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, 131 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.

FamilyIndoor spacesCleanliness

4.98 out of 5 average rating, 178 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.

FamilyKitchenHiking

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, 304 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

KitchenFamilyHiking

4.99 out of 5 average rating, 608 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 spacesKitchenNearby

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!

FamilyKitchenGrill

4.98 out of 5 average rating, 113 reviews

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.

Cottage in Rhinebeck

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 spacesFamilyCleanliness

4.93 out of 5 average rating, 196 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.

Indoor spacesFamilyLayout

4.98 out of 5 average rating, 104 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

Our home is located on an unpaved, private road in a quiet area and features an in-ground, heated, saltwater pool open between Memorial Day and Late September. In 2026, the pool will be available for bookings 5/22 - 9/18. A quiet and private getaway in the Hudson Valley and convenient to many popular activities. NOTE: For bookings during pool season, guests will be asked to review and agree to the safety rules relating to the pool.

KitchenIndoor spacesView

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 spacesKitchenBathroom

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.

Indoor spacesKitchenParking

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, 311 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.

Indoor spacesKitchenLocation

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, 264 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.

Indoor spacesFamilyComfort

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, 158 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

FamilyKitchenSkiing

4.99 out of 5 average rating, 150 reviews

Home in Kingston

Antique Uptown Charmer w/ Five-Star Modern Kitchen

Indoor spacesKitchenQuiet

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, 267 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

Indoor spacesFamilyView

5.0 out of 5 average rating, 118 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

KitchenFamilyAccuracy

4.95 out of 5 average rating, 105 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

KitchenFamilyGetting around

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.

4.98 out of 5 average rating, 128 reviews

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

FamilyKitchenNearby

Barn in Town of Hillsdale

4.97 out of 5 average rating, 185 reviews

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

FamilyIndoor spacesSkiing

A spacious living room features a large gray sectional sofa paired with a coffee table made of rich wood. Natural light fills the space through multiple windows, highlighting the minimalist decor and a cozy fireplace set against a dark stone wall.

4.99 out of 5 average rating, 156 reviews

Hudson Valley Evergreen Treehouse

KitchenFamilySleep quality

Family- and pet-friendly home rentals

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

FamilyIndoor spacesAccess

4.96 out of 5 average rating, 157 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

4.95 out of 5 average rating, 373 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 spacesGrill

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

Indoor spacesKitchenWalkability

4.98 out of 5 average rating, 748 reviews

Cottage in Red Hook

bright serene + spacious barn @barn and bike

FamilyKitchenAmenities

4.96 out of 5 average rating, 138 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

KitchenIndoor spacesGrill

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, 221 reviews

Honeybug Snug near Omega Institute!

KitchenFamilyValue

4.96 out of 5 average rating, 397 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

KitchenIndoor spacesLayout

Family-friendly home rentals with a pool

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.

4.93 out of 5 average rating, 125 reviews

Summer Paradise - Pool, Fire-pit, Nursery!

KitchenIndoor spacesAccess

4.9 out of 5 average rating, 142 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

Indoor spacesFamilyWalkability

Superhost

A view of the farmhouse and guest house from the poolside highlights the spacious yard and surrounding greenery. The in-ground heated pool reflects the sky and is bordered by lounge chairs, with umbrellas providing shade.

Home in Hudson

4.91 out of 5 average rating, 110 reviews

Farmhouse • Secluded • Under 10 mins to Hudson NY

FamilyKitchenGrill

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 spacesHeating

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!

KitchenIndoor spacesWifi

A spacious country house is showcased with a large wraparound deck featuring an umbrella and seating. The well-maintained grounds include greenery and a glimpse of an above-ground pool in the background, complemented by a clear blue sky.

4.93 out of 5 average rating, 127 reviews

Peaceful Hudson Valley Getaway

KitchenFamilyQuiet

4.92 out of 5 average rating, 111 reviews

Home in Hudson

Hudson River Sunset Getaway

FamilyIndoor spacesLayout

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.