Woodstock Vacation Rentals, Homes, & More

18 Rentals

Sort:
Living room w cozy fireplace
1 / 11

Woodstock Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$350

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$350
Per month:$10,500
Pets allowed:Yes
Internet:Yes

Charming house In a compound of two houses in the green rolling hills of Bearsville. It is 5 mins to Woodstock Village Green. Heated, saltwater pool, hot tub, fireplace. Renovated in a relaxed lodge style. Local Spa 5 mins away. To relax your mind spirit and body Come and...

See more

Close x

1 / 13

Woodstock Cabin
1 Bedroom / 1 Bathroom / Sleeps 2

“ Excellent ”16 Reviews

from

$150

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Cabin
Per night:$150
Per month:$4,500
Pets allowed:Yes
Internet:No

Cozy Cabin on 5 acres, woods, meadow, and creek. Private and relaxing,...

See more

Close x

Surrounded by Nature

“ Excellent ”
October 28, 2014
This cozy cabin built was built by the owner. The picture window in living room brings the outdoors in. A window in the loft allows for a view of twinkling stars at night while resting on comfy mattress with plump duvet. Sounds of the playful creek lull you to sleep. The owner, David gives you your privacy while providing helpful information. An ideal place to stay when visiting Woodstock or nearby area.
Elena Oswald, Montville, NJ USA

See all reviews

Close x

1 / 15

Woodstock Home
7 Bedrooms / 4 Bathrooms / Sleeps 32

“ Excellent ”1 Review

from

$400

/ night

Email Owner
Bedrooms:7
Bathrooms:4
Sleeps:32
Type:Home
Per night:$400 - $600
Per week:$3,200
Pets allowed:Yes
Internet:Yes

Looking for a vacation rental in the Catskills? Vacation Rentals Retreats has the solution for you - A beautiful vacation rental house by owner in the Catskills - Located in Saugerties, NY. This home has a great gas fireplace and the kitchen is open to the main living space,...

See more

Close x

FANTASTIC!

“ Excellent ”
June 10, 2014
When up with a group of 25 and it have everything we needed and more! Loved the place so much, the property was amazing!
Jenna Ada Rollino, Long Island, New York

See all reviews

Close x

1 / 24

Woodstock Cottage
3 Bedrooms / 1 Bathroom / Sleeps 4

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$250
Per week:$1,505
Pets allowed:Yes
Internet:No

Sophistication and country charm describes A StreamSide Cottage, a cozy vacation rental cottage nestled in the foothills of the Catskills and offering 1000’ of stream frontage. The perfect destination for that weekend getaway, writing retreat or romantic holiday, A Stream Side...

See more

Close x

Woodstock New York Vacation Rentals - Home
1 / 7

Woodstock Home
2 Bedrooms / 1 Bathroom / Sleeps 6

“ Excellent ”5 Reviews

from

$290

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Home
Per night:$290 - $330
Per month:$8,700 - $9,900
Pets allowed:No
Internet:Yes

FEATURED IN NY MAGAZINE... Charming Woodstock NY Guest House Wonderful Country Escape! (Mountain top Property) Spend a weekend or week in the Country. Near all skiing. Location: Woodstock, Catskills, New York, USA ( 90 miles to NYC) Accommodations: - two bedrooms (See Description)...

See more

Close x

Kick back in the Catskills

“ Excellent ”
September 11, 2012
Home is very clean and well maintained, not lacking anything. The pool is refreshing, the decks are relaxing, the bedrooms are comfortable, the kitchen new appliances, top of the line cookware, its all here. I believe the gem in this home is the downstairs bathroom with the gorgeous two head shower and sauna. Outside, we would see deer in the morning and humming birds and chipmonks during the day. The night sky is clear and loaded with stars, really pretty. We drove throuhout the Catskills enjoying the county and all the small towns. Did the cruise on the Hudson which left out of Kingston which was well worth it. Spent time at Hunter Mtn., Woodstock and every small town in between, All the towns have their own personality and things to do, I think Woodstock was our favorite, plenty of different resturants and things to do and still feels like the 60's. Would we return here again, yes, would we recomend your home, most certainly. A kid friendly and adult friendly get away. Kick back in the Catskills and thanks for sharing your beautiful home with me and my husband. Pat & George
Pat Graham, Bay Shore , New York

See all reviews

Close x

Garlock Artist's Cottage
1 / 15

Woodstock Cabin
2 Bedrooms / 1 Bathroom / Sleeps 4

“ Excellent ”26 Reviews

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cabin
Per night:$150 - $250
Per month:$4,500 - $7,500
Pets allowed:Yes
Internet:Yes

Two bedroom family year round cabin, the original summer home of local Woodstock artist Joseph Garlock. Newly renovated and decorated with his original artwork. Very private location nestled at the foot of Overlook Mountain on six acres of wooded land with brook running by. Unique...

See more

Close x

SUBLIME

“ Excellent ”
September 28, 2014
Where do I begin? This was perfect for my family and two dogs to get away. We truly fell in love with woodstock and Jon's home. He was so nice and the communication was great! The pictures don't give the home the justice it deserves because it was so adorable. Half of the home was a cabin and the other half felt modern. The art around the home was enchanting and it was the perfect place for me to catch up on some drawing myself. I can't say one bad thing about our experience. It was lovely we made camp fires let the dogs run around, we rode our bikes along the roads and hiked up Over Look. Everything in the home was perfect and don't want to tell anyone about how wonderful it was because I don't want all the dates to be booked. (but I will)...Thanks so much for opening your doors to our family and will be booking in the near future!
Hannah Jupiter, New York City

See all reviews

Close x

Woodstock New York Vacation Rentals - Chalet
1 / 19

Woodstock Chalet
3 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$200

/ night

Email Owner
Bedrooms:3
Bathrooms:1.5
Sleeps:6
Type:Chalet
Per night:$200 - $240
Per week:$1,400
Pets allowed:Yes
Internet:Yes

This newly renovated charming Chalet in a secluded Catskill Mountain area near Woodstock will be your Oasis. Sleeps comfortably up to six people. The kitchen fully equipped and has an outdoor grill on a beautiful stone patio. Sitting on the back deck early morning watching the...

See more

Close x

Weekend retreat

“ Excellent ”
June 3, 2013
We just spent 3 days in the Olive Oasis and had a wonderful time. We brought our adult children from NYC for some R&R, and it was just what we needed...a wonderful place to spend time together, so well equipped, with yoga mats for our yoga/meditation and pilates workouts! The spiral staircase takes you to a quiet space for reflection. The hot tub was great, as we had some cool rainy weather. Everything was cheery and colorful, including the dinnerware and utensils! And a very quiet neighborhood, close to Woodstock. The owner was very easy to work with. We hope to go back someday.
Lynne Smith, Waukesha, WI USA

See all reviews

Close x

master bed
1 / 32

Woodstock Cottage
1 Bedroom / 2 Bathrooms / Sleeps 5

“ Excellent ”4 Reviews

from

$175

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:5
Type:Cottage
Per night:$175 - $250
Per week:$1,190
Pets allowed:Yes
Internet:No

A Brand new constructions, 1, 100 sq . ft. two story large and cozy private cottage 1 Br 2 full baths and balcony off the Bedroom. comfortably sleeps 5 (crib for infant available). 2 full baths one on the main floor and one on 2nd floor (with 50 gallon soaking tub / shower), large...

See more

Close x

The Perfect Getaway- Exceeded all expectations!!

“ Excellent ”
August 22, 2013
Always trepidation when you rent, hoping the reality lives up to the description and photos. Well this one exceeds all expectations. Spent two nights here with three friends to celebrate my Birthday and it really was a thoroughly memorable and pleasurable experience. The cottage is a short drive from Woodstock but very secluded. The decoration and amenities are great and modern-nothing musty or old fashioned. Very large upstairs bedroom and en suite bathroom- fantastic modern kitchen and large lounge area with TV/radio. Another bathhroom downstairs and even a washer/dryer.Sleeping was fine with two bed/ sofas also available downstairs. Wi-fi worked great.Everything was provided- just bring booze and food! The cottage has a wonderful outdoor deck where we spent a lot of time plus a small balcony off the upstairs bedroom. . There is also a hot tub and the surrounding grounds and woods are beautiful. Our dog Mac had the time of his life . Boris and Yan were so welcoming, friendly, easy going and unobtrusive. They offered great advice on places to visit and eat which did not disappoint. Woodstock has so much charm with great cafes and shopping, perfect for strolling and relaxing. We also swam on both days in the River and swim hole all in Woodstock. We had beautiful Summer weather but are sure it must be equally enchanting in all seasons. This really was the perfect getaway and is highly recommended. You will not be disappointed! Great value- great place.
Alan Mcdonald, New York NY

