Vacation rentals in Callicoon Center

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Top-rated vacation rentals in Callicoon Center

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Guest favorite

Guest suite in Jeffersonville

4.84 out of 5 average rating, 128 reviews

The Shire

This is a quaint country escape. Separate door from rest of house allows for total privacy. Access to basement (2 cats) and giant barn. Enormous field/forest to explore. Slightly isolated from town center but neighbors close enough if needed. Harmless wild animals are a daily sight. Down country road 1/4M is an amazing farm. Farm animals, fresh eggs & meat if desired. Mornings are glorious with light floating the property. Very pure water/ fresh air aplenty. Additional outdoor shower (May-Nov)!

Sep 13 – 20

G$20,332 GYD per night

Guest favorite

Cottage in Narrowsburg

4.99 out of 5 average rating, 144 reviews

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

Jun 13 – 20

G$27,051 GYD per night

Guest favorite

Guesthouse in Roscoe

4.93 out of 5 average rating, 209 reviews

Comfortable Carriage House Setting in Roscoe, NY

This enchanting carriage house is tucked away a mere five minute drive from the Beaverkill River and about 10 minutes from the hub of the town of Roscoe. Guests have access to the upper dwelling of the carriage house that shares acreage with the main house. Guests can walk the land and explore nature. There is a garden with seating nearby, a pond, a stream running through the property, and a fire pit that guests can enjoy. Perfect get-away spot for a couple that wants to explore the area.

Jun 29 – Jul 6

G$29,243 GYD per night

Guest favorite

Home in Narrowsburg

4.95 out of 5 average rating, 159 reviews

Modern Getaway in the Catskills

Our summer rental has a private entrance adjacent to the main house with kitchen, living & dining rooms, 1 bedroom w/ Queen bed , AC and 1.5 baths. 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 WiFi. A great get-a-way for 2 adults. 20 min. to Bethel Woods 30 mins to Resorts World Casino. No smoking, pets or animals or children. All are welcome. Rainbow Friendly.

Oct 18 – 25

G$17,595 GYD per night

Guest favorite

Tent in Livingston Manor

4.97 out of 5 average rating, 110 reviews

Milkweed Camp - Glamping in the Catskills

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. Please note that temps may dip below 32F in October. We provide a full-size bed (w/ heated mattress pad), fire pit, firewood, propane heater, and solar power. You have access to a composting toilet & outdoor shower on-site, and a conventional shared bathroom if you preferred. We are an LGBTQ+ inclusive space.

Aug 29 – Sep 5

G$22,648 GYD per night

Guest favorite

Farm stay in Callicoon

4.96 out of 5 average rating, 189 reviews

Country road please take me home!!

Are you looking for rest & relaxation or fun in the Catskills. Come enjoy our warm, cozy home away from home. Our guest mobile home is located on a quiet country back road, but yet close to dining and outdoor activities that the Catskills has to offer, rafting down the Delaware & enjoying concerts at Bethelwoods. The possibilities are endless. We now have Spectrum internet. Please note that we do reside on an active farm. This could be a wonderful experience!

Feb 2 – 9

G$18,998 GYD per night

Guest favorite

Farm stay in Roscoe

4.99 out of 5 average rating, 126 reviews

Roscoe Wildlife Retreat

We are open for. the season! You'll be enjoying a 40-foot travel trailer located on 11 acres of land with private entrance and all necessities to be comfortable, including WIFI, heat/AC, hot water, bathroom.FRESH AIR, and so much more. Please note that the trailer is designed for 2 adults/2 children or up to 3 adults/1 child. If you have a special arrangement for your family, just message us, and we will see what we can do.

Sep 8 – 15

G$24,504 GYD per night

Guest favorite

Barn in Roscoe

4.98 out of 5 average rating, 126 reviews

Sleep Above the Alpacas Scenic Farm Getaway

Slumber comfortably atop our 100+ alpacas, Angora rabbits, chickens and potbelly pig named Daisy. BuckBrook Alpacas offers a 3-bedroom loft apartment rental above our barn. You will sleep surrounded by the mountains and the animals on one of the highest peaks of the county. Wake up for a complimentary farm tour and enjoy a 10% off shopping pass in our farm store on our entire selection of alpaca gifts for the whole family.

Aug 16 – 23

G$75,391 GYD per night

Guest favorite

Guesthouse in Long Eddy

4.97 out of 5 average rating, 136 reviews

The Grange

The Grange is a fully renovated 1886 building with 800 sq ft apartment on ground floor. It is located on a quiet country road 4 miles from the Delaware River with great swimming, fishing, kayaking, canoeing, tubing nearby. 15 minutes from Callicoon and 23 minutes from Hancock. Private entrance. Access to my vegetable garden and private lawn. It has fully equipped kitchen and bathroom with bathtub and shower.

Sep 12 – 19

G$30,405 GYD per night

Guest favorite

Cottage in Parksville

4.97 out of 5 average rating, 240 reviews

Rolling River Guest House ~ Cozy & Fun

This charming, private guest house used to be the Rolling River Café, converted into a cozy space with a pellet stove, a queen bed upstairs and futons upstairs and down. Perfect for 1 to 4 guests, such as 2 couples, 3 friends, or a family of 3 or 4. It is private - no sharing with any other guests. It has an open floor plan on both floors.

May 3 – 10

G$20,954 GYD per night

Guest favorite

Home in Livingston Manor

4.93 out of 5 average rating, 188 reviews

Peaceful 4BD Country Retreat

Located near a small country stream, and far away from the bustle of the city, this is the perfect place to disconnect from the your hectic life and recharge. Enjoy fishing, hiking and hunting all nearby or just relax if that is what you want to do. Enjoy country views and wildlife. Three season fire pit for star gazing.

Dec 8 – 15

G$23,321 GYD per night

Guest favorite

Home in Callicoon

4.99 out of 5 average rating, 284 reviews

Paradise in the Catskills

This spacious, fully-renovated old dairy barn looks over the valley with a gorgeous view from the deck. Comprised of large, open rooms, this is a perfect space for a gatherings and getaways with friends and family in the beautiful Catskills. Find us on Instagram! @thecallicoonbarn 4532

Oct 17 – 24

G$46,430 GYD per night