Book Holiday Homes in Highland

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Featured Holiday Homes in Highland

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
The price is AU$400 per night from 6 Apr to 7 Apr
AU$400
includes taxes & fees
6 Apr - 7 Apr
With a stay at this vacation home in Kingston, you'll be on a river, just steps from Catskill State Park and a 4-minute drive from Thorn Preserve - Catskill ...
Esopus Creek modern Tiny house Retreat!
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

Fishkill
The price is AU$531 per night from 15 Apr to 16 Apr
AU$531
includes taxes & fees
15 Apr - 16 Apr
When you stay at this vacation home in Fishkill, you'll be within a 10-minute drive of Northeast Regional Epilepsy Group and SplashDown Beach.
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
HOT TUB w/ POOL,  STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

Woodstock
A stay at this vacation home places you in the heart of Woodstock, steps from Catskill State Park and a 4-minute drive from Woodstock Music Shop.
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
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Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

New Paltz
A stay at this vacation home places you in the heart of New Paltz, a 5-minute drive from Mohonk Preserve Visitor Center and 6 minutes from Testimonial ...
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
Spacious New Luxurious holiday house in lovely Hudson Valley

Spacious New Luxurious holiday house in lovely Hudson Valley

Poughkeepsie
The price is AU$1,493 per night from 1 May to 2 May
AU$1,493
includes taxes & fees
1 May - 2 May
With a stay at this vacation home in Poughkeepsie, you'll be within a 15-minute drive of Vassar College and Marist College.
Spacious New Luxurious holiday house in lovely Hudson Valley
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
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction
Located in Hopewell Junction, this vacation home is in the mountains, within a 10-minute drive of Clarence Fahnestock State Park and Hudson Valley Research ...
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

New Windsor
With a stay at this vacation home in New Windsor, you'll be on a river, within a 10-minute drive of United States Military Academy and Hudson River.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Hidden Charm in Hudson Valley In Dutchess County

Hidden Charm in Hudson Valley In Dutchess County

2 out of 5
Salt Point
Located in Salt Point, this vacation home is in the mountains, within a 15-minute drive of Clinton Vineyards and Institute of Ecosystem Studies.
Hidden Charm in Hudson Valley In Dutchess County
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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.

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
635 Holiday Homes
Lowest Price
AU$194
Highest Price
AU$1,493
Popular accommodation
Esopus Creek modern Tiny house Retreat!, Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo, HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN, Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska, Spacious New Luxurious holiday house in lovely Hudson Valley, Hamptons on the Hudson in South Saugerties, 1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views, Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel. , Hidden Charm in Hudson Valley In Dutchess County

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
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 Vassar ...
SureStay Plus Hotel by Best Western Highland Poughkeepsie
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is AU$194 per night from 20 Apr to 21 Apr
AU$194
includes taxes & fees
20 Apr - 21 Apr
Located in Fishkill, HYATT house Fishkill/Poughkeepsie is a 4-minute drive from SplashDown Beach and 10 minutes from Dia Beacon.
HYATT house Fishkill/Poughkeepsie
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 AU$218 per night from 7 Apr to 8 Apr
AU$218
includes taxes & fees
7 Apr - 8 Apr
A stay at Hyatt Place Poughkeepsie / Hudson Valley places you in the heart of Poughkeepsie, within a 10-minute drive of Marist College and Poughkeepsie ...
Hyatt Place Poughkeepsie / Hudson Valley
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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$214 per night from 20 Apr to 21 Apr
AU$214
includes taxes & fees
20 Apr - 21 Apr
With a stay at DoubleTree by Hilton Poughkeepsie, you'll be centrally located in Poughkeepsie, within a 5-minute drive of Marist College and Vassar College.
DoubleTree by Hilton Poughkeepsie
Don't see what you're looking for?
See all available properties in Highland
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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.

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^Subject to availability and chosen travel dates.