Compare Highland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

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

Highland Rentals

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s

4.24 mi from city center
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and a garden. This family-friendly vacation home also has barbecue grills.
The Scenic Mansion With Breathtaking View

The Scenic Mansion With Breathtaking View

2.74 mi from city center
Guests staying at this villa enjoy free WiFi in public areas, laundry facilities, and barbecue grills.
Private 37 Acre Lake Estate on 164 Acres - 11 BR

Private 37 Acre Lake Estate on 164 Acres - 11 BR

5.69 mi from city center
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2 out of 5
7.93 mi from city center
$907 nightly
The price is $921 total per night
$921 total
Oct 19 - Oct 20
Total with taxes and fees
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

12.1 mi from city center
$294 nightly
The price is $333 total per night
$333 total
Nov 1 - Nov 2
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Chestnut on Willow Lake

Chestnut on Willow Lake

14.46 mi from city center
$508 nightly
The price is $578 total per night
$578 total
Oct 6 - Oct 7
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

19.56 mi from city center
$215 nightly
The price is $240 total per night
$240 total
Oct 14 - Oct 15
Total with taxes and fees
At this vacation home, guests have access to barbecue grills.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

20.07 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2 out of 5
22.33 mi from city center
$203 nightly
The price is $228 total per night
$228 total
Oct 5 - Oct 6
Total with taxes and fees
This apartment is a smoke-free apartment building.
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

22.35 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and laundry facilities. Other amenities at this family-friendly vacation home include local meal delivery service, barbecue grills, and a garden.
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

23.3 mi from city center
$277 nightly
The price is $310 total per night
$310 total
Oct 5 - Oct 6
Total with taxes and fees
At this cottage, guests have access to barbecue grills.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

20.61 mi from city center
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
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.

Highland Large Group Rentals

How to Book Vacation Rentals in Highland



🏠 What is the best price for Highland vacation rentals?

Highland vacation rentals range in price, starting at $228 per night.


🏠 What types of vacation rentals in Highland can I rent?

Orbitz offers a wide range of Highland rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Highland condo rentals.


🏠 Is it free to cancel my Highland vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Highland vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Highland. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Highland?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Highland apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Highland?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Highland package deals will get you even more savings.

More to Explore

More to Explore