Family-friendly holiday rentals in Poughkeepsie

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Poughkeepsie

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

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Guest favourite

Guest suite in Montgomery

4.95 out of 5 average rating, 422 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

27 Dec – 3 Jan

$180 SGD per night

Guest favourite

Cottage in Kerhonkson

4.89 out of 5 average rating, 448 reviews

Mod Scandinavian! HudsonValley! Awesome locale!

Minimalist style Cottage with spacious deck under the stars! Clean, Comfortable. Mountain Views! Very convenient location. Eco friendly. Solar! Passive Activities everywhere! Hiking, skiing!! Yes, it's beautiful here! Memorable. Catskills views. Minnewaska Preserve, Mohonk/Gunjs within 10 minutes. Tall windows. Former Air Traffic Cont. room. Kitchen w/Italian granite,tiled shower. Enjoy, take care of it. Leave as found, pls! We love it! you will too! Pls read detailed listing and other. 🩷😊

24–31 Jul

$240 SGD per night

Guest favourite

Guest suite in Red Hook

4.9 out of 5 average rating, 299 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! Of note, with a 30$ fee, we can set up a 2nd bed in the suite living room. We're happy to do it, it just takes some time to get together. It's a super comfortable mattress, the same model as the queen bed. We are also cycling happy and offer bike rentals and tours.

10–17 Nov

$229 SGD per night

Guest favourite

Flat in New Paltz

4.96 out of 5 average rating, 346 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

19–26 Apr

$160 SGD per night

Guest favourite

Cabin in Chichester

4.99 out of 5 average rating, 514 reviews

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek

30 Sep – 7 Oct

$172 SGD per night

Guest favourite

Flat in New Paltz

4.97 out of 5 average rating, 464 reviews

Relaxing Spa Retreat~Gorgeous View~Walk to Village

Spacious studio apartment including full separate kitchen, with views of wetland, woods, and Mohonk Mountain. Situated within our home, this studio offers you and yours a private entrance, stone patio, and a luxurious spa experience with infrared sauna and hot tub under the stars. One-mile stroll to New Paltz Village on country road or on Wallkill Valley Rail Trail. Kitchen stocked with essentials. Air conditioned. Sleeps three in super comfy beds— one queen and one twin.

23–30 Mar

$487 SGD per night

Guest favourite

Tiny home in New Paltz

4.99 out of 5 average rating, 743 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

1–8 Jul

$153 SGD per night

Guest favourite

Flat in Rosendale

4.96 out of 5 average rating, 201 reviews

Rosendale Trestle View

Enjoy views from your upstairs oasis: 1 bedroom, office, kitchen, & bath. Stay coooool all summer long with our very quiet mini splits. Slip out your private entrance to hike Joppenbergh. Bring or Rent a bike, ride or walk or even X-country ski the #EmpireTrail, the Rosendale trestle and Wallkill Rail-trail. View the trestle and walk 5 minutes to the trail from the house. Walk to local eateries, and cinema, or just relax by the river.

11–18 Sep

$170 SGD per night

Guest favourite

Home in New Paltz

4.97 out of 5 average rating, 679 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

24–31 Jan

$183 SGD per night

Guest favourite

Guest house in Ulster Park

4.85 out of 5 average rating, 457 reviews

Hudson Valley Hideaway

Nestled in the Hudson River Valley an intimate apartment ideal for one or two. 85 miles from NYC, Conveniently located 20 minutes to New Paltz, Mohonk, Woodstock and Bard College. Enjoy a stroll on the land with your morning tea or coffee and visit the koi pond. Check out this wonderful review from the marvelous friends at &north! http://andnorth.com/stay/artist-owned-airbnb-cottage-tucked-away-esopus-ny/

23–30 Mar

$119 SGD per night

Guest favourite

Flat in Beacon

4.99 out of 5 average rating, 487 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)!

12–19 Sep

$260 SGD per night

Guest favourite

Home in Highland

4.96 out of 5 average rating, 107 reviews

House in Highland: Secluded Retreat

Located in Highland, NY, and nearby New Paltz and Poughkeepsie, this home is a retreat with a hot tub and multiple entertaining areas. The stylishly appointed home includes 3 bedrooms, and two deck areas, along with a gas grill and an outdoor wood-burning fireplace. NOTE: WINTER MONTHS REQUIRE A VEHICLE WITH AWD. - This home is not pet friendly, sorry!

3–10 Nov

$749 SGD per night