29

Homes for Rent near Reginald Bennett Elementary School

Section Image Section Image
  • /20

    $3,200 per month

    • 3 Beds
    • 2 Baths
    • 1,542 Sq Ft
    • House for Rent

    17 Elks Park Rd, West Hurley, NY 12491

    Looking for a cozy spot to call home? This fantastic year-round rental will be available starting August 1st! Nestled on 1.40 acres, this charming 3-bedroom, 2-bath home is just minutes from the vibrant village of Woodstock, the West Hurley Hannaford, the NYS Thruway, and right across from the scenic Ashokan Rail Trail.The dining area comfortably seats six, perfect for family dinners or

    Agent Photo

    Catherine Quintard

    Compass Greater NY, LLC

    (845) 622-8236

    17 Elks Park Rd, West Hurley, NY 12491
  • /20

    $10,580 per month

    • 7 Beds
    • 5 Baths
    • 3,798 Sq Ft
    • Condo for Rent

    21 Abbey Rd Unit ID1241292P, Mount Tremper, NY 12457

    Nestled in the heart of tranquil upstate New York, Abbey Road Farmhouse offers an idyllic escape just 2.5 hours from NYC. With ample space for up to 14 guests, the main house boasts 5 beds, 3.5 baths, a cozy living room, a modern kitchen, an office, and a gym. A charming 2-bedroom, 2-bathroom cottage includes a full kitchen, a living room, and a private deck. Outside, enjoy the seasonal pool,

    21 Abbey Rd Unit ID1241292P, Mount Tremper, NY 12457
  • /15

    $2,899 per month

    • 3 Beds
    • 1.5 Baths
    • 1,133 Sq Ft
    • House for Rent

    501 Ohayo Mountain Rd, Woodstock, NY 12498

    Discover your Upstate sanctuary in this contemporary 3-bedroom, 1.5-bath gem on Ohayo Mountain Road. Nestled in wooded bliss, this unfurnished home (or furnished) boasts gleaming hardwood floors, a cozy wood-burning stove, and an open-concept floorplan perfect for modern living. Step outside to your private deck, ideal for entertaining or soaking in the tranquil surroundings. Less than 20 minutes

    James Angelakis BHHS HUDSON VALLEY PROP-WDST

    501 Ohayo Mountain Rd, Woodstock, NY 12498
  • /22

    $1,950 per month

    • Studio
    • 1 Bath
    • 420 Sq Ft
    • House for Rent

    78 Burgher Rd, West Shokan, NY 12494

    Charming Renovated Barn on Private 4-Acre Lot – Available for Long-Term RentalNestled at the end of a quiet dead-end road on a secluded 4-acre property, this beautifully renovated barn offers a unique opportunity for long-term living in a peaceful, natural setting.The residence features a king-sized bed with a memory foam mattress, an oversized bathroom with Kohler fixtures, and a

    78 Burgher Rd, West Shokan, NY 12494
  • /53

    $6,000 per month

    • 3 Beds
    • 2 Baths
    • 1,876 Sq Ft
    • House for Rent

    17 Cross Patch Rd, Willow, NY 12495

    Beautifully renovated farmhouse set on 4.65 private acres with seasonal mountain views. This fully furnished 3BR/2BA home features an open floor plan, custom kitchen with vaulted ceilings, high-end appliances, marble countertops, and hardwood floors throughout. Living room with cobblestone fireplace and French doors to covered porch. Screened porch and large back deck overlook lush grounds.

