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Vacation Rentals in Highland, NY and nearby

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All 31 Rentals in the Highland Area
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From
$550
Per Night
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1 / 7
Highland
3 Bedrooms, 2 Bathrooms, Sleeps 10
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From
$400
Per Night
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1 / 8
Highland
4 Bedrooms, 3 Bathrooms, Sleeps 12
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From
$150
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1 / 18
Highland
4 Bedrooms, 3 Bathrooms, Sleeps 10
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The following rentals are within 15 miles of Highland, New York.

From
$149
Per Night
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1 / 14
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Rhinebeck
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Garden or Yard
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Circa 1840 colonial building, featuring a charming cottage style apartment located in the heart of Rhinebeck Village. This prime location will allow you to walk to every amenity this quaint B&B; community offers, including myriad restaurants, wine bars, boutiques, shops and the famous Dutchess... View all property information
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5 of 5 stars Reviewed November 13, 2014
My wife and I stayed in this cottage apartment one weekend in November, and we loved it. It's in a perfect location -- short walking distance to Rhinebeck's great shops...
4 of 5 stars Reviewed September 24, 2014
So here is the headline: the owner says this apartment's bed is the most comfortable in Rhinebeck - and I think he is right! A fabulous night's sleep on a spacious pillowtop...
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From
$145
Per Night
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1 / 13
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New Paltz
1 Bedroom, 3 Bathrooms, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Garden or Yard
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Spa B&B; of the Hudson Valley is located in Ulster County New York, just 75 minutes North of NYC and 20 minutes from Stewart International Airport. Combining a B&B; with the inhouse Miracles Day Spa is about providing a relaxing setting filled with nature and beauty. Enjoy all natural Spa... View all property information
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4 of 5 stars Reviewed October 21, 2014
We stayed one night. The location of this B&B is very good. You've got excellent views when sitting in the backyard. It is peaceful and beautiful especially at this time of the...
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From
$165
Per Night
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1 / 21
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New Paltz
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (12) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Built in 1847, this Schoolhouse was completely renovated in 2013. It sleeps up to 6 and provides guests a getaway as they look out from the edge of a gorgeous, 120-acre horse farm right near the Shawangunk Mountains (the Gunks). The private house works well for couples, families, friends'... View all property information
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5 of 5 stars Reviewed October 6, 2014
We travelled to the area for a respite from New York City with our two young children. The cottage was perfect for our needs - clean, quiet, well-appointed, and with activities...
5 of 5 stars Reviewed July 14, 2014
Perfect place to spend a few days in the area. Beautiful house, exceptionally clean, and very convenient. My young son loved the hikes, and after a long day in the outdoors it...
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From
$625
Per Night
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1 / 8
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Gardiner
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Beautiful, bright designer renovated house located 90 minutes from GW Bridge on a very quiet secluded dead-end road in the woods adjacent to state land. Designed with contemporary furniture with a queen size bed in each bedroom, the Minimalist inspired flowing 1st fl incorporates all the... View all property information
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5 of 5 stars Reviewed October 23, 2014
We arrived on a Friday afternoon during peak foliage. The house is tucked away in the woods but close enough to hit all the important wineries in Hudson Valley. The house is laid...
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From
$235
Per Night
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1 / 9
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New Paltz
3 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Dishwasher
  • Fireplace
  • Garden or Yard
  • Grill
  • Housekeeping...
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A magical home located at the foothills of the Shawangunk mountain range just 5 min from the Mohonk Mountain House. View all property information
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5 of 5 stars Reviewed September 17, 2014
Two friends and I traveled to New Paltz to participate in a race, and stayed two nights in Amanda's mountain home. She was a gracious host and the dwelling was as described...
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From
$325
Per Night
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1 / 24
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New Paltz
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Fully-furnished, 4-bedroom country house. Drop-dead views of the cliffs from the MBR, the living and dining areas. The house, sits on a 120-acre Horse Farm and is 6 miles from Main Street in New Paltz and 4 miles from Gardiner...about 90+ minutes from NYC. The farmhouse is minutes from the Mohonk... View all property information
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5 of 5 stars Reviewed June 1, 2014
We rented this house for Memorial Day weekend and my daughter’s 16th Birthday. There were eight of us: five girls and three adults. We spent such a wonderful time on the farm and...
