Vacation rentals in Woodstock

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Top-rated vacation rentals in Woodstock

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Guest favourite

Home in Woodstock

4.91 out of 5 average rating, 637 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. 8 – 15

$196 CAD per night

Guest favourite

Home in Woodstock

4.94 out of 5 average rating, 266 reviews

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.

Dec. 16 – 23

$999 CAD per night

Guest favourite

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 299 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.

Oct. 29 – Nov. 5

$184 CAD per night

Guest favourite

Apartment in Woodstock

4.89 out of 5 average rating, 300 reviews

Hotel Woodstock - Tiger Lily Suite

Overlooking the Woodstock village center, this antique hotel has 148 years of history and charm. From the front steps you will feel the same energy that travelers have felt since President Ulysses S. Grant visited Woodstock in 1872. This room 3B is a 1 bedroom apartment with a separate living room with a queen sized sofa bed. There is a full kitchen and a private bath. You do not need a car! The Trailways bus from NYC stops directly across the green, and walk to everything in the village.

Aug. 23 – 30

$188 CAD per night

Guest favourite

Guesthouse in Woodstock

4.95 out of 5 average rating, 301 reviews

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.

Feb. 15 – 22

$216 CAD per night

Guest favourite

Guesthouse in Woodstock

4.86 out of 5 average rating, 826 reviews

Rocket Room - Rock Stars Only

Walk to town, hiking or a swimming hole. A popular vintage look cabin that backs up to a private woods but is steps from all Woodstock has to offer. Long time superhosts. Turn on, Tune in, Drop out in our 70's rock & roll hideaway carved out of a converted 1920s carriage house. This ain't your Grandma's cabin. All our units have been featured in videos, films, and photoshoots. This one has been featured in Playboy and Imperial Publishing arthouse book. Town of Woodstock OP #27.54-1-12

Mar. 25 – Apr. 1

$179 CAD per night

Guest favourite

Guesthouse in Olivebridge

4.97 out of 5 average rating, 223 reviews

Black Olive Cabin in the Woods - Secluded, Tiny

The cabin is nestled into a mossy rock ledge covered with ferns in a secluded part of the Catskills just south of the Ashokan Reservoir. Constructed of large reclaimed hemlock beams and charred cedar siding on the outside, the cabin mixes the old with the new. The open concept design includes high ceilings, hardwood floors, a wood stove, lofted sleeping quarters, a full bathroom, and a kitchen with an induction cooktop and convection oven. It's the perfect weekend getaway.

Sep. 25 – Oct. 2

$215 CAD per night

Guest favourite

Cottage in Saugerties

4.93 out of 5 average rating, 215 reviews

Chic & Cozy Cottage 10 mins to Woodstock

Located on a bucolic country road on the border between Saugerties and Woodstock, this newly renovated 500 sq ft cottage is on a private acre filled with spaces to relax: screened in dining shed, fire pit, BBQ grill, a creek, forest & the magical sound of a hidden waterfall across the road. Just 10 min from Woodstock town square, 8 min to Levon Helm Studios, and 15 from Bearsville Theater, it's the perfect escape. (Pets welcome on a case by case basis. Please ask.)

Mar. 15 – 22

$210 CAD per night

Superhost

Barn in Woodstock

4.84 out of 5 average rating, 163 reviews

The Woodstock Barn Studio

Once a Woodstock chicken barn, your space is the lower level,of a renovated studio apt. that maintains its rustic charm with wide plank pine floors & ceiling beams. Only 2 blocks to down town Woodstock & bus stop to NYC . There are hiking trails for you to enjoy, the beautiful Wilson State Park as well as The stunning views of Cooper Lake, the Ashokan Reservoir & Rail Trail that will help sooth your spirit. Bring your camera! Well behaved pets welcome.

