
Vacation rentals in Woodstock
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Top-rated vacation rentals in Woodstock
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Dutch Touch Woodstock Cottage
The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.
Woodstock Historic Artist Estate - The Pond House
Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star
PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "PREMIER" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1 1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Brand New Modern Cabin walk to town
This brand new cabin was built using green construction and features a living green roof. It is an open concept 1 bedroom with all new fixtures and a soaking tub. You can walk to town in approximately 10-12 minutes. This is in a neighborhood so there are visible neighbors but the architect utilized the natural surroundings to make it feel like you are in the woods. The beauty of this house is it’s access to town. If you look at my past reviews it’s the same location but a new house in front.

Romantic luxury+stream+walk to town=Brook Cottage
Brook Cottage occupies the east wing of a newly renovated authentic 1928 artist’s cottage featuring: 2-story north light windows; cathedral ceiling with skylights; fireplace and fire stove; bluestone patio with gas grill and outdoor seating; newly remodeled cook's kitchen; luxury amenities. Ideally located at the end of a private lane on a spacious shared property bordered by a year-round stream and conservation land, walking distance to the center of Woodstock, the famous "colony of the arts".

Woodstock Dog Friendly Cozy Cottage in Town + Yard
Charming Country Escape – Pet-Friendly & Walk to Village Green! Enjoy country charm and modern comforts in this newly updated 2-bed, 1.5-bath home. Just 2.5 blocks from the Village Green, it’s the perfect getaway for city folk with dogs. Relax in the private backyard with waterfall sounds or stroll to shops, restaurants, and trails. Features include a cozy woodstove, updated kitchen & bath, queen beds, and a master bedroom with an en-suite plus a balcony. You and your pet will love it here!

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace
Snuggle by a roaring fire. Eat in a corner nook or at a rustic wooden counter by a window. This quaint, whimsical home has a private deck w/bbq, a garden with a hammock and fire pit. A full size Murphy bed with a full kitchen (except for an oven). You will have access to the entire guest house. A short drive to the beautiful, eclectic, funky town of Woodstock. Art & culture, restaurants, hiking & biking all nearby. Electric heat, ceiling fan, a standing ac unit and single person shower.

Woodstock retreat with hot tub and deck with view
Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

Fall Fantasy Getaway
This Fall enjoy the changing foliage in your own private forest at the Maverick. As featured in Atomic Ranch & Country Home Magazines, the Maverick is a secluded luxuriously restored 1964 MidCentury deck home furnished with Eames and other iconic era furnishings. The Maverick is secluded yet just 5 minutes from downtown Woodstock as well as beautiful hiking, running, and biking trails. The home is perfectly set up for indoor | outdoor entertainment & dining.

The Carriage House: Studio
We offer a private studio apartment located on the second floor of this wonderfully restored 2 unit carriage house, built in the early roarin' 20's! It offers a blend of modern amenities, with more traditional countryside accents. The traditional design of the studio allows light to pour through the apartment, while making adjustments for sleeping in easy. This truly unique space is a perfect place to take a weekend to relax, and enjoy our exterior grounds!

Woodstock Streamside Cottage
Our streamside cottage is located on a five acre property under a mile to the center of Woodstock. The Sawkill Stream is your backyard with plenty of beautiful trees and meadows your front yard. Quiet sounds of the stream and nature surround you. Central heat and central a/c keeps you comfortable year round. Newly renovated. Please read our reviews and see how you'll feel. Enjoy!

Stunning Woodstock 1 BR Hideaway
Find complete tranquility 5 minutes from Woodstock's bustling Village Green. This sun filled space is situated on a lovely 15-acre owner-occupied property with a private porch and bluestone patio which overlook the forest, seasonal stream and falls. Your only neighbor is the owner, a local painter and sculptor, who lives across the stream.
Popular amenities for Woodstock vacation rentals
Woodstock house rentals

Retro-Chic Cabin in Woodstock - Sauna

Woodstock Retreat -walk to town

Hillside Views in Hudson Valley

Architect's Farmhouse in Woodstock

Beautiful farmhouse with Mountain View- HITS- AC

Whispering Pines: Secluded Retreat near town

Woodstock Catskill Escape: Bright Views & Private

Mt. Wonder: Cold Plunge, Sauna, Hot Tub and View
Woodstock boutique hotels

Village Inn - SoHo suite - Saugerties NY

The Onyx Room Luxury in the Catskills

The Howard Hotel Hudson - Room 301

Hudson Mariner Suite 1

Regal Romantic Luxury Victorian Getaway Catskills

Grace and Favor - welcoming one bedroom suite

Catskill Rose Lodging & Dining

Nautical Nest Boutique Hotel - Suite 4
Other great vacation rentals in Woodstock

Winston's Place - Woodland Cozy Catskills Cabin

The Waterfall Casita: A-frame with 30ft Waterfall

Pet Friendly Cabin Doh-Ray up at 1450 ft

How to Stay in "The Shoe"

Catskill Mtn Streamside Getaway

The Pike Lane Cabin & Nature Preserve

Mountain views, mid-century style! 1 mile to town.

