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^

Featured Holiday Homes in Highland

The Farm at Hyde Park

The Farm at Hyde Park

Staatsburg
Located in Staatsburg, this vacation home is in a rural location, within a 10-minute drive of Margaret Lewis Norrie State Park and Ogden Mills and Ruth Livingston ...
The Farm at Hyde Park
Beautiful Private Stone Home in the Hudson Valley

Beautiful Private Stone Home in the Hudson Valley

Pine Bush
Located in Pine Bush, this vacation home is within a 10-minute drive of Lake Awosting Beach and Minnewaska State Park.
Beautiful Private Stone Home in the Hudson Valley
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

Woodstock
With a stay at this vacation home in Woodstock, you'll be in the mountains, just steps from Catskill State Park and a 3-minute drive from Woodstock Dog ...
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Save an average of 15% on thousands of hotels when you're signed in
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.

Carmel Hamlet
Located in Carmel, this vacation home is in the mountains, a 4-minute drive from Clarence Fahnestock State Park and 8 minutes from Chuang Yen Monastery.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Red Barn Retreat - Shawangunk Mountains Getaway

Red Barn Retreat - Shawangunk Mountains Getaway

Gardiner
When you stay at this vacation home in Gardiner, you'll be on the waterfront, within a 5-minute drive of Whitecliff Vineyard and DM Weil Gallery.
Red Barn Retreat - Shawangunk Mountains Getaway
complete privacy vacation home [private pool]

complete privacy vacation home [private pool]

Newburgh
The price is AU$1,721 per night from 5 Dec to 6 Dec
AU$1,721
includes taxes & fees
5 Dec - 6 Dec
Located in Newburgh, this vacation home is within a 10-minute drive of Chadwick Lake Park and Mount Saint Mary's College Newburgh.
complete privacy vacation home [private pool]
Bright, historic Woodstock home close to town

Bright, historic Woodstock home close to town

Woodstock
With a stay at this vacation home in Woodstock, you'll be a 1-minute walk from Catskill State Park and 8 minutes by foot from Woodstock Golf Club.
Bright, historic Woodstock home close to town
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.

‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.

Saugerties
When you stay at this vacation home in Saugerties, you'll be within a 10-minute drive of Esopus Creek and Hudson Valley Mall.
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
With a stay at this vacation home, you'll be centrally located in Glasco, just a 3-minute walk from Hudson River and 11 minutes by foot from Falling Waters ...
Hamptons on the Hudson in South Saugerties
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 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
501 Holiday Homes
Lowest Price
AU$138
Highest Price
AU$1,721
Popular accommodation
The Farm at Hyde Park, Beautiful Private Stone Home in the Hudson Valley, HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace, Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. , Red Barn Retreat - Shawangunk Mountains Getaway, complete privacy vacation home [private pool], Bright, historic Woodstock home close to town, ‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson., Hamptons on the Hudson in South Saugerties

Top trending hotels in Highland

Rodeway Inn & Suites New Paltz - Hudson Valley

Rodeway Inn & Suites New Paltz - Hudson Valley

2 out of 5
601 Main Street, Highland, NY
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 24 Nov to 25 Nov
AU$138
includes taxes & fees
24 Nov - 25 Nov
A stay at Rodeway Inn & Suites New Paltz - Hudson Valley places you in the heart of Highland, within a 5-minute drive of Apple Greens Golf Course and State University ...
Rodeway Inn & Suites New Paltz - Hudson Valley
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 AU$194 per night from 1 Dec to 2 Dec
AU$194
includes taxes & fees
1 Dec - 2 Dec
With a stay at SureStay Plus Hotel by Best Western Highland Poughkeepsie in Highland, you'll be within a 15-minute drive of Marist College and Culinary Institute ...
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is AU$226 per night from 28 Nov to 29 Nov
AU$226
includes taxes & fees
28 Nov - 29 Nov
Located in Kingston, Best Western Plus Kingston Hotel And Conference Center is in the historical district, a 5-minute walk from Dietz Stadium and 10 minutes ...
Best Western Plus Kingston Hotel And Conference Center
Save an average of 15% on thousands of hotels when you're signed in
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 AU$188 per night from 1 Dec to 2 Dec
AU$188
includes taxes & fees
1 Dec - 2 Dec
With a stay at DoubleTree by Hilton Poughkeepsie, you'll be centrally located in Poughkeepsie, a 2-minute drive from Marist College and 6 minutes from Culinary ...
DoubleTree by Hilton Poughkeepsie
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.