Highland holiday homes

We found 1,752 holiday rentals — enter your dates for availability
Discover a selection of 28 homes and other holiday rentals in Highland that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Highland

Showing deals for:4 Dec - 11 Dec

Kitchen
Hot tub
Fully finished attic: full size bed
Sunroom
Exceptional
(90 reviews)

Start thinking about Fall Foliage! Hot tub, fabulous kitchen, views everywhere!

Tannersville

13% off
NZ$18,276
for 7 nights, 1 home
NZ$2,611 per night
includes taxes & fees
Start thinking about Fall Foliage! Hot tub, fabulous kitchen, views everywhere!
Open kitchen.
Rear Deck, Hot Tub and Screened Porch
Our Sunny Living Room with Wood Stove
A beautiful spot for our comfortable cabin
Exceptional
(119 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off
NZ$5,001
for 7 nights, 1 cabin
NZ$714 per night
includes taxes & fees
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
Exterior
Living area
Property grounds
Private kitchen
Exceptional
(8 reviews)

6 Acre Private Hudson Valley Estate

Highland

8% off
NZ$18,439
for 7 nights, 1 home
NZ$2,634 per night
includes taxes & fees
6 Acre Private Hudson Valley Estate
Interior
Living area
Front porch
Master suite balcony
Exceptional
(34 reviews)

Luxury secluded Catskill log cabin on creek-ski hike great restaurants mins away

Catskill

8% off
NZ$6,723
for 7 nights, 1 cabin
NZ$960 per night
includes taxes & fees
Luxury secluded Catskill log cabin on creek-ski hike great restaurants mins away
Living area
Exterior
Private kitchen
Outdoor dining
Exceptional
(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off
NZ$5,654
for 7 nights, 1 home
NZ$808 per night
includes taxes & fees
Secluded family retreat within minutes of Woodstock village
Private kitchen
Interior
Living area
Terrace/patio
Exceptional
(135 reviews)

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville

11% off
NZ$10,338
for 7 nights, 1 home
NZ$1,477 per night
includes taxes & fees
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Exterior
Living area
Private kitchen
Dining
Exceptional
(40 reviews)

5-Star New Barn Home - Music Studio, Views & Hot Tub

Saugerties

8% off
NZ$10,143
for 7 nights, 1 home
NZ$1,449 per night
includes taxes & fees
5-Star New Barn Home - Music Studio, Views & Hot Tub
A Special Place for Your Special Times!  4 bedroom, 3.5 baths, Full Kitchen, Kitchenette, 2 Living Areas, 2 Dining Areas, Full access to backyard with dining area, fire pit with adirondack chairs, BBQ grill, hammock on 2 acres of land.
Dining
French Doors leading to a veranda offer a wonderful connection to the outdoors, making it the perfect spot to start your day with a cup of morning coffee or tea.
For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.
Exceptional
(25 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
NZ$5,321
for 7 nights, 1 home
NZ$760 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
5 star ensuite bathroom with tub, hand shower, and rain shower.
450sqft of living space: super comfy kingsize bed (+ 2 optional twin beds)
Enjoy your private deck, lawn, firepit, and grill!
Private, luxurious retreat in the heart of an organic farm in the Hudson Valley
Exceptional
(25 reviews)

Luxury retreat w/ private deck, garden, firepit on organic farm

Gardiner

8% off
NZ$2,952
for 7 nights, 1 cabin
NZ$422 per night
includes taxes & fees
Luxury retreat w/ private deck, garden, firepit on organic farm
Enjoy the view of kitchen activities while hanging out on the couch.
View of the cabin from the road. Sitting on just over an acre of land.
A clean, simple hallway that leads to the downstairs bedroom and bathroom.
Living area
Exceptional
(41 reviews)

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Catskill

8% off
NZ$2,869
for 7 nights, 1 cabin
NZ$410 per night
includes taxes & fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Living area
Living area
Exterior
Property grounds
Exceptional
(35 reviews)

