Town of Callicoon, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Callicoon, New York on RentalSaver.com!

Town of Callicoon Rentals

From $408 per night (USD)
VRBO
Shangri-la on Private and Peaceful Lake - Livingston Manor NY
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
Come find Shangri-La on Shandelee Lake outside of downtown Livingston Manor. This five bedroom, two bath house sits on a ...
From $408 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Majestic Farmland A-Frame with Sweeping Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just a little over 2 hours from New York City. The open farmland and rolling hills of Callicoon NY are the perfect ups ...
From $338 per night (USD)
Expedia
From $1191 per night (USD)
VRBO
Dreamy Lakefront Log Cabin - 2hrs from NYC! Sleeps 14 (5Bed/3Bth) 7 private acre
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
Welcome to Clearwater Cabin on Sand Pond. Nestled in the foothills of the Catskill Mountains this lake house offers sere ...
From $1191 per night (USD)
VRBO
$Private Lakefront Cottage, Fish, Row, Panoramic Lake Views.\nPet Friendly!$
From $410 per night (USD)
Expedia
Private Lakefront Cottage, Fish, Row, Panoramic Lake Views.\nPet Friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Lake Jeff Cottage, a private, custom-built, pet-friendly family vacation home nestled in the Catskill Mountai ...
From $410 per night (USD)
Expedia
From $627 per night (USD)
VRBO
My house is unique, welcome EVERYONE to enjoy beautiful VALLEY in Swane Lake.
Bedrooms:
4
Bathrooms:
7
Sleeps:
10
Please come to my house with your family, friends. Come cook together, enjoy every moment with your guests. House is un ...
From $627 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Secluded modern log cabin with picturesque private water fall on 12 acres!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A beautiful escape for you and the family or a memorable romantic getaway in famous Roscoe, New York. Newly built brigh ...
From $386 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Cozy Farm Private Cabin-30% off Spring Special - 183 beautiful acres
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
A truly amazing place to stay. Artistic, eclectic, luxurious, super comfortable, near Calicoon Hills & Bethel Woods—supe ...
From $235 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Charming House Secluded in a 60-Acre Parcel with View
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Charming house secluded in a 60-acre parcel with view is available for rent in the Catskill Region (Callicoon Center, Su ...
From $373 per night (USD)
Expedia
From $264 per night (USD)
VRBO
In the cloud ~your cozy lake house
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Cozy lake house in Catskill,only 2 hrs away from NYC. The property has 2 Bedroom 1-1/2 baths and sleeps 4-6 people . Gue ...
From $264 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Cozy Catskills Chalet
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Sunday Lodge & Mountain House is a peaceful retreat on 5 acres in the Southern Catskill Mountains. Our home is located a ...
From $327 per night (USD)
Expedia
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VRBO
Modern Farmhouse With Expansive Catskills Views
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
The Roscoe Farmhouse is located in the heart of the Catskills with wide open vista views and features thoughtfully appoi ...
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VRBO
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Expedia
Cozy Country Home on an Organic Apple Orchard
Bedrooms:
1
Bathrooms:
3
Sleeps:
3
Family friendly restored home (1,000 sq ft.) in Callicoon Center NY is a 2 hr. drive from the GWB. It has 3 bedrooms, 1 ...
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Expedia
From $186 per night (USD)
VRBO
Charming 2 Bedroom Lakefront Cottage in the Catskill Mountains
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
With only a two hour drive from New York, here's your opportunity to escape to the Catskills to relax and unwind in this ...
From $186 per night (USD)
VRBO
From $939 per night (USD)
VRBO
Catskill Mountain Farmhouses with Private Lake, Sleeps 16
Bedrooms:
3
Bathrooms:
9
Sleeps:
16
Welcome to Buck Brook Valley. Our property offers 2 lovely farmhouses on 52 secluded acres with a private, 9 acre man ma ...
From $939 per night (USD)
VRBO
From $406 per night (USD)
VRBO
Remodeled historical farmhouse with luxury kitchen and bathrooms
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Mertle Farm The Farmy Charmhouse! A 130 year old renovated farmhouse with a private barn, set on 5 acres and surrounded ...
