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 NZ$404 per night from 27 May to 28 May
NZ$404
includes taxes & fees
27 May - 28 May
Stay at this vacation home in Kingston. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Thorn Preserve - Catskill Center and ...
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 NZ$562 per night from 27 Apr to 28 Apr
NZ$562
includes taxes & fees
27 Apr - 28 Apr
Stay at this vacation home in Fishkill. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions SplashDown Beach and Van Wyck Homestead Museum ...
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
Book a stay at this family-friendly vacation home in Woodstock. Enjoy free WiFi, private pools, and a water park. Popular attractions Woodstock Public Library ...
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
Book a stay at this family-friendly vacation home in New Paltz. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Mohonk Preserve Visitor ...
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 NZ$1,546 per night from 1 May to 2 May
NZ$1,546
includes taxes & fees
1 May - 2 May
Stay at this vacation home in Poughkeepsie. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Overlook Drive-In Theater and Richard L. Skimin ...
Spacious New Luxurious holiday house in lovely Hudson Valley
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
Book a stay at this family-friendly vacation home in Glasco. Enjoy free WiFi, private pools, and a garden. Popular attractions Falling Waters Preserve and West ...
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
Stay at this vacation home in Hopewell Junction. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chuang Yen Monastery and Canopus Beach ...
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
Book a stay at this family-friendly vacation home in New Windsor. Enjoy free WiFi, a garden, and patios. Our guests praise the bathrooms in our reviews. Popular ...
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
Book a stay at this family-friendly vacation home in Salt Point. Enjoy free WiFi, a garden, and patios. Popular attractions Innisfree Garden and Clinton Vineyards ...
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
NZ$200
Highest Price
NZ$1,546
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
The price is NZ$322 per night from 10 May to 11 May
NZ$322
includes taxes & fees
10 May - 11 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
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 NZ$213 per night from 4 May to 5 May
NZ$213
includes taxes & fees
4 May - 5 May
Book a stay at this family-friendly hotel in Kingston. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful ...
Best Western Plus Kingston Hotel And Conference Center
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$200 per night from 29 Apr to 30 Apr
NZ$200
includes taxes & fees
29 Apr - 30 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
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Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is NZ$305 per night from 18 May to 19 May
NZ$305
includes taxes & fees
18 May - 19 May
Stay at this 3-star business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
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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.