Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Guest favorite

Rental unit in Margaretville

4.97 out of 5 average rating, 103 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

Bungalow in Margaretville

4.97 out of 5 average rating, 236 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

Rental unit 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, 158 reviews

Groovy Chalet: Cool Mid-Century Mountain Digs!

Now entering our 8th season, the Groovy Chalet is a 750 SqFt mountain pad with a private deck, driveway, and entrance. Our great proximity to hiking trails and skiing was mentioned in Travel and Leisure's "Best Small Towns in the Catskills" feature in 2022. This groovy unit is located between Belleayre and Plattekill mountains and is close to cool towns like Andes, Flesichmans, Pine Hill and Roxbury Well-behaved and housebroken pets are welcome for a $30 fee. NO ADDED CLEANING FEE.

Guest favorite

Rental unit in Arkville

4.94 out of 5 average rating, 170 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!

Guest favorite

Cabin in Margaretville

4.97 out of 5 average rating, 127 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

Guesthouse in Margaretville

4.99 out of 5 average rating, 135 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

4.9 out of 5 average rating, 135 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

Rental unit in Andes

4.96 out of 5 average rating, 263 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, 177 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

Cabin in Arkville

4.97 out of 5 average rating, 296 reviews

Solace: perfect for all seasons; near Belleayre Mt

Less than 15 min from Bellayre Mountain and Pakatakan Reservoir. 4-wheel drive is necessary in winter months. The Catskill Forest Preserve is our backyard-literally (we have 5.9 acres that lead directly into the preserve). Only 5 min to Margaretville town center, grocery store, scenic train rides, restaurants. You'll love Solace for the secluded feel, views, cozy living space, and proximity to activities and necessities. Pets case by case.

Guest favorite

Home in Margaretville

4.87 out of 5 average rating, 143 reviews

Charming Catskills Victorian

Welcome to the absolutely charming and quiet Victorian village of Halcottsville, nestled in the Catskills Mountains. The house sleeps 6 and is great for families, couples, and groups. 10mn to Margaretville and Roxbury Villages. 10mn to Roxbury Barn and Estate, the Inn at West Settlement, and Stone Tavern Farm wedding venues. 15mn to Belleayre and Plattekill Ski Resorts. 40mn to Windham and Hunter Ski Resorts.