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 $373 per night (USD)
VRBO
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)
VRBO
From $343 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 $343 per night (USD)
Expedia
From $215 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 $215 per night (USD)
VRBO
From $970 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 $970 per night (USD)
VRBO
From $499 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 $499 per night (USD)
VRBO
From $505 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 $505 per night (USD)
Expedia
From $237 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 $237 per night (USD)
VRBO
From $362 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 $362 per night (USD)
VRBO
From $303 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 $303 per night (USD)
VRBO
From $277 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 $277 per night (USD)
VRBO
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VRBO
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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VRBO
From $217 per night (USD)
Expedia
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 $217 per night (USD)
Expedia
From $418 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 $418 per night (USD)
VRBO
From $1235 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 $1235 per night (USD)
VRBO
From $288 per night (USD)
VRBO
Great relaxing getaway! Stay at summer home of boxing legend James J Braddock
Bedrooms:
1
Bathrooms:
5
Sleeps:
9
Family friendly farmhouse in North Branch, NY, located within short travel distance to some of the Catskill's Sullivan C ...
From $288 per night (USD)
VRBO
From $380 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 $380 per night (USD)
VRBO
From $416 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 $416 per night (USD)
VRBO
From $1082 per night (USD)
Expedia
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 $1082 per night (USD)
Expedia
From $234 per night (USD)
VRBO
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 $234 per night (USD)
VRBO
From $1326 per night (USD)
Expedia
Newly Restored Catskill Farmhouse w/heated pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Newly restored farmhouse with heated pool on 30 acres of mixed pasture and woods. Perfect for families and entertaining. ...
From $1326 per night (USD)
Expedia
From $884 per night (USD)
VRBO
The Nest At Swiss - Lakefront Luxury In The Catskills
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Your cozy getaway awaits in Jeffersonville at this brilliant house. With 4 bedrooms including a king, queen, twin, and f ...
From $884 per night (USD)
VRBO
From $522 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 $522 per night (USD)
Expedia
From $333 per night (USD)
VRBO
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 $333 per night (USD)
VRBO
From $398 per night (USD)
Expedia
NEW: Chic Home w/ Fireplace & Beautiful Sunsets
Bedrooms:
2
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 $398 per night (USD)
Expedia
$Callicoon Cottage with Private Pond, Fireplace and Fire Pit\nFamily, Pet Friendly$
From $410 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 $410 per night (USD)
VRBO
From $332 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 $332 per night (USD)
Expedia
From $336 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 $336 per night (USD)
VRBO
From $429 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 $429 per night (USD)
VRBO
From $347 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 $347 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
$Spacious 4 Bdrm w/ Indoor Heated Pool+Sauna+Creek\n$
From $679 per night (USD)
VRBO
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 $679 per night (USD)
VRBO
From $420 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 $420 per night (USD)
VRBO
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VRBO
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 ...
Click For Pricing
VRBO
From $318 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 $318 per night (USD)
VRBO
From $234 per night (USD)
VRBO
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 $234 per night (USD)
VRBO
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Expedia
Private Country Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cute side apartment in a mother-in-law house setup. 5 acre property includes an optional outdoor shower in warmer months ...
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Expedia
From $669 per night (USD)
VRBO
Amazing Family Retreat
Bedrooms:
3
Bathrooms:
7
Sleeps:
12
An old farm with a big beautiful garden that you can stroll through and eat directly from. From the seasonal stream to ...
From $669 per night (USD)
VRBO
From $744 per night (USD)
Expedia
Relaxing retreat - Lake - HotTub - Firepit - Gameroom - Pet Friendly - sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Private Hilltop Large A-Frame style Chalet, perfect for gathering friends and family! Sleeps 10 guests max. Enjoy priv ...
From $744 per night (USD)
Expedia
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VRBO
Black Star Cabin on 8 acres, no extra fees
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
About this space Comfortable two bedrooms, two bathroom home in the foothills of Catskill, property has 8 acres of grass ...
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VRBO
From $491 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 $491 per night (USD)
VRBO
From $722 per night (USD)
VRBO
Bright, fun, feature-filled Catskills getaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bright, fun Catskills getaway packed with attractive features, conveniently located, & perfect for hosting. Uniquely des ...
From $722 per night (USD)
VRBO
From $186 per night (USD)
Expedia
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)
Expedia
From $291 per night (USD)
VRBO
Sweet Village Waterfront Cottage w/ Nursery
Bedrooms:
1
Bathrooms:
4
Sleeps:
5
Highlights: In-town location on main street with waterside stone BBQ and patio. Walk to stores and restaurants. Welcom ...
From $291 per night (USD)
VRBO
From $269 per night (USD)
Expedia
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 $269 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Cabin by the Rocks 12 x12 rustic cabin
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
12 x 12 cozy cabin with loft, small outdoor kithchen and compost toilet. Queen bed and two twins on loft. Perfect for a ...
From $240 per night (USD)
VRBO
From $214 per night (USD)
VRBO
The ruffled feather cabin 52 acre farm.
Bedrooms:
2
Bathrooms:
3
Sleeps:
3
The Ruffled Feather Cabin is a beautiful rustic 12 x 12 solar powered unit. Views of the barn and sheep paddock. There ...
From $214 per night (USD)
VRBO
From $327 per night (USD)
VRBO
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 $327 per night (USD)
VRBO
From $419 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 $419 per night (USD)
Expedia
$Private Lakefront Cottage, Fish, Row, Panoramic Lake Views.\nPet Friendly!$
From $443 per night (USD)
VRBO
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 $443 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
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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
From $876 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 $876 per night (USD)
VRBO
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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 $830 per night (USD)
Expedia
House on the Hill: Modern Retreat with Pool, 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 $830 per night (USD)
Expedia
From $304 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 $304 per night (USD)
VRBO
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Expedia
Delightful 5-bedroom house with WiFi, WBFP, acres of woods and fields in Roscoe
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
NEWLY AVAILABLE FOR THANKSGIVING OR XMAS/NEW YEAR HOLIDAYS. Private, charming country getaway in Roscoe, great for maki ...
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Expedia
From $275 per night (USD)
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 ...
From $275 per night (USD)
VRBO
From $1020 per night (USD)
Expedia
NEW: Spacious & Stylish Cabin Just Outside Roscoe
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 $1020 per night (USD)
Expedia
From $803 per night (USD)
VRBO
NEW: Fabulous Mountain Pool Home in Roscoe.
Bedrooms:
2
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 $803 per night (USD)
VRBO
From $328 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 $328 per night (USD)
VRBO
From $438 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 $438 per night (USD)
VRBO
From $478 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 $478 per night (USD)
Expedia
From $317 per night (USD)
VRBO
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 $317 per night (USD)
VRBO
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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 $263 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 $263 per night (USD)
VRBO
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Expedia
Enjoy County Barnhouse Living
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Experience the Country life in my spacious barnhouse. Forget your worries and tell stories by the firepit, enjoy a BBQ a ...
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Expedia
From $624 per night (USD)
VRBO
My house is unique, welcome EVERYONE to enjoy beautiful VALLEY in Swane Lake.
Bedrooms:
4
Bathrooms:
7
Sleeps:
10
When you come to this house you will remember all the time how you enjoy your weekend. I WELCOME ALL TO MY HOUSE You wi ...
From $624 per night (USD)
VRBO
From $415 per night (USD)
VRBO
Beechwoods Pond (private 4acre pond. 30+ acre land)
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Amazing home with separate guest house and private 4 acre pond located on 30+ acres of private land! One of a kind home ...
From $415 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

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Town of Callicoon Rentals

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Results: 69 Rentals