Holiday rentals in Middletown

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.

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.

The Mill House: An Enchanting Stream-Side Retreat

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to the perfect fall retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a recent restoration, marrying its saw mill heritage with contemporary luxuries, including a Nest thermostat, smart speakers, keyless entry, and fast wifi. Original exposed post and beam construction and Scandinavian-inspired design make for a unique and cozy atmosphere.

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.

Luxury Designer Dome Private Oasis in Catskills

* MOST WISHLISTED AIRBNB IN NY STATE! * Welcome to the Shell House, an idyllic and uniquely designed four season retreat nestled on 5 private acres. Enjoy breathtaking mountain views from every room, cozy bedrooms for peaceful nights, and expansive outdoor spaces perfect for relaxation. Just minutes from nearby towns and the best of the Catskills, this light-filled sanctuary invites you to unwind, reconnect with nature, and create lasting memories with loved ones.

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

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.

Charming Cottage on 12 Secluded Acres + Hot Tub

This Catskill cottage is situated on 12 secluded acres with stunning mountain and valley views. The main house features three well-appointed floors with two bedrooms downstairs, a primary bedroom with ensuite on the top floor and a wood burning stove on the main floor. The property also features a separate studio with a large stone patio, fire pit, cedar hot tub, pond, and scenic forest trail beyond. Close to skiing, hiking and golfing!

Stunning Catskills Cabin • Hikes • Lakes • Forest

Welcome to The Pines!! Nestled on 8 acres in the Catskill Mountains. Enjoy beautiful views of the forest, listen to some records, relax by the fireplace, read a book in the hammock, watch a movie on the projector screen, grill on the deck, or soak in the tub. The Pines is close to local shops, breweries, live music, farms, and incredible food. Hiking trails, waterfalls, lakes, kayaking, and skiing are right on your doorstep!

Dry Brook Cabin

The design of the Dry Brook Cabin is inspired by Scandinavian simplicity and functionality. Our aim was to create a space that offers the comfort of modern living while encouraging you to connect with the surrounding landscape. The calming sound of Dry Brook will help you escape the stresses of everyday life, and nature will gently remind you of where we truly belong. We hope you enjoy your stay here as much as we do.

The Porch Upstate Super clean

We are 8 miles away from ski slopes in both directions. .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 have six goats and a mini horse named Batman.

Modern Mountain Retreat with Views on 18 Acres

Relax and find your bliss in this modern stylish retreat on eighteen private acres. Landola Lodge has been recently renovated into a spa-like space that includes cozy beds, luxurious walk-in shower and soaking tub, entertainment lounge with Roku TV, High-Speed Internet, gas fireplace, central AC/Heat, washer/dryer, dishwasher, beautiful mountain views, deck, outdoor grill, and fire pit.