Holiday rentals in Middletown

Mountain View Hideaway

This cabin is a peaceful hideaway with spectacular mountain views tucked into a wooded cove. The hot tub along with the aura of tranquility will provide an oasis after a day of hiking, skiing or snowboarding. It’s an easy 5 minutes to Belleayre Ski Mountain and if looking to work from home, there is high speed wifi available as well as clear cellphone signals at the location. Lookout for the deer, wild turkeys, birds and much more from the porch or lounge. Check out @mountainviewhideaway on IG!

Spacecraft Sanctuary x Stargate Self-Care Retreat

Nestled into a private forested locus in the charming hamlet of Halcottsville, NY is SPACECRAFTX1 SANCTUARY, a transformed single wide trailer with walls of glass sliders that showcase the ultimate designer, Mother Nature with her majestic mountain vistas, perennial x calming Japanese rock gardens. SPACECRAFTX1 STARGATE (separate structure) is a wellness studio for yoga, pilates, barre x meditation with an infrared sauna with chromotherapy for a “Design Your Own” self-care retreat experience.

Catskills Cabin Oasis: Hot Tub, Hike, Creek, Relax

Escape to a secluded Catskills cabin with hot tub, forest views, fireplace, and walkable access to Balsam Lake Trailhead. Relax in the hot tub under the stars, enjoy coffee on the deck beside a babbling creek, and unwind by the historic fireplace built in 1920. Just 10 minutes to Belleayre Mountain for skiing, tubing, hiking, and lake days. Perfect for couples getaways, family weekend escapes, hiking trips, ski weekends, and year-round Catskills adventures. Welcome to Catskill Cabin Oasis!

The Hideaway

Perfect getaway for friends and couples! Kickback, relax and wake up to the stunning mountain view, then cook the perfect brunch in our state of the art kitchen with a brand new range. Cozy up around the wood-burning stove while watching a good movie or playing some board games. At night, watch the stars around the fire pit while listening to the gentle sounds nature. You will feel truly connected to nature while only being 2 hours from NYC. *In winter, a 4x4 vehicle is strongly recommended*

Belleayre GrandHouse 6 BRs w/Hot tub/Sauna/Game RM

Contemporary house located in the heart of Catskills Park. House has a hot tub, sauna, game room, outdoor fire pit and wine bar. 9 mins to Belleayre ski, 13 mins to Plattekill. Total of 3 fls, 3600 SF of living space, sleeps 15, perfect for a group of family or friends gathering together. Granite kitchen countertop w/ tons of cabinet space, eat in kitchen. 15 seats dinning table. 3 modern design bathrooms and 6 large cozy bedrooms. Outdoor lounge area, fire pit with a gorgeous mountain view.

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.

Catskills Mtn. Retreat, Hot Tub, Sauna & Fire Pit

Escape to SOL® Catskills; sustainable opulent living, mountain retreat; breathtaking views and ultimate relaxation. Unwind in the private hot tub, recharge in the sauna, or enjoy a cozy evening by the fire pit. Minutes away from hiking, skiing, and charming Catskills towns, this modern cabin blends seclusion and convenience. With spacious interiors, a fully-equipped kitchen, and all-season outdoor spaces, it’s the perfect destination for your next adventure in the heart of the Catskills!

Cozy Chalet in Margaretville

This cozy chalet sits just outside of Margaretville, right around the corner from the Pakatakan Farmers' Market and Hanah Mountain Resort and Country Club. In town there is a grocery store as well as many wonderful restaurants to dine at. 15 minutes away is Belleayre Mountain Ski Center and Belleayre Beach at Pine Hill Lake. Across the road in Halcottsville you can go kayaking on Lake Wawaka, or 10 minutes down the road in Roxbury Ski Plattekill Mountain and Shephard Hills Golf Course.

FOUR SEASON Huge Catskills Home-Secret Waterfall

Winter wonderland halfway between Belleayre and Plattekill! SUN-DRENCHED 4000 sqf Contemporary sits on 6 wooded acres, adjacent to state lands, private HIKING trails, glorious streams and a hidden WATERFALL. Close popular WEDDING venues,SKI resorts, next to Hanah GOLF Club. Outside large stone FIRE PIT and multiple DECKS for lounging.Great Room boasts a PIANO and ROMANTIC working fireplace,tastefully decorated with a modern flair including a BRAND NEW FULL BATH on the bottom level.

Shell House- Luxury Designer Dome 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.

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.

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.