Location

Dates

Guests

Vacation rentals in Woodstock, New York, United States

Woodstock Manor

Woodstock Manor

Woodstock Manor

Woodstock Manor

Woodstock Manor

Woodstock Manor

3 bedrooms·1 bath

Woodstock • New York

5(2 reviews)

$ 925,60 USD totaal voor 3 nachten

16–19 nov 2026

Modern Mountain Retreat

Front View of house, Photo by: Bertrand Cavalier

Living Room, Photo by: Bertrand Cavalier

Living room, vie of back deck, Photo by: Bertrand Cavalier

Dining table Photo by: Bertrand Cavalier

Modern Mountain Retreat

3 bedrooms·2 baths

Mount Tremper • New York

5(32 reviews)

$ 10.600,00 USD totaal voor 30 nachten

26 okt – 25 nov 2026

Our lil slice of paradise

Idyllic Esopus River Retreat

4 bedrooms·3 baths

Saugerties • New York

$ 3.325,00 USD totaal voor 3 nachten

26–29 okt 2026

exterior- front porch

dining room and lounge area

original wood detailing

Seasonal Rental: 5BR Victorian, Tannersville NY

5 bedrooms·2 baths

Tannersville • New York

4.71(35 reviews)

$ 9.000,00 USD totaal voor 90 nachten

1 dec 2026 – 1 mrt 2027

Villa Gran Sasso

Villa Gran Sasso

Villa Gran Sasso

Villa Gran Sasso

Villa Gran Sasso

Villa Gran Sasso

4 bedrooms·3 baths

Hunter • New York

5(189 reviews)

$ 1.230,00 USD totaal voor 3 nachten

26–29 okt 2026

Enjoy the cozy living room decorated for the holidays.

open dining room

Dog friendly/Generator/ Level 2 EV charger image 3

Fire pit in the backyard

Second bedroom on the second floor with king bed.

Dog friendly/Generator/ Level 2 EV charger

3 bedrooms·2 baths

Lanesville • New York

4.93(94 reviews)

$ 1.227,84 USD totaal voor 3 nachten

26–29 okt 2026

1st Floor Kitchen/Dining/Living Room

3BR Mountain Getaway in the Heart of the Catskills

3BR Mountain Getaway in the Heart of the Catskills

3BR Mountain Getaway in the Heart of the Catskills

3BR Mountain Getaway in the Heart of the Catskills

3 bedrooms·2 baths

Shandaken • New York

$ 930,00 USD totaal voor 3 nachten

26–29 okt 2026

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

Peaceful Cabin on 2.5 wooded acres- 3 Bed/2.5 bath

3 bedrooms·2 baths

Catskill • New York

5(14 reviews)

$ 1.400,00 USD totaal voor 3 nachten

26–29 okt 2026

Birch ladder to loft, star skylight, moon window, bedroom behind the birch wall

Table and chairs, retro fridge and microwave, bay window, love seat, birch sink

Retro Fridge, microwave, coffee maker, electric water boiling kettle

Retro fridge and microwave, custom built birch sink, coffee maker, kettle

View of the custom built sink, love seat, barn style door, two stars skylights

Domeo - Romantic Magical Dome

1 bedroom·1 bath

Windham • New York

4.89(161 reviews)

$ 502,18 USD totaal voor 3 nachten

29 okt – 1 nov 2026

Bedroom - 1 full bed

AC, TV, basic cable, wifi

Catskill Getaway - Ski Windham

Desk, Dining area / kitchenette view from the bedroom

Catskill Getaway - Ski Windham

Catskill Getaway - Ski Windham

1 bedroom·1 bath

Windham • New York

5(52 reviews)

$ 260,82 USD totaal voor 3 nachten

26–29 okt 2026

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

Windham Bliss Chalet w/Game room/ AC. Catskills

4 bedrooms·3 baths

Windham • New York

4.94(18 reviews)

$ 1.570,00 USD totaal voor 3 nachten

26–29 okt 2026

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

Nature Escape: Fire Pit • Games • Near Windham Mtn

3 bedrooms·3 baths

Greene County • New York

$ 1.001,71 USD totaal voor 3 nachten

1–4 jun 2027

Cozy backyard fire pit with Adirondack chairs for relaxing evenings

Peaceful Catskills Getaway - Modern Studio Loft

Charming guest parking with a warm welcome and cottage-style curb appeal

Breathtaking mountain and forest views with vibrant fall color

Stylish black-and-white retreat with elevated deck and serene wooded setting

Peaceful Catskills Getaway - Modern Studio Loft

0 bedrooms·1 bath

Greene County • New York

$ 610,50 USD totaal voor 3 nachten

26–29 okt 2026

Cozy Ranch Retreat in New Paltz

Cozy Ranch Retreat in New Paltz

Cozy Ranch Retreat in New Paltz

Cozy Ranch Retreat in New Paltz

Cozy Ranch Retreat in New Paltz

2 bedrooms·2 baths

New Paltz • New York

5(2 reviews)

