Holiday houses in Callicoon

Guest suite in Narrowsburg

4.95 out of 5 average rating, 206 reviews

Modern Getaway in the Catskills

Our rental unit has a private entrance with kitchen, living & dining rooms and full bath on the first floor. 1 bedroom w/ Queen bed , AC and 1/2 bath on 2nd fl. A porch w/ patio furn. a charcoal BBQ and 50 wooded acres to explore. We supply sheets, towels, kitchenware, coffeemaker and 2 flat screen satellite TVs, Internet and Wi-Fi. A great getaway for 2 adults. 20 min. to Bethel Woods 30 mins to Resorts World Casino. No smoking, pets, animals or children. All are welcome. Rainbow Friendly.

4.98 out of 5 average rating, 179 reviews

Cottage in Narrowsburg

Cozy Cottage in Popular Narrowsburg

A sweet cottage in the artsy hamlet of Narrowsburg welcomes you for a quiet retreat in the country. Moments from the Delaware River and the village, spend hours taking in the serenity of the river and rolling hills of the surrounding countryside, or popping into town for arts and entertainment. There are two separate bedrooms, one with a queen bed and one with a full bed; a well-equipped kitchen; WiFi; a front and back porch; and a deck Come enjoy the all-season splendor of Sullivan County

5 out of 5 average rating, 101 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.

4.95 out of 5 average rating, 157 reviews

Cottage in Kenoza Lake

The Schoolhouse at Kenoza Lake

The Schoolhouse at Kenoza Lake. This late 1800's renovated schoolhouse is the perfect getaway. Only a 2 hour drive from NYC. Old world charm with modern finishes. House features one bedroom plus a sleeping loft, a total of 3 beds plus a bunk bed, claw foot tub, cast iron wood stove, dinner barn, sleeping loft, vegetable garden, outdoor fire pit with bistro lights and Adirondack chairs. 10-20 min driving distance to all of Sullivan County's culinary offerings. 7 min drive to grocery store.

4.99 out of 5 average rating, 189 reviews

Home in Jeffersonville

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!

4.97 out of 5 average rating, 370 reviews

Cabin in Callicoon

Chic Cabin on Callicoon Creek

***FEATURED IN ARCHITECTURAL DIGEST, TRAVEL & LEISURE, APARTMENT THERAPY, AND FODORS TRAVEL*** Set back on a small private road, this cabin dating back to the 1800s is perched above the Callicoon Creek, popular with fly fishermen casting for rainbow trout. Head up the wooded driveway and find yourself in a serene, green clearing all your own. The cabin and studio make for a peaceful getaway, shielded from the surroundings, but incredibly convenient for reaching nearby towns and activities.

4.93 out of 5 average rating, 141 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.

5 out of 5 average rating, 168 reviews

Home in Equinunk

Art House Bird Sanctuary at EBC Sculpture Park

The Art House is set in a Sculpture Park being Developed by the artist Tom and Carol Holmes. The Park is 38 acres of rolling hills, grass land with valley views, bordered by two streams and woodlands. The views are magnificent. The house is set on the second tier of three rolling hills 1000 feet up from the road. The property is the newest building project/ABNB offering from Tom; who creates magical and life changing experiences...in the landscape; at EBC Bird Sanctuary Sculpture Park.

4.98 out of 5 average rating, 47 reviews

Cottage in Callicoon

Old Schoolhouse in Western Catskills

Our one-bedroom cottage was originally built as a school house in 1849. In 1951 the building was turned into a home, and recently renovated with meticulous care, creating a country retreat with modern amenities. Set on an incline with views over rolling hillsides, the home feels like a treehouse with open views that bring the natural surroundings indoors. 8 minutes from village of Callicoon; 15 minutes to Bethel Woods; 20 minutes to Narrowsburg and Livingston Manor; 2 hours from NYC.

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.

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

4.95 out of 5 average rating, 19 reviews

Serene Haven: Nature, Deck, Views & Fireside Fun

MarleyRating, 5 stars3 weeks ago

Our group absolutely loved our stay at the Blue House. It was pristinely clean, cozy, well-decorated, comfortable, and thoughtfully set up. It's so nice to be in an AirBnB where they've clearly thought of everything. The kitchen was well stocked and everything was labeled clearly. The setting was gorgeous and our hosts provided great recommendations. We really hope to go back in the fall for another stay!

4.97 out of 5 average rating, 72 reviews

Guest suite in Callicoon

Catskills Creekside Studio near Livingston Manor

AnnaRating, 5 stars1 month ago

It was a wonderful stay in such a cute town! We really appreciated the fact that it was pet friendly! My boyfriend especially loved the shampoo and conditioner that was in the shower- he said it smelled incredible. Also, the bed was incredibly comfortable. The power ended up going out (while we were at the wedding reception!) and Susanne was proactive and reached out to make sure we were okay and had everything we needed. We will definitely be back and would love to stay again when the time comes!

Superhost

Home in Livingston Manor

5 out of 5 average rating, 3 reviews

Livingston Manor Retreat

CharlieRating, 5 stars10 months ago

A beautiful home on a beautiful piece of land. A river runs through this property and you can hear it flowing all day. The house is beautiful and full of unique pieces. It feels like you’re staying at a friend’s house, not just an airbnb. We will stay here again!

4.88 out of 5 average rating, 49 reviews

Home in Hankins

Peace AND Style: Hot Tub/Fire Pit/Fully Renovated

DestinyRating, 5 stars1 week ago

Our stay was absolutely beautiful and very relaxing . The host was very proactive with answering any questions and making sure we were all set to have a good trip! The house it’s self was stunning as with the area around it.

5 out of 5 average rating, 26 reviews

Five Acres Farm - Charm and Seclusion with 5 BR

StefanoRating, 5 stars1 month ago

We had a great writing retreat here! Hopefully we'll be back at some point.

4.96 out of 5 average rating, 23 reviews

Lighthill Pool is Open plus EV charger

FannyRating, 5 stars3 weeks ago

Great place for a break from the everyday. Extremely well prepared place. Wry thoughtful decoration etc and everything has been considered. Loved our stay!!