House vacation rentals in Pine Hill

5 out of 5 average rating, 180 reviews

A modern living area is highlighted by 20-foot vaulted ceilings and a wall of large picture windows framing lush mountain views. The space features a comfortable sectional sofa, a wooden coffee table, and a television on a media console. A cozy gas fireplace enhances the inviting atmosphere.

Home in Roxbury

Private Mt view escape- 3BR w/firepit near skiing!

Click: "Show more" to read description before booking. NO PETS Perched high on a private road, The Ridge is a 3 BR / 2 bath newly constructed modern farmhouse w/ sweeping mountain views! Relax & dine outdoors on the wrap around deck & discover all of the comforts of home inside the open concept living space. Set on 5 mountainside acres, 3 min to Roxbury town & 10 min to wedding venues. Outdoor adventures await- 4 season activities at ski mountains, hiking, golf, farmers markets & culinary tours

4.99 out of 5 average rating, 112 reviews

Home in Phoenicia

Modern dreamy Hudson Valley home

Gorgeously renovated 3-bedroom home in the heart of the Catskills. Enjoy your own private firepit and outdoor dining, cook and recharge in the light-filled kitchen, feel pampered in the spa-like bathroom with a heated floor - all within 5 minutes of the Phoenicia Diner & Railway Explorers. Nestled in the mountains, this home is the perfect for unwinding & offers green amenities including an EV charger and new eco heating and cooling system. Large windows bring light & views to this dreamy home.

4.99 out of 5 average rating, 108 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

4.95 out of 5 average rating, 209 reviews

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

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.

4.93 out of 5 average rating, 164 reviews

A cozy outdoor seating area is surrounded by trees and fallen leaves. Four red chairs are positioned around a wooden table, with a fire pit in the center. String lights are draped overhead, creating a warm ambiance in the natural setting.

Home in Livingston Manor

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

4.82 out of 5 average rating, 130 reviews

A charming farmhouse is set alongside a serene pond, with lush greenery and mountains in the background. A balcony extends from the upper level, and a small dock is visible on the water. Adjacent structures contribute to the rural appeal.

Home in Arkville

Scenic farmhouse near Belleayre Mountain

Charming farmhouse overlooking the babbling Dry Brook. Entry to a large eat in kitchen that reflects natural light. Beautiful living room with hardwood floors and a stone clad fireplace. Full bathroom downstairs. The second floor offers a master suite with a balcony, large landing, walk in closet, and a full private or shared bathroom as suite has an extra bedroom. The property features a spring fed pond with a dock and pedal boat. Old logging trails that lead you up the scenic mountain.

4.95 out of 5 average rating, 188 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

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

4.95 out of 5 average rating, 137 reviews

The living area features a spacious, light-filled design with high ceilings and warm wood accents. A large sectional sofa surrounds a round coffee table atop a soft area rug. Natural light pours through extensive windows, while a sleek black chair adds a modern touch.

Home in Fleischmanns

Renovated Cozy Catskills Getaway! BBQ, WFH, Relax!

Welcome to Ollies House, named after the my rescue pup Oliver. The home is newly renovated and furnished featuring an indoor wood burning fireplace, 3 bedrooms and 2 full baths. Its located on 5 peaceful and private acres. Ollies House is a great choice for those looking to be active or enjoy a staycation. Located in the heart of the Catskills the house is minutes from Belleayre and 35 mins to Hunter. Situated between Margaretville and Phoenicia with tons of things to do in the area.

4.97 out of 5 average rating, 191 reviews

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

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.

4.99 out of 5 average rating, 140 reviews

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

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.

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.

4.95 out of 5 average rating, 150 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

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.

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 house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 514 reviews

Home in New Paltz

midcentury mod * HOT TUB * walk out trail 2 mohonk

Superhost

Home in Saugerties

4.87 out of 5 average rating, 141 reviews

Catskills SKI HAUS Winter Wonderland

4.88 out of 5 average rating, 185 reviews

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

Scenic River View Escape | New Paltz

4.86 out of 5 average rating, 140 reviews

A panoramic view of distant mountains stretches under a clear blue sky. The landscape features a mix of trees and open areas, showcasing the natural beauty of the surroundings.

