Vacation Home Rentals By Owner In Woodstock, NY

Exceptional(117)

$1080.4
/ Nightly

Private Vacation Home

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

Woodstock, New York, United States
Located just a three-minute drive or a leisurely stroll to the center of Woodstock, this stunning five bedroom contemporary home sited on nearly 5 acres has gorgeous mountain views from almost every window and lots of outdoor space to enjoy the beauty of nature. Perfect for a family vacation or couples who want to rest, relax and take in the mountain air. brbrThe house features 4655 square feet with five bedrooms and four baths, including two master bedroom suites and a separate guest cottage. There is a downstairs living room with a unique wooden ceiling, fireplace and bar, and an upstairs great room with stained glass windows, high ceilings, a large sectional sofa and new high end surround-sound audio system and TV. The upstairs master bedroom has a door out to a private deck with bistro table and chair, and a chaise by the oversized window on which to read or nap. The downstairs master bedroom has a view of the pool and a built-in dresser. The two downstairs bedrooms have queen-sized beds. All the bathrooms are newly renovated. Both master baths have double sinks. The upstairs master bath has a freestanding bathtub as well as a shower. Beautiful wood floors, fully equipped chefs kitchen and tasteful decorations are some of what make this home so special. brbrLounge on the couch in the screen-in porch, or eat at the outdoor dining table on the wooden deck. Swim in the 20 x 40 foot pool, or relax in the outdoor hot tub. Enjoy the newly built fire pit all year long. This is an ideal home for enjoying family, friends, nature and culture. brbrRegistration #20N-050

5
Bed

4
Bath

10
Sleeps

Exceptional(117)

$1080.4
/ Nightly

Private Vacation Home

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

Woodstock, New York, United States
Located just a three-minute drive or a leisurely stroll to the center of Woodstock, this stunning five bedroom contemporary home sited on nearly 5 acres has gorgeous mountain views from almost every window and lots of outdoor space to enjoy the beauty of nature. Perfect for a family vacation or couples who want to rest, relax and take in the mountain air. brbrThe house features 4655 square feet with five bedrooms and four baths, including two master bedroom suites and a separate guest cottage. There is a downstairs living room with a unique wooden ceiling, fireplace and bar, and an upstairs great room with stained glass windows, high ceilings, a large sectional sofa and new high end surround-sound audio system and TV. The upstairs master bedroom has a door out to a private deck with bistro table and chair, and a chaise by the oversized window on which to read or nap. The downstairs master bedroom has a view of the pool and a built-in dresser. The two downstairs bedrooms have queen-sized beds. All the bathrooms are newly renovated. Both master baths have double sinks. The upstairs master bath has a freestanding bathtub as well as a shower. Beautiful wood floors, fully equipped chefs kitchen and tasteful decorations are some of what make this home so special. brbrLounge on the couch in the screen-in porch, or eat at the outdoor dining table on the wooden deck. Swim in the 20 x 40 foot pool, or relax in the outdoor hot tub. Enjoy the newly built fire pit all year long. This is an ideal home for enjoying family, friends, nature and culture. brbrRegistration #20N-050

