Compare Highland Villas

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Featured Villas in Highland

Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery

Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery

Woodbury NY
This villa offers a gym, a sauna, and a hot tub. Other amenities at this family-friendly villa include an arcade/game room, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Dome House Retreat

Dome House Retreat

4 out of 5
116 canaan rd New Paltz NY
At Dome House Retreat, guests have access to free WiFi in public areas, a 24-hour business center, and a library. There's free parking if you drive. Friendly staff can provide tour or ticket assistance, and also offer advice about sightseeing. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a terrace, laundry facilities, and wedding services.
Kitchen
Pet friendly
The Scenic Mansion With Breathtaking View

The Scenic Mansion With Breathtaking View

Highland NY
Guests staying at this villa enjoy free WiFi in public areas, laundry facilities, and barbecue grills.
Pool
Kitchen
New Luxury 5BR3BTh Woodstock Secret Retreat Near all Ski MT Heated Pool& Hot Tub

New Luxury 5BR3BTh Woodstock Secret Retreat Near all Ski MT Heated Pool& Hot Tub

Woodstock NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this golf villa include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
Rhinebrook Estate - 8 Bed/8Bath (Sleeps 20)

Rhinebrook Estate - 8 Bed/8Bath (Sleeps 20)

Hyde Park NY
Guests staying at this villa enjoy a gym, a sauna, and a hot tub. Other amenities at this family-friendly villa include an arcade/game room, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Country home with rock climbing gym, pond & creek.

Country home with rock climbing gym, pond & creek.

New Paltz NY
Guests staying at this villa enjoy a gym, an arcade/game room, and laundry facilities. Additional amenities include barbecue grills and a garden.
Kitchen
Washer
Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Monroe NY
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Retreat Villa: Theater, Yoga Studio, Group Spaces | Dream House in the Gunks

Retreat Villa: Theater, Yoga Studio, Group Spaces | Dream House in the Gunks

Kerhonkson NY
$377 nightly
The price is $382 total per night
$382 total
Jan 15 - Jan 16, 2026
Total with taxes and fees
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool

Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool

Kerhonkson NY
Guests staying at this villa enjoy a hot tub, an arcade/game room, and barbecue grills. This smoke-free villa also has a garden.
Pool
Hot Tub
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Highland

    SureStay Plus Hotel by Best Western Highland Poughkeepsie

    SureStay Plus Hotel by Best Western Highland Poughkeepsie

    3423 US Highway 9W Highland NY
    $80 nightly
    The price is $90 total per night from Jan 4 to Jan 5
    $90 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    7.6/10 Good! (948 reviews)
    Residence Inn by Marriott Kingston

    Residence Inn by Marriott Kingston

    800 Frank Sottile Boulevard Kingston NY
    $114 nightly
    The price is $128 total per night from Jan 1 to Jan 2
    $128 total
    Jan 1 - Jan 2, 2026
    Total with taxes and fees
    8.8/10 Excellent! (802 reviews)
    Hampton Inn & Suites Poughkeepsie

    Hampton Inn & Suites Poughkeepsie

    2361 South Rd Poughkeepsie NY
    $98 nightly
    The price is $113 total per night from Jan 2 to Jan 3
    $113 total
    Jan 2 - Jan 3, 2026
    Total with taxes and fees
    8.8/10 Excellent! (1,006 reviews)

Luxury Villas

Book luxury villas in Highland
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Highland. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Highland, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Highland
You won’t have a problem finding your own space in Highland. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Highland on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Highland rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Highland Villas essential information

Accommodation
14 Villas
Lowest Price
$90
Highest Price
$382
Popular accommodation
Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery, Dome House Retreat, The Scenic Mansion With Breathtaking View, New Luxury 5BR3BTh Woodstock Secret Retreat Near all Ski MT Heated Pool& Hot Tub, Rhinebrook Estate - 8 Bed/8Bath (Sleeps 20), Country home with rock climbing gym, pond & creek., Charming 3-bedroom villa with WiFi, AC in fabulous Monroe, Retreat Villa: Theater, Yoga Studio, Group Spaces | Dream House in the Gunks, Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool