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Pet Friendly Holiday Rentals in Bearsville

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    Don't let other travellers get your favourite Bearsville area holiday rental. You're so close to securing your perfect getaway. Book today.
    26 Matching Rentals in the Bearsville AreaView all 45 rentals
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    Bearsville
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    The following rentals are within 10 kilometres of Bearsville.
    Mid Century Ranch-Hot Tub-Minutes to Center ofTown1 / 164
    (4)Excellent
    Woodstock
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Charming Artist's Cottage1 / 18
    (71)Excellent
    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Spend Xmas at Pet Friendly Cabin Doh-Ray Up At 1450ft!1 / 30
    (6)Excellent
    Woodstock
    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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    Cozy & Serene Cottage in Woodstock1 / 13
    (3)Excellent
    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • 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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    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski1 / 64
    (7)Excellent
    Woodstock
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 December 2017
    Fern Hollow is an absolute gem. From the minute you step into the home you’ll be embraced by very intricate detail followed by beautiful wooden furniture (some appears to be...
    Reviewed 3 December 2017
    It’s hard to describe the amazing time we had staying here. It was an escape, a retreat, an adventure, a delight. To most, the timing of our stay might seem odd. Neither summer...
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    About this property
    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 of town. Tastefully...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Woodstock
    50 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Romantic Country Barn By the Stream1 / 26
    (17)Excellent
    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    • Hot Tub
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 November 2017
    Very nice, clean, pet friendly cottage. Owner was very accommodating and flexible when we had to change our rental date. Home is fully stocked with everything you would need...
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    About this property
    Nestled between two streams, a large, cozy private barn, on five acres of wooded land, and large lawn. A smaller stream just outside your window. Comfortable, with modern accommodation and beautiful artistic details. A perfect place for a peaceful romantic getaway, soak yourself in the outdoor...
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    Woodstock, Catskill Region 12457
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Woodstock Secluded MT Top Home with  Swimming pool1 / 27
    (4)Excellent
    Woodstock
    6 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    • 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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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 15
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    Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts1 / 21
    (1)Excellent
    Woodstock
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home1 / 82
    (3)Excellent
    Woodstock
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • 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 Retreat, Sauna, Steam Shower, Decks1 / 22
    (1)Very good
    Woodstock
    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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    Secluded, Luxury Home with Hot Tub1 / 19
    (9)Excellent
    Woodstock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Zen den1 / 12
    (6)Excellent
    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 December 2017
    Very relaxing and quiet spot, the place was very clean an welcoming from the second we walked through the gates.
    Reviewed 25 September 2017
    Zen Den was a peaceful, beautiful setting-- harmonious, clean, convenient to town. My son and I loved our time together there, and I look forward to bringing my daughter for...
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    About this property
    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 cozy retreat IN TOWN. Located...
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    Woodstock, Catskill Region 12498
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Woodstock
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 minutes from town, surrounded by...
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    Woodstock, Catskill Region 12498
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Woodstock Cabin in the Woods1 / 9
    (8)Excellent
    Willow
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Garden
    • Mountain Views
    • Central Heating
    • Wi-Fi
    • Sauna
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2017
    Rainy days in the woods....Perfect place to snuggle! We brought the city dogs and they loved trekking around woods. Babbling brooks and critters behind the cabin. Artistic town...
    Reviewed 2 May 2017
    The hosts shared with us their camps on their property, it was a perfect set-up. The area is really peaceful. The camp is very comfortable, relaxing and smart. We were their to...
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    About this property
    Relax and enjoy yourself in one of our two beautiful, hand crafted log cabins, located on a wooded mountainside. You will experience the peaceful inspiration of the Catskill Mountain Wild Forrest. Starry nights, fresh air and birdsong await and some nights there might be a giant bonfire to enjoy...
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    Willow, New York 12495
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Woodstock
    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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    Woodstock
    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
    Woodstock
    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
    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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    Woodstock
    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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    Marigold cabin by the stream -  heart of Woodstock1 / 27
    (5)Very good
    Woodstock
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 10 July 2017
    The cabin is updated which is nice, enjoyed the red swivel chairs and tree stump tables. It was fairly clean but appeared to have not seen much activity. Many cobwebs and no...
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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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    Willow
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Mountain Views
    • Internet Access
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan your next relaxing retreat to this private 1-bedroom + loft, 1-bathroom vacation rental cottage in Willow near Woodstock. Nestled on a secluded woodland lot, this home boasts a spacious deck and hot tub, providing a rejuvenating experience for 4 lucky guests! Venture out to explore the...
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    Location Information
    Willow, New York 12495
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    charming woodstock cottage with outdoor hottub1 / 14
    (1)Excellent
    Willow
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    • Grill
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful well-kept cottage on Silver Hollow Road. Available weekends or weekly. 1 +1/2 bedrooms, ( queen size loft sleeping area ) . Very private. Large outdoor hot tub for 6. Located near all local ski areas and hiking trails. $465/weekend ( 3 days 2 nights, includes cleaning ), or $ 1175...
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    Location Information
    Willow, New York 12495
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Olive Oasis Luxury with Hot Tub, Woodstock Area1 / 26
    (9)Very good
    Woodstock
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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