Woodstock vacation rentals

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Top-rated vacation rentals in Woodstock

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Bearsville

4.98 out of 5 average rating, 561 reviews

Mt. Guardian Guest House Exquisite Mountain Views

Exquisite mountain views, immaculate cleanliness, cozy wood stove, beautifully designed, great bed, all amenities, freshly roasted coffee, well-equipped kitchen, excellent Wi-Fi, cable TV, Netflix, and serenity! Close to everything, far from everyone. AirBnB PLUS, Super Hosts, registered with town and county. We follow AirBnB Covid cleaning protocols and run a large HEPA air filter between guests. Pet friendly with prior permission. Over 500 exceptional reviews–many guests return again and again. Winter mid-week discount: book 3 or more nights (Sunday - Thursday) and get one night free! Our little cabin is made and furnished with great care and attention to detail. The space is comfortable and homey, bright and flooded with fresh mountain air. Many of the pieces are hand made and those that are not were chosen for both their aesthetic and functionality. We offer high speed internet access, full service internet TV, Netflix, and a full kitchen with every utensil and pot/pan you need (we've been to a bunch of airbnb's and we hardly ever saw a decent sized spaghetti pot!) and hand crafted bathroom with shower. The views from every window are exquisite - from the front we have miles and miles of national park that change in appearance every day. Whether its covered in fog, changing leaves, bright sunshine or fresh snow Mount Guardian delivers a constantly changing and stunning landscape. Enjoy your morning cup from one of the hammock chairs, the couch, or with a newspaper at the kitchen table... At night , forego the tech and curl up in front of the fire with one of our books, or set up a board game with a glass of wine. The place is cozy warm in the coldest months, and although we have air conditioning, its rare that you'll need it. When you're ready - jump into our queen sized memory foam bed before deciding to get one for yourself (yes - its that good and we're happy to share the details). and gaze up through the skylight at the stars. If you're used to sleeping with constant light and noise you'll be amazed at how well rested you feel after just a couple nights on the mountain. Skiers- we can't guarantee the snow, but the cabin is 20 miles from Hunter, 31 miles to Windham, and 36 miles to Belleayre. Inquire about our mid-week skier specials (Sunday night through Friday morning). We are pet friendly, but only small and medium sized dogs (sorry, we can't allow cats). We charge a cash deposit on arrival, and return it to you at the end of your stay. If you would like to bring a dog, PLEASE SEND AN INQUIRY (DO NOT USE INSTANT BOOKING). We have some pet guidelines which you need to read and agree to first. Nothing huge or surprising, but due to some irresponsible pet owners, we like to be clear before you book. If you are planning to come by motorcycle, PLEASE send an inquiry (do not use instant booking). Special Events in the area: June: Taste of Country and Mountain Jam at Hunter Mountain (Both are great by the way!) June through October: Usually something just about every weekend. Check out what is going on at Levon Helm Studios, Bearsville Theatre, the Colony, Maverick Concerts. Many other music and theater venues a little farther off. Mid October: The view of the changing leaves is spectacular Mid October: Woodstock Film Festival. Book early. This brings big crowds to our little town. Late October: Woodstock Luthier Festival November: Halloween in Woodstock is an event not to be missed. Half for the kids, half for all the folks around here who haven't abandoned their 8 year old. A LOT of fun. Christmas: when Santa comes to Woodstock, most of the town turns out for the welcome party. Like no other. We use a keypad system so you can check-in any time after 3:00pm. If you're coming from the city by bus (Trailways stops in Bearsville and Woodstock), you can get an Uber, Lyft, or a cab- but service can be pretty slow up here (there are only a few drivers.) The cabin is a good 45 minute walk from town, up a pretty good hill. We are generally nearby if you need anything. We also leave very explicit instructions for reaching us if there is an urgent need. The cottage is set in the secluded woods of Mt. Guardian, four miles from the center of Woodstock. Explore artist workshops and colonies, excellent music venues, great restaurants, bars, and plenty of cool little shops. Hiking, skiing, swimming, and tubing are all nearby. Licensed massage therapist available next door or in cabin (please book in advance). It's beautiful up here every season- spring and fall are magical, summer swimming, tubing, exploring and winter skiing and times by the fire. Around here it helps to have a car. Though you can do without one if you're staying in for the most part, the cabs in Woodstock are from Kingston and charge a rather serious call out fee. Uber/Lyft are now available, but you may wait a while to be picked up. As mentioned before Trailways bus service will drop you in Bearsville or Woodstock from the Port Authority and the Amtrak drops in Rhinecliff. Cabs are available at Rhinecliff station but your best bet is to rent a car or drive your own. In winter, the roads up here are plowed frequently. Our driveway is plowed and level, and is accessible to most vehicles throughout the year. We have a dog who lives on the property (next door) - he's very gentle and doesn't bark unless a critter alerts him - though we have a fair few of those up on the mountain! He is an indoor dog and unless you are around while he's being walked or chasing sticks, his presence shouldn't impact your stay. With prior approval, we are happy to welcome quiet well-mannered pets. We require an additional security deposit and provide a receipt and simple "pet deposit agreement" on check-in. We ask pet owners to follow our "pet rules" which include keeping your dog in a suitable pen if you are gone from the cabin. No pups on furniture or bed, pick up after your dog in the yard. You may want to bring a mat or blanket. We will provide full details regarding pets when we get your inquiry. You'll have good wifi in the cabin. Mobile service is great for Verizon, and very limited for other carriers.

