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Woodstock Rentals for Seniors

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    Travelers to Woodstock are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    21 Matching Rentals in WoodstockView all 38 rentals
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    Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski1 / 31
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home1 / 89
    (3)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Woodstock In-town cottage1 / 23
    (45)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Romantic Country Barn By the Stream1 / 26
    (17)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 4 weeks ago
    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 - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Parking
    • Private Yard
    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Zen den1 / 12
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 24, 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...
    Reviewed July 16, 2017
    Awesome, quaint apartment. Minutes from everything. Owners were very quick to respond to emails with any questions. We will definitely be back next time we come to town. We...
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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 Mediterranean Retreat1 / 26
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Private Yard
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    Ayanna's meditaranian retreat was an amazing experience. The house is beautiful all of our needs were met, very clean and nicely decorated we felt so at home. The heated salt...
    Reviewed August 18, 2017
    My family and I stayed 5 nights. We had a great time, the house is beautiful and it's spacious. We were 5 adults and 3 children and we all had our own space. The house is...
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    About this property
    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 neighborhood. The house...
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    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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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 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...
    Reviewed March 1, 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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    Location Information
    Woodstock, Catskill Region 12477
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Woodstock Cottage: walk to Town1 / 22
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Secure Parking
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2017
    We've stayed at this beautiful property three times already. The house has 2 full bedrooms and baths, a spacious and well-equipped kitchen, electric fireplace, gas grill, etc...
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    About this property
    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. No vehicle is necessary....
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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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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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    • 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 September 8, 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 July 29, 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
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 15
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    Stunning Vacation Country & Ski House1 / 23
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Porch
    • Internet Access
    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 12, 2016
    We had a great time. It's secluded so no worries about bothering the neighbors. House was very clean. Kitchen is fully stocked. We spent the whole weekend on the shaded back deck.
    Reviewed November 4, 2013
    My friends and I went there for a relaxing birthday weekend and that's exactly what we had! The house is super private and beautiful! We had a blast! We didn't even leave the...
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    About this property
    This NON SMOKING country home is privately nestled within 15 unspoiled wooded acres overlooking picturesque seasonal trout stream. With sunny, open floor plan the open kitchen / living room / dining room make for great family together time. High quality appliances, comfortable furniture and...
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    Location Information
    Woodstock, Catskill Region 12463
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Mid Century Ranch-Hot Tub-Minutes to Center ofTown1 / 41
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed June 23, 2016
    Nestled appropriately on a street called Holiday Street, Casa Real was a homey vacation rental for our family of 7, some of whom travelled from India for this staycation. a 15...
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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 and a large...
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    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Marigold cabin by the stream -  heart of Woodstock1 / 27
    (5)Very good
    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 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...
    Reviewed July 9, 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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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Parking
    • Wi-Fi
    • Patio
    • DVD Player
    • Private Yard
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 home, 5 mins drive into...
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    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Luxury Secluded Cabin In The Heart of Woodstock1 / 18
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 30, 2017
    We had a wonderful time. Cabin was everything we hoped it would be and more. The hot tub was especially nice!
    Reviewed July 10, 2017
    We celebrated our 12 year anniversary at Sage, what a perfect choice!! the cabin was off-the-floor clean. the bed supper comfortable. The location is great, a minute drive to...
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    About this property
    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 connected with...
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    Location Information
    Woodstock, Catskill Region 12498
    Cabin - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Mountain Views
    • Patio
    • Grill
    • Hot Tub
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 the house. Each room has a...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 11, 2017
    Enjoyed a weekend break here. Beautiful isolated location. Accommodation quite tired looking and very basic especially for the price paid.
    Reviewed September 18, 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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    Woodstock, Catskill Region 12481
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 private haven, offering...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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