    Susanna Scott-Mitchell Compass Greater NY, LLC

    17 Cross Patch Rd, Willow, NY 12495
  • /19

    $2,100 per month

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft
    • House for Rent

    19 Lennox Ave, Glenford, NY 12433

    Discover this charming and versatile home in the peaceful hamlet of Glenford, just minutes from Woodstock and the Ashokan Reservoir. This property includes 1-bed/1-bath , abundant natural light, and cozy living spaces. Situated on a quiet road with off-street parking and scenic surroundings, this home is ideal for those seeking tranquility with easy access to Route 28 and Kingston. Pets

    Cameron Ashkarkhizani Serhant LLC

    19 Lennox Ave, Glenford, NY 12433
  • /38

    $3,500 per month

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    273 Grog Kill Rd, Willow, NY 12495

    We are pleased to present an excellent home available for rent in the Willow/Woodstock area! If you are looking for a home that can be used for year-round living, then this rental home checks all criteria. This property offers great outdoor lighting and provides peaceful window views all throughout the property! Let's take a journey throughout the home, as it sits within a wooded tranquil

    Jorge Lugo Real Broker NY LLC

    273 Grog Kill Rd, Willow, NY 12495
  • /39

    $5,000 per month

    • 2 Beds
    • 1.5 Baths
    • 1,150 Sq Ft
    • House for Rent

    21 Cricket Ridge, Woodstock, NY 12498

    Available by the month.Vintage Shultis family cottage lovingly restored by current owner. Spend the wonderful summer months in this pristine 1,150 square foot cottage. Beamed ceilings, pine floors, high quality windows and doors, newer appliances, fireplace and an all-new HVAC system are just of few of the perks at this charming getaway. Enter through a stunning 3-season, eat-in parlor into

    Gail Cadden Coldwell Banker Village Green

    21 Cricket Ridge, Woodstock, NY 12498
  • /25

    $2,850 per month

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft
    • House for Rent

    50 Galli Curci Rd, Highmount, NY 12441

    Catskills Summer Retreat - Available NowFully furnished 3BR/2BA home offering the perfect balance of comfort and convenience for a seasonal escape. The open kitchen, dining, and living area with a cozy fireplace is ideal for relaxing or entertaining. A separate family room provides additional space to spread out. Two bedrooms are located on the main level, with a spacious third bedroom

    Judy Black Keller Williams Upstate NY Pro

    50 Galli Curci Rd, Highmount, NY 12441
  • /45

    $4,500 per month

    • 2 Beds
    • 3 Baths
    • 2,922 Sq Ft
    • House for Rent

    269 Brown Rd, Olivebridge, NY 12461

    Tucked away on over six private acres in Olivebridge, this nearly 3,000-square-foot home offers the kind of space and quiet that's hard to come by. Inside, the layout is open and bright, with oversized windows throughout and plenty of room to spread out—whether you're here for a season or something more long-term. The main level features a spacious living/dining/kitchen area that opens right out

    Briana Cermak BHHS HUDSON VALLEY PROP-WDST

    269 Brown Rd, Olivebridge, NY 12461
  • /29

    $3,750 per month

    • 4 Beds
    • 2 Baths
    • 2,500 Sq Ft
    • House for Rent

    20 Mary Lou Ln, Shokan, NY 12481

    This bright and beautifully updated raised ranch seamlessly blends classic charm with the modern appeal of a new build. Nestled in a serene neighborhood on a quiet cul-de-sac in the low-tax town of Olive, ideally situated between Woodstock and Phoenicia, this fully-renovated home offers the perfect combination of style, comfort, and convenience. At its heart is a stunning kitchen featuring a

    Benjamin Armento Coldwell Banker Village Green

    20 Mary Lou Ln, Shokan, NY 12481
  • /6

    $1,950 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Apartment for Rent

    18 Rock City Rd Unit A, Wood Stock, NY 12498

    Welcome to this beautifully renovated 1

    James Angelakis BHHS HUDSON VALLEY PROP-WDST

    18 Rock City Rd Unit A, Wood Stock, NY 12498
  • /33

    $13,000 per month

    • 3 Beds
    • 2.5 Baths
    • 3,076 Sq Ft
    • House for Rent

    16 Juniper Ln, Woodstock, NY 12498

    Welcome to Juniper Woods. Available for monthly rentals with flexible lease terms ranging from 3 to 6 months or longer.Nestled on four serene acres just minutes from the center of Woodstock, Juniper Woods is a custom-designed, exquisitely renovated residence offering the perfect balance of sophistication, tranquility, and convenience. With over 3,000 square feet of thoughtfully curated living

