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Vacation Rentals & Apartments in Woodstock

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251 apartments

mid century modern ranch woodstock pool

Bearsville house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$520

Margaret's Cottage in Woodstock Village

Woodstock log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$192

Fabulous Family House nr Woodstock Center

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$316

Woodstock Village Serene & Spacious

Woodstock house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$262

Teahouse Cottage

Woodstock cottage

50 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 58 minutes

Price per night from

$201

Mid Century Ranch-Hot Tub-Minutes to Center ofTown

Woodstock house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$384

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

Woodstock house

5 bedrooms / 3 bathrooms / sleeps 13

Responds fast! avg. 3 hours 34 minutes

Price per night from

$805

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

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$339

Charming Converted Barn On 2+ Acres Walk To Town

Woodstock house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$494

Event-Friendly Home - 5 Mins to Central Woodstock

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$156

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 high tech. Somehow we did something wrong with the remotes and lost the tv connection, but Raymond was extremely patient troubleshooting over the phone. Kitchen is nicely equipped. Bathrooms, full upstairs and half downstairs (not pictured), were standard but fine. The views of the woods from the many windows were really pretty, especially in the snow. It was a bit of an adventure driving up the somewhat steep mountain road. Definitely need 4wd in bad weather, so car rental was a little expensive. Overall, we had a lovely stay and hope to have a chance to come back in the summer.

Responds fast! avg. 3 minutes

Price per night from

$334

Woodstock Peace, Privacy, Views

Woodstock house

4 bedrooms / 5 bathrooms / sleeps 9

Price per night from

$1,161

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

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 12 minutes

Price per night from

$313

Stunning Vacation Country & Ski House

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 12

“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 family time, pony rides and a local zoo just 5 min away. we were all able to enjoy our time together and separately thanks to the large livingroom and nice basement . We found the house very clean and with everything we needed in it.

Responds fast! avg. 2 hours 24 minutes

Price per night from

$523

Woodstock Mediterranean Retreat

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$518

Woodstock Carriage House

Woodstock house

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$262

'Casa Reál' Expansive Woodstock House w/ Hot Tub!

Woodstock house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 5 minutes

Price per night from

$391

Updated/Pet-Friendly Cabin By Hikes and Woodstock!

Bearsville cottage

2 bedrooms / 1 bathroom / sleeps 3

Responds fast! avg. 4 minutes

Price per night from

$184

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

Woodstock house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 51 minutes

Price per night from

$343

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

Woodstock house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$459

Cozy & Serene Cottage in Woodstock

Woodstock cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$262

Woodstock gorgeous cottage & pool. on 10 acres

Woodstock house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$374

Woodstock Town Center Studio Apt.

Woodstock apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$134

Schoolhouse Cottage

Woodstock house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 58 minutes

Price per night from

$221

Historic Southwestern Chalet

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$407

Relaxing Zen Cabin

Woodstock house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$186

Spectacular Mountaintop Estate

Woodstock apartment

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$581

Charming Cottage Home

Woodstock house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$175

Tentrr - Woodstock's Dreamcatcher Cabana Campsite

Woodstock tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$316

Tentrr - Woodstock Dreamcatcher

Woodstock tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$174

Tentrr Signature - Shady Knolls

Bearsville tented camp

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$144

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

Woodstock tented camp

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$432

2 BR Cabin, Hot Tub, Fireplace, Heart of Woodstock

Woodstock log cabin

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$262

Marigold cabin by the stream - Heart of Woodstock with Hot Tub & Fireplace

Woodstock cottage

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 18 minutes

Price per night from

$259

Secluded, Luxury Home with Hot Tub

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 6

“Woodstock cabin with hotel” Great place, great service, clean and very nice, looking forward to renting this on a yearly basis , lots to do around the surrounding towns., visited the overlook mountain hiking trail and the Christmas light shows.

Responds fast! avg. 17 minutes

Price per night from

$270

Romantic Country Barn By the Stream

Woodstock log cabin

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 33 minutes

Price per night from

$259

Charming Artist's Cottage

Woodstock house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

Price per night from

$196

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 9 minutes

Price per night from

$288

Viewing 38 of 251
rentals in Woodstock

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About Woodstock

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.

