Holiday houses in Callicoon Center

5 out of 5 average rating, 5 reviews

Cabin in Roscoe

Callicoon Cottage

Welcome to Callicoon Cottage, a quiet & charming 2BR farmhouse in the Catskills, perfect for romantic getaways, friend gatherings and family adventures. Enjoy a modern kitchen, spacious dining, a deep soaking tub, a backyard fire pit and a creek. A 1-min walk to Callicoon Hills Resort offers dining, sauna, yoga, a pool, a gym & skating. Nearby towns of Callicoon, Livingston Manor & Jeffersonville offer restaurants, shopping, hiking & more. Family-friendly with crib, highchair & baby essentials.

4.89 out of 5 average rating, 120 reviews

Home in North Branch

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.

5 out of 5 average rating, 100 reviews

Cabin in Damascus

Cozy A-Frame | Hot Tub, Fire Pit & Pet-Friendly

Escape to the Cedar Haven A-Frame in Damascus, PA – the perfect romantic hideaway just a short drive from NYC. Nestled in peaceful woods, this cozy 400-square-foot retreat offers all you need for a relaxing escape. Soak in the private hot tub, roast marshmallows by the fire pit, or unwind to music as you watch the forest through wide windows. Whether celebrating a special occasion or just needing time away, the tiny cabin invites you to unplug, reconnect, and make memories in nature’s embrace.

4.98 out of 5 average rating, 105 reviews

Cabin in Roscoe

Cabin@Crow Hill: unplug and reconnect with nature

Escape it all, listen to the birds and near by Buck Brook. Explore the Catskills with plenty of hiking, lakes, and fly fishing. The stars are incredible, so as you sit on the balcony or at the fire pit look up. Crow Hill is located on a quiet road away from the bustle of town. The wifi is moderate due to the location, so it allows you to unplug. Crow Hill is dog friendly ( no cats) and perfect for a family getaway. The cabin is deep cleaned and sanitized between guests. Come take a break!

4.99 out of 5 average rating, 188 reviews

BirchRidge A-Frame: Sauna/Firepit/Hiking/King Bed

Nestled in the Catskills Forest, less than 2 hrs from NYC you'll find Birch Ridge A-frame! This gorgeous 2 bedroom cabin is set on 6 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that create a magical stay with breathtaking views. This is the perfect place to relax, sit in the barrel sauna, hike through the private forest, roast marshmallows over the fire, and soak up the sounds of nature. A space that’s made for creating memories that will last a lifetime!

4.99 out of 5 average rating, 136 reviews

Cabin in Roscoe

Wonder's Never Cease: Hot Tub, Sauna & Cold Plunge

Hi, I'm Wonder! Welcome to my magical Catskills cabin escape - quiet & with a private spa. Ideal for romantic getaways, vacations w family & friends, or wellness retreats. Nestled in nature, our clean log cabin offers a natural, chemical-free hot tub, sauna & cold plunge. Enjoy views from the porch, cozy by the wood stove, grill epic meals, indulge in the spa & explore hikes & cute towns. Child, infant, pet friendly. Helpful host! Book to reconnect with nature, one another & yourself.

4.93 out of 5 average rating, 140 reviews

Home in Livingston Manor

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

4.94 out of 5 average rating, 155 reviews

Cabin in Walton

The Mill House: Creekside Catskills Spring Escape

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to a winter retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a meticulous restoration in 2021, marrying its saw mill heritage with contemporary luxuries, including a Nest thermostat, smart speakers, keyless entry, and fast wifi. Original exposed post and beam construction and Scandinavian-inspired design make for a unique and cozy atmosphere.

4.97 out of 5 average rating, 208 reviews

Chalet in Obernburg

King Of The Hill

Romantic Mountain Top Retreat with Million Dollar Views Escape to this incredibly private, mountaintop vacation home, nestled on 80 acres of pristine land. Offering breathtaking, panoramic views. This peaceful retreat is the perfect getaway for relaxation and romance. Just 2 hours from the GW Bridge, enjoy the tranquility of nature without sacrificing modern comforts, including high-speed internet service. The ideal escape for those seeking both privacy and convenience.

Guesthouse in Callicoon Center

4.98 out of 5 average rating, 53 reviews

Beautiful Mtn Cozy Cabin-183 acres-Amazing Views

Truly beautiful mountain cabin. Artistic, eclectic, luxurious—super hi-speed internet—private patio & picnic table—comfy beds, bathrooms with 2 person deep Jacuzzi tubs—house-wide stereo—induction cooking–air-fryer/oven—dishwasher— linens–snacks and drinks included. Geothermal heat/hot water, solar electric — EV charging. Private chef and masseuse available. Farm-to-table restaurants, skiing, hiking, bike rentals, tons of trails, fishing and 183 acres to explore!

