Family-friendly holiday rentals in Poughkeepsie

Guest suite in Wappingers Falls

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.

4.82 out of 5 average rating, 124 reviews

Private ground floor guest suite in Hudson Valley

Guest favorite/newly renovated/private, ground floor guest suite. 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. Car suggested.

4.89 out of 5 average rating, 655 reviews

The exterior of the Little Yellow Cottage features a charming yellow facade with white trim. A round window and a cupola add character to the roof. Surrounding greenery provides a natural setting, while a small white statue of a goat sits in front of the entrance steps.

Cottage in Highland

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

4.97 out of 5 average rating, 341 reviews

A modern living area features a gray sofa adorned with patterned cushions. Two sleek black tables are positioned on a striped rug, with a small plant on one of the tables. Tall, dark curtains frame the window, allowing natural light to enter the space.

Condo in Poughkeepsie

Spacious and stylish entire one bedroom apartment.

Enjoy a stylish experience at this centrally-located one bedroom apartment in Poughkeepsie. Apt is located in a quiet Victorian townhouse on the 3rd floor. Entire rental unit, Parking is included for one vehicle. Located downtown. Walking distance to: Post Office, Courts, County Bldgs, Police Station, City Hall, Nesheiwat Convention Center (fka Civic Center), Poughkeepsie Grand Hotel, Walkway Over The Hudson, Bardavon Opera House, The Academy, train station, waterfront, bus depot, and more.

4.84 out of 5 average rating, 339 reviews

A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.

Apartment in Newburgh

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Apartment in Poughkeepsie

A spacious bed with a white striped blanket is centered in the room, accompanied by two patterned pillows. A yellow accent chair and a small side table with a lamp are visible in the background, contributing to a cozy, inviting atmosphere.

4.95 out of 5 average rating, 129 reviews

Spacious Studio in Historic home, near Metro North

1st floor studio apartment in a private home. Located in the historic Mt Carmel/Little Italy section of Poughkeepsie. 5 minute walk to Metro North train station and entrance to the Walkway over the Hudson. Many restaurants, coffee/pastry shops within walking distance. There is off street parking and a lovely yard in back. Convenient to Marist College, Vassar College, the CIA, FDR home , Vanderbilt Mansion, Locust Grove, breweries, Rail trails and Wineries. NO third party booking allowed.

4.84 out of 5 average rating, 235 reviews

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

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.

Guest suite in Marlboro Township

A spacious bedroom features a large queen bed with a contrasting striped blanket. Nightstands are positioned on either side, and a lamp provides soft lighting. Two windows with light-filtering curtains allow natural light to fill the room, complemented by a beige carpet.

4.97 out of 5 average rating, 502 reviews

Spacious & Private Hudson Valley Getaway

Welcome to Marlboro! This private space in our home features a private entrance, private bathroom with a nice standing shower, eating area (not a kitchen) with tea kettle and coffee machine, toaster, microwave and refrigerator with freezer. There is a table and chairs, love seat couch that transforms into a small cot, queen bed, walk in closet and 55 inch smart TV with a full motion TV stand. We are permitted to operate in the town of Marlboro and a yearly fire inspection is conducted.

Tiny home in Poughkeepsie

A cozy outdoor seating area features two light blue chairs positioned around a circular fire pit, with firewood stacked beside it. In the background, a compact cabin is set among the trees, showcasing a contrasting dark exterior and bright yellow door.

4.86 out of 5 average rating, 148 reviews

Lake Side Tiny House

Reconnect with nature at this unforgettable escape. Sitting on a beautiful 5 acre property, tucked back in the woods along a beautiful lake. Come stay and unwind. Plenty to explore and just be. Lake access for swimming or with paddle board, canoe, or kayak. Just ask and can be assisted with. The whole property has been curated to be a playground. Full bathroom inside unit. Brand new Mini Split heat and AC unit. Works amazing Has most kitchen amenities besides an oven. Enjoy

4.9 out of 5 average rating, 154 reviews

A spacious room is showcased with a cozy bed, a small wooden table, and two chairs. A wooden bench is positioned near the entrance. The bathroom doorway is visible, along with a bright mirror and light fixtures. Natural light enters the room through a window.

Guest suite in New Paltz

Newly built apartment steps from Mohonk preserve.