5
Bed

4
Bath

10
Sleeps

$388.99
/ Nightly

Private Vacation Home

Maison Noir: Upstate Oasis | Chic Design | Pool + Hot Tub

Woodstock, New York, United States
Summary:brbrMaison Noir is a stunning 3 bed, 3 bath contemporary sanctuary just 2 hours from NYC. Designed with elegance and energy efficiency in mind, it features the unique Wabi Sabi Design Philosophy. Indulge in a resort calibre oasis, boasting a heated pool, cedar hot tub, chic lounge seating, firepit, BBQ, and alfresco dining! All just 5 minutes to the Village of Woodstock.brbrbrbrNearby Attractions: Woodstock Golf Course (2 mins), Tennis Club (5 mins), Woodstock Day Camp (6 mins)brbrNearby towns: Saugerties (15mins), Kingston (20mins), Catskill (30min), New Paltz (35mins), Hudson (35mins)brbrbrbrThe Space:brbrExperience unparalleled luxury at Maison Noir, an exquisitely designed getaway with calming neutral tones, boasting the unique Wabi Sabi Interior Design Philosophy.brbrbrbrThe open-concept space is framed by nature, with soaring ceilings, clean lines, and carefully curated furnishings that radiate sophistication. The main living area features a striking double-height ceiling with an abundance of natural light streaming through a full wall of windows.brbrbrbrThe sleek kitchen features a long poured-concrete counter, open shelving, and matte black fixtures. Industrial wire-frame stools offer casual seating along the counter, perfect for sipping morning coffee or a shared bottle of wine. Adjacent, the dining area centers around a beautiful matte-black table, with matching high-back spindle chairs—great for shared meals.brbrbrbrA cozy lounge area with a low-profile black sectional invites you to relax with a book or enjoy a quiet moment while taking in the views through oversized windows. Thoughtful artwork, a statement fireplace, 2 designer wire chairs and a comfy sofa, provide ultimate comfort and style. brbrbrbrThe master bedroom, located on the main floor, features a king size bed and ensuite bathroom with a walk in shower. The master bedroom has a Smart TV (this is the only TV in the house). Upstairs are two guest bedrooms each with a queen size bed and a twin day bed. These rooms share a bathroom with a walk in shower. brbrbrbrStep outside into a boutique style haven designed for elevated outdoor living. The expansive, heated pool sets the tone for total relaxation surrounded by an elegant dark grey flagstone deck with modern lounge chairs. A separate deck offers a cedar hot tub and sun loungers ideal for peaceful morning soaks. Gather around the glowing fire pit with a glass of wine, enjoy alfresco meals fresh off the grill, or settle into chic lounge seating.brbrbrbrMaison Noir is a dream for design lovers, nature seekers, and anyone craving a beautiful, intentional space to reset and recharge. Soak, swim, lounge, and dine in style beneath the open sky - indulge in a truly luxurious experience.brbrbrbrThe Neighborhood:brbrWe love sharing our Red Cottage picks with our guests, and Maison Noir puts you close to it all. For amazing meals, check out Silvia and Cucina for seasonal, locally inspired dishes, or try Good Night for creative Southeast Asian flavors. For something more casual, grab coffee and pastries at Caffe Woodstock or a wood-fired bagel from The Mud Club.brbrbrbrWhen the sun goes down, head to Woodstock Brewing for craft beer, Small Talk for great cocktails in a cozy setting, or catch some local flavor at Tinker Street Tavern.brbrbrbrNeed provisions Sunflower Market has everything you’ll need, while Woodstock Meats, Fruition Chocolate, and Bread Alone offer the best local specialties.brbrbrbrFor shopping, we love browsing Three Turtle Doves, Gilded Carriage, and Pacama Furniture. Book lovers should stop into The Golden Notebook, and wine enthusiasts will appreciate the curated selections at Unfiltered Wine.brbrbrbrFor fresh air and amazing views, hike Overlook Mountain. And if you're here for music, don’t miss a show at The Colony or legendary Levon Helm Studios—two unforgettable local venues.brbrbrbrGetting Around:brbrMaison Noir is just 2 hours from New York City. A car is essential for getting there and exploring the area. The main access routes are the I-87 S, NJ-17 S and FDR Dr. We strongly recommend a 4x4 or a car with four-wheel drive, especially in winter, to handle snow and gravel roads.brbrbrbrOther Things to Note:brbrNOTE: The property does not have window shades or blinds. The pool and hot tub close during the fall season shortly after Labor Day, and opens up again in late Spring/early summer.

3
Bed

3
Bath

6
Sleeps

Exceptional(90)

$350.0
/ Nightly

Private Vacation Home

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

Woodstock, New York, United States
Perfect romantic getaway, totally private.brBeautiful 1600 sq. ft modern house, newly constructed, 2 bedrooms/2 baths, tucked away in the woods on a 6 acres lot, at the heart of enchanted Woodstock, in the historic Byrdcliffe area.brEnjoy your private hot tub, relax and watch the meandering deer. Or step up to the 2nd floor deck to take it all in.brA gas fireplace for the ultimate unwinding experience. Stay connected with wi-fi, digital cable, and Netflix enabled smart TV. Large, fully stocked kitchen, radiant heat, central AC. Two queen beds, and a full size sofa bed in living room. Sleeps 6.brWalking distance to NYC bus route and River Rock health spa. Great restaurants nearby. 1 and a half hours from George Washington bridge.

2
Bed

2
Bath

6
Sleeps

$565.97
/ Nightly

Private Vacation Home

Boutique Luxury Retreat in the Town of Woodstock. Short or Long Term

Woodstock, New York, United States
Summer Rental (May-Sept) or Annual Getaway (30% off) The Artist’s Cottage at Library Lane is a circa 1925 Vervoordt-inspired home in a private setting near the vibrant town of Woodstock. Built by the iconic Woodstock artist Paul Arndt as his sprawling art studio, this property is steeped in the history of the region’s most influential generation of artists and has been featured in the TV series Design Defined and the prestigious Francis York publication, known for featuring historic estates. The cottage has an original stone fireplace fitted with a Stub Belgian insert, soaring high ceilings, and wide pine floors, along with modern touches like skylights and a Venetian plastered bathroom by artist Anthony Chase. Creature comforts abound George Smith sofas, oak sawhorse dining table, custom barn wood cabinetry stocked with Le Creuset cookware, Sabatier knives, a Nespresso coffeemaker, and a cold-pressed juicer and blender. The screened-in porch with its cathedral-style ceilings is a perfect spot to practice yoga, read, meditate, or simply take in the beauty of the Michael Trapp landscape-designed property, and enjoy elegant outdoor dining and barbecue. Equally restorative is a low EMF Sunlighten far-infrared sauna located on the porch. Library Lane is a peaceful, quiet haven just a five-minute walk to downtown Woodstock, and near the area’s most beloved skiing, hiking, and wild swimming spots.

