Family-friendly holiday rentals in Pine Hill

4.96 out of 5 average rating, 303 reviews

Cabin in Big Indian

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.

4.93 out of 5 average rating, 152 reviews

A peaceful outdoor scene features red Adirondack chairs positioned on lush green grass. The morning sun casts long shadows, illuminating the surrounding trees and the misty mountain view in the background.

Cabin in Arkville

Mountain View Hideaway

This cabin is a peaceful hideaway with spectacular mountain views tucked into a wooded cove. The hot tub along with the aura of tranquility will provide an oasis after a day of hiking, skiing or snowboarding. It’s an easy 5 minutes to Belleayre Ski Mountain and if looking to work from home, there is high speed wifi available as well as clear cellphone signals at the location. Lookout for the deer, wild turkeys, birds and much more from the porch or lounge. Check out @mountainviewhideaway on IG!

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.

4.92 out of 5 average rating, 155 reviews

Private Creek in Backyard: Catskills BelleHouse!

Our clean, bright home is the ultimate Catskills escape. Unwind to the sounds of gorgeous Birch Creek right outside the back door and feel free to take a dip! • Quick walk to Pine Hill Lake for swimming & boating. • Close to so many spectacular hiking trails • One minute to Peekamoose, the best restaurant in the Catskills! • Easy 5-minute drive to Belleayre Ski Center. • Fast Wi-Fi perfect for remote work. • Pets welcome w/ fee. • Located next door to our other property, Birch Creek Retreat!

A charming house is nestled among trees at the edge of a gently flowing stream. Smooth stone steps lead up to the home, which features a wide porch that extends out, offering a view of the lush greenery surrounding it.

4.99 out of 5 average rating, 100 reviews

Peaceful streamside in nature near skiing & hike

Find yourself at the base of Rose Mountain in a beautiful architect designed home. Relax to the sound of a beautiful year around stream. Easily accessible 5+ acres surrounded by State park land. Hiking trail right out the door. 5 mins to Bellearye Mountain, 15 minute to Full moon Resort and 1 minute Peekamoose restaurant and Pine Hill Lake. 14 minutes to Phoenicia. Gourmet kitchen, big dining room with an outstanding view. We have Air Conditioning, but it is rarely needed. #2025-str-AO-012

4.99 out of 5 average rating, 113 reviews

A serene pond reflects vibrant autumn foliage and a gentle slope of trees. The surrounding area is lush with greenery, while the clear blue sky adds depth to the picturesque landscape, creating a peaceful retreat in nature.

Cottage in Big Indian

The Pond House ~ 5 Min to Belleayre ~Outdoor Fun

Bring your family to this spacious and entertaining 8BR 3Bath oasis. Find your inner peace sitting by the pond and watching the ducks glide through the water. Let the soft rumble of Birch Creek flowing through the back of the property lull you into daydreaming. The comfy design and rich amenity list will leave you in awe. ✔ 8 Comfortable BRs ✔ Fully Equipped Kitchen ✔ Pond and Creek Access ✔ Outdoors (BBQ, Fire Pit, Hammock) ✔ Game Room ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

4.87 out of 5 average rating, 136 reviews

A cozy campfire area is surrounded by wooden Adirondack chairs, set upon a gravel surface. In the background, the A-frame cabin stands under the tree canopy, with multiple illuminated windows providing a warm glow.

Cabin in Pine Hill

Modern A-Frame in Catskills Park

The Pine Hill Aframe curates a modern and intentionally designed A-frame retreat on 1.6 acres just 3 mins to Belleayre Ski resort & 20 min. to Plattekill. Centrally located in the heart of the Catskills, surrounded by world renown trails and fishing. Rest, hike, ski, relax, create amongst the renovated interior or forest bathe outdoors. We invite you to come build memories! As seen on Dwell Mag & Cabin Chronicles Season 3. Find us on IG @pinehillaframe STR License #2022-STR-AO-073P

4.96 out of 5 average rating, 113 reviews

A large hot tub is positioned beneath a wooden shelter, surrounded by lush greenery. Adirondack chairs are placed nearby, providing a comfortable seating area. The bubbling water of the hot tub invites relaxation, set against a backdrop of tall trees and vibrant foliage.

Home in Arkville

Mountain Escape with a Large Hot Tub and more!

Escape to a serene retreat with a large 6-person hot tub, Adirondack chairs by the firepit, and a grill for perfect evenings. Just minutes from Belleayre skiing, hiking trails, world-class fishing, and year-round activities. Enjoy wildlife from the wrap-around deck, practice yoga, read, or listen to the soothing mountain creek. Embrace the moment and forget your worries! Nestled on a private road, this haven requires 4-wheel drive in winter. Book now for an unforgettable experience!