4.87 out of 5 average rating, 102 reviews

The Blue Hill House...A modern Catskills getaway

The Blue Hill House is a modern Catskills cabin featuring 3 large bedrooms, 2 bathrooms, a fully equipped kitchen, and much more. Nestled on 7 private acres just a few minutes away from Livingston Manor, the Blue Hill House is the perfect mix of Catskills mountain escape and modern getaway. Enjoy the stunning mountain views from the large deck, or explore the nearby hiking trails, lakes, dining options, and shops. Follow us on insta @thebluehillhouse.

4.98 out of 5 average rating, 142 reviews

Tent in Livingston Manor

Milkweed Camp - Glamping in a Blueberry Field

Our off-grid canvas tent is situated at the edge of a meadow, surrounded by blueberry bushes. It's just 4.5 miles to Main St in Livingston Manor, and 35 minutes to Bethel Woods. We provide a full-size bed (w/ heated mattress pad), fire pit, firewood, propane heater, and solar power. You have access to a private outhouse with composting toilet & outdoor shower on-site, and a conventional shared bathroom if you preferred. We are an LGBTQ+ inclusive space.

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Other great holiday rentals in Callicoon Center

4.95 out of 5 average rating, 95 reviews

The Swiss Hill Farmhouse

YuliyaRating, 5 stars2 weeks ago

We rented the house to celebrate my birthday, its was peaceful, calm and just relaxing. The house itself has charm of an old farm house. Very bright, with great details of a old house that was billed in 1912. The little mystery there, who is the man on the big portrait. ;)) Comfortable furnishings, all to our liking. The host is incredible. Flexible check in hours, host responded with minutes, everything was ready and working. Its was incredible stay! Will recommend this to our friends and family!!! Thank you so much!!

4.98 out of 5 average rating, 94 reviews

The Nest At Swiss - Lakefront In The Catskills

SamRating, 5 stars3 weeks ago

We had an amazing weekend in the Catskills thanks to The Nest at Swiss. We brought five kids and 5 adults and we had the greatest time. Plenty of room to spread out while also a ton to do. We watched movies, played cards, made pop corn, built fires, smoked meat, went fishing, kayaking, played endless games of manhunt and monopoly. The Nest was set up for everything. We really enjoyed the short walks into Jeffersonville and hanging out on the decks. Even though the weather wasn’t perfect for Memorial Day weekend it did not matter to us. The Nest is also really close to Bethel Woods and we took him to concert on Saturday night super convenient location. The house was fully stocked and had everything we can think of. Well done Matthew!

5 out of 5 average rating, 31 reviews

Charming Village House - Walk Everywhere

CorrinRating, 5 stars3 weeks ago

Great place to stay for a concert at Bethel Woods. Only 20 minutes away. On top of that the town is so cute, we wished we had more time to spend in town or out back by the creek! We used the grill and made a great dinner. Kitchen was equipped with everything we needed. The host was very responsive and sent us everything we needed to know prior to arriving! We would definitely stay here again!

4.97 out of 5 average rating, 96 reviews

Cabin in Jeffersonville

1930's Vintage Cabin · Hot Tub · Kohler Cabin

AlexandraRating, 5 stars1 week ago

This was a beautiful tranquil home with a cute town right down the road for local eats. We came to this area because of a race behind held at Bethel Arts Center. It was 15 minutes away and a perfect location. The home was spotless and so cozy!

4.97 out of 5 average rating, 71 reviews

Cabin in Youngsville

Cutbow Cabin Secluded Home near Livingston Manor

EricaRating, 5 stars3 weeks ago

Our second visit to Matt’s place was just as magical as the first, if not more so! It's the perfect place to immerse yourself in nature, offering a wonderfully isolated feel while still being conveniently close to quaint towns, great hikes and breweries. The light and the land surrounding the house are truly breathtaking, and we’re grateful it’s dog friendly. We absolutely loved our time here and can't wait to return.

4.99 out of 5 average rating, 109 reviews

Guesthouse in Roscoe

Map Maker's Cabin

Gottfried Rating, 5 stars1 week ago

Our 5th time here and we are going to plan the next round. Because we love it. It is an extremely peaceful location, a wonderful cozy cabin surrounded by a beautiful nature, and a host that is just unbelievable great. This is the paradise.

4.98 out of 5 average rating, 47 reviews

Cottage in Callicoon

Old Schoolhouse in Western Catskills

DonnaRating, 5 stars5 months ago

Great location, close to downtown and the Villa Roma. The house is a bedroom one bath home with a very open living and kitchen area. Cynthia kept in contact with us throughout our stay to make sure everything was going smoothly. Would definitely stay there again.