Magnolia Cottage
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ863 | ﺩ.ﺇ918 | ﺩ.ﺇ790 | ﺩ.ﺇ867 | ﺩ.ﺇ918 | ﺩ.ﺇ918 | ﺩ.ﺇ918 | ﺩ.ﺇ951 | ﺩ.ﺇ918 | ﺩ.ﺇ936 | ﺩ.ﺇ918 | ﺩ.ﺇ911 | 
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C | 
Frequently Asked Questions
What types of vacation rentals are available in Woodstock?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Woodstock. From over 110 house rentals to over 20 cottage rentals, we've got you covered.
Are there vacation rentals with a dedicated workspace in Woodstock?
Yes! Work meets play with ease at over 150 vacation rentals in Woodstock featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Woodstock?
Four-legged friends are welcome in Woodstock. Choose from more than 110 vacation rentals for guests traveling with pets.
Are there Woodstock vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Woodstock, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in hotel rentals in Woodstock?
Experience the best of Woodstock with our hotel rentals, starting at about $280 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Woodstock have self check-in?
Absolutely! We offer over 10 cottage rentals with self check-in in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodstock have a gym?
Absolutely! We offer over 20 house rentals with a gym in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Woodstock have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Woodstock have wifi?
Absolutely! We offer over 20 cottage rentals with wifi in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Woodstock?
Woodstock has more than 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
All about Woodstock
Despite the fact that the 1969 Woodstock Festival took place a 90-minute drive to the southwest at Bethel Woods Center for the Arts, the town of Woodstock is the exact cross-section of arts and nature that you’d expect from its association with the famous music fest. Sitting in the foothills of the Catskills, the arts colony was established here in 1902, drawing artists of all types — ranging from craftspeople and photographers to actors and musicians. Free-spirited creativity has a certain kind of purity here, inspired by the vast forests, peaks, and waters — in fact, the Ashokan Reservoir is so crisp that it supplies 40 percent of New York City’s drinking water.
What are the top things to do in Woodstock?
Overlook Mountain Wild Forest
While most mountain hikes lure visitors with their sprawling mountaintop views, Overlook Mountain (with the Hudson River Valley in the foreground and five states in the distance) does that and so much more. Along the way up the Spur Trail, you’ll find the ruins of the never-finished Overlook Mountain House. At the summit, an impressive fire tower reaches 3,140 feet high. Also worth a visit: The Karma Triyana Dharmachakra Tibetan Buddhist monastery across the street from the trailhead.
The Center for Photography at Woodstock
What started as an artists’ colony’s urge to give photographers their own space has grown into a gallery and workshop center that both showcases and supports photography in every kind of light.
Opus 40
Just a 10-minute drive to the east in Saugerties is a 6.5-acre earthwork sculpture that was hand-shaped from bluestone by artist Harvey Fite over the course of 37 years. Sitting on 50 acres of meadows, forest, and quarries, the site — often likened to Stonehenge — also hosts theatrical and musical performances.
Quick stats about vacation rentals in Woodstock

Total vacation rentals
Explore 230 vacation rentals in Woodstock

Nightly prices starting at
Woodstock vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 29,210 verified reviews to help you choose

Family-friendly vacation rentals
130 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
220 of Woodstock vacation rentals include wi-fi access

Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Woodstock rentals

4.9 Average rating
Woodstock stays are highly rated by guests—averaging 4.9 out of 5!
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- Hunter Mountain
 - Bethel Woods Center for the Arts
 - Belleayre Mountain Ski Center
 - Minnewaska State Park Preserve
 - Thunder Ridge Ski Area
 - Windham Mountain
 - Resorts World Catskills
 - John Boyd Thacher State Park
 - Howe Caverns
 - Bash Bish Falls State Park
 - Kent Falls State Park
 - Hudson Highlands State Park
 - Brotherhood, America's Oldest Winery
 - Zoom Flume
 - Walkway Over the Hudson State Historic Park
 - Catamount Mountain Ski Resort
 - Norman Rockwell Museum
 - Taconic State Park
 - Villa Roma Ski Resort
 - Plattekill Mountain
 - Mohawk Mountain Ski Area
 - Opus 40
 - Beartown State Forest
 - Hunter Mountain Resort