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Highland Holiday Homes

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    Don't let other travellers get your favourite Highland area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 22 Rentals in Highland
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    Secluded Country Getaway1 / 29
    (1)Excellent
    Highland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Sam's Cottage on the Greens1 / 19
    (1)Excellent
    Highland
    1 Bedroom, 3 Bathrooms, Sleeps 3 Quick View
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    Hudson Valley 40 Acres With Lake And Hiking1 / 18
    (12)Excellent
    Highland
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Highland
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Sauna
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breathtaking Glass, Wood & Stone Modern Villa On 12 Acres. Secluded luxury cantilevered on a 200' granite bluff peninsula over the Hudson River. As fine an estate as any in Europe yet only 1.5 hrs from Manhattan. Gourmet kitchen. 10' screen media room. Huge riverside deck, hot tub & heated...
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    Highland, New York 12528
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    Highland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Washer
    • Mountain Views
    • Grill
    • Central Heating
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely A-frame house nestled in a quiet wooded lot on a culdesac. Just minutes from local attractions including historic sites, outdoor activities and easy access to NYC.<BR><BR>House is completely furnished with new furniture and appliances. Lovely outdoor eating area overlooks woods and quiet...
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    Highland, New York 12528 1006
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 15 kilometres of Highland.
    Serene Vista Spa B and B of the Hudson Valley 11 / 13
    (3)Very good
    New Paltz
    1 Bedroom, 3 Bathrooms, Sleeps 2 Quick View
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Porch
    • Patio
    • DVD Player
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 March 2017
    i just went for the 1 hour facial. It was HEAVENLY. All natural essential oils. It was more like a full body "facial". I have "fine lines" on my face...
    Reviewed 8 January 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...
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    About this property
    Serene Vista 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....
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    New Paltz, New York 12589
    Private Room - 1 Bedroom, 3 Bathrooms, Sleeps 2
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    Earth Berm House at Terra Casa Retreat Center1 / 11
    (5)Very good
    Plattekill
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 2017
    My first contact with america! I was 1 month in Casa Terra, I shared a very interesting project with john and amber. A month that I spend quickly to feel at home. I shared jobs...
    Reviewed 29 April 2017
    Staying as John + Ambers first long term guest along with another fellow volunteer, I believe was it was a good learning experience for everyone in many ways. There is a lot of...
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    About this property
    The house features picturesque forrest landscapes, warm lighting, wide plank wood floors, rustic hard wood beams, and modern kitchen. Venture on the grass roof of the earth sheltered house, as well as hike trails, snow shoe, XC ski and explore nature on the 150 acres of land we have :) Great space...
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    Plattekill, New York 12589
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cozy Apple House1 / 18
    (1)Excellent
    Gardiner
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    House was so sweet and cozy. Decorated very cute!! Very clean I felt more than comfortable having my 9 month old son crawl all over the floors. The owner Rhonda was a great...
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    About this property
    Come stay at our quaint cottage in the shadow of the Shawangunk Mountains. A sweet alternative from the beach. There's so much to do: Hiking, Walking, Biking, Swimming, Apple Picking. Grab a tube and float down a cool lazy river or go for a hike and take in the amazing mountain air, not to...
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    Gardiner, New York 12525
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Renovated Schoolhouse - Hudson Valley Getaway1 / 21
    (17)Excellent
    New Paltz
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Parking
    • Satellite TV
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2017
    This is a perfect location and house for a weekend away with plenty of ways to enjoy the outdoors! For the sports enthusiasts, there is great road cycling (right out the door...
    Reviewed 3 May 2016
    We stayed at the Schoolhouse Cottage over a weekend while some of us were participating in the Rock The Ridge 50-Mile Endurance Challenge taking place in the Mohonk Preserve and...
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    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'...
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    New Paltz, New York 12561
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Marlboro
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Satellite TV
    • Housekeeping Included
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large 3 bedroom first floor house located on top of a hill in a quiet neighborhood. Home owned by family for over 40 years. - Owner will rent for 7-120 days at 1st, after the renter will be able to renew the lease if they choose & if owner approves. The Space Looking to rent the first floor of a...
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    Marlboro, New York 12542
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    New Paltz meets Cape May1 / 24
    (1)Excellent
    New Paltz
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Washer
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2016
    Gayle is a delight to work with...accessible and helpful. Her home is an absolute dream and is every bit as charming in person as it appears in photos. One of my favorite things...
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    About this property
    4 beds -- baths 3,400 sqft NEW PALTZ MEETS CAPE MAY ON THE WATERFRONT WITH MOUNTAIN VIEWS- Spend the summer watching the eagles soar from your own nature preserve and the conveniences of village living with easy access to the NYC express bus. Enjoy the mountain views while relaxing on your...
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    New Paltz, New York 12561
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Modern, Eclectic, Tranquil Mountain Retreat1 / 8
    (2)Excellent
    Gardiner
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • DVD Player
    • Grill
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2017
    Amazing house that felt like home the moment we stepped in the door!Such a cool house with 2 fab sound systems, some cool artwork, furniture and decorations. Lovely outside...
