Holiday houses in Pine Hill

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Top-rated holiday rentals in Pine Hill

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Top Guest favourite
The living area features large windows that provide natural light and views of the surrounding woods. A blue sofa and a matching loveseat are positioned around a coffee table on a patterned area rug. Wooden beams and a stone fireplace add to the cabin's character.
Cabin in Big Indian
4.96 out of 5 average rating, 287 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 favourite
The A-frame cabin is surrounded by vibrant autumn foliage, showcasing hues of gold and orange. A welcoming red door stands out against the green exterior. A wooden deck extends from the cabin, providing an inviting entry point amidst the natural landscape.
Cabin in Margaretville
5 out of 5 average rating, 211 reviews

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

Top Guest favourite
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, 334 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.

Superhost
Cabin in Pine Hill
4.86 out of 5 average rating, 122 reviews

Modern A-Frame in Catskills Park & 3 mins to Ski

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

Top Guest favourite
Holiday home in Pine Hill
4.99 out of 5 average rating, 146 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 favourite
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
4.95 out of 5 average rating, 189 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 favourite
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.
Home in Big Indian
4.98 out of 5 average rating, 189 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.

Guest favourite
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, 143 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.

Guest favourite
A back deck overlooks the scenic Catskill Mountain range, featuring a recessed hot tub and a fire pit. Soft lighting from string lights enhances the outdoor space, inviting relaxation while taking in gentle mountain views at sunset.
Chalet in Fleischmanns
4.99 out of 5 average rating, 243 reviews

Crows Nest Mtn. Chalet

Elevated into the Mountainside, Crow’s Nest looks out onto a spectacular view of the Catskill Mountain range of Belleayre. Grab a cup of coffee and watch the sunrise from the back deck or bask in the glow of the sunset while relaxing in the hot tub or hammock. This is an incredible place to unwind and take in that fresh mountain air or retreat to one of the many hangout spots in this newly renovated home. Follow us on IG : @crows_nest_catskills

Top Guest favourite
A charming Swiss chalet is nestled among tall trees, surrounded by lush greenery. The house features a welcoming deck and multiple windows that provide natural light. A stone path leads to the entrance, inviting guests to explore the tranquil outdoor setting.
Home in Big Indian
4.98 out of 5 average rating, 133 reviews

Gingerbread House- a 1950s Catskills Chalet

Perched high among the trees, Gingerbread is a 1950’s Swiss chalet that sits on 4 acres. This is the house everyone slows down for, points and says ‘ that’s the house I would want Upstate’. Well ….she's taken. But I am so happy to welcome you as guests for a short period of time. Gingerbread comes with all the little touches making it feel like the perfect home away for a week, weekend or however long you can escape your regular life.

Guest favourite
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
4.95 out of 5 average rating, 149 reviews

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

Top Guest favourite
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
4.86 out of 5 average rating, 162 reviews

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 holiday rentals

When is the best time to visit Pine Hill?

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Avg. price$455 NZD$448 NZD$457 NZD$395 NZD$422 NZD$441 NZD$443 NZD$450 NZD$441 NZD$443 NZD$431 NZD$468 NZD
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Frequently Asked Questions

  • What are the most popular amenities for House Rentals in Pine Hill?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with wifi, over 10 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Pine Hill?

    Yes! Work meets play with ease at over 30 vacation rentals in Pine Hill featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Pine Hill?

    Pine Hill has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Pine Hill have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Pine Hill. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Pine Hill?

    Four-legged friends are welcome in Pine Hill. Choose from more than 30 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in house rentals in Pine Hill?

    Experience the best of Pine Hill with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do bed and breakfast rentals in Pine Hill have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Pine Hill. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Pine Hill have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Pine Hill. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Pine Hill

  • Total holiday rentals

    Explore 60 holiday rentals in Pine Hill

  • Nightly prices starting at

    Pine Hill holiday rentals start at $141 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Pine Hill holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Pine Hill rentals

  • 4.9 Average rating

    Pine Hill stays are highly rated by guests—averaging 4.9 out of 5!

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