Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Guest favorite

Apartment in Margaretville

4.97 out of 5 average rating, 101 reviews

Margaretville Village Views, Apt 3

Bright Cozy Apt in the heart of Margaretville Village features a queen-sized bed in the cozy sleeping loft, the couch opens to a twin size as well. The vaulted ceilings give the space a roomy feel, you can cook in and watch your favorite streaming channels on wifi, or go for a stroll out to dinner. We are within walking distance of all the amenities, hiking, fishing, antiques, shopping, cafes and more. We are close to Skiing, Fishing, Hiking, Wedding Venues, and all the Catskills have to offer.

Guest favorite

Home in Prattsville

4.91 out of 5 average rating, 273 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

Guest favorite

Bungalow in Margaretville

4.97 out of 5 average rating, 230 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.

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, and the kitchen. Our place is good for couples, solo adventurers, and business travelers. WIFI is 300mbps. We have security cameras and an EV Charging station on the property. We now have an outdoor fireplace (wood not included). We also have a standby generator in case of a power failure.

Guest favorite

Guest suite in Margaretville

4.94 out of 5 average rating, 155 reviews

Groovy Chalet: Cool Mid-Century Mountain Digs!

Very spacious, 750 SqFt sunny mountain pad in Margaretville with private deck, driveway and entrance. Close to hiking trails, kayaking, skiing, wedding venues, Andes and Pine Hill. This groovy unit is nestled between Plattekill and Belleayre mountains. Hike, kayak, ski or shop your heart out, and come back and relax by the wood stove with your glass of vino. This retro-styled space is here for you! Well behaved and house broken pets are welcome for a $30 fee. NO ADDED CLEANING FEE.

Guest favorite

Cabin in Margaretville

4.97 out of 5 average rating, 121 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.

Guest favorite

Apartment in Arkville

4.92 out of 5 average rating, 234 reviews

Catskills Hideaway - West

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. A queen size bed, en suite bath, kitchen, fireplace, & luxurious amenities await in your perfect Hideaway.

Guest favorite

Guesthouse in Margaretville

4.99 out of 5 average rating, 134 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.

Guest favorite

Cabin in Margaretville

4.91 out of 5 average rating, 133 reviews

Catskill Mountain Retreat With 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!

Guest favorite

Apartment in Andes

4.96 out of 5 average rating, 261 reviews

Andes Modern-Open-Streamside-Retreat

The only gas/instant/clean/ no smoke Fireplace in the area! no hauling wood, trying to start a fire, smoke, etc. 2 bedrooms (queen beds). Luxury modern bathroom w/ huge walk in tiled shower. Fully equipped gourmet open kitchen. Back deck (with BBQ grill), front deck dining & rockers. Juliet balcony directly above a babbling brook off one bedroom. New SmartTV. Hi-Speed WiFi. Long Farm table seats 8. Large stone desk w/comfy chair if you need to work remotely.

Superhost

Home in Arkville

4.86 out of 5 average rating, 176 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)

Guest favorite

Chalet in Fleischmanns

4.99 out of 5 average rating, 170 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