30 Best Woodstock Apartments on Holiday Lettings - Vacation rentals

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33 Vacation rentals

(45) Excellent 

Certificate of Excellence

23

Vacation cottage in Woodstock

Catskill Region / Woodstock

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Car not necessary
Located right in the middle of Woodstock, this recently renovated cottage with a cozy, open floor plan affords you both privacy and convenience. There's no need for a car. Walk to everything, including the NYC bus stop, Woodstock's unique shops and galleries, or hiking …see more

Certificate of Excellence

from $150 / night

$800 - $930 / week

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Responds fast!
avg. 25 minutes

from $150 / night

(6) Excellent 

30

Ski home to rent in Woodstock

Catskill Region / Woodstock

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ski
  • Child friendly
  • Pet friendly
Pet Friendly Cabin surrounded by the forests of Mt. Guardian at an altitude of 1500 feet. + Large summer porch overlooks a beautiful pond + Stays cool in the summer (has only reached the 90s two summers in the last 10 years) + Beautifully furnished + P …see more

from $260 / night

$1500 - $1650 / week

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Responds fast!
avg. 3 hours 10 minutes

from $260 / night

(3) Excellent 

29

Woodstock Vacation log cabin rental

Catskill Region / Woodstock

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Margaret's Cottage Located the in the village of Woodstock , stroll to restaurants, Tinker St movie theater, take a dip in the Millstream, or follow the Comeau trail past the steam through the woods to the meadow with the best mountain vista in town. On the NYC bus rou …see more

from $165 / night

$950 - $1020 / week

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from $165 / night

20

Home rental in Woodstock

Catskill Region / Woodstock

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Salutations from this sunlit, solar powered house with mountain views! We are little over a mile to the village green/Woodstock central! Four bedrooms (two master suites) sleep eight comfortably, with one king bed, two queens and two twin beds (ACs in each bedroom in th …see more

from $199 / night

$1625 - $1975 / week

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from $199 / night

(1) Excellent 

22

Woodstock ski home to rent.

Catskill Region / Woodstock

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
*****PLEASE SEE THE PAGE WITH ALL DETAILS JANNA RITZ DOTT COME****quintessential woodstock stone cottage with original large 11 ft artist window and stone fireplace. completely gutted and new everything but with cottage flair. new kitchen huge thermador pro range, bath …see more

from $300 / night

$2100 / week

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Responds fast!
avg. 2 hours 58 minutes

from $300 / night

(3) Excellent 

22

Vacation cottage in Woodstock

Catskill Region / Woodstock

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
WALK TO EVERYTHING IN THE VILLAGE FROM THIS NEWLY RENOVATED COTTAGE WITH GORGEOUS VIEWS! Located in the center of the village, this newly renovated cottage is open, cozy, and perfect for a Woodstock vacation or weekend getaway. Convenience is the name of the game here …see more

from $295 / night

$1695 - $1895 / week

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from $295 / night

(1) Excellent 

10

Woodstock Vacation home rental

Catskill Region / Woodstock

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Car not necessary
  • Air conditioning
This is a two bedroom modern house on a small hill. The location is perfect, walking distance to downtown Woodstock, easy access to community swimming holes, town events, galleries, shops & restaurants. You can enjoy the peace and quiet in the woods, and only 10 minutes …see more

from $220 / night

$1300 / week

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from $220 / night

(4) Excellent 

9

Home rental in Woodstock

Catskill Region / Woodstock

6 15 2 nights min

  • 6 bedrooms
  • Sleeps 15
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This home has 3600 sq ft of space 6 bedrooms, 3 baths, an extra sunroom that can be used as another bedroom and can accomodate a group of 12-15 or an average size family . Though it is very private on 15 acres its just 1 and half mile to the center of Woodstock.The vill …see more

from $500 / night

$2800 / week

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from $500 / night

(5) Excellent 

31

Woodstock Vacation home accommodation

Catskill Region / Woodstock

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxurious 3 BR / 3 BA, handmade craftsman style home, in the heart of Woodstock! Pamper yourself with a private pool, spa and stream. Enjoy serenity and privacy, as this property is located on 7 acres, at the end of a private road, yet is still only 5 min to the heart …see more

from $295 / night

$2065 / week

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Responds fast!
avg. 1 hour 33 minutes

from $295 / night

(1) Good 

8

Woodstock Vacation home rental

Catskill Region / Woodstock

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Aspects Inn and Spa! Lio and Sharon invite you to their Aspects Inn and Spa in the heart of the historic artists colony of Woodstock, NY. Nestled in the gentle streams and valleys of the ancient Catskill Mountains, Woodstock is just a two hour scenic drive up the …see more

from $250 / night

$1750 / week

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from $250 / night

(3) Excellent 

89

Home rental in Woodstock with golf nearby

Catskill Region / Woodstock

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Woodstock! This spacious 5 bedroom/3 bathroom home features wide open spaces, a master bedroom with an en suite bathroom, an in ground pool, and game room with a ping pong table, a toasty wood stove for chilly nights, and all the benefits of being a two to th …see more

