Holiday rentals in Sundown

4.95 out of 5 average rating, 172 reviews

Chalet in Grahamsville

Catskills mountain view chalet

Come and enjoy our Catskills mountain view chalet. Escape the chaos of the city for peace and serenity. In our home you'll find an open concept kitchen/dining and living room space, a huge deck, 2 bedrooms, a newly renovated bathroom and a loft work space. Take in the country skyline view with a glass of wine on the deck while listening to meditative sounds of the babbling brook. Don't forget to bring groceries as the best way to enjoy the chalet is with a home cooked meal with those you love

4.99 out of 5 average rating, 154 reviews

Cabin in Kerhonkson

Lovely Cabin w/Piano No Car Needed Best Hiking

When you truly want to get away from it all, come experience the wilderness of the Catskills. We're nestled next to 30k acres of the Sundown Wild Forest inside the 300k acres Catskill Park, 2 hrs from NYC. Enjoy any of the 3 fireplaces located in and around the cabin after your choice of 8 hiking trails you can take from our doorstep including the cascading pools of the secluded Vernooy Kill Falls. Ecology History tour available RT private transportation from New Paltz Trailways Bus available.

4.98 out of 5 average rating, 129 reviews

Home in Claryville

The Old Farmhouse on Red Hill - Catskill Mountains

The Red Hill Farmhouse is one of the original farmhouses in the Catskills from 1849; a gut renovation labor of love, where owner John McCormick, (designer of popular spots in the city such as St Mazie, Cafe Moto/ Bar Velo, Five Leaves, Smith and Mills and Maison Premiere), has completely redone the house while keeping the integrity of its history through salvaging and using the original materials wherever possible and “barn diving” to reinstall other original features adding to its rustic charm.

4.99 out of 5 average rating, 159 reviews

Cabin in Rochester

The Black Dymond A Private Streamside Cabin

A 2.5 hour drive from NYC to a serene, private, woodland, streamside home. This cabin sits on the very edge of the Catskill Mountains. It's cozy, modern, and minimalistic with a touch of rustic elegance. All new appliances with all the cooking necessities, a comfortable bed with large screen smart tv, excellent wifi service, a romantic gas-powered fireplace and the most private back deck away from the world to get lost for a weekend in the beauty of the woods.*Now offering mid-week price deals!

4.85 out of 5 average rating, 227 reviews

Chalet in Claryville

Secluded Cabin in Catskills Park on 20 acres

It's a secluded cabin and we kept it small and pristine for a reason. We also just planted cherry trees and apple tree...We kept it pristine so one can feel nature. And we dont have internet or Tv there otherwize it would be like being in the city. Get a feel for what it is like to be in a cabin in the woods. There is a whole flourishing ecosystem there with family of rabits, foxes, humming birds, bees, butterflies and birds. We are planting a garden and flowers. A place for hiking lovers.

4.93 out of 5 average rating, 140 reviews

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.

Guest suite in West Shokan

4.94 out of 5 average rating, 133 reviews

Stylish and Cozy Mountain Retreat

Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

4.93 out of 5 average rating, 123 reviews

Home in Claryville

Modern Catskills Tiny House Near Hiking Trails

A modern and well- designed home located in the Neversink area of the Catskills. The Tiny House has been updated with high-speed 200 Mbps wifi and a separate landline. There is no cell phone service in the immediate area. The house is a short drive to some of the best hiking trails in the area. Enjoy walks in the woods, country drives, or relax on the deck overlooking the pond. 3- night minimum stay. We require our guests to be 24 and over. Maximum of 2 adults. No pets .

4.81 out of 5 average rating, 903 reviews

Cottage in Kerhonkson

Cozy Cottage w/ Infrared Sauna

Escape to a serene, nature-inspired cottage nestled on the Shawangunk Ridge. Relax by the warm gas fireplace, gather around the handmade dining table crafted from 100-year-old reclaimed wood, or unwind in the private infrared sauna, accessible from the master bedroom. Explore nearby hiking trails, discover hidden messages throughout the space, and enjoy a curated "meaningful library." Perfect for relaxation, adventure, and meaningful moments with loved ones.

4.93 out of 5 average rating, 159 reviews

Cabin in Grahamsville

A Secluded Catskills Getaway: The Red Hill House

Situated on five acres inside the Catskills Park alongside a babbling brook, this mountain escape is perfect for couples, a friends retreat, or family getaway. Wake up with pour over coffee and take in the fresh air with a trek through our woods or the nearby Red Hill Fire Tower hike. Later, enjoy a nap in the hammock followed by a nighttime bonfire. Or put on a record and get cozy indoors with the woodburning stove and a variety of board games!

4.99 out of 5 average rating, 313 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Cabin in Livingston Manor

4.95 out of 5 average rating, 347 reviews

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek, gaze out XL windows, or cozy up by the fire—every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor—a quintessential Catskills town—and less than 2 hours from NYC.

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Other great holiday rentals in Sundown

4.87 out of 5 average rating, 46 reviews

Cabin in Kerhonkson

Black A-Frame: Catskills Cabin

AnatolyRating, 5 stars2 weeks ago

Amazing place in a very peaceful area! Very cozy and charming. Erica was very friendly and provided us with everything we could possibly need, as well as a very detailed guide for the local experience.

4.74 out of 5 average rating, 711 reviews

Cottage in Neversink

Cozy Catskills Lakefront Cottage

MichaelRating, 5 stars2 days ago

Lovely little get away, beautiful inside layout with a gorgeous backyard, a very comfortable place to stay definitely recommend

5 out of 5 average rating, 20 reviews

Home in Kerhonkson

Kerhonkson Forest House

HilaryRating, 5 stars1 week ago

We absolutely adored our stay at Insaff’s cozy home in the woods! The house was exactly as described and very comfortable. We really loved the heated floors in the bathroom and the shower. Super luxe. The woodland setting was picturesque and peaceful. The house was well stocked with everything we needed. A perfect getaway spot.

5 out of 5 average rating, 38 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

BingRating, 5 stars5 days ago

We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!

5 out of 5 average rating, 84 reviews

Cottage in Grahamsville

“Green Meadow Cottage”, updated 1850’s farmhouse.

IngaRating, 5 stars3 weeks ago

Tom’s place was super clean, lovely decorated and furnished. It has a lot to offer for the price- great value! Super easy communication, as well.

Guest house in Kerhonkson

5 out of 5 average rating, 15 reviews

Rustic Retreat in Hudson Valley

MarioRating, 5 stars3 weeks ago

Our stay was amazing. We completed our goal which was to disconnect from they city for a weekend and felt re-charged, re-energized and at peace during and after the trip. The setup is very practical. The deck was perfect for us to work on our own things throughout the day like journaling, cooking or just basking in the sun and napping. The outhouse, shower and BBQ area are all within 20-30 feet from the main deck and we just couldn't ask for a better layout. There's even a little trail down the main road that we explored that took us around the area and looped back to the house. Max was very responsive with any questions we had and he was very helpful in making us feel comfortable throughout the trip.

Cabin in Livingston Manor

4.88 out of 5 average rating, 58 reviews

Modern Catskills Creekfront A-Frame w/ Fly Fishing

ThomasRating, 5 stars2 weeks ago

Overall a great place to stay. View of the willowemoc was incredible. Truly beautiful. Heating system was pretty loud. Could easily hear it inside. WiFi was pretty much non-existent Those were my only complaints. Place itself very nice and tastefully done.