Jun 11 – 18

€ 172 per night
Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 634 reviews

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.

Feb 9 – 16

€ 132 per night
Guest favorite

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 298 reviews

Artful and Serene Woodstock Getaway

Please read description thoroughly before booking. Relax with a comfortable mix of rustic and elegant in this colorful studio with loft bedroom in the Catskill Mountains of NY. Midway between lovely towns, Woodstock and Phoenicia. Full kitchen and bath, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. We use fragrance free laundry detergent. No smoking or vaping. This listing is not suitable for children or infants.

Sep 19 – 26

€ 124 per night

Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Colony153 locals recommend
Bearsville Theater195 locals recommend
Garden Cafe Woodstock234 locals recommend
Bread Alone Bakery204 locals recommend
SILVIA275 locals recommend
Levon Helm Studios98 locals recommend

Other great vacation rentals in Woodstock

Guest favorite

Cabin in Boiceville

4.98 out of 5 average rating, 434 reviews

Winston's Place - Woodland Cozy Catskills Cabin

Feb 14 – 21

€ 160 per night
Guest favorite

Cottage in Saugerties

4.93 out of 5 average rating, 210 reviews

Chic & Cozy Cottage 10 mins to Woodstock

Jan 15 – 22

€ 142 per night
Guest favorite

Guesthouse in Olivebridge

4.97 out of 5 average rating, 222 reviews

Black Olive Cabin in the Woods - Secluded, Tiny

Aug 9 – 16

€ 153 per night
Guest favorite

Cabin in Woodstock

4.93 out of 5 average rating, 609 reviews

Byrdcliffe Artist Studio (27.1-1-70)

Nov 5 – 12

€ 200 per night
Guest favorite

Guest suite in Woodstock

4.94 out of 5 average rating, 313 reviews

Perfect Woodstock Location- Short Walk to Town

Apr 13 – 20

€ 173 per night
Guest favorite

Cabin in Woodstock

4.93 out of 5 average rating, 579 reviews

Restored Farmhouse with Yoga Studio

Feb 5 – 12

€ 192 per night
Guest favorite

Cabin in Boiceville

5.0 out of 5 average rating, 119 reviews

Come enjoy our wee cabin!