Top Destination reviews

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub
Perfect Location, Hidden Gem

We stayed with our two grown children in the cabin over a long weekend in the summer. The house at first sight is somewhat quirky: tall with a large outdoor porch on the second floor. All of us were looking forward to spend some quality time together, but also were concerned about privacy. To our delight the second floor proved to be a huge master suit with it’s own outdoor space and totally private entrance in addition to the spiral stairway connecting to the lower level. Clearly the design of the house was well thought out to provide for entertainment as well as privacy. The weekend was an all around huge success. Our younger son, the chef, took advantage of the gourmet kitchen and delighted us with a festive dinner the first night. Fresh organic corn, prepared on the outdoor grill, complimented the meal. Our older son was working on his second book in the quite shade on the upper deck and my husband was enjoying the hot tub on the stone patio with his favorite bourbon at hand. I, of course was helping with dinner. The next day we drove to what the locals call the ‘blue hole’ and completed a short hike alongside the stream. We spent the afternoon souvenir shopping in down town Woodstock. For our last day we have decided to stay at the vacation rental, which proved to offer the relaxation and pampering we needed so much.see more
Secluded, Luxury Home with Hot Tub
Comfortable, Relaxing Private Cottage

We had a wonderful time relaxing by the fire. Close trip to the adorable town of Woodstock and convenient ride to Overlook Mountain for a nice 5 mile hike. We loved everything from the open floor plan and bubbling hot tub. It was a perfect setting for a much needed weekend away. Thank you! … see more
Chic Retreat in Bearsville 2 m to Woodstock, Saline Pool, Fireplace and Hot tub.
A place to relax.

The first thing I do upon arrival to a rental is wash any kitchen items I will be using(plates, silverware, glasses, pots and pans, etc.) Not here! Everything was immaculate! As was the entire house. The furniture was of quality, the beds wonderfully comfortable, and all else beyond expectations. It was the most comfortable, well set up rental I have ever stayed at. Everything was as described and more. I will most certainly stay here again! The owner was pleasant and very helpful. She made everything easy. The hot tub was so nice. We used it every day. The location was as pretty as could be. One felt remote, though Woodstock was five minutes away. I can't wait to come back.see more
Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts
A blissful get-away ...

Starry nights, a cozy fire and an a groovy town with lots of music and the great outdoors. Janna's style is classic, vintage and cool, her attention to detail is amazing. I would recommend this rental to everyone I know looking for a get-away. … see more
Pet Friendly Cabin Doh-Ray Up At 1450ft
Perfect New Year's Getaway!

This place was exactly what my friend and I were hoping for, for a much needed respite to celebrate the end of a very hectic year! Clean, cozy, comfortable, a truly idyllic setting to get away from it all. Not far from NYC, we took a train to Poughkeepsie, rented an SUV from there and drove another hour to the cabin, very easy. Raymond and Maura were super wonderful to work with and we totally felt at home here. Loved the modern amenities (tv system, internet) and fully stocked kitchen. Woodstove was simple and toasty warm. Lots of light, open space, loved the screened porch- I even sat out there to watch the snow come down (with a jacket on), so picturesque. And even with other homes nearby, the place still felt very private and peaceful, super quiet. Only about a 10-15 minute drive into town. Definitely rent/take a 4 wheel drive vehicle, esp in winter, the hills are quite steep. Great supermarket in Hurley (West Hurley Market) with a liquor/wine store next door, very convenient. Beds were super comfortable, slept like a lamb each night. My only regret is that we weren't able to stay for longer, would've loved a chance to hike, check out Cooper Lake and the restaurants in town, and spend a few more lazy days next to the fire, reading/watching movies but hopefully will be back again soon!see more
Contemporary, Secluded Cabin In The Heart of Woodstock
Completely worth it!!!! Had a blast!!!

My husband and I are celebrating our 5th wedding anniversary this year and saw this cabin on flip key and decided to try it! What a pleasure it was to deal with the owner. Quick response and he was sure to provide cell phone numbers for us to contact if we had any questions. House was clean and ready by check-in time. My husband had his coffee every morning relaxing in the hot tub. Located on 6 private acres but very close town of woodstock (which was a bonus for me). Redrock spa right down the road from the cabin, we walked there to get a couple's massage which was AMAZING!!! Can't say enough great things about the whole experience from booking it to staying there, the only bad part was our stay coming to and end and having to leave this peaceful paradise and head home :( Already talking about coming back next year!!!see more

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