Family-friendly holiday rentals in Pine Hill

4.96 out of 5 average rating, 301 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.

KitchenFamilyOutdoor spaces

4.85 out of 5 average rating, 162 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

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

KitchenFamilySkiing

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, 154 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!

FamilyKitchenBackyard

4.99 out of 5 average rating, 112 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!

KitchenIndoor spacesOutdoor spaces

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

KitchenFamilyCondition

Holiday home in Pine Hill

4.99 out of 5 average rating, 154 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.

KitchenFamilyLocation

4.96 out of 5 average rating, 111 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!

Indoor spacesKitchenAccess

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, 139 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.

KitchenIndoor spacesQuiet

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, 195 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.

Indoor spacesFamilyCondition

Apartment 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, 124 reviews

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

Escape to a calm Catskills retreat at the base of Belleayre Mountain 🌲🏔️ Where natural fineness meets charming, relaxed style ✨ Thoughtfully designed with a focus on healthy living, sustainability, and connection to nature 🌱 Surrounded by miles of forest, enjoy mountain views, fresh air, and quiet moments in every season 🌿 Wake up to the beauty of the outdoors—deer passing by, birds overhead, and the occasional glimpse of local wildlife 🦌🐻

Indoor spacesKitchenLocation

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

Indoor spacesKitchenPets

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

FamilyIndoor spacesTV

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

4.93 out of 5 average rating, 150 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

KitchenFamilyLong stay

4.98 out of 5 average rating, 469 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!

FamilyIndoor spacesBarbecue

4.98 out of 5 average rating, 176 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

Indoor spacesKitchenWalkability

4.93 out of 5 average rating, 215 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

Indoor spacesKitchenCleanliness

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

KitchenFamilyCheckout

4.99 out of 5 average rating, 150 reviews

The A-frame chalet is framed by lush greenery, featuring a dark exterior with large windows. A bright blue door welcomes guests, and a private balcony extends from the upper level. Natural light reflects off the exterior, highlighting the home's inviting design.

Home in Prattsville

Scandi A-Frame w/Hot Tub & Sauna

Indoor spacesKitchenAccuracy

4.96 out of 5 average rating, 229 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

KitchenFamilyBreakfast

4.9 out of 5 average rating, 131 reviews

The image features a modern hot tub in the foreground, with bubbling water and a clear dome structure nearby. The dome showcases a seating area surrounded by nature, with trees visible in the background against a bright blue sky.

Chalet in Prattsville

White Holiday Cozy Chalet Pool/Hot Tub/bubble room

Indoor spacesFamilyPets

Family- and pet-friendly home rentals

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, 163 reviews

Storybook Creekside Retreat: 8 Acres + Epic Views

KitchenFamilySleep quality

Bungalow in Margaretville

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.

4.96 out of 5 average rating, 385 reviews

The Porch Upstate Super clean

KitchenIndoor spacesCleanliness

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, 222 reviews

Catskills Mountain House with a Separate Cottage on a Creek

Indoor spacesKitchenAccuracy

4.93 out of 5 average rating, 211 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

KitchenFamilyLayout

4.94 out of 5 average rating, 178 reviews

An aerial view of a spacious property with well-maintained green grass, surrounded by trees exhibiting autumn colors. The house, positioned centrally, is complemented by a firepit area with seating in the foreground, providing an inviting space for outdoor gatherings.

Cottage in Margaretville

Cozy Catskills Cottage with Mountain Views

KitchenIndoor spacesAir conditioning

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, 178 reviews

Catskills Cedar House | central Catskills retreat

FamilyKitchenOutdoor spaces

4.87 out of 5 average rating, 99 reviews

A serene view of a private lake surrounded by lush greenery, featuring a fountain at its center. Four red Adirondack chairs are arranged around a fire pit on the grassy shore, inviting outdoor relaxation. A solitary tree rises from the water, enhancing the tranquil atmosphere.

Barn in Big Indian

Barn-Again|Lakefront Mountain Retreat by Belleayre

KitchenIndoor spacesComfort

The charming mountainside house features a rustic wooden deck with railings, providing an inviting outdoor space. A mixture of blue siding and stone accents characterize the exterior, surrounded by lush greenery and trees, creating a peaceful natural setting.

4.93 out of 5 average rating, 158 reviews

Catskills Hiking Skiing Belleayre Full Moon Resort

Indoor spacesKitchenComfort

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 186 reviews

Farm stay in Saugerties

Catskills Family Retreat: Pool, Sauna and Animals!

KitchenIndoor spacesBiking

4.95 out of 5 average rating, 104 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

Indoor spacesKitchenBarbecue

4.98 out of 5 average rating, 173 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

KitchenIndoor spacesHospitality

4.95 out of 5 average rating, 108 reviews

Home in Windham

Catskill Villa | 6BDRM, Pool, Hot Tub & Movie Room

FamilyKitchenTV

4.97 out of 5 average rating, 109 reviews

A welcoming living area features a stone fireplace and wood-beamed ceiling. Two comfortable armchairs and a sofa are arranged around a circular coffee table. Large windows, framed by sheer curtains, allow natural light to brighten the space. A television is mounted on the wall, enhancing the cozy atmosphere.

Townhouse in Windham

Cozy, peaceful-3Br (5 beds)2.5 Bath townhouse

FamilyKitchenComfort

4.91 out of 5 average rating, 125 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!

Indoor spacesFamilyLaundry

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

Indoor spacesKitchenValue