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Vacation Rentals in Highland, NY and nearby

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All 29 Rentals in the Highland Area
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From
$185
Per Night
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1 / 13
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Highland
1 Bedroom, 3 Bathrooms, Sleeps 3
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From
$550
Per Night
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1 / 7
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Highland
3 Bedrooms, 2 Bathrooms, Sleeps 10
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From
$163
Per Night
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1 / 18
Highland
4 Bedrooms, 3 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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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
4500 Sq. Ft Stone House 4 Bedrooms, 3 Bath On 40 Acres. Property is 90 miles from New York City, five minutes from the Hudson River. Rental house and property are available for weddings, events and filming. Very large living room with fireplace, and deck, large eat in kitchen and dining room off... View all property information
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The following rentals are within 15 miles of Highland, New York.

From
$160
Per Night
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1 / 13
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Accord
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • 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
$275
Per Night
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1 / 9
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Rhinebeck
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Dishwasher
  • Dryer
  • Internet Access
  • Washer
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. Walk outside and decide to either visit the farm next door, complete with cows, or the Northern Dutchess County Botanical Gardens. Light filled home welcomes you as you enter into slate floors and wide wood... View all property information
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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
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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
$165
Per Night
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1 / 21
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New Paltz
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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
$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
  • Gym
  • Hot Tub
  • 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
$825
Per Night
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1 / 8
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Hyde Park
4 Bedrooms, 4 Bathrooms, Sleeps 11
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Safe
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
$250
Per Night
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1 / 21
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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
  • 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
$159
Per Night
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1 / 14
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Rhinebeck
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Air Conditioning
  • 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 December 7, 2014
We spent this past weekend at the cottage. We had a great time and loved the space. Cosy, warm and right in town. The owner, Joseph was really helpful, amazing friendly and...
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...
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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
  • 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
$225
Per Night
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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
$260
Per Night
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1 / 23
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Beacon
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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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
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
$235
Per Night
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1 / 9
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New Paltz
3 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
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
$395
Per Night
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1 / 9
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Accord
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (7) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Mountain Views
  • Satellite TV
  • Washer
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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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
  • 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
$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
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
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
$750
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
$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
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • 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
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
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
$145
Per Night
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1 / 13
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New Paltz
1 Bedroom, 3 Bathrooms, Sleeps 2
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
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 a boutique vacation destination that combines everything you expect from an upscale bed and breakfast, clean airy rooms, lovely living areas, and delicious breakfasts with the opportunity to benefit from spa treatments at the in-house Miracles Day Spa. Spa B&B of the... View all property information
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5 of 5 stars Reviewed January 7, 2015
From the moment we arrived our hosts Daniel & Christina could not have been more accommodating. Nothing was too much trouble, they advised on restaurants and places to visit...
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
$145
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1 / 13
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Wallkill
1 Bedroom, 3 Bathrooms, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Housekeeping...
  • Mountain Views
  • Wi-Fi
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 a boutique vacation destination that combines everything you expect from an upscale bed and breakfast, clean airy rooms, lovely living areas, and delicious breakfasts with the opportunity to benefit from spa treatments at the in-house Miracles Day Spa. Spa B&B of the... 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
$225
Per Night
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1 / 23
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Millbrook
4 Bedrooms, 3 Bathrooms, Sleeps 2
Details Reviews (1) Make Inquiry
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
$150
Per Night
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1 / 4
New Paltz
1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
RESERVE TODAY to ensure time for you and your special someone in this charming cottage. Or get some needed solitude for yourself to write, read and relax in total privacy! This eclectic one bedroom cottage is the perfect place to take time out while still having quick access to all that the... View all property information
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From
$317
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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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
  • Private Outdoor...
  • 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, In ground Pool, game room,Internet, lg deck with view of Shawangunk mountain. 10 minute from Mohonk Mountain House and Town of New Paltz GOLF COURSE. 82 miles from NYC. (Pets not allowed) Beds: 2 Queen Beds, 2 Twin Beds View all property information
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