from $350 / night

$1950 - $4760 / week

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Responds fast!
avg. 25 minutes

from $350 / night

(1) Excellent 

16

Woodstock Vacation b&b rental

Catskill Region / Woodstock

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Private garden
Coldbrook B&B is exclusively a Bed & Breakfast and located 2 hours north of New York City in the heart of the Catskill Mountains and 10 minutes to the center of famous Woodstock, NY. Peace and quiet are abundant with the option to peruse the charming shops in the quain …see more

from $645 / night

$2000 / week

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Responds fast!
avg. 2 hours 24 minutes

from $645 / night

(4) Excellent 

12

Woodstock Vacation apartment rental

Catskill Region / Woodstock

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Welcome to the Zen Den! Enjoy our beautiful, newly constructed, 2 story apt 60 seconds from the heart of town. Free parking, covered porch in the expansive back yard, full kitchen, full bathroom, BBQ, perfect for enjoying your stay in Woodstock! Enjoy this sweet and c …see more

from $120 / night

$600 / week

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Responds fast!
avg. 2 hours 26 minutes

from $120 / night

(4) Excellent 

Certificate of Excellence

41

Vacation home in Woodstock

Catskill Region / Woodstock

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Welcome to "Casa Reál" this Spanish style ranch is tastefully decorated with mid-century modern furnishing. It's got large open spaces, good flow and contemporary floor plan. This home also features a sunken living-room, formal dining room, sunken family room with wood- …see more

Certificate of Excellence

from $325 / night

$1800 - $2150 / week

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Responds fast!
avg. 1 hour 24 minutes

from $325 / night

12

Vacation tipi/teepee in Woodstock

Catskill Region / Woodstock

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
--------Authentic 18 foot Sioux Tipi, handmade and painted by the artists at Nomadics Tipi Makers in Oregon. The tipi overlooks a waterfall on the Sawkill Creek that runs through our estate. Across the river is Comeau Park, with a 2 mile walking trail. The center …see more

from $150 / night

$1050 / week

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Responds fast!
avg. 3 hours 22 minutes

from $150 / night

14

Woodstock Vacation home rental

Catskill Region / Woodstock

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
  • Air conditioning
This special home is a converted barn with the original 1790's foundation. We want our guests to feel at peace and have a relaxing vacation! The house is filled with unique collectibles and folk art. You'll find an eclectic collection of original paintings throughout th …see more

from $425 / night

$2000 / week

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Responds fast!
avg. 58 minutes

from $425 / night

13

Vacation cottage in Woodstock

Catskill Region / Woodstock

50 4 1 night min

  • 50 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Originally built in the 1870's as a small barn on the estate. The cottage was fully renovated, new bath, new kitchen, refinished hardwood floors, pillow top mattress in the sleeping loft, and a queen size Murphy bed if you prefer not to use the sleeping loft. This is …see more

from $140 / night

$980 / week

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Responds fast!
avg. 3 hours 22 minutes

from $140 / night

17

Vacation home in Woodstock

Catskill Region / Woodstock

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This comfortable and spacious family home (2,500sq ft) has four bedrooms upstairs and plenty of socializing space downstairs including a screened in porch, deck & bbq, a great room, playroom, fireplace room, surrounded by 80 ft pine trees and a level lawn. This spacious …see more

from $255 / night

$1600 - $1850 / week

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Responds fast!
avg. 3 hours 47 minutes

from $255 / night

(5) Very Good 

10

Home rental in Woodstock

Catskill Region / Woodstock

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
  • Air conditioning
  • Ask about pets
Choose from two newly renovated private two bedroom suite/deplex apartments ( Citrus and Plum) in a turn of the century country Victorian designed to make your stay in Woodstock memorable. Unplug and leave your worries behind. You can walk to all destinations on Tink …see more

from $225 / night

$1400 / week

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from $225 / night

(1) Very Good 

13

Vacation home in Woodstock

Catskill Region / Woodstock

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Ask about children
  • Car not necessary
Newly built 3-story cedar Farmhouse sleeps 9, secluded on 5+ acres of wooded land surrounded by mountains, mature trees and wildflowers. Finely decorated with antiques in bright airy rooms and pine wood floors. Every window has amazing views of nature yet The Woodstock …see more

from $450 / night

$2500 / week

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from $450 / night

14

Woodstock Vacation home rental

Catskill Region / Woodstock

4 6 2 nights min

  • 4 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
This charming English Tudor Carriage House is the perfect retreat and located in a wooded setting on 10+ acres on a wooded estate only 1.5 miles to the center of Woodstock. It is a spacious 4 bedroom, 1 1/2 bath home with a lovely stone fireplace. The Carriage House i …see more

