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!

Value · Family · Indoor spaces

Cupcake Cottage! 1838 renovated barn, with views.

The Airbnb 15.5% service fee is now built directly into the nightly price. New for 2026: Kitchen Aid stand mixer, towels, frying pans. Cupcake Cottage has had a total renovation: the same light, charm, and views remain but inside there is a new kitchen, flooring, and heating system. And outside, a new deck and porch configuration, windows, siding, roof and dormers. The house is an 1838 barn with old beams and rafters, and modern finishes of hemlock, red oak, and western red cedar throughout.

Family · Location · View

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.

Value · Family · Pool

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.

Family · Location · Pool

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!

Location · Family · Cleanliness

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*

Family · Location · Check-in

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.

Value · Family · Condition

Catskills Home with SAUNA, near Belleayre Beach

Nestled in the hills of the Catskills, Yellow Door Cabin offers a tranquil getaway 2.5 hours from New York City. The cabin is equipped with modern amenities - high speed WiFi, smart TV and AC/heat. Relax at the brand new private Sauna on the property. Located between Asheville & Roxbury NY, you will be minutes away from local cafes, dining, farmers markets, hiking and skiing. Enjoy year round outdoor adventures at Belleayre, Plattekill ski mountains and Phoenecia Diner all ~20 minutes away.

Location · Value · View

Cozy Catskill Ski Cabin Margaretville/Arkville

Contemporary & rustic log cabin, < 2. 5 hrs. from NYC nestled in the Catskills; well-appointed, perfect getaway/retreat/ski cabin - quiet, private - <15 minutes to Belleayre & Plattekill Mtns.- steps from Catskill fitness center w/Olympic-size pool, walk to Union Grove Distillery; kayaking and farmer’s market 5 min. drive. Fireplace indoors/ firepit out. Great for remote work, families, or romantic getaways. Enjoy hiking, fishing, local shops, antiquing, art galleries, restaurants.

Value · Family · Long stay

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.

Location · Family · Hiking

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. No cats allowed only dogs under 20 pounds and you need to let us know..

Location · Value · Layout

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.

Value · Family · Skiing