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From
$160
Per Night
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1 / 13
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Accord
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Dishwasher
  • Garden or Yard
  • Grill
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Tranquil majestic 1400 sf.cottage with soaring ceilings on a meadow in the woods. Walk to the stream and be transported by nature all around. Hike, and enjoy the Mohonk Mountains nearby, or rest at home surrounded by beauty and privacy . Every season is lovely, especially rainy days. Brand new... View all property information
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From
$250
Per Night
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1 / 16
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High Falls
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Our historic 4 bedroom French Huguenot style farmhouse was built in 1796 and is bordered by 17,500 acres of the forests, streams and lakes of the Mohonk Preserve and Minnewaska State Park. You can literally step out of the house onto over 80 miles of hiking and biking trails. The entire home was... View all property information
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From
$225
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1 / 1
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Beacon
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Private getaway at the base of Mt. Beacon. Easy access to hiking trails and walking distance to downtown Beacon. Views of the Hudson Valley from the front exposure, and mountains to the rear. Large airy bedroom with a beautiful tiled bath. The Space The maid's wing of our brick Dutch colonial... View all property information
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From
$205
Per Night
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1 / 8
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Millbrook
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Garden or Yard
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
One bedroom garden cottage with a full bath, galley kitchen, and outside garden terrace. You can drive to local horse ranches, go antiquing in town, or walk to really great restaurants right in town. You can walk to the local grocery stores, get some fresh baked bread, fresh fish and local farm... View all property information
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From
$250
Per Night
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1 / 9
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Rhinebeck
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This newly renovated modern farmhouse style home is situated on a serene, country road. Very cozy house will welcome you to relax and enjoy the peaceful surroundings. Light filled home welcomes you as you enter into slate floors and wide wood floors throughout. All custom colors by Farrow and Ball... View all property information
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From
$145
Per Night
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1 / 13
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Wallkill
1 Bedroom, 3 Bathrooms, Sleeps 2
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Spa B&B; of the Hudson Valley is located in Ulster County New York, just 75 minutes North of NYC and 20 minutes from Stewart International Airport. Combining a B&B; with the inhouse Miracles Day Spa is about providing a relaxing setting filled with nature and beauty. Enjoy all natural Spa... View all property information
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From
$400
Per Night
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1 / 20
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Stormville
4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Housekeeping...
  • Mountain Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Far View Farm is located on Stormville Mountain. This offers breath taking views of the Hudson Valley. This farmhouse goes back to the early 1800's but has everything to make it a private retreat from your busy life. It has 25 private acres with trails and no neighbors to be seen. Enjoy the views... View all property information
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From
$100
Per Night
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1 / 12
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Accord
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Garden or Yard
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • x
About this property
Located in the Hudson Valley, 2 hours North of NYC, our 27 acre Farm is home to horses, chickens, bunnies, dogs, cats and other farm animals. Enjoy our walking trails, creek and luxurious hot tub. Our property is far from any large roads and is perfect for families with children and pets or for... View all property information
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5 of 5 stars Reviewed July 9, 2014
The farm was very peaceful and relaxing. We were there in July and the fireflies put on an amazing performance for us. It was great to be in that wonderful natural settling and...
5 of 5 stars Reviewed January 28, 2014
My boyfriend and I stayed here for four nights and had a relaxing and great stay. We stayed in the apartment which was a wonderful space for two people. Great kitchen for cooking...
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From
$825
Per Night
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1 / 8
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Hyde Park
4 Bedrooms, 4 Bathrooms, Sleeps 11
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautiful pond views on a forty acre estate. When you reserve le Petit Chateau you will enjoy a huge gourmet breakfast that we can help you stock with all local ingredients. You will be supporting our area farmers when you reserve the Chateau for your Vacation Rental. For ten years we have been... View all property information
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From
$375
Per Night
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1 / 28
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New Paltz
4 Bedrooms, 4 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Garden or Yard
  • Grill
  • Hot Tub
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautiful farmhouse style country home with an open floor plan on a serene 6-acre property in Gardiner, NY. Features gorgeous, unobstructed views of the Shawangunk Mountains (The Gunks). Our property is a short 90 minute drive North of NYC. The house features 4 bedrooms (up to 8 people) and 4... View all property information
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5 of 5 stars Reviewed October 27, 2014
No one in our group could have asked for anything more. The estate was just perfect. Cindy was not on site but always available to help with any questions. Her recommendations...
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From
$235
Per Night
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1 / 23
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Beacon
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
PLEASE NOTE: I DO NOT RENT FOR FOR 1 NIGHT. THERE IS A 2 NIGHT MINIMUM. Continue reading further down in this box for 5***** Reviews. Here's a sample: "More like a boutique hotel." "This house is a dream come true." "Great owner, great location!" This home in beautiful Hudson Valley is a... View all property information
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From
$714
Per Night
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1 / 8
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Millbrook
5 Bedrooms, 5 Bathrooms, Sleeps 10
Bookings
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Idle Hour Farm is located in the heart of Hunt Country, Dutchess County NY. It is a peaceful place among rolling hills, horse farms and dairy farms. It is conveniently located 1 1/2 hours from NYC, 1 hour from the Catskill Mountains, 4 hours from the Adirondack Mountains. It is situated on 16... View all property information
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5 of 5 stars Reviewed September 10, 2014
The house is beautifully furnished, the grounds are lovely, we had a most wonderful stay. We swam in the pond which is a perfect temperature and has a small sandy 'beach' making...
