Family-friendly vacation rentals in Dutchess County

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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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Guest favourite

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Oct. 17 – 24

$1,186 CAD per night

Guest favourite

Guest suite in Millerton

4.93 out of 5 average rating, 322 reviews

Romantic Sunset-50 mile view!

ROMANTIC LUXURY! Spring/Summer is beginning now. Flowers are starting to bloom 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;

Dec. 23 – 30

$261 CAD per night

Guest favourite

Home in Salt Point

4.95 out of 5 average rating, 133 reviews

The Literary Inn-entire house

This 3 bedroom guest house located in Salt Point, Dutchess County in New York State. This quiet private place on a 4 acre property is less than 10 minutes from the Taconic Parkway. The house has cable TV, free wifi, central air and heat, a full kitchen with a dishwasher, a full bathroom, a large deck and private patio. The Hudson Valley is home to Colleges, Museums, historic towns, and great State Parks. There are restaurants offering vegetarian and vegan dishes and super markets are nearby.

Sep. 1 – 8

$305 CAD per night

Guest favourite

Guest suite in Red Hook

4.9 out of 5 average rating, 296 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.

Nov. 22 – 29

$228 CAD per night

Guest favourite

Apartment 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)!

Oct. 16 – 23

$283 CAD per night

Guest favourite

Tiny homes in Hopewell Junction

4.96 out of 5 average rating, 463 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!

May 17 – 24

$451 CAD per night

Guest favourite

Guesthouse in Millbrook

4.86 out of 5 average rating, 223 reviews

Quaint Cottage near Millbrook Village

This space is a small cottage on our property located just a mile from the Village of Millbrook. The cottage is very private and removed from the main house. It features a queen-size bed, small bath with shower, and modest kitchenette with coffee/tea maker and refrigerator but no stove. The cottage is good for couples or solo adventurers. Small house-broken dogs are welcome. No cats, please.

Jul. 9 – 16

$220 CAD per night

Guest favourite

Apartment in Millerton

4.8 out of 5 average rating, 230 reviews

Gardens Galore and Village Whimsy Retreat

My place is close to restaurants and dining, the city center, and parks. My place is good for couples, solo adventurers, business travelers, and families (with kids). It is a steal for the price. nothing is as good around here, a true bargin. The apartment is below the 1850's victorian house. During the day you can hear children's feet pitter patter. After 7 The place is quite.

Mar. 8 – 15

$154 CAD per night

Guest favourite

Cabin in Red Hook

4.96 out of 5 average rating, 305 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.

Sep. 21 – 28

$695 CAD 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!

Feb. 22 – Mar. 1

$468 CAD per night

Guest favourite

Apartment in Carmel

4.87 out of 5 average rating, 275 reviews

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.

Nov. 2 – 9

$201 CAD per night

Guest favourite

Cottage in Poughkeepsie

4.91 out of 5 average rating, 301 reviews

Be in Nature at this Gorgeous Riverfront Cabin

Wappinger Cottage is a Scandinavian-inspired home featuring landscaped gardens leading to the shimmering Wappinger Creek. Inside, contemporary furnishings accented by bold patterns and pops of color create a sophisticated and inviting space. The house is designed to be cooled by cross ventilation. There are tower fans, but no AC. Pets allowed.

Jan. 9 – 16

$474 CAD per night