23

Homes for Rent near Woodstock Day School

Section Image
  • /29

    $6,000 per month

    • 2 Beds
    • 2 Baths
    • 1,655 Sq Ft
    • House for Rent

    25 Boggs Hill Rd, Woodstock, NY 12498

    Privately nestled in the woods, yet just a short distance from Woodstock Village, this just completed total restoration and modernization offers finest in quality finishes throughout. Open main level design ideal for your lifestyle features complete chef's kitchen with huge farmhouse sink, slide out pantry, top of the line appliances, and access to outside ideal for placement of a grill. Living

    25 Boggs Hill Rd, Woodstock, NY 12498
  • /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
  • /15

    $2,100 per month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    200 Van Dale Rd Unit Retreat, Woodstock, NY 12498

    Property Id: 1792319Beautiful, quiet, one-bedroom apartment located on a secluded 4 acre lot, only 2 miles from town. Washer/Dryer in the apartment. RENT INCLUDES UTILITIES, FUEL OIL, ULTRA HIGH-SPEED WIFI, and STREAMING CONENT. Streaming content paid subscriptions currently include; Disney+, Apple+, Netflix, Amazon Prime, Paramount+, Peacock, Hulu, HBOMax, Spotify, ESPN+, NFL+,… and

    200 Van Dale Rd Unit Retreat, Woodstock, NY 12498
  • /21

    $18,000 per month

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

    125 Morey Hill Rd, Kingston, NY 12401

    The Woodstock Barn - A Private Retreat in NatureTucked away on two serene acres surrounded by lush woodlands, The Woodstock Barn is a stunning retreat designed for comfort, relaxation, and effortless entertaining. This spacious 2,200 sq. ft. home offers four bedrooms, three full bathrooms, and multiple inviting communal spaces, making it perfect for hosting guests or simply unwinding in

    Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

    125 Morey Hill Rd, Kingston, NY 12401
  • /15

    $2,100 per month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    200 Van Dale Rd Unit Retreat, Woodstock, NY 12498

    Beautiful, quiet, one-bedroom apartment located on a secluded 4 acre lot, only 2 miles from town. Washer/Dryer in the apartment. RENT INCLUDES UTILITIES, FUEL OIL, ULTRA HIGH-SPEED WIFI, and STREAMING CONENT. Streaming content paid subscriptions currently include; Disney+, Apple+, Netflix, Amazon Prime, Paramount+, Peacock, Hulu, HBOMax, Spotify, ESPN+, NFL+,… and more. Large kitchen, living

    200 Van Dale Rd Unit Retreat, Woodstock, NY 12498
  • /14

    $1,900 per month

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

    20 Tannery Brook Rd, Woodstock, NY 12498

    Beautifully renovated first floor, one bedroom apartment located steps from the center of Woodstock with a level backyard & frontage on the Millstream. Spacious tiled bathroom and fully equipped kitchen. This apartment is being offered fully furnished and has flexible term options. Enjoy dining, art galleries, entertainment and shopping right outside your door, as well as the Trailways bus stop.

    Sarah Finch The Kinderhook Group, Inc.

    20 Tannery Brook Rd, Woodstock, NY 12498
  • /2

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    15 Larson Ln Unit 15, Woodstock, NY 12498

    A rustic vibe down a dirt road very close to town. If you’re looking to unwind and have a bright space to do it this might be your place.

    15 Larson Ln Unit 15, Woodstock, NY 12498
  • /9

    $4,500 per month

    • 3 Beds
    • 3 Baths
    • 1,949 Sq Ft
    • House for Rent

    82 Cooper Lake Rd, Bearsville, NY 12409

    Price listed for annual/ long term rental. Available 9/1/25 Quintessential Woodstock home on lovely, bucolic road 3 bedrooms, 3 baths, hardwood floors, exposed beam ceilings, stone fireplace Drenched in light with open floor plan yet cozy charm All modern amenities with radiant heat, stainless steel appliances and beautifully decorated French doors out to stone patio perfect for summer days

    Johanna Trimboli Halter Associates Realty

    82 Cooper Lake Rd, Bearsville, NY 12409
  • /30

    $11,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,333 Sq Ft
    • House for Rent

    10 Purdy Hollow Rd, Woodstock, NY 12498

    Summer Rental Opportunity. Nestled in the serene hamlet of Zena, just five minutes from the heart of Woodstock, this exquisitely renovated cedar contemporary home offers a blend of elegance, comfort, and modern convenience. It is a sanctuary of refined living, set on three private acres directly across from the pristine 60-acre Thorn Preserve, which offers breathtaking views of the Catskill

    Leslie Foti Coldwell Banker Village Green

    10 Purdy Hollow Rd, Woodstock, NY 12498
  • /23

    $6,500 per month

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

    11 Shultis Farm Rd, Bearsville, NY 12409

    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 to town.Step inside

    Alexis Li Corcoran Country Living

    11 Shultis Farm Rd, Bearsville, NY 12409
  • /18

    $2,400 per month

    • 3 Beds
    • 1.5 Baths
    • 1,128 Sq Ft
    • Apartment for Rent

    39 Tannery Brook Rd, Woodstock, NY 12498

    This lovely 3 bedroom duplex apartment has been newly renovated and is available immediately. Located in the village, it is a 2 mimute walk to the center of town and all the shops and restaurants, Utilities and water bill to be paid by tenant.