Nestled amongst the trees below Bonticou Crag this is a great base camp for climbing, hiking and biking. Five minutes from New Paltz; I do recommend having a car to access the area. Shared yard and fire pit right outside. My family and I live in the main part of the house. The outside area and house are still under construction, I’m working on it but its not put together yet. The apartment and inside area are clean and newly built with their own mini split and air circulation.

Apartment in Poughkeepsie

The living room features a variety of seating options including a blue accent chair, a brown sofa, and woven armchair. A coffee table rests on a patterned rug, while natural light filters through sheer curtains, illuminating the space. A television is positioned on an antique cabinet.

4.93 out of 5 average rating, 363 reviews

3 Bdrm. Near Hudson Valley Colleges & Attractions

Built in 1910, this 3 bedroom apartment is located close to many Hudson Valley attractions - only 0.5 miles from the Poughkeepsie train station. Located within 2 miles of both Marist and Vassar Colleges, as well as a short drive from The Culinary Institute of America. Historic villages of Hyde Park and Rhinebeck are just a short drive along the river. As well as fast access to hiking and biking trails in local Shawangunk mountains, Mohonk Preserve, and Minnewaska State Park.

4.96 out of 5 average rating, 275 reviews

A sunlit living room features a spacious gray sofa and a decorative coffee table. A large television is mounted on the wall, displaying a serene sunset. An archway leads to a dining area with white chairs and a dining table, enhancing the open concept design.

Home in Poughkeepsie

The whole group will enjoy easy access to everything from this centrally located home. Ample space inside and out for creativity, relaxing and enjoying! Located in a quiet, residential, family-oriented neighborhood. This retreat is less than 1 mile from Marist College, and the Walkway Over the Hudson. A ten-minute drive to The Culinary, Vassar College and all FDR historic sites/attractions. Also, enjoy 125 cable and Roku tv Channels. Make this home your home away from home!

4.95 out of 5 average rating, 110 reviews

A spacious living room features two comfortable gray sofas and a light blue accent chair arranged around a glass coffee table. Natural light illuminates the room, highlighting the hardwood floor. Wall art featuring greenery adds a fresh touch to the inviting atmosphere.

Home in Poughkeepsie

Poughkeepsie 3br home near Vassar college/hospital

The Atala is a two story 3BR/2Bath house, nestled in a quiet neighborhood close to the city's excitement and attractions. Warm up by the fireplace in the living room while watching your favorite shows on a 75” flat screen TV, or brew a cup of coffee in our convenient coffee bar. Enjoy three inviting bedrooms with air conditioning/heating and a fully equipped kitchen. Our backyard with furniture, fire pit, and gas grill, is perfect for relaxing with family and friends.

Popular amenities for Poughkeepsie family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 586 reviews

A hot tub is positioned on a wooden deck, surrounded by lush greenery and trees. It offers expansive views of the natural landscape, with gentle hills visible in the distance under a soft, overcast sky.

Apartment in New Paltz

Relaxing Spa Retreat~Gorgeous View~Walk to Village

4.97 out of 5 average rating, 354 reviews

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

Relaxing secluded stay with loving social animals.

4.83 out of 5 average rating, 110 reviews

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

Entire Home (private pool), Event Friendly

4.98 out of 5 average rating, 173 reviews

An inviting hot tub bubbles gently under a covered deck, framed by lush greenery. The scenic backdrop features rolling hills and trees under a partly cloudy sky, creating a tranquil outdoor space for relaxation.

Home in Gardiner

4 BR Stunning Mountain Retreat w Hot Tub!

4.89 out of 5 average rating, 168 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

4.89 out of 5 average rating, 209 reviews

An outdoor space features a hot tub surrounded by a gravel area. Two lounge chairs and a glass table are placed near a striped rug. Potted plants are hung along the wooden fence, enhancing the cozy atmosphere.

Apartment in Kingston

Charming Pet Friendly Getaway w Hot Tub & Fire Pit

4.94 out of 5 average rating, 317 reviews

The living room features large windows offering views of the river and surrounding trees. A blue sofa and a beige tufted couch are positioned around a wooden coffee table, while a colorful area rug adds warmth to the space. Bright yellow walls enhance the inviting atmosphere.

Home in New Paltz

Welcome to The Boathouse! Waterfront/Boats/Hot tub

4.96 out of 5 average rating, 225 reviews

A spacious living area is furnished with a large sectional sofa, adorned with decorative throw pillows. Natural light filters through multiple tall windows, illuminating a central coffee table accompanied by simple decor. In the background, a large dining table and green accents enhance the inviting atmosphere.

