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

A cozy studio space features a full-size bed with a neutral comforter, a desk and chair set against a wall, and a small television mounted above a radiator. Natural light enters through a window, with patterned curtains framing the view. The bathroom doorway is visible in the background.

Apartment in Amenia

4.93 out of 5 average rating, 114 reviews

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

Top guest favorite

A well-maintained exterior view showcases a single-story house with a gray siding. A small patio area features a wooden picnic table surrounded by flower beds and a stone pathway. Lush greenery frames the space, while a clear blue sky fills the backdrop.

Apartment in Verbank

4.96 out of 5 average rating, 152 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.

Top guest favorite

The living area features a comfortable black leather couch positioned near a wooden coffee table. A large television is mounted on the wall opposite the seating. Light-colored walls and wood flooring create a spacious ambiance, with a door leading outside visible in the background.

Guest suite in Wappingers Falls

4.81 out of 5 average rating, 115 reviews

Private ground floor guest suite in Hudson Valley

Newly renovated private, ground floor guest suite returning for 2025 rentals! Br, full bath, large LR w/big TV/frig/mw/coffee in centrally located area in the heart of Hudson Valley. Walk to Dutchess Rail Trail/Uber accessible/self ck in. Close to Poughkeepsie, Beacon, Vassar/Marist/DCC colleges, Walkway over Hudson, Culinary Institute, Vassar Hospital, Hyde Park, New Paltz, Rhinebeck. Couch only in LR would be ok for a child. Pets considered for $15/night fee w/inquiry prior. No full kitchen.

Top guest favorite

The exterior of a modern wooden house is surrounded by lush greenery. Large windows allow natural light to fill the interior. A neat lawn leads to the entrance, which is framed by manicured bushes and trees in the background.

Home in Millbrook

5 out of 5 average rating, 116 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.

Superhost

A charming cottage is depicted, featuring a dark exterior with bright pink doors. Two pink chairs and a small table are positioned outside on a gravel area, surrounded by potted plants. Trees frame the backdrop, contributing to a serene setting.

Guesthouse in Dover Plains

4.87 out of 5 average rating, 123 reviews

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Top guest favorite

The kitchen features modern white cabinetry with black handles, complemented by a light-colored countertop. A stainless steel sink is positioned under a wall-mounted faucet. A tile backsplash in neutral tones adds texture, while a fire extinguisher is mounted for safety.

Apartment in Pine Plains

4.98 out of 5 average rating, 202 reviews

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Guest favorite

The front entry of the house is framed by flower pots and flanked by twin windows with dark shutters. A welcome mat lies outside the dark front door, which features a decorative door handle and is set against a pale yellow exterior. An American flag gently sways in the breeze.

Home in Hyde Park

4.84 out of 5 average rating, 224 reviews

Village Cape Getaway

Village Cape on Albany Post Rd in the historic town of Hyde Park. Surrounded by gardens, stone walls, private parking/entry. This 2 story house offers a 1 bdrm apartment that sleeps 3 on the 2nd floor. Close to markets, shops, restaurants. 1 mi to Vanderbilt Mansion, FDR house and library. 2mi to the Culinary Institute of America. 4mi to Marist College. Hiking trails walking distance. Historic drive-in movie in town. Metro north Poughkeepsie sta 6mi south offering taxi and bus service.

Top guest favorite

A bright living room features a sofa facing large glass doors that open to a view of the forest. A cozy armchair is situated nearby, along with a simple coffee table. A bookshelf contains various items, and a wood stove is positioned in the corner.

Guesthouse in Stanfordville

4.93 out of 5 average rating, 186 reviews

Eco Cottage in the Woods

The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Top guest favorite

A yellow sign is displayed among green foliage, featuring a goat and two ducks illustrated on it. The bold text indicates 'SLOW FREE RANGE DUCKS & GOATS at PLAY,' emphasizing the friendly atmosphere surrounding the property.

Farm stay in Ancram

4.97 out of 5 average rating, 349 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

Guest favorite

A warmly colored wooden front door features a large window at the top and is adorned with a seasonal wreath. Two carved bear statues stand on either side, complementing a welcome mat placed at the entrance.

Apartment in Millbrook

4.93 out of 5 average rating, 234 reviews

Red Tail Ridge

One BR with bath, full kitchen, eating area and living room. Separate entrance and sliding glass door in rear with country views. Located on 12 acre parcel. Close to village of Millbrook (less than 4 miles). We are located in center of Dutchess County. There is great antique shopping, historic sites and some of the finest restaurants and chefs with tastes to suit most everyone. .

Top guest favorite

A private deck features a circular table accompanied by two chairs, surrounded by greenery and offering panoramic views of rolling hills and meadows. A potted plant with white flowers is placed on the table, enhancing the outdoor setting under a clear blue sky.

Loft in Stanfordville

4.99 out of 5 average rating, 117 reviews

Harley's Hideaway - Cozy Furnished Apartment

A comfortable and welcoming one bedroom apartment that is separate from our main house. Includes single bedroom with queen bed sleeper, full bathroom, equipped kitchen with ceramic tiling, dining area and living room with hardwood flooring, private deck with panoramic views, 42" cable TV, keyless entry, onsite parking and wireless internet access.

Top guest favorite

The exterior of the Strand House is showcased, featuring warm orange brick and large windows. A stylish sign is displayed prominently across the top, while stairs lead to a welcoming entrance. Planters with yellow flowers are positioned beside the entrance, enhancing the building's charm.

Apartment in Kingston

4.93 out of 5 average rating, 270 reviews

Historic Strand House -Unit 1 Capt. Anderson Suite

Brand new luxury apartments in a restored historic building located in the heart of the historic Rondout District in downtown Kingston. A five minute walk from the waterfront, restaurants, bars, galleries, shops and marina. The Strand House consists of 4 units: (2) studios and (2) two-bedrooms all individually decorated and thoughtfully curated.