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Woodstock Rentals

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Woodstock Rentals

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42 apartments

Sun Salutations in Woodstock, a mile to the village & a stop on Trailways

Woodstock house

4 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 2 hours 8 minutes

$247

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Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong

Woodstock house

2 bedrooms / 2 bathrooms / Sleeps 4

$293

1 / 14

Charming Converted Barn On 2+ Acres Walk To Town

Woodstock house

5 bedrooms / 2 bathrooms / Sleeps 10

$425

1 / 14

Zen the

Woodstock apartment

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 2 hours 44 minutes

$120

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Woodstock Village Serene & Spacious

Woodstock house

2 bedrooms / 1 bathroom / Sleeps 6

$225

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Stunning Vacation Country & Ski House

Woodstock house

4 bedrooms / 3 bathrooms / Sleeps 10

“One of a kind, secluded, comfortable, & friendly.” We had the best weekend here in this beautiful spacious house. The huge windows all around the living area give such a peaceful feeling looking at the forst or the stream in the backyard. We enjoyed f

Responds fast! avg. 2 hours 9 minutes

$450

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Pet Friendly Cabin Doh-Ray Up At 1450ft!

Woodstock house

2 bedrooms / 2 bathrooms / Sleeps 5

“Relaxing mountain retreat” We enjoyed a very pleasant Thanksgiving week getaway at the cabin, which looks just like the pictures -- nice combination of modern and rustic design. Also very comfortable, clean and well organized. Tv and sound system very

Responds fast! avg. 2 hours 34 minutes

$260

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Woodstock Cottage: walk to Town

Woodstock cottage

2 bedrooms / 3 bathrooms / Sleeps 4

“Very well kept and extremely caring owners” The cottage seems as though it was renovated yesterday because it is so clean and well kept. The kitchen has everything you need to cook, and the living room is comfortable. There are many games and movies a

Responds fast! avg. 3 hours 50 minutes

$315

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Woodstock Secluded MT Top Home with Swimming pool

Woodstock house

6 bedrooms / 3 bathrooms / Sleeps 15

$500

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Woodstock Town Center Studio Apt.

Woodstock apartment

1 bedroom / 1 bathroom / Sleeps 2

$115

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Teahouse Cottage

Woodstock cottage

50 bedrooms / 1 bathroom / Sleeps 4

Responds fast! avg. 2 hours 59 minutes

$155

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A Little Woodstock Love Nest. Walk to everything!

Woodstock apartment

1 bedroom / 1 bathroom / Sleeps 4

$100

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A Little Woodstock Love Inn. Walk to everything!

Woodstock apartment

1 bedroom / 1 bathroom / Sleeps 4

$96

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Woodstock In-town cottage

Woodstock cottage

1 bedroom / 1 bathroom / Sleeps 2

“Perfect” This little gem was the perfect getaway for me, my friend and my dog Amber. The location was private yet walking distance into town, near a beautiful stream and gentle, peaceful hiking trails. The owners El and Eric personally met us when we

Responds fast! avg. 10 minutes

$150

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Coldbrook B&B 2 hours North of NYC Woodstock, NY

Woodstock b and b

3 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 3 hours 44 minutes

$645

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Margaret's Cottage in Woodstock Village

Woodstock log cabin

2 bedrooms / 1 bathroom / Sleeps 4

$165

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Mid Century Ranch-Hot Tub-Minutes to Center ofTown

Woodstock house

4 bedrooms / 4 bathrooms / Sleeps 8

Responds fast! avg. 1 hour 45 minutes

$263

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Sioux Tipi on the waterfall

Woodstock tipi/teepee

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 2 hours 59 minutes

$150

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Schoolhouse Cottage

Woodstock house

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 2 hours 59 minutes

$190

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New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home

Woodstock house

5 bedrooms / 3 bathrooms / Sleeps 13

Responds fast! avg. 25 minutes

$450

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Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts

Woodstock house

4 bedrooms / 2 bathrooms / Sleeps 8

Responds fast! avg. 2 hours 3 minutes

$293

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Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski

Woodstock house

3 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 2 hours 10 minutes

$295

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Woodstock Retreat, Sauna, Steam Shower, Decks

Woodstock house

2 bedrooms / 2 bathrooms / Sleeps 8

Responds fast! avg. 3 hours 17 minutes

$295

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Woodstock Mediterranean Retreat

Woodstock house

4 bedrooms / 3 bathrooms / Sleeps 11

Responds fast! avg. 3 hours 49 minutes

$450

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Cozy & Serene Cottage in Woodstock

Woodstock cottage

1 bedroom / 1 bathroom / Sleeps 3

$200

1 / 13

Mountain Woodland Private Elegant Peacefull MAGIC

Woodstock house

3 bedrooms / 3 bathrooms / Sleeps 6

$375

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Olive Oasis Luxury with Hot Tub, Woodstock Area

Woodstock house

3 bedrooms / 2 bathrooms / Sleeps 6

“A true escape into nature and solitude!” Olive Oasis is a true gem in the gorgeous area of the ashokan Reservoir and Catskill Mountains. The home is uniquely and tastefully decorated and impeccably clean with an open and spacious layout. Large kitch

$219

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Woodstock Modern House with a Pool

Woodstock house

4 bedrooms / 2 bathrooms / Sleeps 10

$350

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NEW!Event-Friendly Home 5 Min to Central Woodstock

Woodstock house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 23 minutes

$125

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Woodstock gorgeous cottage & pool. on 10 acres

Woodstock house

2 bedrooms / 1 bathroom / Sleeps 6

$323

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Woodstock Peace, Privacy, Views

Woodstock house

4 bedrooms / 5 bathrooms / Sleeps 9

$1,000

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Classic Mid-Century Modern in Woodstock, 5 minutes from town.

Woodstock house

5 bedrooms / 4 bathrooms / Sleeps 8

$395

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Chic Retreat in Bearsville 2 m to Woodstock, Saline Pool, Fireplace and Hot tub.

Woodstock house

2 bedrooms / 3 bathrooms / Sleeps 6

“Clean & Comfortable... Quiet & Relaxing...” My wife, 2 dogs and I very much enjoyed our 3 day stay here at the Bearsville Retreat. We arrived on the morning of Super Bowl Sunday, skied Belleayre with friends, had a nice dinner in Woodstock and then ca

$500

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Expansive 4BR Woodstock House w/ Hot Tub!

Woodstock house

4 bedrooms / 4 bathrooms / Sleeps 8

Responds fast! avg. 7 minutes

$335

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Spacious Family Retreat, Woodstock, 2hrs from NYC

Woodstock house

4 bedrooms / 3 bathrooms / Sleeps 9

$255

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Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities)

Woodstock tented camp

2 bedrooms / 1 bathroom / Sleeps 4

$197

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Woodstock Carriage House

Woodstock house

4 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 44 minutes

$200

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Romantic Country Barn By the Stream

Woodstock log cabin

2 bedrooms / 1 bathroom / Sleeps 4

Responds fast! avg. 47 minutes

$195

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About Woodstock

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With a surprisingly large arts community, rolling green hills, and friendly locals, the small and picturesque town of Woodstock has it all! The primary street that hosts a row of boutiques and charming restaurants is known as Tinker Street, but don't limit yourself to this one area. There are plenty of things to see and do across the entire town.

Here are just a few additional suggestions of things to do in Woodstock:

  • Shawangunk Mountains: This mountain range attracts people from all over the area with its rock climbing, hiking, and camping options.
  • SweetHeart Gallery: Overlooking a beautiful waterfall, this popular local gallery features artwork and crafts pieces from some of the best artists in the region.
  • Karma Triyana Dharmachakra Tibetan Buddhist Monastery: This beautiful and serene monastery is the perfect place to spend an afternoon learning about Buddhism or just simply clearing your head.

For those looking to attend local events and festivals, head to Ulster County, a short drive from Woodstock. In Ulster County you can cheer on the competitors participating in the Shandaken Primitive Biathlon in January, watch the boat rally on the Wallkill River at the New Paltz Regatta in May, or take home a piece of art from one of the best artists in the region at the Woodstock-New Paltz Art and Crafts Fair in September.

Luckily, there's a vacation rental available in Woodstock that has everything you are looking for in a getaway home. Book a luxury condo downtown or rent a secluded cabin in the woods just steps from the mountains for an unforgettable vacation experience.

If you're looking to explore the surrounding area, there are several other towns just outside of Woodstock that make for great day trips. The busy college town of Binghamton and the rolling fields of Oswego can both be reached within an hour by car.

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