Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Guest favorite

Apartment in Margaretville

4.95 out of 5 average rating, 166 reviews

Binnekill Getaway Apt.5 in the Catskill Mountains

Binnekill Getaway Apt. has a hunting lodge feel, located in the heart of Margaretville Village, yet it's quiet and cozy inside, overlooks the Binnekill stream with views of the mountains, there is a deck to sit and relax outside. We're located in close walking distance to all the amenities, restaurants and shopping, outdoor activities and the Trailways bus stop. There's plenty to do close by such as Golf, hiking, kayaking, shopping, bowling, fishing, antiquing and wedding venues. Great location!

May 22 – 29

€ 123 per night

Guest favorite

Home in Prattsville

4.91 out of 5 average rating, 270 reviews

Yanity House

You will have access to the entire house fully furnished. Pet's are welcome just keep paws clean its a beige rug. We want everyone to be comfortable, so please let us know how and what you would like to see improved if you rent the unit. We will improve the unit as per guest suggestions. Currently we do not have cable but we do have a dvd and game system in the living room - All the bedrooms have TV's, dvd players or bring your streaming device There currently is no phone but cell service works

Apr 26 – May 3

€ 102 per night

Guest favorite

Bungalow in Margaretville

4.97 out of 5 average rating, 225 reviews

The Porch Upstate Super clean

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 will definitely will share our veggies and fruit with you . We have 3 sheep , 10 chickens and 5 barn cats .Halcottsville has its own post office ,voluntary fire department and a beautiful Lake.

Nov 30 – Dec 7

€ 146 per night

Guest favorite

Bungalow in Big Indian

4.93 out of 5 average rating, 120 reviews

The Den @ Oliverea - Minutes to Hiking and Skiing!

Nestled into a quiet through road that goes to some of the best hiking nearby (hello Slide Mt.!) and just 10 minutes away from skiing at powder-coated Belleayre, my charming little two bedroom cottage is ready for your family or group's adventures. There is no cell service here, but fast Internet awaits the remote worker, with a modern mesh network providing indoor/outdoor coverage. Comfy beds, a stocked kitchen, a hot shower, and mountain peace await! Shandaken STR License #2022-STR-001P

Dec 10 – 17

€ 157 per night

Guest favorite

Apartment in Halcott Center

4.97 out of 5 average rating, 130 reviews

Mountain View Apartment

We offer a quiet and extremely clean place. We are only 6 miles from Belleayre Mtn Ski Center. Restaurants are nearby. You’ll love our place because of the neighborhood, the outdoors space, the light, the comfy bed, and the kitchen. Our place is good for couples, solo adventurers, and business travelers. For all of you that work from home, our WIFI is 300mbps. We have security cameras and an EV Charging station on the property. We also have a standby generator in case of a power failure.

Jan 30 – Feb 6

€ 114 per night

Guest favorite

Apartment in Arkville

4.94 out of 5 average rating, 164 reviews

Catskills Hideaway - East

Enjoy the serenity of the scenic Catskill Mountains - relax in a lovely tranquil setting nestled in nature yet minutes from restaurants, galleries & shops. This spacious studio with private exterior stair access in a unique Brick House built in 1965 - the original "Guest House" on a spectacular estate - welcomes guests with breathtaking beauty & magnificent views. Luxurious amenities await in your perfect Hideaway: king size bed, en suite bathroom, kitchen, fireplace, & more!

Jun 7 – 14

€ 91 per night

Guest favorite

Cabin in Margaretville

4.97 out of 5 average rating, 116 reviews

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.

Feb 16 – 23

€ 299 per night

Guest favorite

Guesthouse in Margaretville

4.98 out of 5 average rating, 133 reviews

Sunny Arts & Crafts Loft

Catskill Mtn. Summer: hiking, swimming, relaxing. Explore fun towns like Margaretville, Andes & more. May & June are almost fully booked, but lots of great summer and fall dates available. Situated on a peaceful mountainside, the loft is a cozy, private place to unwind as you enjoy a Catskill Mtn. adventure. Super savings on longer stays, too! Our road is plowed & sanded, but you will definitely need AWD & good tires to ensure smooth travels in the WINTER months.

Jul 25 – Aug 1

€ 107 per night

Guest favorite

Cabin in Margaretville

4.91 out of 5 average rating, 132 reviews

Catskill Mountain Gem With Outdoor Deck & Fire Pit

The Trillium Cabin is the perfect place to simply spend time in nature! The Trillium Cabin is set on a private 2 acre lot. Hike in your own backyard bordering 35 acres of state land filled with hiking trails and wildlife. Located at the end of a town maintained road, get here rain or shine. Close to many wedding venues, Platekill Mountain, Bellayre Beach/Ski Mountain and hiking trails. Enjoy our outdoor fire pit as well as our newly installed wood stove!

Aug 19 – 26

€ 163 per night

Superhost

Home in Arkville

4.86 out of 5 average rating, 173 reviews

Little Red Schoolhouse

A charming Schoolhouse from the mid-nineteeth century with a separate sleeping cabin and bathroom approximately twelve feet away from the Schoolhouse itself. Open from March through the beginning of December. Remote, yet accessible. Two night stay minimum. PLEASE PARK IN THE PARKING LOT BY THE ROAD -- not on the dirt road itself, nor on the grass as it leaves tire marks on the grass (apologies for my obsession with a maintaining a nice lawn)

Jun 22 – 29

€ 134 per night

Guest favorite

Chalet in Fleischmanns

4.99 out of 5 average rating, 168 reviews

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

Jan 30 – Feb 6

€ 333 per night

Guest favorite

Cabin in Margaretville

4.98 out of 5 average rating, 325 reviews

Modern & Chic Log Home-Spectacular Mountain Views!

Welcome to Fox Ridge Chalet! 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.

Sep 27 – Oct 4

€ 559 per night