From $406 per night (USD)
VRBO
From $407 per night (USD)
Expedia
3-bedroom chalet just 13 minutes drive to Bethel Woods
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
In Jeffersonville's center lies a cozy three-bedroom cottage, providing a peaceful retreat during your upcoming holiday. ...
From $407 per night (USD)
Expedia
From $1195 per night (USD)
VRBO
Luxury Getaway in Jeffersonville, NY
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Home away from home. You will find yourselves in a peaceful, and cozy place that you will not want to leave. Surrounded ...
From $1195 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Private Chalet with Fire Pit, Deck and Large Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Nestled on six acres of serene and untouched Catskills forest, our charming A-frame chalet invites you to relax ...
From $236 per night (USD)
Expedia
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VRBO
Swan Lake Estate w/ Sauna & Game Room!
Bedrooms:
5
Bathrooms:
4
Sleeps:
14
5,456 Sq Ft | Antique Furniture | Year-Round Activities Step into the tranquility of Swan Lake when you stay at this 4- ...
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VRBO
From $446 per night (USD)
VRBO
Lilac Hill - VIEWS, Privacy, and Design
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Lilac Hill is a stunning escape in the heart of the Catskills, located just 2 hours from NYC. Set on 39 priva ...
From $446 per night (USD)
VRBO
From $415 per night (USD)
VRBO
Brookside Manor - Elegance near Livingston Manor
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Summary: Brookside Manor is an elegant country escape in the heart of the Catskills, located 2 hours from NYC. Set on ...
From $415 per night (USD)
VRBO
$Spacious 4 Bdrm w/ Indoor Heated Pool+Sauna+Creek\n$
From $691 per night (USD)
Expedia
Spacious 4 Bdrm w/ Indoor Heated Pool+Sauna+Creek\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This c ...
From $691 per night (USD)
Expedia
From $510 per night (USD)
VRBO
Clancy House - Cedar Hot Tub, Sleeps 10
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Escape to this breathtaking 4-bed, 4 bath retreat in Livingston Manor. On a serene 5-acre lot, this modern home ...
From $510 per night (USD)
VRBO
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Expedia
Private 12 acres
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to the Trout House! A 10 minute drive from Livingston Manor or Roscoe brings you up a dirt road to this totally ...
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Expedia
From $294 per night (USD)
VRBO
Serene Haven: Nature, Deck, Views & Fireside Fun
Bedrooms:
1
Bathrooms:
17
Sleeps:
8
Summary: “The Blue House” is a modern, newly renovated, two-story Catskill ranch house that sits atop a hill with five p ...
From $294 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Modern Manor on Maple
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Modern Manor on Maple! Built in the 1920s, this charming two-story farmhouse is located in the heart of Jeff ...
From $244 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Creekside Cottage
Bedrooms:
1
Bathrooms:
4
Sleeps:
5
Highlights: In-town location on main street with waterside stone BBQ and patio. Walk to stores and restaurants. Welc ...
From $252 per night (USD)
VRBO
From $336 per night (USD)
VRBO
Immerse in your private woods in our modern cabin
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our cabin is a stylish retreat set on 5 private wooded acres. All houses in this private neighborhood have at least 5 ac ...
From $336 per night (USD)
VRBO
From $225 per night (USD)
VRBO
Renovated Chalet with Hot Tub and Pond
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to Winterberry Pond, our completely renovated converted barn which is nestled on 7+ private acres. This ...
From $225 per night (USD)
VRBO
From $332 per night (USD)
Expedia
Bethel Woods Escape: Fire Pit~BBQ~Hiking~On 5 acres~Cute A-Frame
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*Private Chef Services Available* ~5 acres of land ~Fireplace ~Fast wifi ~Fire Pit and solo stove ~Back Patio w/ Weber ...
From $332 per night (USD)
Expedia
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VRBO
Aparment in the woods - 10 min. to Bethel Woods
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
7 miles from the original site of the 1969 Woodstock music festival, now the home of Bethel Woods Performing Arts Center ...
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VRBO
From $582 per night (USD)
Expedia
BirchRidge A-Frame:Catskills Retreat-Sauna-Firepit
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in the Catskills Forest, less than 2 hours from NYC you'll find Birch Ridge A-frame! This custom-built 2 bed/ 1 ...