    Victoria Stent Coldwell Banker Village Green

    16 Juniper Ln, Woodstock, NY 12498
  • /18

    $2,750 per month

    • 1 Bed
    • 1 Bath
    • 727 Sq Ft
    • House for Rent

    195 Glenford Wittenberg Rd, Glenford, NY 12433

    Charming, Sundrenched Cottage on lovely Glenford Wittenberg Road looking for its nextlucky tenant. Lots of windows, vaulted ceilings, knotty pine flooring, woodstove, nestle in and enjoy the simple life! Washer and Dryer on site, Carport and Shed too!Easy to show! Look at the Photos! Great outdoor space!

    Mary Orapello Howard Hanna Rand Realty

    195 Glenford Wittenberg Rd, Glenford, NY 12433
  • /37

    $5,500 per month

    • 3 Beds
    • 2 Baths
    • 2,739 Sq Ft
    • House for Rent

    33 Race Track Rd, Bearsville, NY 12409

    ANNUAL FURNISHED RENTAL w POOL Lovely, meticulously maintained 3 bd/2 ba home with flex room and finished basement on amazing road. 3 plus bucolic acres minutes to the center of Woodstock HW floors, gourmet kitchen, living room with beautiful stone fireplace. Stone patio perfect for eating al fresco Sprawling grounds and gardens. Plenty of room to enjoy hosting family and friends.

    Johanna Trimboli Halter Associates Realty

    33 Race Track Rd, Bearsville, NY 12409
  • /24

    $7,000 per month

    • 3 Beds
    • 2 Baths
    • 1,483 Sq Ft
    • House for Rent

    673 Acorn Hill Rd, Olivebridge, NY 12461

    Woodstock NY area. Seasonal Summer Rental 20K...Great Summer Vacation Rental, Available June 1st thru Labor day weekend -- Enjoy the Catskill Mountains to the fullest in this large, updated home! This private country oasis features a Salt Water Lap Pool that's 8 feet wide and 60 feet long! The fenced in yard includes an 8-foot-high deer fence, with a gate into the property... minutes to the

    Sara Gorman Maliha Coldwell Banker Village GreenK

    673 Acorn Hill Rd, Olivebridge, NY 12461
  • /10

    $3,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,620 Sq Ft
    • House for Rent

    5262 Route 28, Mount Tremper, NY 12457

    Mid-Century Modern Ranch with nice Open Floor Plan, Three Bedrooms and 1.5 Baths. Beamed Ceilings, Wood Floors and Mountain Views add Charm. Large Carport, big enough for 2 vehicles keeps your autos protected from the elements.

    Edwin Maldonado Howard Hanna Rand Realty

    5262 Route 28, Mount Tremper, NY 12457
  • /11

    $3,000 per month

    • 4 Beds
    • 2 Baths
    • 1,579 Sq Ft
    • House for Rent

    14 Jay St, Phoenicia, NY 12464

    Charming 4-Bedroom Home in the Heart of PhoeniciaThis inviting 4-bedroom, 2-bathroom home offers the perfect blend of comfort and convenience, just a short walk to Main Street Phoenicia for dining, shopping, and all the charm of this beloved Catskills town.Step inside to find easy-to-maintain hardwood floors throughout, a bright and airy living space, and a well-appointed kitchen. A screened-in

    Teresa Falkowski Keller Williams Realty HV Nort

    14 Jay St, Phoenicia, NY 12464
  • /24

    $14,250 per month

    • 3 Beds
    • 3 Baths
    • 3,200 Sq Ft
    • House for Rent

    106 Chestnut Hill Rd, Woodstock, NY 12498

    Summer or Long-Term Rental Opportunity. Let Pictures do the talking. Nestled on a secluded lot, just 10 minutes' walk from the heart of Woodstock, this exquisitely designed brand new home offers a blend of elegance, comfort, and modern convenience. It is a sanctuary of refined living, set on five private acres right next to the Woodstock Golf Course. The Woodstock Tennis Club is also 5