See all reviews

Close x

Woodstock New York Vacation Rentals - Cabin
1 / 14

Woodstock Cabin
2 Bedrooms / 1 Bathroom / Sleeps 6

“ Excellent ”1 Review

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Cabin
Per night:$225 - $275
Per week:$1,500
Pets allowed:Yes
Internet:Yes

Located in the heart of Woodstock (Glasco Tpyk & Ricks Rd. ) this cabin is the perfect romantic getaway. With 6 acres of of forest and open land as your back yard. Newly renovated, 2 bedrooms 1 bath, with wood- burning fireplace, Soak in the private hot tub and watch deer meander,...

See more

Close x

Amazing Experience!

“ Excellent ”
June 6, 2013
We stayed at the cabin on March 27th-29th with our 2 sons and we fell in love with it! The place is perfect!! The bedrooms are cozy, the kitchen is fully equipped, the outdoor tub is a real treat, and there was enough space in the living room for the kids to play and watch DVDs. We really liked the fact that it's close to Woodstock but also quiet and relaxing. You can take a nice walk; drink coffee down the road and go back "home" to the cabin. Highly recommended!!! Tal and Eyal Redler, Toronto
Tal Sion-Redler, Toronto, ON, Canada

See all reviews

Close x

Woodstock New York Vacation Rentals - Home
1 / 19

Woodstock Home
2 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ Excellent ”7 Reviews

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Home
Per night:$225 - $285
Per week:$1,850
Pets allowed:Yes
Internet:No

Drive down a private country road to Saddle Hill where you will find a completely secluded retreat nestled between the Catskill Mountains and rolling fields. Beautifully renovated, spacious contemporary home features two large bedrooms with ensuite bathrooms, a full gourmet...

See more

Close x

WONDERFUL,PEACEFUL AND RELAXING SIMPLY LOVED IT!

“ Excellent ”
December 10, 2014
Hi my name is Laura and me and my boyfriend Ty really enjoyed the seclusion and the view of nature. We loved the hut tub and the big spacious window which was perfect when the 6-7 deer came on the lawn to eat it was beautiful. The kitchen was to die for and our first night there was spent inside the kitchen making shrimps with pasta. The fir place reaaly made the nights even more romantic it was chilly in November but we still spent some time on the patio enjoying the view. To put it simply WE LOVED IT!
Laura Foster, Manhattan New York

See all reviews

Close x

1 / 23

Woodstock Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

from

$350

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$350 - $450
Per month:$10,500 - $13,500
Pets allowed:Yes
Internet:Yes

At the Bearsville end of Woodstock, and off the famous and beautiful Cooper Lake Rd, this idyllic and romantic private country home awaits you, to care for you and to let you unwind. Private and quiet, set way back on a teeny dirt road with virtually no traffic, this perfectly...

See more

Close x

Woodstock New York Vacation Rentals - Home
1 / 19

Woodstock Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$250

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$250 - $295
Per week:$1,850
Pets allowed:No
Internet:Yes

Perfect romantic getaway, totally private. Beautiful 1600 sq. ft modern house, newly constructed, 2 bedrooms/2 baths, tucked away in the woods on a 6 acres lot, at the heart of enchanted Woodstock, in the historic Byrdcliffe area. Enjoy your private hot tub, relax and watch...

See more

Close x

Woodstock New York Vacation Rentals - Cabin
1 / 12

Woodstock Cabin
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”1 Review

from

$195

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Cabin
Per night:$195 - $260
Per week:$1,350 - $1,500
Pets allowed:Yes
Internet:No

Come for the perfect romantic getaway. Newly renovated, one bedroom, luxury cabin, in the heart of Woodstock. Secluded and private on 6 acres of forest and open land. Soak in the hot tub and watch deer meander, wild turkey and woodpeckers. Large deck to BBQ and entertain on. Stay...

