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Bearsville Holiday Vacation with Pools

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    Don't let other travellers get your favourite Bearsville area vacation rental. You're so close to securing your perfect getaway. Book today.
    13 Matching Rentals in the Bearsville AreaView all 49 rentals
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    Woodstock Modern House with Pool and Hot Tub1 / 29
    (1)Excellent
    Bearsville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Bearsville
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 10 kilometres of Bearsville.
    Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski1 / 66
    (7)Excellent
    Woodstock
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Woodstock Secluded MT Top Home with  Swimming pool1 / 9
    (4)Excellent
    Woodstock
    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 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
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 15
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    Woodstock Mediterranean Retreat1 / 26
    (3)Excellent
    Woodstock
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Private Garden
    • 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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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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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 June 2, 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 May 30, 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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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Woodstock
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 the Catskill Mountains, the...
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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Chic Retreat in Bearsville 2 m to Woodstock, Saline Pool, Fireplace and Hot tub.1 / 54
    (14)Excellent
    Woodstock
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    I cannot emphasize how glad I am that I found this place most of our honeymoon trip. It is truly magical. We did not want to leave and hope to go back as soon as possible. The...
    Reviewed October 9, 2015
    My husband and I escaped from the city to The Bearsville Retreat for a weekend and could not have been happier with the home. Everything was pristine, but cosy enough to feel...
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    About this property
    Charming house In a compound consisting of of two houses in the green rolling hills of Bearsville. It's 5 mins to Woodstock Village Green. Heated, saltwater pool, outdoor (hotwater) shower, hot tub, fireplace. Renovated in a relaxed lodge style. Local Spa 5 mins away to relax your mind spirit and...
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    Location Information
    Woodstock, Catskill Region 12409
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lake Hill
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful mountain views on 6.5 acres a few miles from Woodstock, NY. This homestead features 3 bedrooms, 2 bath in Lake Hill. Nightly, weekly or monthly rental available. Great for those seeking seclusion and privacy. Outdoor jacuzzi, pool. Great for ski season. House can sleep up to 6 people....
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    Location Information
    Lake Hill, New York 12448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Woodstock Modern House with a Pool1 / 37
    (1)Excellent
    Woodstock
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Parking
    • Mountain Views
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 5, 2018
    Love everything about this house. It is specious, bright, modern and very comfortable. The house is very clean and has everything you need. You can relax in the living room or...
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    About this property
    Welcome! Note: We have plenty of 5 star reviews, please asks and we can send you a link. This beautiful 2,000 sq. ft house is modern and clean. It sits on 3 acres of beautiful landscape and has a great 18 yard pool. The house, recently renovated and conveniently located between Woodstock and...
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    Location Information
    Woodstock, Catskill Region 12477
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Woodstock
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Woodstock, Catskill Region 12401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Woodstock
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Woodstock, Catskill Region 12498
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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