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.

4.95 out of 5 average rating, 140 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.

An open living space features a stone fireplace at its center, flanked by large windows that provide natural light. Comfortable seating is arranged around a coffee table, and a dining area with chairs is visible in the background, all designed with rustic cedar beams overhead.

4.97 out of 5 average rating, 196 reviews

Contemporary MOUNTAINSIDE home

The contemporary mountain side house is located between Woodstock and the Belleayre Ski Resort. Designed by an award winning architect, featuring cedar beams, vaulted ceiling, and walls of windows. Lower level houses the media/billiards room and 4 en-suite bedrooms all with individual private outdoor patios. Close to Peekamoose and Zephyr restaurants. Few minuets from Phoenicia and a little further is the historic Town of Woodstock with its long history in the arts and music.

4.98 out of 5 average rating, 471 reviews

A spacious living area features a high A-frame ceiling with large triangular windows, allowing for abundant natural light and scenic views. A wood-burning stove sits in the center, surrounded by elegant seating arrangements on a plush area rug, enhancing a cozy atmosphere.

Cabin in Margaretville

Modern & Chic Log Home-Spectacular Mountain Views!

Welcome to Fox Ridge Chalet! Minimum age to book 21. A newly renovated, stylish log cabin nestled on 7 private acres above the village of Margaretville, in the heart of Catskills Park. Though the home is secluded, offering spectacular mountain views and total privacy, it’s just a three-minute drive to Margaretville’s restaurants, shops and galleries and under ten minutes to Belleayre Ski Resort as well many other local attractions.

4.96 out of 5 average rating, 160 reviews

A spacious country house is surrounded by lush greenery and mature trees. A gazebo is elegantly positioned on the lawn, while a meandering stream flows gently nearby, enhancing the natural setting.

Home in Pine Hill

Birch Creek Retreat ~ 8BR/8BA New Hot Tub + Sauna

Charming, spacious, historical place for families to bunker up in a natural setting. Stay at this private, sprawling country house situated on 23 acres of woodlands. There is a barn and a rare keystone bridge on the property with a meandering stream that runs throughout. Perfect place to host memorable family reunions, friends gatherings & all season getaways! :) Please inquire for use of the barn. License #2024-STR-AO-027P

4.87 out of 5 average rating, 167 reviews

An open living space is viewed through arched doorways, showcasing wood flooring and natural light. A central seating area features a sofa and minimalist décor, while two cozy sleeping areas are visible in the background. Two pendant lights hang from the ceiling, enhancing the airy feel.

Home in Pine Hill

The Carriage House/Pine Hill Studio

Charming light-filled renovated 1200 SF carriage house in the lovely Catskills hamlet of Pine Hill. Two bedrooms with two additional daybeds in open loft-like space. Full kitchen and bath. Walk to Pine Hill Lake, hiking and restaurants and stores in town. Close to Phoenicia, Belleayre and Woodstock. Perfect for staying in the area for hiking, leaf peeping, weddings, and skiing ! Shandaken STR License #2023-STR-030

Popular amenities for Pine Hill family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 180 reviews

A serene view of the cabin set amidst lush greenery, with a calm stream flowing nearby. The deck is visible, and seating areas are arranged on the manicured lawn. Surrounding trees offer a sense of seclusion, enhancing the natural ambiance of the location.

Cabin in Hardenburgh

Catskills Cabin Oasis: Hot Tub, Hike, Creek, Relax

4.99 out of 5 average rating, 169 reviews

A cozy outdoor space features comfortable seating and a modern fireplace, set against a stunning backdrop of lush trees and a colorful sunset. A hot tub is visible nearby, inviting relaxation. Soft lighting adds a warm touch to the tranquil atmosphere.

Home in Lexington

Valley View Chalet: AC, Hot Tub, Firepit, Games

4.92 out of 5 average rating, 217 reviews

The contemporary house is set against a backdrop of trees with autumn foliage. It features a spacious deck and large windows that invite natural light. A paved area is visible in front, with organized landscaping and clear access to the entrance.

Home in Margaretville

Belleayre GrandHouse 6 BRs w/Hot tub/Sauna/Game RM

4.96 out of 5 average rating, 232 reviews

A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.

Home in Hunter

Modern House with Mountain View @Getawind

4.97 out of 5 average rating, 105 reviews

A rustic wooden cabin features a vibrant yellow door and large windows, surrounded by manicured greenery. The property is set against a backdrop of lush trees and a clear blue sky with scattered clouds, inviting an appreciation of the natural landscape.

Home in Fleischmanns

Secluded Cabin w/ Chefs Kitchen & Hot Tub!

