Family-friendly vacation rentals in Pine Plains

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Pine Plains

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

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Top guest favorite

The exterior of the modern rustic apartment showcases a wooden structure with a stylish sloped roof. The well-maintained front yard features lush green grass and ornamental plants, while a spacious deck is visible above, complemented by outdoor furniture and shade options.

Guesthouse in Woodstock

5 out of 5 average rating, 378 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO ALL 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE on deck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Guest favorite

A cozy living room features a stone fireplace as the focal point, complemented by large windows that offer views of the outdoor deck. A wooden coffee table is surrounded by wicker chairs, and a decorative plant adds a touch of greenery.

Home in Windham

4.88 out of 5 average rating, 136 reviews

Catskills Retreat: Hot Tub | Fireplace | Firepit

Year-Round Catskills Retreat Escape to Five Star Cottage in Windham, NY, just 2 hours from NYC. This spacious 4-bedroom, 2.5-bath home features stunning mountain views, a cozy wood-burning fireplace, a hot tub, and a large deck for year-round enjoyment. Ski in the winter, and explore nearby hiking trails, lakes, and waterfalls in the warmer months. Ideal for families and groups seeking adventure, wellness, or a peaceful retreat. Book your stay today and experience the beauty of the Catskills!

Top guest favorite

A spacious retreat is seen from above, featuring a large deck with seating and modern design elements. Surrounding foliage displays vibrant autumn colors, while a gravel pathway leads to the house. The serene landscape emphasizes the property's natural setting.

Home in Round Top

4.96 out of 5 average rating, 195 reviews

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Top guest favorite

An enclosed porch features two metal-framed chairs with cushions, positioned near a small table. A decorative rug with vibrant floral patterns covers the floor. A potted plant and a lantern add to the decor, with sunlight streaming through the windows overlooking the water.

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Superhost

A two-story house features a dark blue exterior, surrounded by lush greenery. A spacious deck is accessed by a set of stairs, and a circle of red Adirondack chairs is arranged around a fire pit in the backyard.

Home in Lanesville

4.94 out of 5 average rating, 159 reviews

Waterfront, outdoor deck with fire pit

Enjoy the fresh mountain air and relaxing vibe hosted by Mother Nature herself. Located on Main St. in Hunter - 3 min walk from the bus stop, 8 min walk to Hunter Mt if you choose (2 min drive w. Car/ski equipment) Cozy and comfortable house that overlooks Hunter Mountain. Private waterfront access to the Schoharie creek, good sized sunken backyard w fire, upper and lower patios - Sleeps 6 in beds, 2 more on the sofa bed. 2 full baths, washer and dryer, wifi and Smart Tv's with built in Roku

Top guest favorite

A wooden playset is situated in a shaded area, featuring a slide, climbing wall, and swings. Nearby, a grassy space with pebbled pathways leads to a rustic barn surrounded by trees. Natural light filters through the forest canopy, creating a serene atmosphere.

Home in Saugerties

5 out of 5 average rating, 149 reviews

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

Superhost

A well-lit bathroom features a dark wood vanity with a sink and ample counter space. A white toilet is positioned next to the door, which is framed by a light beige wall. Natural light from a nearby window illuminates the space.

Home in New Milford

4.88 out of 5 average rating, 188 reviews

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Guest favorite

A charming two-story house features a welcoming porch bordered by colorful flower beds. Blue trim accents the white exterior, highlighting the architectural details. A pathway leads to the entrance, which is framed by a decorative arch and supported by columns.

Home in Athens

4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Guest favorite

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

4.95 out of 5 average rating, 354 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Guest favorite

A wooden dining table is centered in the room, surrounded by yellow and red metal chairs. A rustic American flag art piece is displayed on the wall alongside framed pictures. Light enters through a glass door, enhancing the cozy ambiance.

Apartment in Shandaken

4.81 out of 5 average rating, 190 reviews

Catskill Cabin, Chill Apartment, 1st Fl * * * * *

Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-full life. We focus on healthy living, the environment & sustainability. Every day something in nature, a bear in the bushes, picturesque autumn foliage perfect for hipsters and dudes, kids and us grownups. Enjoy the mountain views. The Farmhouse is surrounded by miles of preserved forest land. Enjoy the mountain views. Parties or events are not allowed.