    Soiti Anderson Curated By Soiti

    106 Chestnut Hill Rd, Woodstock, NY 12498
  • /14

    $3,500 per month

    • 4 Beds
    • 2 Baths
    • 2,158 Sq Ft
    • House for Rent

    295 Grog Kill Rd, Willow, NY 12495

    SUMMER RENTAL: Private, fully furnished Woodstock Oasis with mountain views, is ready to be your Spring getaway! On a dead-end rd. up high on a hill, this Willow home has everything you need, close to hiking, skiing, restaurants and shopping, just minutes from Woodstock, Phoenicia and the NYS Thruway, this private retreat is available beginning July 1st through April 30th, 2026.

    Mark Kanter BHHS HUDSON VALLEY PROP-WDST

    295 Grog Kill Rd, Willow, NY 12495
  • /23

    $6,500 per month

    • 4 Beds
    • 2.5 Baths
    • 1,853 Sq Ft
    • House for Rent

    11 Shultis Farm Rd, Bearsville, NY 12409

    AVAIL FROM SEPT 2025. Private & Serene Modern Farmhouse Near Woodstock - Nestled on a private road just minutes from the heart of Woodstock, this beautifully renovated 4-bedroom, 2.5-bathroom modern farmhouse offers the perfect blend of charm, space, and privacy. Surrounded by mature trees, stone walls, and tall hedges, this home feels like a secluded retreat while remaining conveniently close

    Alexis Li Corcoran Country Living

    11 Shultis Farm Rd, Bearsville, NY 12409
  • /36

    $16,500 per month

    • 4 Beds
    • 2.5 Baths
    • 4,400 Sq Ft
    • House for Rent

    75 Hill 99, Woodstock, NY 12498

    AVAIL FROM SEPT 2025. Secluded Mountain Chalet with Breathtaking Views and Poolside Lodge - Set atop nine private acres, this stunning mountaintop chalet offers a rare combination of serenity, seclusion, and spectacular views. A long, private driveway winds through the property, leading to a retreat unlike any other. The property features a three-story main house and a separate two-story Poolside

    Alexis Li Corcoran Country Living

    75 Hill 99, Woodstock, NY 12498
  • /32

    $3,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,480 Sq Ft
    • House for Rent

    4666 New York 212, Willow, NY 12495

    What a delightful country retreat and artist home this is! Located in an idyllic setting with mountain views and a gorgeous and famous trout stream, this beautifully maintained farm house exudes charm and comfort. With 3 bedrooms, 2 1/2 baths, formal dining room, a spacious kitchen with fireplace, a living room to die for with beamed ceiling and a stone fireplace with a woodstove insert, you

    Sylvie Ross Halter Associates Realty Inc

    4666 New York 212, Willow, NY 12495
  • /43

    $3,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,480 Sq Ft
    • House for Rent

    4666 New York 212 Unit House, Willow, NY 12495

    What a delightful country retreat and artist home this is! Located in an idyllic setting with mountain views and a gorgeous and famous trout stream, this beautifully maintained farm house exudes charm and comfort. With 3 bedrooms, 2 1/2 baths, formal dining room, a spacious kitchen with fireplace, a living room to die for with beamed ceiling and a stone fireplace with a woodstove insert, you

    Sylvie Ross Halter Associates Realty

    4666 New York 212 Unit House, Willow, NY 12495
  • /30

    $4,000 per month

    • 1 Bed
    • 1 Bath
    • 1,587 Sq Ft
    • House for Rent

    272 Yerry Hill Rd Unit Studio, Woodstock, NY 12498

    Imagine immersing yourself in a world of natural beauty. As you enter the property and travel on the quarter-mile driveway, you'll be greeted by trees on both sides with a view of a large pond (though not part of the property), to your right. As you continue, you will reach a fork; to your left is a small cottage; keep to the right, Trees all around...It feels like an enchanted forest. Follow the

    Naomi Castillo Smith BHHS HUDSON VALLEY PROP-WDST

    272 Yerry Hill Rd Unit Studio, Woodstock, NY 12498
How to Rent a Home