    Brenda Graf Corcoran Country Living

    39 Tannery Brook Rd, Woodstock, NY 12498
  • /29

    $3,575 per month

    • 3 Beds
    • 2.5 Baths
    • 1,369 Sq Ft
    • House for Rent

    333 Mink Hollow Rd, Woodstock, NY 12448

    Lease term 1 year or more.If you're looking for a tranquil place to live and work, this may be the house. Sitting on a knoll, this 2025, sq. ft. split-level offers 3 Bedrooms and 2.5 baths and is sited on 1.44 level acres. Open front yard, trees, and across the road a seasonal view of the Beaver Kill stream. Newer roof, appliances, new bathrooms, painted interior and exterior. Comfortable

    Naomi Castillo Smith BHHS HUDSON VALLEY PROP-WDST

    333 Mink Hollow Rd, Woodstock, NY 12448
  • /36

    $16,500 per month

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

    75 Hill 99, Woodstock, NY 12498

    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 Lodge, both connected

    Alexis Li Corcoran Country Living

    75 Hill 99, Woodstock, NY 12498
  • /24

    $3,900 per month

    • 4 Beds
    • 2 Baths
    • 1,930 Sq Ft
    • House for Rent

    128 Cole Bank Rd, Saugerties, NY 12477

    Newly renovated farmhouse with gorgeous mountain views and sounds of gushing waterfall across the street. Enjoy the views from your hot tub, and watch a movie in the outdoor theater! Here are the details:Upstairs-3 large bedrooms with closets, ceiling fans and wide plank wood floors-1 smaller bedroom-1 bath with showerDownstairs-Full living room -Full

    sharon freedman eXp Realty

    128 Cole Bank Rd, Saugerties, NY 12477
  • /13

    $3,300 per month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • House for Rent

    88 Rock City Rd Unit 90, Woodstock, NY 12498

    This free standing cottage is ideally located to enjoy all of Woodstock's charm. It is 1200 square feet with two bedrooms, located only 1/2 mile from the Woodstock Village Green. It is available either furnished or unfurnished.Owner is providing heat, electric, water, waste removal, landscaping and snow removal. The rental includes full use of the ground level pool and deck, fire pit and outdoor

    Michael Shaughnessy Halter Associates Realty

    88 Rock City Rd Unit 90, Woodstock, NY 12498
  • /20

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,233 Sq Ft
    • House for Rent

    607 Wittenberg Rd Unit Main House, Mount Tremper, NY 12457

    Situated in a forested setting with access to both sides of Little Beaver Kill and mountain views. Off the entrance foyer is a large living room/office with vaulted ceilings (extra closet space) that opens onto a balcony and the easy flowing Beaver Kill Stream. On the other side of the foyer is the kitchen with breakfast bar and cozy light-filled dining area with built-in banquette seating.

    Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

    607 Wittenberg Rd Unit Main House, Mount Tremper, NY 12457
  • /14

    $1,950 per month

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

    35 Chestnut Hill Rd Unit 2, Saugerties, NY 12477

    Located between Woodstock and Saugerties, this unfurnished contemporary 700-square-foot 1 bedroom/1 bath 2nd floor apartment offers modern living in the Hudson Valley. The private entrance leads up to an open-concept living and dining area filled with natural light through new windows.The kitchen features modern appliances including a dishwasher and built-in microwave. A comfortable

    Pieta Williams Halter Associates Realty

    35 Chestnut Hill Rd Unit 2, Saugerties, NY 12477
  • /7

    $2,250 per month

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

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

    Move in now and enjoy FREE rent until January 1st! Located in the heart of Woodstock is this beautiful newly renovated 1 bedroom apartment looking for its first residents. Walking distance to an array of fine dining restaurants, bars, boutique shops, local markets, artisanal bakeries, pharmacies, galleries, and entertainment venues including a cinema and theater. Just two hours from NYC, this

    James Angelakis BHHS HUDSON VALLEY PROP-WDST

    18 Rock City Rd Unit A, Wood Stock, NY 12498
  • /10

    $3,750 per month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Apartment for Rent

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

    Move in now and enjoy FREE rent until January 1st! Welcome to your modern living oasis in the heart of Woodstock. This beautiful newly renovated 2 bedroom home is waiting for its first residents. Just two hours from the heart of NYC. Walk to numerous restaurants, bars, shops, markets, bakeries, pharmacies, galleries, the cinema, and the theater.This 1890's farmhouse has been reimagined

    James Angelakis BHHS HUDSON VALLEY PROP-WDST

    18 Rock City Rd Unit B, Wood Stock, NY 12498
  • /22

    $6,500 per month

    • 2 Beds
    • 1 Bath
    • 1,323 Sq Ft
    • House for Rent

    10 Sled Hill Rd, Woodstock, NY 12498

    Discover this enchanting 2-bedroom, 1-bath home tucked away in a quiet corner of Woodstock village. Perfectly located within walking distance to all the vibrant restaurants, shops, grocery stores, and pharmacies, this home offers the ideal blend of convenience and tranquility.Step inside to find a cozy wood-burning stove that adds warmth and character to the space. The upstairs room has

    Genevieve Geaney BHHS Hudson Valley Properties

    10 Sled Hill Rd, Woodstock, NY 12498
  • /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