Family-friendly vacation rentals in Pine Hill

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Top-rated family-friendly rentals in Pine Hill

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

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Guest favorite

A bright living area features large windows that allow natural light to fill the space. A comfortable sofa is centered on a patterned area rug, complemented by a glass coffee table. Shelves hold various books and decorative items, while a wood-burning stove provides warmth.

Cabin in Big Indian

4.96 out of 5 average rating, 284 reviews

Retro Modern Paradise in the Catskills

Our spacious home is nestled at the top of Rose Mountain in The Catskills, perfect for a family retreat. Approximately 2.5 hour drive from New York City and only 10 minutes from Belleayre. Spend your time relaxing in our cabin with the seclusion and privacy of 5 acres of forest and meadow. Our property runs along a small creek in Big Indian, NY, with sweeping views of Slide Mountain. Centered in the middle of the Catskills its easy to explore many local restaurants and bars within an hour drive.

Top guest favorite

A gravel driveway winds through a well-maintained yard, leading towards distant mountains under a clear blue sky. Sparse trees and an American flag add to the serene landscape, indicating a peaceful outdoor setting.

Apartment in Halcott Center

4.97 out of 5 average rating, 145 reviews

Mountain View Apartment

We offer a quiet and extremely clean place. We are only 6 miles from Belleayre Mtn Ski Center. Restaurants are nearby. You’ll love our place because of the neighborhood, the outdoors space, the light, and the kitchen. Our place is good for couples, solo adventurers, and business travelers. WIFI is 300mbps. We have security cameras outside only, EV Charging station on the property. We now have an outdoor fire pit (wood not included). We also have a standby generator in case of a power failure.

Superhost

A modern living area features a leather sofa paired with a wooden coffee table, accented by a ceramic vase. A cozy patterned wall hanging adds texture. A dining space is visible in the background, complemented by natural light from the windows.

Cabin in Big Indian

4.9 out of 5 average rating, 125 reviews

Birch Creek House - Private & Cozy Creekside Cabin

Hidden, fully renovated, modernized cabin off Rte 28 in Big Indian. Located on 5 acres of private forest, down a long driveway, with a private wrap around deck, outdoor dining + firepit + indoor fireplace. Just a few min drive to notable shopping and dining, along with several mountains, ski resorts like Belleayre, world-class hiking, and outdoor everything that upstate NY has to offer. @birchcreekhouse on IG. 5 min to Belleayre Mtn 25 min from Hunter Mtn 15 min to Phoenicia Diner SBL#414137

Top guest favorite

A garden brimming with vibrant orange flowers is set in front of a dark structure. A red building is visible in the background, surrounded by lush trees, adding to the green landscape. This serene outdoor space emphasizes a natural and welcoming environment.

Bungalow in Margaretville

4.97 out of 5 average rating, 319 reviews

The Porch Upstate Super clean

Halcottsville is a tiny hamlet In the heart of the Catskills .The porch is a compound with an old general store built in 1890 which is available for rent .We also have a restored barn , gardens and Apple orchard . The Bungalow is super private and still right on Main Street in Halcottsville. We will definitely will share our veggies and fruit with you . We have 3 sheep , 10 chickens and 5 barn cats .Halcottsville has its own post office ,voluntary fire department and a beautiful Lake.

Top guest favorite

A charming cottage is nestled among lush greenery, featuring a white exterior with brown shutters. The entrance is framed by well-maintained shrubs and a wooden deck extends from the front. Tall trees create a serene backdrop, enhancing the peaceful environment.

Bungalow in Big Indian

4.95 out of 5 average rating, 176 reviews

The Den @ Oliverea - Minutes to Hiking and Skiing!

Nestled into a quiet through road that goes to some of the best hiking nearby (hello Slide Mt.!) and just 10 minutes away from skiing at powder-coated Belleayre, my charming little two bedroom cottage is ready for your family or group's adventures. There is no cell service here, but fast Internet awaits the remote worker, with a modern mesh network providing indoor/outdoor coverage. Comfy beds, a stocked kitchen, a hot shower, and mountain peace await! Shandaken STR License #2022-STR-001P

Guest favorite

The exterior of a charming blue house features large windows surrounded by lush greenery. A small guest cottage is visible nearby, set in a well-maintained yard with a grassy area and trees. A distinctive sculpture rests on a rock in the foreground.

Home in Shandaken

4.96 out of 5 average rating, 202 reviews

Catskills Mountain House with a Separate Cottage on a Creek

Beautifully furnished & charming with plenty of outdoor space to play around, have a fire, grill- and beautiful barn. A small stream runs on the edge of the property, perfect to sit beside, and a guest cottage with extra sleeping space (queen, trundle and aerobeds/ bathroom). It's full of unique, hand-crafted and antique furnishing and decor, (fun-fact, former residence of Freakonomics author Stephen Dubner). You'll have free range of the whole place! Shandaken STR Licence #2024-STR-AO-105.