Jun. 18 – 25

$176 CAD per night

Guest favourite

Tiny homes in Saugerties

4.94 out of 5 average rating, 217 reviews

Gorgeous Tiny House with Mountain View

Enjoy our little cabin and feel off the grid, without being far from the charming village of Saugerties and close to Woodstock. Enjoy the beautiful Catskills area and retreat in our beautifully renovated “tiny haven” ... complete with a Mountain View! “The Haven” at Blue Mountain! ******Can also be booked together with the Main House on the property, listed as Blue Mountain Haven! https://abnb.me/SMQTSu5LQpb

Nov. 26 – Dec. 3

$181 CAD per night

Guest favourite

Guest suite in Woodstock

4.94 out of 5 average rating, 315 reviews

Perfect Woodstock Location- Short Walk to Town

Perfect location! Short walk (350 yards) to center of Woodstock yet enjoy Catskill mountain and meadow views from home and patio in a serene private setting. NO CAR NEEDED. Easy Walk to bus stop, dining, shopping, flea market, farmer's market and movie theater. Close to hiking trails, swimming holes and beautiful forests. Security deposit is not charged upfront. Registered with town of Woodstock #19H-013.

Nov. 1 – 8

$258 CAD per night

Guest favourite

Cabin in Boiceville

5.0 out of 5 average rating, 120 reviews

Come enjoy our wee cabin!

Our Wee Cabin is 25 mins to Belleayre and ready for your visit! Enjoy the bucolic view, modern yet cozy decor and convenient location while you explore the beautiful Catskills. Our Wee Cabin has a full kitchen & bathroom and a bedroom with a Queen-sized bed. Town of Olive Short Term Rental permit Registration No: STR-22-15 Please note: Property shared with another Airbnb: Our Wee Cottage.

Jun. 6 – 13

$207 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Woodstock vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

The Woodstock Inn on the Millstream4 locals recommend

Other great vacation rentals in Woodstock

Guest favourite

Cabin in Saugerties

4.94 out of 5 average rating, 162 reviews

Cozy Cottage for Two

Jan. 6 – 13

$229 CAD per night

Guest favourite

Villa in Woodstock

4.92 out of 5 average rating, 128 reviews

The Falls

Dec. 5 – 12

$290 CAD per night

Guest favourite

Cabin in Woodstock

4.85 out of 5 average rating, 154 reviews

Brand New Modern Cabin walk to town

Oct. 3 – 10

$295 CAD per night

Guest favourite

Cottage in Woodstock

4.99 out of 5 average rating, 276 reviews

Grapevine Cottage

Jan. 22 – 29

$480 CAD per night

Guest favourite

Home in Kingston

4.97 out of 5 average rating, 274 reviews

This New House

Feb. 2 – 9

$223 CAD per night

Guest favourite

Guesthouse in Bearsville

4.98 out of 5 average rating, 464 reviews

Relax on the Ridge - 2 miles from Woodstock

Aug. 28 – Sep. 4

$262 CAD per night

Guest favourite

Apartment in Woodstock

4.99 out of 5 average rating, 135 reviews

Redbird 1926

May 15 – 22

$185 CAD per night

Guest favourite

Cabin in Kingston

4.98 out of 5 average rating, 332 reviews

Come Stay in "The Shoe"

Jan. 31 – Feb. 7

$198 CAD per night

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Quick stats about vacation rentals in Woodstock

Total rentals	270 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	150 properties are a good fit for families
Total number of reviews	32K reviews

Vacation rentals in Woodstock

Top-rated vacation rentals in Woodstock

Home in Woodstock

Home in Woodstock

Guesthouse in Mount Tremper

Apartment in Woodstock

Guesthouse in Woodstock

Guesthouse in Woodstock

Guesthouse in Olivebridge

Cottage in Saugerties

Barn in Woodstock

Tiny homes in Saugerties

Guest suite in Woodstock

Cabin in Boiceville

Vacation rentals for every style

Houses

Cabins

Apartments

Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Other great vacation rentals in Woodstock

Cabin in Saugerties

Villa in Woodstock

Cabin in Woodstock

Cottage in Woodstock

Home in Kingston

Guesthouse in Bearsville

Apartment in Woodstock

Cabin in Kingston

Quick stats about vacation rentals in Woodstock

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore