
Holiday houses in Middletown
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Top-rated holiday rentals in Middletown
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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!

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.

Andes Valley View
This home is a beautiful mix of cozy and modern. You’ll love cooking in the kitchen and taking in the view from the second story deck. The property is stunning, with wide meadows and dense woods. There are 140 acres to explore and utilize for events like weddings or a retreats. There is a half acre pond with a pond house at the top of the property and a trout stream running along the bottom. It’s everything you could hope for in a Catskills getaway, all nestled overlooking the town of Andes.

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.

Cozy Cottage with Stunning Mountain Views
Welcome to Solheim Cottage! Featuring gorgeous mountain views, less than two and a half hours from NYC, and ten minutes from Belleayre Ski Center, this cozy and private cottage is perfect for a romantic couples retreat, two couples, a small family, or a group of friends looking for a relaxing and quiet escape in the historic Catskills. The cottage is a short drive to Phoenicia, Woodstock, Andes, and Margaretville for shopping, dining, antiquing, skiing and exploring.

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.
Popular amenities for Middletown holiday rentals
Other great holiday rentals in Middletown

Catskills Home with SAUNA, near Belleayre Ski

Whitetail Chalet Catskills

Serenity Cabin Catskills Getaway

Hog Mountain Haus

Designer Chalet with Hot Tub and Fire Pit

Luxurious A-Frame Retreat with Hiking Trail

Hawke House

The Borderless Retreat Chalet
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Hunter Mountain
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- Resorts World Catskills
- Windham Mountain
- Howe Caverns
- Glimmerglass State Park
- Thacher State Park
- Hunter Mountain Resort
- Plattekill Mountain
- Zoom Flume
- Opus 40
- Walkway Over the Hudson State Historic Park
- Cooperstown All Star Village
- Woodloch Resort
- Poets' Walk Park
- Mohonk Preserve
- Peekamoose Blue Hole
- Lake Minnewaska
- The Culinary Institute of America
- Saugerties Lighthouse
- Upper Delaware Scenic and Recreational River
- The Andes Hotel