Hidden Charm in Hudson Valley In Dutchess County

Salt Point

8% off
NZ$7,300
for 7 nights, 1 home
NZ$1,043 per night
includes taxes & fees
Hidden Charm in Hudson Valley In Dutchess County
View of valley and lush evergreens. Queen bed. Spacious closet
Whip up delicious meals in the spacious, bright kitchen with ample counter space
Sit together outside, enjoy fresh Hudson Valley air,  share stories and memories
Settle into the many comfy seats in the Family Room.
Exceptional
(40 reviews)

Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Highland

8% off
NZ$7,516
for 7 nights, 1 home
NZ$1,074 per night
includes taxes & fees
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
Open floor kitchen, LR, and DR, with panoramic view of lake.
Breathtaking View, Situated on Orange Lake
Through the front door to spectacular lake beauty
Winter beauty
Exceptional
(330 reviews)

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh

8% off
NZ$5,717
for 7 nights, 1 home
NZ$817 per night
includes taxes & fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Property grounds
Room
Interior
Interior
Exceptional
(86 reviews)

for the creative spirit, swimming dock on pond, horses to pet, Fire pit

Ulster Park

8% off
NZ$3,957
for 7 nights, 1 home
NZ$565 per night
includes taxes & fees
for the creative spirit, swimming dock on pond, horses to pet, Fire pit
Property grounds
Exterior
Property grounds
Living area
Exceptional
(13 reviews)

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

8% off
NZ$2,351
for 7 nights, 1 home
NZ$336 per night
includes taxes & fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Sitting in the living room area, you feel nestled in the woods.
Feel the awe of the 20 foot vaulted ceilings and windows onto the woods
It's mesmerizing to watch and hear the roaring waterfall from this bridge.
The Enchanted Forest beckons!
Exceptional
(20 reviews)

Hudson Valley stunning lake side modern barn in an Enchanted Forest

Clinton Corners

8% off
NZ$6,362
for 7 nights, 1 home
NZ$909 per night
includes taxes & fees
Hudson Valley stunning lake side modern barn in an Enchanted Forest
Room
Dining room table with bay window.
Private kitchen
The den is wide open with an oversized couch, coffee tables and stool seating.
Exceptional
(40 reviews)

Spacious, Private, Close to Town, Work From Home

Woodstock

7% off
NZ$5,424
for 7 nights, 1 home
NZ$775 per night
includes taxes & fees
Spacious, Private, Close to Town, Work From Home
Bedroom 2 has a Roku-enabled TV and a queen bed.
George Washington was president when these original hardwood floors were made!
This sitting area is another great space to gather around the faux fireplace.
Here's the spacious farmhouse kitchen. A leaf expands the table to seat 6.
Exceptional
(19 reviews)

Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres

Milton

16% off
NZ$4,361
for 7 nights, 1 home
NZ$623 per night
includes taxes & fees
Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
Walk way to back yard from side of the house
View of the dining room
Original mahogany wood work and French Chandliers though out the house
Hallway with pocket doors on main floor
Exceptional
(17 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

20% off
NZ$9,755
for 7 nights, 1 home
NZ$1,394 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
Fern garden in summer
Welcome to Bridge House
In winter, stay toasty warm by the fire
Cooking is a breeze in this recently remodeled kitchen
Exceptional
(128 reviews)

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

Willow

8% off
NZ$4,325
for 7 nights, 1 home
NZ$618 per night
includes taxes & fees
Waterfront Mid-century Modern Gem Surround by Forever Wild Land
Private kitchen
Terrace/patio
Dining
Exterior
Exceptional
(29 reviews)

Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!

Hurley

12% off
NZ$3,218
for 7 nights, 1 cabin
NZ$460 per night
includes taxes & fees
Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!
Interior
Exterior
Private kitchen
Terrace/patio
Exceptional
(10 reviews)

Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road

High Falls

16% off
NZ$8,413
for 7 nights, 1 home
NZ$1,202 per night
includes taxes & fees
Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road
Interior
Exterior
Terrace/patio
Property grounds
Exceptional
(46 reviews)

Cosy lakefront cottage in Hudson Valley

Walden

8% off
NZ$2,800
for 7 nights, 1 cottage
NZ$400 per night
includes taxes & fees
Cosy lakefront cottage in Hudson Valley
Private kitchen
Interior
Living area
Welcome!!
Exceptional
(26 reviews)

Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals

Saugerties

8% off
NZ$11,099
for 7 nights, 1 home
NZ$1,586 per night
includes taxes & fees
Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The scenic city of Highland awaits you

The riverfront, wildlife and mountains are the perfect backdrop to your holiday home in Highland. This scenic city attracts visitors thanks to its boating and hiking. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Highland

Are you hoping to discover attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Highland a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • New Paltz Golf Course (7.1 mi / 11.4 km)
  • Benmarl Vineyards and Winery (8.9 mi / 14.4 km)
  • Mohonk Golf Course (9.9 mi / 15.9 km)
  • Robibero Winery (10.4 mi / 16.8 km)
  • SplashDown Beach (12.3 mi / 19.8 km)
  • Ice Time Sports Complex (15.7 mi / 25.2 km)

Exploring the natural features in Highland

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Highland is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Walkway Over the Hudson State Historic Park (0.9 mi / 1.4 km)
  • Bowdoin Park (8.5 mi / 13.6 km)
  • Mohonk Lake (10.6 mi / 17.1 km)
  • Mohonk Preserve Visitor Center (11.7 mi / 18.9 km)
  • Shawangunk Mountains (13.4 mi / 21.6 km)
  • Lake Minnewaska Beach (14.3 mi / 23.1 km)

How to get to and around Highland

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 16.6 mi (26.7 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Highland?
According to our research, houses are considered the most popular type of holiday property in Highland. But as you'd expect, everyone's idea of the perfect trip is bound to be different. Bookabach has holiday homes in a variety of shapes and sizes, so you're sure to find the best fit for your needs.
How much does it cost to rent a holiday home in Highland?
A range of things affect what you'll pay for a holiday home in Highland, like the length of stay, season and type of property. But, all of our holiday homes have one thing in common — incredible value. Simply enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Highland?
Prices for beach houses in Highland may vary depending on the style and size of the property and when you're travelling. Simply enter your dates of travel into Bookabach and how many guests to see available options and prices. From there you can use our filters to refine your search by amenities, ratings, nearby activities and more.
Are there pet-friendly holiday homes in Highland?
With five holiday homes that welcome pets, your furry little friend can join you on your Highland holiday. Use our filter tool to search our pet-friendly holiday homes and find a pad that'll set tails wagging on Bookabach.
What are popular home amenities in Highland?
Mountain views, a fireplace and a garden are rated the most popular home amenities in Highland. Whether you plan to travel as a party of one, with your other half or a group of family members, Bookabach will help you find a holiday home that suits your style with all the features you're looking for.
Are there large group holiday homes in Highland?
There are four holiday homes in Highland that can host a group of five or more people. From family reunions to special occasions, these stays have enough room to spend time with the people you love.
Are there holiday homes in Highland that welcome kids?
Highland has five family-friendly holiday homes to pick from. And discovering a stay that welcomes youngsters is simple with our "Properties good for families" filter. On top of having the entire place to yourselves, you'll also enjoy access to perks and conveniences such as bunk beds, full kitchens and private pools.
What are the top attractions for families in Highland?
There are loads of amazing things to do and see with the family in Highland, including:
  • Berean Park Beach
  • Franny Reese State Park
  • Franklin D Roosevelt Library & Museum
Are there holiday homes with WiFi in Highland?
You'll find three holiday homes with WiFi in Highland. If you want to disconnect from daily life during your escape, but still need to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Highland?
There are five holiday homes with air conditioning in Highland giving you that cooling breeze and extra bit of comfort. Just enter your desired travel dates and then use our handy filter tool to find stays with air conditioning.
How old do you have to be to rent a holiday home in Highland?
It's a good idea to check with the Highland holiday home you're looking at on Bookabach as the minimum age differs. However, it's normally 16, 18 or 21.
How long can I rent a holiday home in Highland for?
It's up to the Highland property. To browse a list of options offering extended stays, just enter your travel dates and guest number into the Bookabach search page. You can enjoy having the entire property to yourself, as well as comforts such as air conditioning, a fully-equipped kitchen and a yard to run around in. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.