3
Bed

2
Bath

5
Sleeps

Exceptional(90)

$350.0
/ Nightly

Private Vacation Home

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

Woodstock, New York, United States
Perfect romantic getaway, totally private.brBeautiful 1600 sq. ft modern house, newly constructed, 2 bedrooms/2 baths, tucked away in the woods on a 6 acres lot, at the heart of enchanted Woodstock, in the historic Byrdcliffe area.brEnjoy your private hot tub, relax and watch the meandering deer. Or step up to the 2nd floor deck to take it all in.brA gas fireplace for the ultimate unwinding experience. Stay connected with wi-fi, digital cable, and Netflix enabled smart TV. Large, fully stocked kitchen, radiant heat, central AC. Two queen beds, and a full size sofa bed in living room. Sleeps 6.brWalking distance to NYC bus route and River Rock health spa. Great restaurants nearby. 1 and a half hours from George Washington bridge.

2
Bed

2
Bath

6
Sleeps

$565.97
/ Nightly

Private Vacation Home

Boutique Luxury Retreat in the Town of Woodstock. Short or Long Term

Woodstock, New York, United States
Summer Rental (May-Sept) or Annual Getaway (30% off) The Artist’s Cottage at Library Lane is a circa 1925 Vervoordt-inspired home in a private setting near the vibrant town of Woodstock. Built by the iconic Woodstock artist Paul Arndt as his sprawling art studio, this property is steeped in the history of the region’s most influential generation of artists and has been featured in the TV series Design Defined and the prestigious Francis York publication, known for featuring historic estates. The cottage has an original stone fireplace fitted with a Stub Belgian insert, soaring high ceilings, and wide pine floors, along with modern touches like skylights and a Venetian plastered bathroom by artist Anthony Chase. Creature comforts abound George Smith sofas, oak sawhorse dining table, custom barn wood cabinetry stocked with Le Creuset cookware, Sabatier knives, a Nespresso coffeemaker, and a cold-pressed juicer and blender. The screened-in porch with its cathedral-style ceilings is a perfect spot to practice yoga, read, meditate, or simply take in the beauty of the Michael Trapp landscape-designed property, and enjoy elegant outdoor dining and barbecue. Equally restorative is a low EMF Sunlighten far-infrared sauna located on the porch. Library Lane is a peaceful, quiet haven just a five-minute walk to downtown Woodstock, and near the area’s most beloved skiing, hiking, and wild swimming spots.

3
Bed

2
Bath

5
Sleeps

$722.38
/ Nightly

Private vacation home

Woodstock historic artist estate - The Pond House

Woodstock, New York, United States

3
Bed

1
Bath

5
Sleeps

$749.28
/ Nightly

Private vacation home

Cozy Mid-Century Retreat with Spa Hot Tub

Woodstock, New York, United States

2
Bed

2
Bath

7
Sleeps

$775.78
/ Nightly

Private vacation home

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

Woodstock, New York, United States

3
Bed

2
Bath

6
Sleeps

$777.25
/ Nightly

Private vacation home

Mid-Century Modern Gem, Heated Pool, 1 Mile from Town

Woodstock, New York, United States

3
Bed

2
Bath

6
Sleeps

$778.40
/ Nightly

Private vacation home

Peaceful, stunning property 3 min to Woodstock-truly a \"Blissful Getaway\"

Woodstock, New York, United States

3
Bed

2
Bath

6
Sleeps

$790.10
/ Nightly

Private vacation home

Modern Farmhouse Getaway

Woodstock, New York, United States

4
Bed

2
Bath

10
Sleeps

$966.56
/ Nightly

Private vacation home

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

Woodstock, New York, United States

3
Bed

3
Bath

8
Sleeps

$1049.49
/ Nightly

Private vacation home

NEW: Architect-designed historic CARRIAGE HOUSE w/heated pool, AC, walk to town!

Woodstock, New York, United States

3
Bed

2
Bath

6
Sleeps

$1080.40
/ Nightly

Private vacation home

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

Woodstock, New York, United States

5
Bed

4
Bath

10
Sleeps

$1370.55
/ Nightly

Private vacation home

Woodstock Ridge / Hot Tub, Pool & Fire Pit

Woodstock, New York, United States

4
Bed

3
Bath

8
Sleeps