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Vacation Rentals & Apartments in Woodstock

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190 apartments

Margaret's Cottage in Woodstock Village

Woodstock log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$189

Teahouse Cottage

Woodstock cottage

50 bedrooms / 1 bathroom / sleeps 4

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

$458

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

Woodstock house

5 bedrooms / 3 bathrooms / sleeps 13

Price per night from

$1,021

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

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$341

Charming Converted Barn On 2+ Acres Walk To Town

Woodstock house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$484

Family-Friendly Home: 5 Mins to Central Woodstock

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$132

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.

Price per night from

$361

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 8 minutes

Price per night from

$630

Woodstock Mediterranean Retreat

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$859

Woodstock Carriage House

Woodstock house

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$376

Updated/Pet-Friendly Cabin By Hikes and Woodstock!

Bearsville cottage

2 bedrooms / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 17 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. 3 hours 6 minutes

Price per night from

$682

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

$1,065

Tentrr Signature Site - Shady Knolls

Bearsville tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 30 minutes

Price per night from

$182

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

Woodstock tented camp

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$431

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

Woodstock log cabin

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$294

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

Woodstock cottage

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 25 minutes

Price per night from

$287

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. 27 minutes

Price per night from

$287

Romantic Country Barn By the Stream

Woodstock log cabin

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 37 minutes

Price per night from

$288

Charming Artist's Cottage

Woodstock house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$229

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 14 minutes

Price per night from

$317

Contemporary, Secluded Cabin In The Heart of Woodstock

Woodstock log cabin

1 bedroom / 1 bathroom / sleeps 4

“A place to do everything, or nothing” I must confess, that I did not expect much, hearing from a local friend who drove by the property. While previous vacations advertised themselves as located in Woodstock, this one truly is. Took us an hour and fourty minutes from manhattan, door to door. While it looked a little quirky at first sight, with an extension above the living room, once we entered we realized that it serves as a giant sky light, opening the space to the surrounding woods. The living area is spacious,filled with light, while the adjacent bedroom is cozy and rather romantic. Out of the woods and just down the road is the 'sunfrost' market and deli where we had our best juice ever at lunch time. After an afternoon stroll in Woodstock we spent the evening on the deck with a glass of Pinot. A red tailed hawk joined us for a while perched on a branch above a neat pile of cut wood, but soon lost interest and flew away. With the wine in-tow we plunged into the hot tub the way of adam and Eve. The next day I mostly lazed around, while wify practiced her graceful Tai-Chi on the deck. we had a great dinner at the 'red onion' which can not be put to shame by any New York establishment triple it's price. In short; secluded, romantic and a perfect weekend escape.

Responds fast! avg. 17 minutes

Price per night from

$287

Sioux Tipi on the waterfall

Woodstock tipi/teepee

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$189

Woodstock Sanctuary Spa Retreat - walk to town!

Woodstock house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$855

Great rentals within 20 miles that match your search

Church Des Artistes

Kingston villa

4 bedrooms / 5 bathrooms / sleeps 14

“Wonderful!” This was one of the most unusual places we've ever stayed- a renovated old church, at the same time classic, modern, absolutely spotless, warm, bright, cozy and if you appreciate the arts you are in for a treat as both Julie and Peter are accomplished artists (Julie is a painter and Peter a musician).

Price per night from

$1,132

LOVELY SAUGERTIES RENTAL (Pool)

Saugerties house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$484

Spectacular Ski Vacation House - Incredible Views!

Shandaken house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$455

Tumblin' Falls House

Catskill house

5 bedrooms / 4 bathrooms / sleeps 12

“Our second home!” Tumblin' Falls has been our home away from home since we first discovered it in the mid-1990s. There's no better place to kick back and enjoy the mountain air, the beautiful waterfall, the company of wonderful people, and the warm feeling of a small town. The house is beautifully nostalgic and comfortable, and it's located within range of destinations like the Windham ski area, and the Cobleskill caves, Secret Caverns and Howe Caverns. We love Linda and Hugh, who greet us with "welcome home" each time we arrive. There is no better place to leave your cares behind, and embrace the beauty of the Catskills!

Responds fast! avg. 3 hours 3 minutes

Price per night from

$796

***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

Windham house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 55 minutes

Price per night from

$199

3 BR Ski in Ski out Condo at The Hunter Highlands

Hunter apartment

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$398

West Kill Retreat

West Kill house

3 bedrooms / 1 bathroom / sleeps 6

“Awesome getaway!” I came here with a group of friends for a getaway weekend, and it was awesome! The house is big and comfortable. Huge backyard where you can relax and nearby is a little river where you can walk to. The owners of the house are super friendly and always tried to make you feel comfortable. Definitely would recommend this to others and I would sure be coming back.

Price per night from

$296

Catskill Mountains Retreat for Large Groups

Big Indian villa

20 bedrooms / 8 bathrooms / sleeps 40

Price per night from

$2,787

Expanded Cabin facing Hunter Mountain in NY

Hunter log cabin

4 bedrooms / 2 bathrooms / sleeps 7

“Love it--would return again!” Jeffrey was very friendly, accommodating, helpful and professional as we were booking the cabin. Cabin was beautifully furnished and large enough to fit 8 of us. 5 min drive to Hunter Mountain. Very cozy and comfortable--loved it and would love to return again sometime in the future!

Responds fast! avg. 1 hour 16 minutes

Price per night from

$683

Winter Rental For Upstate New York

Hunter apartment

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$133

Creekside Log Cottage With Sunroom, Big Indian, NY

Big Indian cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 19 minutes

Price per night from

$342

OUR LOVELY VACATION HOME IS LOCATED IN THE CATSKIL

Catskill finca

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 12 minutes

Price per night from

$569

The Warehouse

Saugerties studio

Studio / 1 bathroom / sleeps 4

Price per night from

$171

Viewing 38 of 190
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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