970s architectural gem located in the convenient upstate NY town of Staatsburg. It has been thoughtfully modernized and designed to encourage maximum serenity and enjoyment of both the indoor and outdoor spaces. The floating staircase, huge picture windows, expansive deck and wooded outdoor space make this home perfect for an upstate getaway - while still being close to some of the major area attractions and towns. Our historic street also features 1700s homes and a farm/brewery.

Indoor spacesFamilyAmenities

4.98 out of 5 average rating, 176 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

Named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' First Floor Open Space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer, Dryer, FridgeFreezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Decorative Fireplace, Smart TV & Cable Second floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

FamilyKitchenCondition

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, 303 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

FamilyIndoor spacesLayout

4.99 out of 5 average rating, 607 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.

Indoor spacesKitchenLayout

4.97 out of 5 average rating, 146 reviews

The exterior of the house features a curved metal roof and large glass doors, allowing natural light to fill the interior. The surrounding area includes vibrant greenery and well-maintained landscaping, with a wooden deck extending in front, providing an inviting outdoor space.

Cottage in Rhinebeck

Extra Large Rhinebeck Village Guest House

Large loft-like house located in historic Rhinebeck Village. An easy walk to fine and casual dining, shopping and the County fair grounds. The lower level has 2 huge rooms with large beds and living area in each. One side has a TV, stereo and vinyl collection, the other a kitchen area, dining table, couch, and wood burning stove. The loft (accessible by step-ladder) has 2 more beds. The bathroom (separate rooms for bathing and WC) is between the two lower level rooms. Truly a rare find!

KitchenIndoor spacesLayout

4.93 out of 5 average rating, 195 reviews

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.

Cottage in Rhinebeck

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.

FamilyKitchenSleep quality

4.94 out of 5 average rating, 181 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!

Indoor spacesFamilyWifi

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, 194 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.

Indoor spacesKitchenHiking

4.99 out of 5 average rating, 192 reviews

The exterior of the house showcases a charming two-story structure with light siding and a vibrant red front door. Lush greenery surrounds the property, complemented by a well-maintained lawn and a pathway leading to the entrance.

Cottage in Port Ewen

Swan Cottage with Expansive Hudson River Views

The Swan Cottage was built in 1923 and was fully renovated in 2020. The idyllic location, on a bluff overlooking the Hudson River, is the perfect perch to relax and get away from it all. The front porch is a nice spot to have a cup of coffee and watch the sailboats on the river, while the huge wraparound porch affords terrific views of the river as well as the forest that gives this home a feeling of being high in the tree tops.

KitchenIndoor spacesWalkability

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.

4.9 out of 5 average rating, 310 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.

FamilyIndoor spacesBackyard

The exterior of the house showcases a modern rustic design, featuring a stone and wood façade. Large picture windows reflect the surrounding nature, while an outdoor fire pit is surrounded by several Adirondack chairs on a grassy area. A dining table and chairs are positioned nearby.

5.0 out of 5 average rating, 263 reviews

Eagle Rock House

FRESH AIR • SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Eagle Rock 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.

KitchenFamilyAmenities

Popular amenities for Rhinebeck family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 149 reviews

Home in Kingston

Antique Uptown Charmer w/ Five-Star Modern Kitchen

FamilyKitchenGetting around

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, 266 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

KitchenFamilyTV

5.0 out of 5 average rating, 117 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

KitchenFamilyWalkability

Superhost

Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

Indoor spacesKitchenSleep quality

4.91 out of 5 average rating, 149 reviews

4.94 out of 5 average rating, 159 reviews

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.

Home in Saugerties

Bluestone Escape - Where everyone is at home.

KitchenFamilyHiking

4.95 out of 5 average rating, 106 reviews

A fire pit is surrounded by four wooden Adirondack chairs on a gravel circle, positioned near a serene waterfront. Lush green trees frame the scene, providing a natural backdrop to this inviting outdoor gathering space.

Home in Lake Katrine

Waterfront Cottage - Hot Tub, Kayaks and Fire Pit

FamilyKitchenGetting around

4.94 out of 5 average rating, 296 reviews

The exterior of a large farmhouse features a welcoming porch with a wooden bench and decorative elements. Lush greenery surrounds the pathway leading to the entrance, enhancing the inviting appearance of the dark wood siding and multiple windows reflecting natural light.

Home in Hudson

Livingston Farmhouse Escape with hot tub and sauna

Indoor spacesFamilyCheckout

4.98 out of 5 average rating, 128 reviews

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.

Home in Saugerties

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

KitchenFamilyCheckout

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 156 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

KitchenIndoor spacesShared spaces

4.98 out of 5 average rating, 102 reviews

A two-story house stands on a gently sloping hill, surrounded by lush green grass. The property features a large, covered porch that wraps around part of the home, offering views of the expansive yard and surrounding trees.

Home in Tivoli

Upstate Getaway btw Rhinebeck+Hudson

Indoor spacesKitchenWifi

4.95 out of 5 average rating, 370 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!

KitchenFamilyCheckout

4.91 out of 5 average rating, 117 reviews

Cabin in Kingston

Modern Getaway in Kingston - 1.5hr from NYC

FamilyIndoor spacesDecor

4.96 out of 5 average rating, 137 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

FamilyIndoor spacesRiver

4.99 out of 5 average rating, 215 reviews

Cabin in Saugerties

Timberwall Ranger Station | Your Upstate Base Camp

KitchenIndoor spacesCheck-in

4.98 out of 5 average rating, 748 reviews

Cottage in Red Hook

bright serene + spacious barn @barn and bike

KitchenIndoor spacesLayout

4.99 out of 5 average rating, 374 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

FamilyKitchenOutdoor spaces

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 128 reviews

A bright living area features large windows that invite natural light. A circular rug provides a soft contrast to the wooden flooring, and a modern sectional sofa is accompanied by two armchairs. A decorative mirror and artwork enhance the elegant ambiance.

Home in Kingston

Luxury Retreat with pool in historic Kingston

FamilyKitchenHospitality

4.93 out of 5 average rating, 124 reviews

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

Home in Saugerties

Summer Paradise - Pool, Fire-pit, Nursery!

Indoor spacesFamilyAccuracy

4.99 out of 5 average rating, 114 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!

FamilyIndoor spacesBathroom

4.9 out of 5 average rating, 140 reviews

An aerial view showcases the spacious home surrounded by trees and a manicured lawn. Outdoor seating is featured on the deck, illuminated by string lights. A fire pit area is visible, enhancing the outdoor gathering space for relaxation and socializing.

Chalet in Ruby

Enchanting Upstate Cabin w Pool, Firepit

FamilyKitchenBathroom

4.94 out of 5 average rating, 398 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

FamilyIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 172 reviews

A spacious living area features two modern armchairs with orange accent pillows facing a large picture window. The serene view of the wooded area surrounding the private pond is visible, inviting natural light into the space. A low coffee table occupies the center, complemented by a soft sofa nearby.

Cottage in Saugerties

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

KitchenIndoor spacesLayout

4.91 out of 5 average rating, 174 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

KitchenFamilyBackyard