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Family-friendly vacation rentals in Dutchess County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Dutchess County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Home in Milton

4.75 out of 5 average rating, 174 reviews

Historic 1 BR Family Home Near Buttermilk Falls

This historic upstate New York family home was lovingly restored by 4th generation owners. Once a 1790 Stagecoach Stop, this 1 BR home is now the perfect stay for guests visiting Buttermilk Falls Resort & Spa, coming for a wedding in the Hudson Valley, or exploring local agritourism. Enjoy our large kitchen and sitting area, 180-degree sunroom, and newly-renovated bathroom. Our home is a duplex that sits on 5 wooded acres, and the other side of the home is also available for rent on AirBnB.

Home in Millbrook

5 out of 5 average rating, 105 reviews

Stunning Views, Light and Open - The Beech House

Named for one of it's giant beech trees, The Beech House is a modern, sunlit home with gorgeous views of the Catskills. All are welcome to come, relax, and unwind in our warm, open, comfortable home. The Beech House sits on 4 lush acres, off a quiet lane, just an easy walk to the village of Millbrook in Dutchess County. The house is perfect for relaxing or playing, staying in or going out, couples, friends, or families. We absolutely love it and it is our great pleasure to share it with you.

Guesthouse in Beacon

4.94 out of 5 average rating, 380 reviews

Cozy Mountainside Suite - Minutes from Beacon

The Equestrian Suite at Lambs Hill is a private estate with panoramic views overlooking the Hudson River & downtown Beacon. This beautifully-designed luxury suite sits atop a barn home to Icelandic horses & miniature donkeys, & features an outdoor hot tub, gourmet kitchen appliances, & wrap-around decks. 1 mile to Beacon's Main St, 2 miles to Metro North train station & DIA: Beacon. We can host a max of 2 guests & have some dangerous features for kids so guests should be adults only.

Rental unit in Beacon

4.91 out of 5 average rating, 564 reviews

Cozy Beacon Studio

Studio apartment in an 1870 brick house, gut renovated in 2022 with Hudson Valley designer Simone Eisold. Property backs up to Beacon's famous Fishkill Creek and abandoned railway tracks (future rail trail). Take a nature walk on the tracks to Main St, the Roundhouse and the waterfall in ~10 min. The property has a separate patio & treetop hot tub with view of the creek and Mt Beacon for private additional rental (pending availability). Inquire for details. [Permit: 2024-0027-STR]

Guest suite in Millerton

4.93 out of 5 average rating, 347 reviews

Romantic Sunset-50 mile view!

ROMANTIC LUXURY! Fall is beginning now. Lesves are starting to turn and the nights are crisp and cool. Fresh mountain air. Clear starry nights. Your own private suite, entrance, kitchen, bathroom, outdoor dining facilities, bar b q grill. Located atop a mountain with magnificent SUNSET view 50 miles overlooking the Hudson River Valley. Completely steam cleaned, disinfected and sterilized before each guest. HEPA Air filters installed. High speed WIFI, 500mbps! 55” 4K HD TV;

Guest suite in Red Hook

4.91 out of 5 average rating, 334 reviews

the farmhouse suite at gallatin farmstead

A 575 sq ft. fully private suite with your own entrance in a beautiful early American eyebrow colonial. The mid-century farmhouse style is highlighted by a darling kitchenette. And don't forget the bathroom hot steam shower! Please note the kitchenette has an induction stove top and convection air fryer toaster oven. It's a great for light cooking. Please ask for a grill for cooking meat and greasy food. We are also have a cycling side business offering bike rentals and tours.

Home in Lagrangeville

4.84 out of 5 average rating, 133 reviews

Classic Hudson Valley Farmhouse Nestled in 9 Rolling Acres

Whether you seek a nook to escape to or room to gather all together, this expansive and historic farmhouse offers the chance to do so in comfort. Highlights include multiple working fireplaces and a piano, with plenty of space to lounge by either, as well as an expansive library. The formal dining room has a 10 foot table, and the kitchen is well-equipped to support it. Pool season is Memorial Day - Labor Day.