From $582 per night (USD)
Expedia
From $340 per night (USD)
VRBO
Stonebridge Hideaway - Enchanting 3 Bedroom Cabin
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Escape to Stonebridge Hideaway, a 3-bed, 1.5-bath Cape Cod style home in Callicoon, NY, just 2 hours from NYC. ...
From $340 per night (USD)
VRBO
From $464 per night (USD)
VRBO
Hemlock Hill Barn - Hillside Views, Hot Tub + Pond
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Escape to Hemlock Hill Barn, a beautifully constructed barn with 3-bedrooms and 1.5 bathroom - just 2.5 hours f ...
From $464 per night (USD)
VRBO
$Callicoon Cottage with Private Pond, Fireplace and Fire Pit\nFamily, Pet Friendly$
From $329 per night (USD)
VRBO
Callicoon Cottage with Private Pond, Fireplace and Fire Pit\nFamily, Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our enchanting retreat, where two distinctive homes—a cozy cottage and a charming farmhouse—await you on a pi ...
From $329 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Architectural Gem - Catskill Chalet, hot tub, wraparound deck on 6 acres
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unwind in a secluded and cozy upstate escape on 6+ wooded acres off a dead-end road while relaxing to the tune of Callic ...
From $346 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Fireplace, Hot Tub, Sauna– Adventure & Charming Towns!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
<p>A short distance from kayaking, birdwatching, and more, this pet-friendly cottage lets you experience it all. With co ...
From $319 per night (USD)
VRBO
From $962 per night (USD)
VRBO
Livingston Manor Lodge - brand new, modern upstate house - 10 min from town
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
The ultimate family or friend luxury retreat in the Western Catskills, just two hours outside of New York City. Come enj ...
From $962 per night (USD)
VRBO
From $508 per night (USD)
VRBO
Catskills Creekside House near Livingston Manor
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Immerse yourself in a memorable Catskills getaway at The Shirley Main House! Nestled in the charming village of Youngsvi ...
From $508 per night (USD)
VRBO
From $346 per night (USD)
Expedia
1930's Vintage Cabin · Hot Tub · Kohler Cabin
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Discover the enchanting allure of Kohler Cabin, nestled in the quaint town of Jeffersonville. This vintage-inspired retr ...
From $346 per night (USD)
Expedia
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Expedia
The Farmstead at 373 Willi Hill Rd, Swan Lake NY 12783
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The farmstead at Willie Hill, nestled at the base of the old Bossley Farm, is a picturesque haven surrounded by rolling ...
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Expedia
From $334 per night (USD)
Expedia
Dancing Doe Estate with Wood Stove, Hot Tub & Firepit
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
SUMMARY Perched on a hill above the Village of Jeffersonville, Dancing Doe Estate, is a perfect marriage of country char ...
From $334 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Charming 2-bedroom Country Cottage with Hot Tub
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Relax and recharge in the secluded garden hot tub at this charming 1900s farm cottage and take in charming country views ...
From $291 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Beechwood Beacon
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Highlights: If your stay wish list includes a bright, modern home, with morning coffee on the deck, nearby hiking, farme ...
From $362 per night (USD)
Expedia
From $678 per night (USD)
VRBO
House on the Hill: Modern Retreat with Sauna, Hot Tub + Fire Pit
Bedrooms:
4
Bathrooms:
1
Sleeps:
10
This sweeping and spacious modern retreat with 180-degree views is your personal oasis in the country. With a grand livi ...
From $678 per night (USD)
VRBO
From $443 per night (USD)
Expedia
Onyx Ridge · Breathtaking Views · 14 Acres
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to Onyx Cabin, a luxurious upscale retreat perched atop a Catskills mountain and accessible via a secluded privat ...
From $443 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Fall & Winter Comfort in Roscoe Mountain Home
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Highlights: If a heated pool, chefs kitchen, private seasonal trout stream, and a warm, cozy home with great beds and lu ...
From $465 per night (USD)
VRBO
From $521 per night (USD)
Expedia
Wellness Retreat with Hot Tub, Gym, Cold Plunge, Office
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Koto House is a rejuvenating wellness retreat designed for those who are seeking a peaceful getaway to reconnect with na ...
From $521 per night (USD)
Expedia
From $266 per night (USD)
VRBO
The Farmstead at 373 Willi Hill Rd, Swan Lake NY 12783
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The farmstead at Willie Hill, nestled at the base of the old Bossley Farm, is a picturesque haven surrounded by rolling ...
