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

From
$149
Per Night
1 / 14
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Rhinebeck
1 Bedroom, 1 Bathroom, Sleeps 2
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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
$625
Per Night
1 / 8
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Gardiner
3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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$145
Per Night
1 / 13
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New Paltz
1 Bedroom, 3 Bathrooms, Sleeps 2
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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
1 / 21
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New Paltz
2 Bedrooms, 1 Bathroom, Sleeps 6
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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
$235
Per Night
1 / 9
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New Paltz
3 Bedrooms, 1 Bathroom, Sleeps 4
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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
1 / 24
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New Paltz
3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
1 / 13
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Accord
2 Bedrooms, 1 Bathroom, Sleeps 4
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From
$250
Per Night
1 / 9
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Rhinebeck
3 Bedrooms, 3 Bathrooms, Sleeps 6
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From
$145
Per Night
1 / 13
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Wallkill
1 Bedroom, 3 Bathrooms, Sleeps 2
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From
$400
Per Night
1 / 20
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Stormville
4 Bedrooms, 3 Bathrooms, Sleeps 10
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From
$205
Per Night
1 / 8
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Millbrook
1 Bedroom, 1 Bathroom, Sleeps 2
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From
$250
Per Night
1 / 16
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High Falls
4 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$225
Per Night
1 / 1
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Beacon
1 Bedroom, 1 Bathroom, Sleeps 2
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From
$100
Per Night
1 / 12
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Accord
1 Bedroom, 1 Bathroom, Sleeps 3
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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
1 / 8
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Hyde Park
4 Bedrooms, 4 Bathrooms, Sleeps 11
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From
$375
Per Night
1 / 28
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New Paltz
4 Bedrooms, 4 Bathrooms, Sleeps 8
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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
1 / 23
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Beacon
2 Bedrooms, 1 Bathroom, Sleeps 6
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From
$714
Per Night
1 / 8
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Millbrook
5 Bedrooms, 5 Bathrooms, Sleeps 10
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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
$501
Per Night
1 / 22
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Rhinebeck
4 Bedrooms, 2 Bathrooms, Sleeps 8
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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
1 / 12
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Accord
1 Bedroom, 1 Bathroom, Sleeps 4
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From
$129
Per Night
1 / 12
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West Park
3 Bedrooms, 2 Bathrooms, Sleeps 7
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From
$250
Per Night
1 / 14
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Rhinebeck
3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$300
Per Night
1 / 14
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Clinton Corners
4 Bedrooms, 3 Bathrooms, Sleeps 5
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From
$200
Per Night
1 / 11
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Fishkill
2 Bedrooms, 4 Bathrooms, Sleeps 4
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From
$395
Per Night
1 / 9
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Accord
3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
$225
Per Night
1 / 23
Millbrook
4 Bedrooms, 3 Bathrooms, Sleeps 2
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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
$357
Per Night
1 / 15
Clinton Corners
6 Bedrooms, 5 Bathrooms, Sleeps 12
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From
$1,600
Per Week
1 / 14
Gardiner
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability

  • Wheelchair access (3)
  • Elder access (13)
  • Suitable for children (20)
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  • Internet (25)
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Suitability

  • Wheelchair access (3)
  • Elder access (13)
  • Suitable for children (20)
  • Pet friendly (7)
  • Smoking allowed (1)

Amenities

  • Internet (25)
  • Other outdoor space (25)
  • Grill (22)
  • Air Conditioning (20)
  • Parking (19)
  • View all amenities