$ 911,40 USD totaal voor 3 nachten

26–29 okt 2026

Enjoy a private, secluded spot away from the hustle and bustle, tucked amongst the trees and mountains. Experience the country life!

Enjoy a nice cup of coffee on the balcony after a peaceful slumber while you listen to the sounds of nature (no sirens or constant construction here!).

Picture yourself spending a perfect evening in the backyard—relaxing in the barrel sauna, sharing a meal with friends at the dining table (seats 8) under charming bistro lights, and unwinding by the firepit as the stars come out. Perfect night!

Sink into your leather couch after a day of exploring the beauty of the Catkills. Your open concept living and dining space is perfect for relaxing with friends and family, connecting and making memories.

How lovely to enjoy a hot tub soak as a family - perfect when the weather starts to turn a bit brisk on fall days. Kids will want to get off the slopes and return to their private hot tub after a busy day of skiing!

Scandi A-Frame w/Hot Tub & Sauna

3 bedrooms·2 baths

Prattsville • New York

5(103 reviews)

$ 1.790,50 USD totaal voor 4 nachten

8–12 nov 2026

Exterior - Back Yard

Exterior - Hot Tub

Deck with rocking chairs and valley views

Fire pit at sunset

Hilltop Horizons

6 bedrooms·4½ baths

Cornwallville • New York

$ 1.904,05 USD $ 1.847,09 USD totaal voor 3 nachten

26–29 okt 2026

Cemetery Schoolhouse l image 1

Cemetery Schoolhouse l image 2

Cemetery Schoolhouse l image 3

Cemetery Schoolhouse l image 4

Cemetery Schoolhouse l image 5

Cemetery Schoolhouse l

1 bedroom·1 bath

Hudson • New York

4.88(238 reviews)

$ 2.250,00 USD totaal voor 30 nachten

7 dec 2026 – 6 jan 2027

Asian Cemetery Schoolhouse image 1

Chinese Wedding- Opium Bed!!!!!

a really long table for all your imaginary friends

Painting by Marie Stella. Dresser to stash all the goodies you get on Warren

this looks really nice doesnt it? thanks.

Asian Cemetery Schoolhouse

1 bedroom·1 bath

Hudson • New York

$ 2.250,00 USD totaal voor 30 nachten

26 okt – 25 nov 2026

Dining area with a wood burning stove

Living room with Smart TV and a fireplace

Treetops Mountain House - 5 Mins to Belleayre

3 bedrooms·2 baths

Arkville • New York

5(2 reviews)

$ 930,00 USD totaal voor 3 nachten

26–29 okt 2026

Hudson Haven image 2

Hudson Haven

3 bedrooms·2 baths

Hudson • New York

4.82(104 reviews)

$ 935,00 USD totaal voor 3 nachten

1–4 nov 2026

Side view of cottage

Garden view of cottage

Queen-sized bedroom

Secluded Country Getaway

2 bedrooms·1 bath

Lloyd • New York

4.74(27 reviews)

$ 977,00 USD totaal voor 3 nachten

31 dec 2026 – 3 jan 2027

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

Catskill Bungalow - Tiny House by Windham & Hunter

1 bedroom·1 bath

Prattsville • New York

5(34 reviews)

$ 281,52 USD totaal voor 3 nachten

28–31 okt 2026

Dining and kitchen area, view to bedroom 1

View to the dining and living room area from bedroom 1

Bedroom 1(included when renting for up to 3 guests). Queen and single bed

Bedroom 1 (queen bed)

Catskill Cottage - 2 bedroom by Windham and Hunter

2 bedrooms·1 bath

Prattsville • New York

4.9(30 reviews)

$ 289,80 USD totaal voor 3 nachten

26–29 okt 2026

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

Secluded Open Air Cabin Spring fed swimming pond

4 bedrooms·2 baths

Fleischmanns • New York

4.91(79 reviews)

$ 1.210,00 USD totaal voor 3 nachten

26–29 okt 2026