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Pet Friendly Holiday Rentals in Woodstock

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    Travellers to Woodstock are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    23 Matching Rentals in WoodstockView all 40 rentals
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    Charming Artist's Cottage1 / 126
    (74)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski1 / 33
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Romantic Country Barn By the Stream1 / 26
    (18)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Woodstock Retreat, Sauna, Steam Shower, Decks1 / 22
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 December 2016
    The accommodations were very comfortable even with 3 kids. Location was very private with lots of skylights and scenic views. We enjoyed the sauna and steamy showers and...
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    About this property
    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 center of Woodstock, a lively,...
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    Woodstock, Catskill Region 12495
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    JUNE SALE! Jun 14-17 $230/night at Pet Friendly Cabin Doh-Ray Up At 1450ft1 / 30
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Porch
    • Central Heating
    • Washer
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    The cabin is comfortable and well equipped. The grounds are well kept and lovely. There is easy access to Woodstock and other towns. We were there when the weather was hot...
    Reviewed 15 November 2014
    My family and I wanted to get away from all the noise and hectic schedule of our everyday lives. Cabin Doh-Ray was the perfect home away from home. The cozy house had all the...
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    About this property
    Pet Friendly Cabin surrounded by the forests of Mt. Guardian at an altitude of 1500 feet. 3 Day Minimum Christmas. + 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 + Pine...
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    Woodstock, Catskill Region 12409
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    50 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Garden
    • Parking
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 a petite one room studio...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 50 Bedrooms, 1 Bathroom, Sleeps 4
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    New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home1 / 82
    (3)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Mountain Views
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2017
    Very clean,spacious and relaxing house ! enjoyed every moment staying there.!Owner was very friendly and responsivw when needed. definitely will come again soon !!!!
    Reviewed 31 May 2017
    We rented this house for a long weekend -- several adults and a few babies included. Our travel time from Brooklyn was a little over 2 hours, so it's a great getaway that's not...
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    About this property
    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 three minute drive from...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Woodstock In-town cottage1 / 23
    (46)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    • Hot Tub
    • Mountain Views
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2018
    Loved this cottage. Had a great time, and it was cozy and comfy. Super friendly people. Highly recommended.
    Reviewed 23 November 2016
    Ellen could not have been more accomodating or gracious a hostess. She met us in the parking lot, saving us a spot - all smiles and happy energy. She put some basic...
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    About this property
    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 trails. Cook your own meals...
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    Woodstock, Catskill Region 12477
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Mid Century Ranch-Hot Tub-Minutes to Center ofTown1 / 36
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2018
    What a great place to gather with friends and family for an extended weekend! The decor of Casa Real is so much fun and the spacious interior and property on which the Casa is...
    Reviewed 3 August 2016
    The house is beautiful, interesting, spacious, and cozy, with so many different places to sit, gather, read, perfect for our group of 8 consisting of 3 generations including 4...
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    About this property
    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-burning fireplace- 'we...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 the summer). Two and a half...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Woodstock Secluded MT Top Home with  Swimming pool1 / 9
    (4)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2015
    The Pictures of this Glorious....Peaceful Place does not do it justice as too how Stunning it truly is......The house was Immaculate......The Swimming Pool was not just inviting...
    Reviewed 29 July 2015
    I don't often right reviews but I really wanted to share with everyone how wonderful this location is. This is our third year renting homes as a family of 15 and this house was...
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    About this property
    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 village of Woodstock has many...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 15
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    . 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 condition, as are the hardwood...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Parking
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ”. 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 has a wonderful assortment of...
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    Woodstock, Catskill Region 12401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 BR Cabin, Hot Tub, Fireplace, Heart of Woodstock1 / 20
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Porch
    • Air Conditioning
    • Washer
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, wild turkey...
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    Woodstock, Catskill Region 12498
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts1 / 21
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Housekeeping Included
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *****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, baths, plumbing, electric,...
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    Woodstock, Catskill Region 12457
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy & Serene Cottage in Woodstock1 / 13
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Housekeeping Included
    • Patio
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2017
    V's place was cozy, clean, and very quiet. The deck was our favorite! Lovely spot to sit and enjoy the country -- especially the outstanding view of Overlook Mountain. It was...
    Reviewed 30 June 2017
    Fascinating artistic community with unique shops, great restaurants and beautiful mountain vistas.This was my first trip to Woodstock and I can’t wait to come back to the...
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    About this property
    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 4.5 acre property but is less...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Sioux Tipi on the waterfall1 / 12
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    --------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 of Woodstock Village [and...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Marigold cabin by the stream -  Heart of Woodstock with Hot Tub & Fireplace1 / 27
    (6)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2018
    Cute little well designed cabin a couple of miles walk from the village of Woodstock. As the weather was unseasonably miserable when we stayed, we certainly enjoyed the hot tub...
    Reviewed 11 July 2017
    We had an amazing time. the place was clean, well designed. Everything we needed was there. The hot tub under the starts was a great treat. LOVED the covered deck, we were able...
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    About this property
    Located at the heart of woodstock (on Ricks Rd) this newly built cabin is a dream gateway. Spacious, with all modern amenities, free wi-fi, cable TV, Netflix enabled, Gas fireplace, whisper quiet AC, romantic outdoor hot tub, large covered deck with infrared BBQ grill. Great lounging chairs to...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Secluded, Luxury Home with Hot Tub1 / 19
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • DVD Player
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2017
    Mirav was very responsive and friendly. The house was perfect and had everything you needed. The hot tub was a very nice addition as well. My hubby and i had a very relaxing...
    Reviewed 2 March 2017
    this place is perfect. the house has all the amenities you will need, its warm and welcoming. the owners were very communicative. its close to both Woodstock and Saugerties. we...
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    About this property
    On the border line of Woodstock & Saugerties. 4.5 miles from the center of Woodstock village. Drive down a private country road to Saddle Hill where you will find a completely secluded retreat nestled, on 2.5 acres, between the Catskill Mountains and rolling fields. Beautifully renovated, spacious...
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    Woodstock, Catskill Region 12477
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 & shower, hand hewn beams,...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 on both sides of the house. The master...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *25% Winter/Spring Special (Stays 4 - 7 Nights Long)* 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...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Olive Oasis Luxury with Hot Tub, Woodstock Area1 / 26
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 October 2017
    Enjoyed a weekend break here. Beautiful isolated location. Accommodation quite tired looking and very basic especially for the price paid.
    Reviewed 18 September 2014
    The place is as nice as promised, with the hot tub, grill, entertainment center, all in good working order. My only caveat, is that this rental is best for 2 couples. The...
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    About this property
    The perfect getaway for family and groups, artists, writers, yoga and meditation lovers all are welcome. Escape to a magical land- private and secluded with a hot tub out door, relax, hike, ski, meditate or create your new masterpiece. The place invoke your imagination and stimulate your...
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    Location Information
    Woodstock, Catskill Region 12481
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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