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From
$129
Per Night
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1 / 12
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West Park
3 Bedrooms, 2 Bathrooms, Sleeps 7
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
Be my guest, enjoy tropical paradise at the large beautiful backyard filled with palms and other exotic fruit trees. I grow coconuts, mangoes, papaya, grapes, and pineapples. Depending on the season all for your enjoyment. Fenced backyard will give you privacy you need while sunbathing by the... View all property information
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From
$501
Per Night
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1 / 22
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Rhinebeck
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Arrive to bedrooms made up with Egyptian cotton linens from The White Company London, with towels to match (bath, hand and face towels provided for every guest). Enjoy bathrooms with locally-made soaps, shampoos and conditioners which we encourage you to take home at the end of your stay. When... View all property information
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5 of 5 stars Reviewed June 6, 2014
We stayed here for a ski week and it was awesome with four resorts at our fingertips. Plattekill is only a few minutes down the road and is a bit of a hidden gem with some...
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From
$200
Per Night
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1 / 12
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Accord
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Garden or Yard
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Woods Retreat is located in the heart of Ulster County, and the foothills of the Catskill mountains in the High Falls/Stone Ridge area. Close to New Paltz, Kingston, Woodstock, minutes from Mohonk Mountain, Minnewaska State Park and the Ashokan reservoir, the Woods Retreat is right across the... View all property information
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From
$250
Per Night
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1 / 14
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Rhinebeck
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Dishwasher
  • Fireplace
  • Garden or Yard
  • Grill
  • Housekeeping...
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A perfect home away from home in the beautiful Hudson Valley “Gracious, clean, well appointed home with a cozy vibe. Living quarters all on one floor, no stairs to worry about. Great location close to town and neighboring amenities. Explore the Hudson Valley in comfort from this charming country... View all property information
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From
$300
Per Night
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1 / 14
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Clinton Corners
4 Bedrooms, 3 Bathrooms, Sleeps 5
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Spacious, gracious colonial on 5.2 acres surrounded by trees and lawns, with 40' heated in-ground pool, a pond and back deck. Enjoy the great room and open eat-in kitchen with 4 bedrooms, a jacuzzi in the master bathroom, 2.5 bathrooms and finished basement with in-home theater. Only 90 minutes... View all property information
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From
$200
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1 / 11
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Fishkill
2 Bedrooms, 4 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Housekeeping...
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This two bedroom home is spotless, comfortable and conveniently located. It includes a fireplace, state-of-the-art washer and dryer, and a full kitchen with amenities like a great stove, dishwasher and garbage disposal. There is also a futon in the loft area that could sleep a fifth person. The... View all property information
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From
$395
Per Night
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1 / 9
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Accord
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This charming 3 bedroom Adirondack style cottage offers privacy and serenity. Relax in the pool, along the private banks of a trout stream, or just stretch out on the large screened-in porch. It's located on a quiet country road, surrounded by 32 acres of enchanting woodland. Close to Stone Ridge... View all property information
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5 of 5 stars Reviewed July 29, 2014
We really enjoyed our time at the Lawrence/Kim cottage. We felt like we were at our own private resort. Inside, the cottage is spacious and tastefully furnished. Outside, we...
5 of 5 stars Reviewed July 13, 2014
A lovely cottage in a lovely setting. Our dogs ran around all day--no leashes!! The pool was refreshing and a good size for swimming laps. Private, quiet, and beautiful.
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$225
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1 / 23
Millbrook
4 Bedrooms, 3 Bathrooms, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Castle , Wing's Castle is a true Hudson Valley stone castle Sweeping views of the entire Mid-Hudson Valley, on the High hills of Dutchess county New York. 75 miles north of New York City and 75 miles south of Albany. Rooms are a Dungeon and a Tower room for now. We also have a Fairy Tale Cottage... View all property information
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4 of 5 stars Reviewed January 7, 2014
My boyfriend and I went to Wing's Castle for New Year's Eve...and we had a nice, relaxing time. We were looking for no tv's...no outside world..no drama. It was very peaceful...
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From
$1,600
Per Week
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1 / 14
Gardiner
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Spacious cozy home with Lg. kitchen,living room, 3 bedrooms, 2 bathrooms, Inground Pool, game room,Internet, lg deck with view of Shawangunk mountain. 82 miles from NYC. 10 minutes from Mohonk Mountain House and Tow of New Paltz (Pets not allowed) Beds: 2 Queen Beds, 2 Twin Beds View all property information
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From
$357
Per Night
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1 / 15
Clinton Corners
6 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A 2004 COMPLETELY FURNISHED HOME WITH A HUGE OPEN FLOOR PLAN GREAT ROOM FEATURING A 32 FOOT SOARING WOOD CLAD CEILINGS. THIS SPECTACULAR RETREAT OVERLOOKS A HEART SHAPED POND EQUIPPED WITH A PADDLE BOAT STOCKED WITH TROUT,SUNNIES AND BLUE GILLS FOR YOUR CATCH AND RELEASE PLEASURE. THE HOUSE WAS... View all property information
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