Holiday rentals in Middletown

4.96 out of 5 average rating, 124 reviews

Flat in Margaretville

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.

Bungalow in Margaretville

4.97 out of 5 average rating, 301 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.

4.95 out of 5 average rating, 123 reviews

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.

4.95 out of 5 average rating, 222 reviews

Flat in Arkville

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!

4.94 out of 5 average rating, 166 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.

4.9 out of 5 average rating, 182 reviews

Serene Catskills Cabin | Fire Pit & Outdoor Dining

The Trillium Cabin is the perfect place to simply spend time in nature! Follow us @thetrilliumcabin 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 wood stove!

Guest house in Margaretville

4.98 out of 5 average rating, 167 reviews

Sunny Arts & Crafts Loft

Warm weather is finally here - prime time for Catskill Mountain outdoor warm weather activities - hiking, biking, swimming, fishing, golf. - all conveniently accessible nearby. Explore fun towns like Margaretville, Andes & more. The loft is a cozy, private place to unwind in a peaceful mountainside location. Super savings on longer stays, too! No need for AWD the rest of the year, but AWD & WINTER TIRES a must for smooth travels during WINTER visits.

4.98 out of 5 average rating, 101 reviews

Cabin in Hardenburgh

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!

4.99 out of 5 average rating, 224 reviews

Chalet in Fleischmanns

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

4.97 out of 5 average rating, 329 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.

4.98 out of 5 average rating, 404 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.

4.97 out of 5 average rating, 120 reviews

Hike & Sauna! Modern Mountain Escape

Welcome to a brand new Catskills getaway. Inspired by Japanese and Scandinavian design, every detail has been thought through to create the perfect private retreat where interiors blend seamlessly with the surrounding mountains. You’ll see high end finishes throughout the space and all the amenities you could desire. Welcome to a relaxing stay at your home away from home.

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Other great holiday rentals in Middletown

5 out of 5 average rating, 19 reviews

Home in Fleischmanns

Tree Top Chalet

IdoRating, 5 stars2 months ago

Great quality sublet in upstate New York. Furnished with sophisticated upscale furniture (yet very cozy and comfortable), large rooms (super comfortable beds), new bathrooms and excellent outdoor amenities like a large hot tub and a fire pit. Two things that set this place apart: (a) the atmosphere - this is a modern mid century cabin feel with a lot of attention put into small details: fantastic classic Hi-Fi receiver and speakers (with a turntable and LPs if you don't want to stream music), great sofa and Eames chair, a heat stove and fire place and a large TV with many streaming choices all make your time in the living room feel special. (b) The host - Omar is attentive, incredibly friendly and proactive. He did above and beyond to make our stay comfortable and was available for anything we needed. We barely left the house because we had such a great time there. Will absolutely come again.

Superhost

Home in Denver

4.79 out of 5 average rating, 57 reviews

Creekside Cabin

JuliahRating, 5 stars1 week ago

the space was beautiful! loved being surrounded by nature and had lots of fun with local experiences and some fishing! super cute place :)

4.89 out of 5 average rating, 95 reviews

Mountain View Hideaway

MarcRating, 5 stars2 weeks ago

This was such a gorgeous stay in the early summer. The house is beautifully located, tucked away in the forest with an absolutely stunning view of Bellayre Mountain. It’s well equipped and spacious for two, even three, couples. Although it was just two of us, it would be great to return with friends. The hot tub is lovely and the perfect way to unwind after a long hike. The house is beautifully decorated and cooking is easy with the well appointed kitchen and outdoor grill. Highly recommended!

4.94 out of 5 average rating, 18 reviews

Loft in Arkville

Historic Catskills Firehouse

NicoleRating, 5 stars3 months ago

The old firehouse in Arkville was great. Lots of that Catskills charm decorated with antiques. The apartment is spacious and comfortable. We almost regret making dinner reservations because there was a full kitchen, fully stocked and there was a large dining table. The furniture is also big and comfy for a chill evening in. The location is really convenient, a 10 min drive to Belleayre, 3 mins to the grocery store. I also like that the host didn’t have a ton of rules about clean up and laundry. We are pretty neat but it’s nice to not have to worry about removing linens or finding a remote trash location. The host and her partner were super friendly and helpful!

Superhost

4.76 out of 5 average rating, 90 reviews

Cute Cabin w/ Hot Tub, Private Pond & Fire Pit

BruceRating, 5 stars4 days ago

This was our first Air BnB and we were very pleased with the experience. It was very easy to book, easy to use the cabin and the amenities, comfy beds with nice comforters, AC and heat units worked great, enjoyed hanging out on the deck and on the balcony off the upstairs balcony. After dinner from the grill, it was really relaxing to sit around a wood fire in the pit outside. It is set up very nicely, the beach towels for the hot tub were a nice touch, and we easily found everything we looked for (kitchen and grill stuff, etc.). Enjoyed listening to the frogs and watching birds flying around the pond. Very pleasant!

5 out of 5 average rating, 18 reviews

Home in Margaretville

11 Priv Acre - Sleeps 15 - Firepit, Sauna, Karaoke

BrookRating, 5 stars3 days ago

Francesca’s place was perfect for a long weekend with three families and our kids. The house was beautiful, spotless and had everything we needed. The mattresses and pillows in the bedrooms were comfortable and the bathrooms were beautiful. All amenities like the bbq and fire pit were well stocked with charcoal or wood for burning. The kids had a ball in the basement using the ping pong table and karaoke. Clean up and check out were simple and straightforward. Importantly, Francesca was a wonderful and responsive communicator. We would highly recommend this home in the Catskills!

4.97 out of 5 average rating, 64 reviews

Cabin in Roxbury

Zen Catskills Cabin w/ Firepit, Tatami, Mtn Views

PriyaRating, 5 stars3 weeks ago

had an incredible stay here for a weekend away! great communication with the host and helpful tips and recommendations