Home in Town of Shandaken

A fully renovated kitchen features stainless steel appliances, including a gas stove and refrigerator. Open shelving displays a variety of cookware and small appliances. Natural light enters through a window, enhancing the bright and clean workspace with warm wood accents on the countertops.

4.91 out of 5 average rating, 108 reviews

Modern Mountain Getaway with Fire Pit

4.97 out of 5 average rating, 399 reviews

An outdoor wood-fired hot tub is positioned on a deck, offering views of the lush green landscape and distant mountains. Sunlight reflects off the water's surface, while a wooden paddle rests against the side. The serene setting invites relaxation amidst nature.

Cabin in Big Indian

Romantic Cabin with Sauna & Wood Fired Hot Tub

4.94 out of 5 average rating, 154 reviews

The inviting living area features a comfortable gray sofa adorned with accent pillows. A wooden coffee table is centrally placed, while a modern lamp and a cozy rug enhance the space. Large sliding doors open onto the deck, offering natural light and views of the surroundings.

Cottage in Chichester

Stream Come True | Hot Tub, Ski, Hike, Relax

Family- and pet-friendly home rentals

4.85 out of 5 average rating, 163 reviews

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

Birch Creek House - Private & Cozy Creekside Cabin

Holiday home in Pine Hill

4.99 out of 5 average rating, 154 reviews

The Perfect Catskills Escape for Families and Groups

Cabin in Town of Shandaken

A spacious living area features a wood-paneled ceiling with four skylights, allowing natural light to brighten the room. A cozy sectional sofa offers a comfortable seating option. A stone fireplace is positioned next to a wall-mounted television, with large glass doors leading to the outdoor deck.

4.97 out of 5 average rating, 181 reviews

Catskills Cedar House | central Catskills retreat

Cabin in Town of Shandaken

The cabin's exterior showcases a charming green facade adorned with decorative stars. A spacious deck is visible, equipped with a dining area and umbrellas for shade. Surrounding lush grass and colorful flowering bushes enhance the natural setting, while seating arrangements offer inviting spots to relax outdoors.

4.98 out of 5 average rating, 164 reviews

Storybook Creekside Retreat: 8 Acres w/ Epic Views

Flat in Town of Shandaken

A serene bedroom features a light lavender bed with plush pillows. A golden accent pillow adds color. A wall mural depicting a tree with birds in flight creates a calming backdrop, while natural light brightens the space from a nearby door.

4.94 out of 5 average rating, 125 reviews

Catskill Cabin, Zen Mantra Apt. #9 * * * * *

4.93 out of 5 average rating, 212 reviews

A charming cabin, constructed with dark wood, sits surrounded by lush greenery. A stone pathway leads to the front entrance, where steps are flanked by ornamental plants. The backdrop features rolling hills, showcasing a blend of nature and tranquility.

Cabin in Arkville

Dry Brook Cabin

Home in Town of Shandaken

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.

4.95 out of 5 average rating, 223 reviews

Catskills Mountain House with a Separate Cottage on a Creek

4.84 out of 5 average rating, 112 reviews

A serene waterfall cascades over smooth rock formations, surrounded by lush green foliage and autumn leaves. Gentle water flows create a calming sound, while amber sunlight filters through the trees, illuminating the natural landscape.

Home in Margaretville

FOUR SEASON Huge Catskills Home-Secret Waterfall

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 174 reviews

A modern cabin stands against a backdrop of lush greenery and mountains. Large windows invite natural light, while a deck with seating is visible in the foreground. Surrounding landscaping includes trees and shrubs, creating a serene and private outdoor space.

Cabin in Arkville

Hike & Sauna! Modern Mountain Escape

4.95 out of 5 average rating, 105 reviews

A tranquil heated saltwater pool is framed by lush greenery and sun loungers, inviting relaxation. An orange inflatable ring floats on the water, and a wooden fence provides some separation from the surrounding area. Bright sunlight casts a refreshing glow on the pool's surface.

Cabin in Roxbury

Blissful Mountain House

4.94 out of 5 average rating, 398 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

4.95 out of 5 average rating, 109 reviews

Home in Windham

Windham Manor | 6BDRM, Pool, Hot Tub & Movie Room

4.91 out of 5 average rating, 127 reviews

An aerial view showcases a charming farmhouse surrounded by lush greenery and the Catskill Mountains. A rectangular in-ground pool is visible in the backyard, bordered by a grassy area. A quiet country road runs alongside the property, contributing to the tranquil setting.

Home in Grahamsville

Spacious Catskills Farmhouse on over 5 acres!

4.95 out of 5 average rating, 412 reviews

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

A Very Cozy House With a Very Big Yard

4.99 out of 5 average rating, 278 reviews

An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

Home in Woodstock

The Woodstock Barn House - Sauna, Gym, Jacuzzi