    Reviewed 23 October 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...
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    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...
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    Gardiner, New York 12566
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Thornwood Guesthouse - historic w/ modern comforts1 / 69
    (3)Excellent
    New Paltz
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Balcony
    • Satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2016
    Kim and Tom have done an amazing job at creating a charming, enchanting, and sacred space. Thornwood always feels like home away from home. We can't wait for our next stay!
    Reviewed 18 April 2016
    My friends and I visited Thornwood last Spring/Summer, and it took our breaths away. From the immaculate condition of the centuries-old house to its calm, serene surroundings...
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    About this property
    MAKING YOUR STAY PERFECT: Step Into History - Walk to Town - Play - Feed Chickens -- Multi-Cook Kitchen - Quiet Spaces - Peaceful Five minutes from bus and NY Thruway. Check-in and check-out times often flexible, please ask. This 250+ year-old gem has been fourteen years in the remaking. We...
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    Location Information
    New Paltz, New York 12561
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Poughkeepsie
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be welcome and comfortable for work or pleasure in my 1 bedroom apartment near Vassar College, Marist College and the Culinary Institute of America. The apartment sleeps 4. The rooms are spacious and professionally decorated. Full kitchen with all necessary cooking and eating equipment...
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    Poughkeepsie, New York 12603
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    New Paltz
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Hot Tub
    • Mountain Views
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4000 sq ft home, tastefully decorated with flat sceen HDTV, DVD player and Wii. Gourmet kitchen. Forgot to pick up wine for dinner, choose from our selection and save yourself a trip. Pool with 5000 sq ft deck. BBQ grill. 3000 sq ft art gallery. Upstairs gym, upright piano in house, grand piano in...
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    New Paltz, New York 12561
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Poughkeepsie
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located on the border of Poughkeepsie and the Historic Hyde Park, home to Franklin and Eleanor Roosevelt. The Culinary Institute of America is a five minute drive and has not only wonderful classes but also restaurants that are open to the public (get reservations!). Marist college is...
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    Location Information
    Poughkeepsie, New York 12601
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    New Paltz
    7 Bedrooms, 8 Bathrooms, Sleeps 13 Quick View
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    • Sauna
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Hot Tub
    • Patio
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the HeartsEase Mansion, a Hudson Valley National Registry Historic estate. As a guest to our Hudson Valley home, you join a long tradition of people who have made their way to this spectacular region known for its natural beauty, art, and cultural innovation. <BR><BR>Some background in...
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    Location Information
    New Paltz, New York 12493
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 13
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    Private King Bed w/Bath in SHARED Charming House, good for business travelers1 / 10
    (3)Excellent
    New Paltz
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Central Heating
    • Patio
    • Parking
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    Really enjoyed the quiet and quaintness of the historic house along with the closeness to all kinds of sites including New Paltz. Liz and Matt were very attentive and always a...
    Reviewed 18 June 2017
    My room in this house just outside the commercial center of the college town of New Paltz, in New York's Hudson River Valley, offered a pleasant and unique place to stay for...
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    About this property
    Our place is all about comfort and convenience! It is under 5 mins from the NYS Thruway and not far from public transport. This is a perfect place for business travelers! Please email for availability or questions. Close to nature, Minnewaska State Park, Mohonk Preserve, rock climbing, skydiving,...
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    Location Information
    New Paltz, New York 12561
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    New Paltz
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Mountain Views
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Farmhouse and Guest Cottage are situated on two secluded acres of land on the Wallkill River in New York's Hudson Valley, just 90 miles North of New York City. Set in a rural environment, surrounded by New York State land and in between family run farms, we are still only a few minutes from...
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    New Paltz, New York 12561
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Paltz
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Satellite TV
    • Washer
    • Mountain Views
    • Wi-Fi
    • Secure Parking
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New Home with great views of Mohonk and The Gunks! Minutes from town, or walk the mile and a half down the scenic Walkill Valley Rail Trail to historic New Paltz. This spacious 3 br/2 bath home has everything you need for a great getaway! Just one mile south of Main Street via road or the...
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    New Paltz, New York 12561
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    New Paltz
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Farmhouse and Guest Cottage are situated on two secluded acres of land on the Wallkill River in New York's Hudson Valley, just 90 miles North of New York City. Set in a rural environment, surrounded by New York State land and in between family run farms, we are still only a few minutes from...
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    New Paltz, New York 12561
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Eclectic One Bedroom Cottage in the Hudson Valley1 / 4
    (16)Excellent
    New Paltz
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Private Garden
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2016
    10 minutes from new paltz pet friendly lovely patio to sit out everything you need. ..why stay in a hotel?
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    About this property
    Bring that special someone to our charming cottage in New Paltz and take that much needed break. Or get some needed solitude for yourself to write, read and relax in total privacy. You can even bring your dog! This eclectic one bedroom cottage is the perfect place to take time out while still...
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    New Paltz, New York 12561
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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