Compare Highland Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Highland

Perfect home for a dream retreat + POOL

Perfect home for a dream retreat + POOL

At this villa, guests have access to barbecue grills.
Fireplace
Pool
Kick back & relax in this peaceful, stylish place to stay with the whole family.

Kick back & relax in this peaceful, stylish place to stay with the whole family.

This villa offers a gym, a sauna, and a spa tub. Other amenities at this family-friendly villa include an arcade/game room, a garden, and barbecue grills.
Hot Tub
Fireplace
4-Acre Hudson Valley Estate with Pool, Sauna, Yard

4-Acre Hudson Valley Estate with Pool, Sauna, Yard

This villa features a sauna and a garden. This smoke-free villa also has barbecue grills.
Fireplace
Pet friendly
The Scenic Mansion With Breathtaking View

The Scenic Mansion With Breathtaking View

This villa features free WiFi in public areas and barbecue grills.
Fireplace
Pool
Rhinebrook Estate - 8 Bed/8Bath (Sleeps 20)

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

Guests staying at this villa enjoy a gym, a sauna, and a spa tub. Other amenities at this family-friendly villa include an arcade/game room, a garden, and barbecue grills.
Hot Tub
Fireplace
Beautiful modern villa with pool suana hot tub...

Beautiful modern villa with pool suana hot tub...

At this villa, guests have access to an outdoor pool, an arcade/game room, and barbecue grills. This smoke-free villa also has a garden.
Pet friendly
Pool
Villa Retreat in nature with private yoga studio

Villa Retreat in nature with private yoga studio

The price is $265 per night
$265
per night
Jun 3 - Jun 4
Guests of this villa enjoy features like a gym, a spa tub, and an arcade/game room. Other amenities at this family-friendly villa include local meal delivery service, a garden, and barbecue grills.
Hot Tub
Fireplace
Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool

Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool

Guests staying at this villa enjoy a spa tub, an arcade/game room, and barbecue grills. This smoke-free villa also has a garden.
Hot Tub
Fireplace
: Spring is here!! Pool opening soon!! Looking forward to being your host!

: Spring is here!! Pool opening soon!! Looking forward to being your host!

Guests of this villa enjoy features like an outdoor pool, a gym, and an arcade/game room. Additional amenities include barbecue grills and a garden.
Fireplace
Pet friendly
Don't see what you're looking for?
See all available properties in Highland
View all properties
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

    Rodeway Inn & Suites New Paltz - Hudson Valley

    Rodeway Inn & Suites New Paltz - Hudson Valley

    601 Main Street, Highland, NY
    The price is $75 per night from Jun 2 to Jun 3
    $75
    per night
    Jun 2 - Jun 3
    7/10 Good! (557 reviews)
    SureStay Plus Hotel by Best Western Highland Poughkeepsie

    SureStay Plus Hotel by Best Western Highland Poughkeepsie

    3423 US Highway 9W, I-87 Exit 18 to I-9W, Highland, NY
    The price is $99 per night from Jun 17 to Jun 18
    $99
    per night
    Jun 17 - Jun 18
    7.4/10 Good! (707 reviews)
    HYATT house Fishkill/Poughkeepsie

    HYATT house Fishkill/Poughkeepsie

    100 Westage Business Center Dr., Fishkill, NY
    The price is $142 per night from Jun 9 to Jun 10
    $142
    per night
    Jun 9 - Jun 10
    8.6/10 Excellent! (1,000 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!

Villas in Highland

Most Popular

More Places To Stay in Highland