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Woodstock Pet Friendly Vacation Rentals

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    Travellers to Woodstock are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    21 Matching Rentals in WoodstockView all 39 rentals
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    New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home1 / 85
    (5)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Charming Artist's Cottage1 / 18
    (83)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet Friendly Cabin Doh-Ray Up At 1450ft1 / 60
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Secluded, Luxury Home with Hot Tub1 / 32
    (10)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 April 26, 2019
    Place super clean, kudos to Housekeeping. Owner very kind/professional. Village Diner best breakfast/kind staff. Saugerties Lighthouse/nice excursion. So many nice spots to see...
    Reviewed September 8, 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...
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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
    2 BR Cabin, Hot Tub, Fireplace, Heart of Woodstock1 / 20
    (3)Average
    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
    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 April 10, 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 July 10, 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
    Romantic Country Barn By the Stream1 / 26
    (21)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    • Hot Tub
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 20, 2019
    We loved everything about the barn, it was easy to find, had a great hot tub and roomy interior. We finally relaxed after a long week and we enjoyed the local wildlife across...
    Reviewed March 5, 2019
    The Romantic Country Barn was a fabulous place to stay. While you're right next door to the owner, you would never know it. The placement of the barn makes you feel like you're...
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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
    Mid Century Ranch-Hot Tub-Minutes to Center ofTown1 / 72
    (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 June 2, 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 August 2, 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
    Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski1 / 23
    (8)Excellent
    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 August 8, 2018
    This is a very handsome house in a spectacular setting. The house itself, a mid-century contemporary.. Lots of wood and glass, and you'll appreciate all that glass because...
    Reviewed December 17, 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...
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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
    Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts1 / 85
    (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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    Location Information
    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 July 11, 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 June 29, 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
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Tentrr Shady Knolls campsite is a secluded mountainside campsite overlooking thousands of acres of State Forest Preserve. This site is accessible by SUV or a short walk. Enjoy the breathtaking mountain views from the campsite or hike to a nearby cool mountain trout stream. Many local swimming...
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    Location Information
    Bearsville, Woodstock 12409
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Teahouse Cottage1 / 13
    (1)Excellent
    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
    Reviewed July 7, 2018
    Great place for 4th of July activities grill n chill hikes river wades Woodstock town close by for provisions
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    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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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 50 Bedrooms, 1 Bathroom, Sleeps 4
    Woodstock Retreat, Sauna, Steam Shower, Decks1 / 22
    (3)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 July 16, 2019
    This home is beautiful! The beauty can be seen as you drive up the road to it. When first seeing it you get the feeling that it is going to be just what you are looking for...
    Reviewed August 10, 2018
    Lovely residence with all the amenities and creature comforts for a relaxing and quiet getaway. Lots of light and multiple decks! The swimming pond was further away than...
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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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    Location Information
    Woodstock, Catskill Region 12495
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    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
    Olive Oasis Luxury with Hot Tub, Woodstock Area1 / 52
    (9)Very good
    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 yesterday
    I think this is the 5th or 6th year. This time without my beloved wife who passed from cancer. Anyway, this place is gorgeous in and out. The weather wasn't as cooperative as I...
    Reviewed October 11, 2017
    Enjoyed a weekend break here. Beautiful isolated location. Accommodation quite tired looking and very basic especially for the price paid.
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    About this property
    private and magical with out door hot tub , relax, hike, ski, meditate or do yoga, cook and enjoy friends and family. The perfect getaway for family and groups. Artists, writers, yoga and meditation lovers all are welcome. located in the Shokan Village in the Town of Olive next to Woodstock. Sleeps...
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    Location Information
    Woodstock, Catskill Region 12481
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Bearsville retreat begins at this 2-bedroom, 1-bathroom vacation rental cabin. The perfect home-base for a group of 3 guests, this adorable abode features all the comforts and amenities you'll need to settle in. Situated just a short drive from local markets and other attractions, there's...
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    Location Information
    Bearsville, Woodstock 12409
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    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
    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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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    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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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
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    • Grill
    • Washer
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in this beautiful restored barn built in the 1840s. Three bedrooms, large living room and a big kitchen for a small group. Enjoy beautiful natural views on the porch in the quiet evenings. Grill in the backyard next to the creek. Relax with hot drinks around the fireplace. Watch deer and wild...
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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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