From $266 per night (USD)
VRBO
From $469 per night (USD)
VRBO
Hilltop Retreat with Hot Tub in Livingston Manor
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**NEW TO VRBO! 5-STAR SUPERHOST AND GUEST FAVORITE ON ABNB** It’s always the perfect time to book a getaway to the west ...
From $469 per night (USD)
VRBO
From $266 per night (USD)
VRBO
Charming 3-Bedroom Country Escape in Scenic Livingston Manor
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Get ready to relax and recharge in this cozy 3-bedroom country house in the heart of Livingston Manor. Ideal for familie ...
From $266 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Private Escape, Stunning Views in Jeffersonville
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this cozy one-bedroom home with an additional loft featuring two twin beds, perfect for small families or coup ...
From $245 per night (USD)
VRBO
From $252 per night (USD)
VRBO
Milk House @ Indigo Bunting Farm
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We invite you to enjoy our renovated guesthouse, once the milk house on a productive dairy farm in the mid-twentieth cen ...
From $252 per night (USD)
VRBO
From $503 per night (USD)
VRBO
Shandelee Brook House: Hot Tub Serenity | Peaceful Surroundings | 5 Mins to Livi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Shandelee Brook House is a 4 bed, 2.5 bath cottage just 2.5 hours from NYC with access to Shandelee Lake. The n ...
From $503 per night (USD)
VRBO
From $370 per night (USD)
VRBO
Red Hill House: Farmhouse Charm | Natural Views
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Red Hill House is a beautiful 3 bed 1.5 bath farmhouse just over 2 hours from NYC. With an artful flair, covere ...
From $370 per night (USD)
VRBO
From $841 per night (USD)
Expedia
The Lodge at Roscoe Peak!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Highlights: If your dream getaway includes airy, modern interiors, a cozy fireplace, foodie and brewery stops in charmin ...
From $841 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Serene Duplex w/ On-Site Brook in Callicoon Center
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private Balcony | Local Brews Nearby | 8 Mi to Livingston Manor | 9 Mi to Beaverkill Creek, Birthplace of U.S. Fly-Fishi ...
From $295 per night (USD)
VRBO
From $269 per night (USD)
VRBO
Serene Home w/ On-Site Brook in Callicoon Center
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Tranquil Location | Near Hiking | 8 Mi to Livingston Manor | Remote Work Ready Capture the essence of countryside livin ...
From $269 per night (USD)
VRBO
From $364 per night (USD)
VRBO
Red Tail Ridge Cabin in North Branch
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tucked in the woods above North Branch, Red Tail Ridge offers a peaceful escape with sweeping views and quiet charm. A s ...
From $364 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Charming 3BR farmhouse on a quiet country road—pet-friendly, cozy, and close to Callicoon, North Branch Inn & the Cider Mill. Perfect for couples, families, or remote work with a full kitchen, comfy spaces & room to roam.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This stylish yet cozy 3BR/2BA farmhouse is your perfect upstate escape—pet-friendly and full of charm. Set on a quiet co ...
From $373 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Catskills Chalet - 5 acres Full Kitchen Fire Pit Office Pets OK BBQ WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to Shady Fox Farm Catskills, your charming and spacious chalet retreat! This newly and fully rehabbed home is se ...
From $344 per night (USD)
VRBO
From $466 per night (USD)
Expedia
Nature, Comfort and Culture in the Catskills
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover a beautiful home on East Hill surrounded by forests, lakes, farmland, and bohemian towns. Just 2-2.5 hours from ...
From $466 per night (USD)
Expedia
From $4633 per night (USD)
VRBO
Ro House - A Modern Cabin w/ Hot Tub!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in the picturesque Catskills region, the Ro House offers the perfect balance of convenience and tranquillity in ...
From $4633 per night (USD)
VRBO
From $379 per night (USD)
VRBO
Red Hill House: Farmhouse Charm | Natural Views
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Red Hill House is a beautiful 3 bed 1.5 bath farmhouse just over 2 hours from NYC. With an artful flair, covere ...
From $379 per night (USD)
VRBO

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Town of Callicoon Rentals

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Results: 64 Rentals