Book Holiday Homes in Highland

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Highland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Highland vacation homes are the perfect way for you to wing it.

Holiday houses in Highland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Highland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Highland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Highland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Highland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Highland Holiday Homes essential information

Accommodation
Holiday Homes
Lowest Price
NZ$184
Highest Price
NZ$221
Popular accommodation
SureStay Plus Hotel by Best Western Highland Poughkeepsie, DoubleTree by Hilton Poughkeepsie, HYATT house Fishkill/Poughkeepsie, Hyatt Place Poughkeepsie / Hudson Valley

Top trending hotels in Highland

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W, I-87 Exit 18 to I-9W, Highland, NY
Fully refundableReserve now, pay when you stay
The price is NZ$184 per night from 5 May to 6 May
NZ$184
includes taxes & fees
5 May - 6 May
Book a stay at this business-friendly hotel in Highland. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
SureStay Plus Hotel by Best Western Highland Poughkeepsie
DoubleTree by Hilton Poughkeepsie

DoubleTree by Hilton Poughkeepsie

4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is NZ$221 per night from 20 Apr to 21 Apr
NZ$221
includes taxes & fees
20 Apr - 21 Apr
Stay at this 4-star business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
DoubleTree by Hilton Poughkeepsie
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is NZ$214 per night from 8 Apr to 9 Apr
NZ$214
includes taxes & fees
8 Apr - 9 Apr
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
HYATT house Fishkill/Poughkeepsie
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is NZ$210 per night from 13 Apr to 14 Apr
NZ$210
includes taxes & fees
13 Apr - 14 Apr
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Poughkeepsie / Hudson Valley
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.