from $200 / night

$1200 / week

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Responds fast!
avg. 53 minutes

from $200 / night

14

Home rental in Woodstock

Catskill Region / Woodstock

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
. This is an 1870's post and beam barn. For 20 years, before we owned it, the barn was a Montessori school. After we purchased the property, we converted the school to a guest cottage. The hand hewn beams you see in the photos are preserved in their original c …see more

from $150 / night

$1050 / week

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Responds fast!
avg. 3 hours 22 minutes

from $150 / night

26

Woodstock Vacation home rental

Catskill Region / Woodstock

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Say hello to your perfect vacation home! Bright and airy Woodstock home with all the amenities you will need. Located only 4 minutes from the Village of Woodstock. Four-bedroom house with 3 full bathrooms located on private roadway perfect for walking & running around n …see more

from $380 / night

$2660 / week

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from $380 / night

17

Home rental in Woodstock

Catskill Region / Woodstock

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Two miles from the center of the renowned artist colony of Woodstock, New York, a long driveway off a peaceful country road leads you to the grace and charm of this turn of the century farm house.Set amidst acres of rolling meadows and magnificent pines, encircled by th …see more

from $1000 / night

$6000 / week

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Responds fast!
avg. 19 minutes

from $1000 / night

19

Vacation home with shared pool in Woodstock

Catskill Region / Woodstock

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Woodstock New York--- Sunset cottage is an award winning vacation home. This home has been featured in NY Magazine and architectural Digest It is fully furnished, has a completely equipped stainless steel kitchen, wifi, cable TV DVD, AC & HEAT, tile bathroom with tub …see more

from $325 / night

$2100 / week

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from $325 / night

(1) Very Good 

21

Woodstock Vacation home rental

Catskill Region / Woodstock

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Restore yourself at this lovely vacation home while you explore Woodstock, the Hudson Valley and the Catskills. You will be surrounded by woods, mountains and hundreds of acres of public land, and visited often by deer and turkeys -- but you are 10 minutes from the cent …see more

from $275 / night

$1800 - $2150 / week

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Responds fast!
avg. 2 hours 8 minutes

from $275 / night

15

Vacation home in Woodstock

Catskill Region / Woodstock

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
”. The home is a classic saltbox contemporary and sits on approx. 5 private acres. The area is dotted with waterways and rock outcroppings that are part of the local landscape. This is a beautiful time of year to be here. The summer months are special and the area ha …see more

from $475 / night

$2850 - $3200 / week

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from $475 / night

(12) Very Good 

13

Vacation hotel apartment with indoor pool in Woodstock

Catskill Region / Woodstock

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Aspects Inn & Spa in the heart of Woodstock, NY offers a unique retreat with a two apartment 2 bedroom each w/ full kitchen and all amenities with direct access to our indoor spa with 40' saline pool, ionized Jacuzzi and infrared sauna. at the rate of $250 per n …see more

from $500 / night

$3000 / week

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from $500 / night

21

Woodstock Vacation home rental

Catskill Region / Woodstock

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Located 150 miles from New York City is one of the most beautiful vacation homes in the Catskill region. You and your loved ones will be able to relax in this beautiful mountainous area which was made famous by Washington Irving when he published the famous short story …see more

from $325 / night

$2275 / week

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from $325 / night

(3) Excellent 

13

Woodstock Vacation cottage rental

Catskill Region / Woodstock

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Cozy, clean & light-filled cottage designed for all-season comfort, relaxation & rejuvenation set on serene landscaped grounds & woods. Cottage is perfect for romantic weekends, country getaways, or solo retreats. Dreamcatcher is unique. The cottage sits on a beautiful …see more

from $200 / night

$1400 / week

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from $200 / night

37

Woodstock Vacation home rental

Catskill Region / Woodstock

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
Welcome to "Casa Reál," an exquisite 4-bedroom, 4-bathroom Spanish-style vacation rental house in Woodstock, New York, with accommodations for 8. This wonderful ranch home is ideally situated on a semi-private lot with, scenic tree views and a private hot tub, mere minu …see more

from $350 / night

$1800 / week

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Responds fast!
avg. 18 minutes

from $350 / night

27

Woodstock Vacation home rental

Catskill Region / Woodstock

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Built in 1964, this classic mid century modern boasts its original kitchen cabinets as well as a wall of Danish storage units in the living room. It comfortably sleeps 8 in its 5 air conditioned second floor bedrooms, all of which have access to the balconies that run o …see more

from $395 / night

$2650 - $3950 / week

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from $395 / night

4

Tented camp rental in Woodstock

Catskill Region / Woodstock

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
Lying within the borders of the Catskill Park, these breathtaking tent rentals are located in the quaint and historic town of Woodstock. "Glampers" will find many things to keep them inspired and entertained during this getaway. This truly beautiful property is its own …see more

from $198 / night

$1386 / week

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from $198 / night