Top guest favorite

A bright living area features a blue couch adorned with decorative pillows. A wooden coffee table sits in front, complemented by a woven bowl. Vibrant artwork is displayed on the walls, and a stained glass door invites natural light. A staircase leads to the upper level.

Home in Phoenicia

4.98 out of 5 average rating, 310 reviews

Stony Clove Cottage - sleeps 6, *maximum 4 adults*

Welcome! Stony Clove Cottage sleeps a maximum 4 adults and 2 children. There are 2 queen beds and a bunkbed for children only. Located in the beautiful Catskill Mountains just 2 hours 15 mins. from NYC. Two great ski mountains, Hunter and Belleayre, are each 15 minutes away. Close to amazing hiking trails. Listen to the sound of the Stony Clove Creek and enjoy being in nature, while just 1 mile from Phoenicia's Main Street. Beautiful in all seasons! Shandaken STR License # 2023-STR-AO-059

Top guest favorite

The charming blue house features a spacious front porch supported by white columns. Set back from a tree-lined path, the property showcases well-maintained gardens with low stone walls and vibrant green grass, creating a welcoming entrance.

Vacation home in Pine Hill

4.99 out of 5 average rating, 142 reviews

The Perfect Catskills Escape for Families and Groups

Pine Hill House is a renovated 1870s boarding house with loads of old charm mixed in with new luxuries. Take a left from the house to find miles of hiking trails. Take a right and walk to town with its vibrant restaurant scene and a lively community center. Belleayre Beach and Belleayre ski area are both a 5-minute drive away, as are some of the Catskills' hottest restaurants, spas, and cider houses. Don't want to leave? Relax around the woodburning stove and soak in the clawfoot tub.

Guest favorite

A circular stone fire pit area is surrounded by five red Adirondack chairs on a well-maintained grassy lawn. Lush green trees provide shade, with a view of a charming house in the background, contributing to a serene outdoor setting.

Home in Big Indian

4.94 out of 5 average rating, 124 reviews

Birch Creek Mountain House

The Birch Creek Mountain House is a beautiful newly renovated 4 bedroom 2 bath 2400 sq. ft. home on Birch Creek. Only 3 minutes to Belleayre Mountain and the new high-speed Gondola. You will love listening to the sound of Birch Creek in the backyard or sitting by the warm fire in the Great Room. There is hiking, skiing, biking and fishing nearby with a quick walk to Belleayre Beach. Only 2 hrs. 15 mins. from NYC, it's the perfect place to escape and relax with family and friends.

Guest favorite

The log cabin features a sloped metal roof and large windows, surrounded by trees. A spacious wooden deck with a railing offers outdoor seating options. The area is adorned with fallen leaves, enhancing the natural setting.

Cabin in Margaretville

4.94 out of 5 average rating, 179 reviews

Catskills log cabin in the sky with mountain views

Welcome to Cabin in the Sky! At 1,671 ft elevation, Cabin in the Sky is a newly renovated log cabin nestled in the mountainside with tranquil views. The home offers the perfect combination of seclusion and convenience. In the mornings/evenings, enjoy a cup of coffee or glass of wine from the private deck which overlooks pure nature (not a car, street or building in sight). During the day, take advantage of the local hiking, skiing, farmer's markets, restaurants and shopping.

Top guest favorite

Three rustic cabins are nestled among vibrant autumn foliage, showcasing warm wooden exteriors and covered porches. A grassy area is visible in the foreground, inviting guests to relax and enjoy the natural surroundings. A gravel path leads to the cabins, enhancing the peaceful ambiance.

Tiny home in Shandaken

4.88 out of 5 average rating, 130 reviews

Simple, cozy cabin in the Central Catskills

"Joan" is our Simple, cozy cabin just 10 minutes to Phoenicia and Pine Hill and all the great hiking of the Central Catskills. Part of a 1940s bungalow colony lovingly restored, “Joan” is one of three cabins which sits next to each other. She sits between Shelly and Georgie, still offering each guest privacy without isolation. Joan is good for couples, and at 215 square feet, Joan will give you a nice, cozy feel. You’ll love my place because of the views and the outdoor space.

Guest favorite

The exterior of the house is viewed from the backyard, showcasing a spacious deck with a red umbrella. Lush green grass surrounds the area, with tall trees providing shade. The backdrop features rolling hills, creating a serene outdoor environment.

Home in Big Indian

4.91 out of 5 average rating, 134 reviews

5 minutes to Belleayre! The Birch Creek BelleHouse

Our modern home is clean and bright. Just minutes from skiing, hiking, swimming, and fine dining - The gorgeous Birch Creek is right outside . Feel free to take a dip. - A quick walk to Pine Hill Lake for swimming, boating and more. - Many spectacular hiking trails nearby. - It's an easy five minute drive to Belleayre Ski Center - Close to the best restaurants in NY State. - Pets are welcome with an additional fee. - Next door to our other property, the Birch Creek Cottage.