Home in High Falls

Clove Schoolhouse on Mohonk Preserve

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 992 reviews

An exterior view of an old milk barn, featuring a wooden door and overgrown greenery surrounding the structure. The rustic charm is highlighted by exposed brick and an angled roof. A few outdoor furniture pieces are positioned nearby, complementing the natural setting.

Farm stay in High Falls

Dave's Milk Barn

4.98 out of 5 average rating, 124 reviews

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

Hillside Views in Hudson Valley

4.94 out of 5 average rating, 149 reviews

A wide view of a grassy field is presented, bordered by trees and rolling hills in the distance. The sky appears clear and blue, creating a serene backdrop for outdoor activities. A small firepit made of stone is positioned on the lower left.

Campsite in Kerhonkson

tent camping $25/person/night -stunning mt views.

4.96 out of 5 average rating, 274 reviews

The front of the cabin is showcased with a welcoming door decorated with a wreath. Two blue chairs and one white chair are positioned on either side, complemented by a small table and potted flowers near the entrance. Lush greenery surrounds the cabin.

Tiny home in Newburgh

Cabin in the heart of the Hudson Valley, Cabin 3

4.93 out of 5 average rating, 365 reviews

A spacious main area is highlighted by a large bed covered with a floral quilt. A comfortable sofa is positioned nearby, while a wooden café counter with four chairs overlooks natural light coming through the three windows. A coffee bar and kitchen appliances are integrated into the space.

Apartment in New Paltz

Peaceful and Private Boutique Apartment *Pool*

4.91 out of 5 average rating, 776 reviews

A spacious bedroom is shown with a queen bed adorned in floral bedding. A cozy fireplace is built from natural stone, surrounded by decorative elements. A small breakfast table with black chairs is positioned near windows draped in bright yellow curtains, allowing natural light to fill the room.

Farm stay in New Paltz

The 1772 Lefevre Stonehouse Suite

4.94 out of 5 average rating, 121 reviews

A spacious living room is presented, featuring a comfortable green sectional sofa with decorative pillows. A wooden coffee table with magazines rests in front, and a mirror is mounted above a side table adorned with a lamp. A cozy armchair is positioned nearby.

Home in Hyde Park

Hyde Parks Hideaway

4.93 out of 5 average rating, 378 reviews

Loft in New Paltz

Peaceful Couples Retreat Near Trails, Town & SUNY

Family-friendly home rentals with a pool

4.82 out of 5 average rating, 194 reviews

A serene outdoor pool area is surrounded by a wooden deck and natural greenery. Pool floats lie on the water's surface, and a few lounge chairs are arranged nearby. Lush trees and shrubs create a tranquil backdrop, enhancing the connection to nature.

Cottage in Kingston

Cottage with Private Deck on 8 acres of Woods

4.92 out of 5 average rating, 333 reviews

A large, serene pool reflects the surrounding greenery and the stone facade of a historic guesthouse. Sun loungers are positioned beside the water, and well-maintained gardens and patios are visible in the backyard, inviting relaxation and outdoor enjoyment.

Guesthouse in Kingston

The Antique Stone House

Apartment in Wappingers Falls

5 out of 5 average rating, 229 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

4.93 out of 5 average rating, 393 reviews

A cozy living space is highlighted by a light wooden floor and a white shiplap ceiling. A comfortable brown leather couch and an orange accent chair provide seating. A wooden coffee table sits in front of the sofa. Wall art and a floor lamp add warmth to the room.

Cottage in Kingston

Kapitan’s Cottage Private Upstate Catskill Retreat

4.95 out of 5 average rating, 154 reviews

A small red cabin is framed by lush greenery, with a welcoming porch featuring two wooden rocking chairs. Natural stone path leads to the entrance, surrounded by a forest of tall trees and soft moss-covered ground.

Cabin in New Paltz

Le Petit Abris at Gunks EcoLodge

Guesthouse in Stanfordville

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.

4.93 out of 5 average rating, 187 reviews

Eco Cottage in the Woods

4.92 out of 5 average rating, 290 reviews

A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.

Apartment in Brookfield

Peaceful apartment on 3.5 acres w/ Artist studio.