See more

Close x

Amazing Experience

“ Excellent ”
June 6, 2013
We stayed at the cabin on March 27th-29th with our 2 sons and we fell in love with it!The place is perfect!! The bedrooms are cozy, the kitchen is fully equipped, the outdoor tub is a real treat, and there was enough space in the living room for the kids to play and watch DVDs. We really liked the fact that it's close to Woodstock but also quiet and relaxing. You can take a nice walk; drink coffee down the road and go back "home" to the cabin. Highly recommended!!!Tal and Eyal Redler, Toronto
Tal Redler, Toronto, ON, Canada

See all reviews

Close x

1 / 10

Woodstock Home
6 Bedrooms / 2 Bathrooms / Sleeps 17

from

$195

/ night

Email Owner
Bedrooms:6
Bathrooms:2
Sleeps:17
Type:Home
Per night:$195 - $495
Per week:$1,295 - $2,500
Pets allowed:No
Internet:Yes

Beautiful 1800's farm house on 2 acres surrounded by mountains and streams. Recently renovated, large bright and airy rooms, with views, refinished original hard wood floors, one and a half miles from Woodstock, sleeps 17. This is our personal vacation home and as such is well-...

See more

Close x

1 / 5

Woodstock Apartment
1 Bedroom / 1 Bathroom / Sleeps 4

from

$225

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$225 - $250
Per week:$1,575 - $1,750
Pets allowed:No
Internet:Yes

Large, new studio, with kitchen and bath. free WIFI sleeps 2- 4 no pets NOW BOOKING SPRING AND SUMMER 2013 We have a perfect setting for your stay. Escape to the country this weekend. Sunset Studio is a large new vacation rental 90 minutes from the GW Bridge. When you stay you’ll...

See more

Close x

Woodstock New York Vacation Rentals - Cottage
1 / 10

Woodstock Cottage
2 Bedrooms / 1 Bathroom / Sleeps 4

“ Excellent ”14 Reviews

from

$195

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$195 - $225
Per month:$5,850 - $6,750
Pets allowed:Yes
Internet:Yes

A large, cozy private barn, on five acres of wooded land, with a stream outside your window. Comfortable, with modern accommodation and beautiful artistic details. A perfect place for a peaceful romantic getaway, soak yourself in the outdoor hot tub, or stay in touch with the...

See more

Close x

Lovely stay

“ Excellent ”
November 17, 2014
The cottage was clean and had a lovely décor. The landlord was quick to send directions and all the information we needed shortly after receiving our deposit. Directions were well written and accurate, and there is a great informational binder on what to see and do when you arrive. You do have to put the heater on considerably high in the colder months to get a comfortable feeling but the heater works fairly quickly. There is a third bedroom on the upper level of a spiral staircase. I do not know how warm it was up there as I slept on the main floor. The main bed's bedsheets are super soft! I give special thanks to this landowner for allowing us to bring our dog with no questions asked. I only initially wrote that he was medium sized, housebroken and never chews household items. There were no inquires by her in turn, asking about weight, breed, pictures, vaccinations or anything else. There was a good deal of trust and relaxation with this person. I say this because it's refreshing in such a day and age where everyone is worried about liability. I expect that by stating this, responsible people will do her the courtesy of being honest, managing any dogs you may wish to bring, and leaving everything clean and in order. Dog owners today cannot afford to ruin trust. There IS a considerable amount of extra money involved if you bring a pet, but it was well worth it. I would stay here again!
Laura Osanitch, Queens, NYC.

See all reviews

Close x

Woodstock New York Vacation Rentals - Home
1 / 24

Woodstock Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 10

from

$250

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:10
Type:Home
Per night:$250 - $600
Per week:$1,800 - $3,500
Pets allowed:Yes
Internet:Yes

Welcome to our beautiful home set on the bank of the Sawkill stream, amongst the trees. Have a swim in the pool, Swing in the forest, Barbecue, roast Marshmallows on the camp fire, or just hang out, cook, chill, read and enjoy this kid/pet friendly house. We are right ...

See more

Close x

1 / 16

Woodstock Home
Studio / 4 Bathrooms / Sleeps 8

from

$500

/ night

Email Owner
Bedrooms:Studio
Bathrooms:4
Sleeps:8
Type:Home
Per night:$500 - $600
Per week:$3,500 - $4,200
Pets allowed:No
Internet:Yes

Welcome and please contact us for more updated pictures and guests reviews! This beautiful 2, 000 sq. ft house is modern and clean. It sits on 3 acres of beautiful landscape and has a great 18 yard pool. The house, recently renovated and conveniently located between Woodstock...

See more

Close x

Loading...
Click for larger map
Loading...
Show Big Map
  • Price

  • Bedrooms

    Guests

  • Amenities

    • More