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 favorite

Home in Poughquag

4.99 out of 5 average rating, 139 reviews

The Beekman Salt Box - Historic Hudson Valley Home

Step back in time in this gorgeous 1860 Cottage in Duchess County, 2 miles off the Taconic in the historic Hamlet of Beekmanville, just 75 minutes north of the GW Bridge and 5 minutes from the Appalachian Trail. Five acres bisected by the Fishkill Creek. Huge patio with fire pit. Indoor wood-burning stove. Super-fast Xfinity/Comcast Wi-Fi makes this the perfect place to relax or to work away from work! Grocery store and gas and Dunkin less than 2 miles away.

Guest favorite

Rental unit in Verbank

4.95 out of 5 average rating, 130 reviews

Large, private apartment in scenic Hudson Valley

We are located right in the middle of the Dutchess County so access to all points is convenient. Many attractions are: historical Hyde Park, Walkway Over The Hudson, Culinary Institute, Vassar & Marist colleges, wineries, breweries, the quaint towns of Millbrook & Rhinebeck, Dutchess County Fairgrounds, and The Links At Unionvale golf course and banquet hall. Great for couples, adventurers and business travelers who love activity but appreciate a comfortable quiet place at the end of the day.

Guest favorite

Home in Millbrook

5 out of 5 average rating, 106 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.

Guest favorite

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.

Guest favorite

Guest suite in Millerton

4.93 out of 5 average rating, 348 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 favorite

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.

Superhost

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.

Guest favorite

Rental unit in Beacon

4.99 out of 5 average rating, 536 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)!

Guest favorite

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!

Guest favorite

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.

Guest favorite

Rental unit in Carmel

4.87 out of 5 average rating, 292 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.

Guest favorite

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!