Jun 3 – 10

€ 159 per night
Guest favorite

Guesthouse in Woodstock

5.0 out of 5 average rating, 292 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

Dec 22 – 29

€ 216 per night
Guest favorite

Cottage in Saugerties

4.93 out of 5 average rating, 204 reviews

New:Cozy Barn-Style Retreat Minutes From Woodstock

Sep 6 – 13

€ 331 per night
Guest favorite

Cottage in Woodstock

4.99 out of 5 average rating, 274 reviews

Grapevine Cottage

Jan 7 – 14

€ 322 per night
Guest favorite

Home in Kingston

4.97 out of 5 average rating, 269 reviews

This New House

Dec 16 – 23

€ 150 per night
Guest favorite

Guesthouse in Bearsville

4.98 out of 5 average rating, 463 reviews

Relax on the Ridge - 2 miles from Woodstock

Mar 24 – 31

€ 176 per night

Other great vacation rentals in Woodstock

Guest favorite

Guesthouse in Woodstock

4.96 out of 5 average rating, 185 reviews

Top of the Hill

Feb 26 – Mar 5

€ 142 per night
Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 738 reviews

Hudson Valley Tiny House

Jun 11 – 18

€ 112 per night
Superhost

Farm stay in High Falls

4.86 out of 5 average rating, 795 reviews

Dave's Milk Barn

Nov 24 – Dec 1

€ 124 per night
Guest favorite

Guesthouse in Kingston

5.0 out of 5 average rating, 125 reviews

Cultivate Quietude: Beautiful views, Modern design

Apr 9 – 16

€ 157 per night
Guest favorite

Cottage in Saugerties

4.98 out of 5 average rating, 123 reviews

Cozy Cottage, just off exit 20, 1/2 hr to Hunter

Dec 2 – 9

€ 149 per night
Guest favorite

Townhouse in Saugerties

4.92 out of 5 average rating, 288 reviews

15 min to Woodstock/Saugerties/Hunter (2 bedroom)

Apr 21 – 28

€ 136 per night
Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 108 reviews

Spacious, Private, Close to Town, Work From Home

Oct 8 – 15

€ 458 per night
Guest favorite

Treehouse in Willow

4.96 out of 5 average rating, 703 reviews

Willow Treehouse - secluded, unique, romantic

Jan 28 – Feb 4

€ 437 per night
Guest favorite

Bungalow in Big Indian

4.93 out of 5 average rating, 117 reviews

The Den @ Oliverea - Minutes to Hiking and Skiing!

Apr 11 – 18

€ 116 per night
Guest favorite

Cabin in Woodstock

4.92 out of 5 average rating, 232 reviews

Margaret's Cottage-WoodstockVillage

May 20 – 27

€ 166 per night
Guest favorite

Home in Hurley

4.92 out of 5 average rating, 111 reviews

Stunning Mountain Views, 5 minutes to Woodstock

Dec 4 – 11

€ 312 per night
Guest favorite

Guest suite in Woodstock

4.98 out of 5 average rating, 92 reviews

Woodstock retreat with hot tub and deck with view

Dec 20 – 27

€ 116 per night

Quick stats about vacation rentals in Woodstock

Total rentals

260 properties

Rentals with dedicated workspaces

160 properties have a dedicated workspace

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

120 properties allow pets

Family-friendly rentals

140 properties are a good fit for families

Total number of reviews

31K reviews

Your guide to Woodstock

Welcome to 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.


The best time to stay in a vacation rental in Woodstock

Woodstock is at its best in the summer months with comfortable temperatures from day to night, though a burst of summer rain isn’t unusual. Events are also in full swing, such as the Maverick Festival, with chamber music from June to September; Mower’s Saturday Market flea market and the Woodstock Farm Festival from May through the fall; and the Woodstock-New Paltz Arts & Craft Show, with a spring edition in May and fall one in September. Summer is also prime time to book one of the area’s house rentals and revel in the greenery with outdoor activities such as hiking and biking. Autumn brings its own delights with stunning fall colors, especially around the second week of October. While snow tends to blanket the area in the coldest months, the Catskills’ winter sports offerings can’t be topped. As the snow melts away, spring brings back the tourists, as the temperature works its way up to its comfy zone.


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.

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Woodstock?

    Yes! Work meets play with ease at over 160 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 120 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 40 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 guesthouse rentals in Woodstock?

    Experience the best of Woodstock with our guesthouse rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Woodstock have self check-in?

    Absolutely! We offer over 80 house 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 10 house rentals with a gym in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodstock have a bbq area?

    Absolutely! We offer over 110 house rentals with a bbq area in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Woodstock have wifi?

    Absolutely! We offer over 20 guesthouse 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 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Woodstock?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with wifi, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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