Home in Woodstock

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

4.98 out of 5 average rating, 129 reviews

A spacious deck features two comfortable chairs and a round table at its center, offering a clear view of the expansive Catskill Mountain landscape. Lush greenery and rolling hills stretch into the distance under a bright blue sky.

Home in Stamford

Hawk View

4.99 out of 5 average rating, 107 reviews

An aerial view captures The Evergreen retreat set on three acres, showcasing a spacious yard surrounded by trees. A heated pool is visible beside a patio area with a dining table, while a fire pit is centrally located, enhancing the outdoor experience.

Home in Saugerties

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

5 out of 5 average rating, 160 reviews

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

4.9 out of 5 average rating, 110 reviews

Home in Grahamsville

Spacious Catskills Farmhouse on over 5 acres!

Weekly house rentals

4.97 out of 5 average rating, 137 reviews

The exterior of the home is showcased, featuring a prominent front porch with decorative railings. Lush green lawns surround the house, and trees line the background. The structure has a steep roof with dormer windows and a central door framed by elegant sidelights.

Home in Roxbury

Modern Getaway with Mountain Views

A spacious living room is arranged with a large sectional couch and a wooden coffee table. A modern television is mounted on the wall, while a gas woodstove provides warmth. Natural light enters through multiple windows, enhancing the relaxed atmosphere.

4.9 out of 5 average rating, 29 reviews

Creekside. Near Belleayre skiing & lake, shopping

A charming retreat is nestled in a snowy landscape, featuring a dark exterior with warm light emanating from multiple windows. The stone chimney adds a rustic touch, while a pathway leads to the entrance, framed by snow-covered landscaping.

5 out of 5 average rating, 16 reviews

littleburnthouse in Highmount NY

4.99 out of 5 average rating, 91 reviews

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.

Home in Big Indian

Peaceful streamside in nature near skiing & hike

4.98 out of 5 average rating, 168 reviews

A fire pit made of stacked logs is in the foreground, with bright flames dancing above. In the background, a serene lake is flanked by lush trees, reflecting the surrounding mountains bathed in early morning light.

Home in Chichester

Stunning Pvte Lakehouse•SKI•Hike•Mntn Views•F/pit

4.95 out of 5 average rating, 456 reviews

A spacious interior features exposed wooden beams and light-colored flooring. Large windows allow natural light to illuminate the room, highlighting comfortable seating areas and a dining table. A staircase is visible, leading to the upper level, enhancing the open and airy design.

Home in Germantown

Rustic Swedish Barn/Featured in Airbnb Magazine

4.99 out of 5 average rating, 108 reviews

Home in Roxbury

Peaceful Designer Farmhouse~Hot Tub~Sunset Porch

5 out of 5 average rating, 134 reviews

The exterior view showcases the two-story Flatrock House, featuring a combination of wood and stone siding. A welcoming entryway is complemented by a stone pathway lined with greenery, while surrounding trees and a lush yard enhance the natural setting.

Home in Shandaken

Swim in the Esopus, Close to Phoenicia and Skiing

Private house rentals

5 out of 5 average rating, 25 reviews

Home in Arkville

Artist’s Home in the Catskills-5 Minutes to Skiing

A sitting area features dual windows that bring in natural light, complemented by built-in seating adorned with striped and solid cushions. A small white table occupies the center, while a comfortable chair invites relaxation. A plush area rug enhances the warm ambiance.

4.86 out of 5 average rating, 43 reviews

Modern Farmhouse 5 min to Belleayre | Wood Stove

5 out of 5 average rating, 39 reviews

Home in Margaretville

Luxurious A-Frame Ski Retreat in the Catskills

4.99 out of 5 average rating, 76 reviews

Home in Arkville

Mountain Escape with a Large Hot Tub and more!

4.98 out of 5 average rating, 90 reviews

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

5 out of 5 average rating, 6 reviews

Home in Mount Tremper

Catskill Mountains Forest Nest for 2

4.99 out of 5 average rating, 70 reviews

Home in Lanesville

Stylish Catskills A-Frame Cabin w/ Hot Tub

The exterior of Pine Hill Chateau showcases a modern two-story structure with white siding and black accents. Large windows invite natural light, while a stone pathway leads to the entrance. The surrounding yard features well-maintained grass and scattered autumn leaves.