Rental unit in Beacon

4.99 out of 5 average rating, 535 reviews

Rustic Spa Retreat

10 minute walk to Main Street (many restaurants, cafes, galleries, etc) 10 minute walk to Mt Beacon TrailHead. (It's not a hotel and not on Main Street: it's in a residential neighborhood) Cozy, small space set up for a couple (or solo traveler) looking for a relaxing short escape from "The Real World". A couple days here really feels likes so much longer (especially if you take a steam and a jacuzzi)!

Tiny home in Hopewell Junction

4.95 out of 5 average rating, 497 reviews

The GlassHouse: Hudson Valley Tiny Home w/Firepit

The GlassHouse is the much talked-about experience that we had crafted within a sprawling forest preserve. Its wrap-around windows allow breathtaking views to bring out the romantic in all of us! We are stone’s throw up against the Appalachian Trail right on the Dutchess/Putnam line and are less than an hour from Manhattan. Minutes from Fahnestock & Hudson Highlands State Parks & the Empire State Trail!

Cabin in Red Hook

4.96 out of 5 average rating, 335 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

Cottage in Staatsburg

4.91 out of 5 average rating, 183 reviews

Charming Creek side Getaway 3.5 mi. from Omega

Nestled in a creek side hollow, this private and cozy cottage offers a welcoming space to relax and refresh in. The house has a charm all its own, featuring beautiful furnished rooms with the accent on comfortable. Combine that with the creek side setting without another visible house from the property and it truly feels like a "nature's getaway".

Home in Rhinebeck

4.92 out of 5 average rating, 271 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!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Dutchess County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Villa in Hopewell Junction

4.96 out of 5 average rating, 289 reviews

The Mission House Sanctuary

Home in Rhinebeck

4.91 out of 5 average rating, 224 reviews

Rhinebeck Modern Home with amazing outdoor space

Farm stay in Kent

4.88 out of 5 average rating, 293 reviews

(°) The Wandering Peacock (°)

Home in Ancramdale

4.93 out of 5 average rating, 135 reviews

Unwind in the country, stargaze in hot tub

Home in Cold Spring

4.91 out of 5 average rating, 253 reviews

1834 Farm House

Home in Red Hook

4.88 out of 5 average rating, 225 reviews

Wooded Retreat w/ Hot Tub and Trout River

Home in Beacon

4.8 out of 5 average rating, 5 reviews

House in Beacon, Just Off Main Street

Family- and pet-friendly home rentals

Home in Millerton

4.89 out of 5 average rating, 149 reviews

The 1913 House, book 6 days get the 7th free.

Home in Saugerties

4.89 out of 5 average rating, 114 reviews

The Esopus Creek Charmer | a waterfront home

Camper/RV in Wappingers Falls

4.87 out of 5 average rating, 204 reviews

Camping(Pebble base camp) private campsite

Home in Beacon

4.97 out of 5 average rating, 234 reviews

Mt hikes, city strolls river walks

Home in Lake Katrine

4.95 out of 5 average rating, 110 reviews

Magical Waterfront Escape on the Esopus Creek

Cottage in Pine Plains

5 out of 5 average rating, 140 reviews

Patchin Mills Quaint Country Cottage

Rental unit in Saugerties

4.86 out of 5 average rating, 147 reviews

Saugerties Marina Peaceful Setting On the Water

Home in Verbank

4.98 out of 5 average rating, 179 reviews

The Waterfall House

Family-friendly home rentals with a pool

Home in Saugerties

5 out of 5 average rating, 94 reviews

Saugerties Luxury Rental Close to hikes, festivals

Home in Stormville

4.94 out of 5 average rating, 176 reviews

Private Hudson Valley Country Retreat

Home in Stormville

5 out of 5 average rating, 11 reviews

2 MasterSuites Heated SaltWater Pool+HotTub&More

Home in Saugerties

4.93 out of 5 average rating, 120 reviews

Bluestone Escape - Where everyone is at home.

Home in Staatsburg

4.86 out of 5 average rating, 119 reviews

Private Country Home near Rhinebeck

Farm stay in Rhinebeck

4.94 out of 5 average rating, 179 reviews

Majestic Oasis in Rhinebeck w/ Hot Tub & Pool

Cottage in Dover Plains

5 out of 5 average rating, 15 reviews

Charming Country House

Home in Saugerties

4.8 out of 5 average rating, 130 reviews

Hillside Escape: HITS Home w/ Pool & Hot Tub

Destinations to explore