Vacation 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.

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.

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.

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.

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.

Catskill Cabin Oasis: Ski, Hot Tub, Creek, Hike!

Imagine waking up in a tranquil cabin & then walking out to your deck where you enjoy your morning cup of coffee in the NEW hot tub while listening to the babbling brook at your feet. Well you don't have to imagine ...the Catskills Cabin Oasis is here! For adventurous types, there's a hiking trail steps away & Bellayre Mountain is 10 minutes away complete with a lake & biking for the Summer & Skiing/Tubing for the Winter! Come here & have it all!

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.

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 Lookout

Perfect getaway for friends and couples! Find a new state of relaxation as you wake up to a stunning mountain/pond view from the wrap-around, covered porch. Cozy up around the wood-burning stove while watching a good movie or take a stroll around the property. At night, watch the stars around the fire pit or solve a puzzle or two. You will feel truly connected to nature while only being 2 hours from NYC.

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.