Guest favorite

A cabin is shown nestled among trees, with a wooden deck overlooking a gently flowing stream. Vibrant autumn leaves contrast against the dark exterior of the cabin, enhancing the natural setting. The scene captures the peacefulness of the surrounding landscape, inviting relaxation.

Cabin in Accord

4.94 out of 5 average rating, 112 reviews

Peaceful Cabins by the river, excellent wifi!

Just figured out availability for our cabins this summer! The Big Cabin, located 15 feet from the water’s edge, will easily sleep six. The Little Cabin, 30 yards from the House with a water view and plenty of privacy, is perfect for a couple. Located on a secluded, non-thoroughfare road, it includes access to a private swimming hole and waterfall. Near the Shawangunk climbing mountain and hiking/cycling trails, Accord “downtown” and super chic Inness.

Guest favorite

Home in Palenville

4.96 out of 5 average rating, 162 reviews

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

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What guests are saying

Beautiful Lakefront Retreat with Private Dock

4.92 out of 5 average rating, 116 reviews2 weeks ago

It was our first experience with Airbnb. We were there to tour the World Headquarters for Jehovah’s Witnesses and this proved to be our evening haven. The house was well stocked as others had commented. We enjoyed relaxing and spent much time in living room with the beautiful view. It was perfect for our stay. Our thanks to our Host.

Home in New Fairfield

What guests are saying

Sweet Farm Stay

4.93 out of 5 average rating, 294 reviews1 week ago

So grateful for our weekend getaway at Larissa's. Everything was so peaceful and cozy. We have two little boys and Larissa was wonderful with making them comfortable to join in on the farm responsibilities, from feeding animals to gathering eggs and cleaning the barn. Our boys kept talking about Farmer Larissa and when they would see her and the animals again, (Finn and Bugsy especially!). We felt so warmly welcomed, in naturally good company and really can't wait to come back again for a longer stay.

Apartment in Earlton

What guests are saying

Modern Home with Stunning Views

4.95 out of 5 average rating, 114 reviews5 months ago

Full recommend. One of the most beautifully appointed Air Bnb's I've stayed at both inside and out. Gorgeous views and serene surroundings. Clean, comfortable and close to food & fun. One note, there is no TV - that is indicated on the amenities list - but you might miss it. So get outside when you're there!

Home in Rosendale

What guests are saying

A sunny, quiet chalet beautifully decorated.

4.98 out of 5 average rating, 135 reviews2 months ago

Beautiful, clean and great location! We were up skiing at Catamount so the location was ideal, and the sauna was a nice treat everyday. The house is beautifully decorated and spacious and open. There are a few different levels so plenty of room to spread around with a separate spacious TV/exercise/bunk room in one of the levels. The 2 king beds and twin beds in the bedrooms were all very comfortable and each of the bedroom had their own bathroom next door. The kitchen is fully stocked with kitchenware and necessities/spices etc. Kids went sledding and we even hiked up several times to the top of the hill with great views. Carolyn was very responsive and accommodating.

Home in Egremont

What guests are saying

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

4.91 out of 5 average rating, 117 reviews2 months ago

Sally responded to questions right away. She was really attentive - making sure snow was cleared and ice salted so that we could leave early in the morning after a big snow storm. The place was really conveniently located 15 minutes from ski Butternut. And it was immaculately clean and so cozy. It was a really nice stay.

Home in Sheffield

What guests are saying

Mountain view on Stream beauty

4.83 out of 5 average rating, 120 reviews10 months ago

David’s place is an absolute dream. Like others have said, the pictures don’t do it justice. With the stream in the yard, fire pit, hammock, VHS collection, cozy living room, and lofted bedroom, you could easily spend a week here without going anywhere else. We booked last minute and David was extremly accommodating and quick to respond when we had questions, even going so far as to send me a hand drawn map to help us find our way to a local swimming hole. I’ll absolutely be back! My dogs were bummed to return back to our crammed NYC apartmenr after a dreamy weekend here :)

Home in Phoenicia