Highland holiday rentals

We found 1,764 holiday rentals — enter your dates for availability
Discover a selection of 24 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:6 Nov - 13 Nov

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Why visit Highland

  • Historic charm: Highland celebrates its rich heritage with well-preserved historic sites, bridges and period houses that offer a glimpse into its storied past.
  • Scenic outdoors: Enjoy picturesque landscapes along the Hudson River and lush parks ideal for leisurely walks and family picnics.
  • Neighbourhood appeal: Experience the quaint, family-friendly atmosphere of local communities, perfect for a relaxed holiday.
  • Outdoor adventures: Abundant opportunities for hiking and exploring the natural beauty of the area await outdoor enthusiasts.
  • Serene escapes: Discover a peaceful retreat with charming rural vistas and a calm, inviting ambience.

Popular types of accommodation in Highland

Discover the charm of Highland, New York, a picturesque town nestled along the banks of the Hudson River. With an array of attractions, from scenic parks to historical sites, Highland offers a perfect backdrop for your holiday. Our visitors often prefer private holiday homes, cosy cottages, and rustic cabins for a comfortable stay. Whether you’re seeking hillside homes or family-friendly accommodations, Highland provides a delightful experience for every traveller.

  • Private Holiday Homes: These spacious and fully-equipped residences offer a perfect retreat for families or groups seeking comfort and privacy during their stay in Highland.
  • Cottages: Charming and quaint, these traditional dwellings provide a cosy atmosphere, ideal for a romantic getaway or a peaceful escape.
  • Cabins: Nestled in nature, these rustic lodgings offer a unique experience, combining the outdoors with homely comforts for an adventurous stay.
  • Apartments: Conveniently located, these self-contained units are perfect for those wanting easy access to local amenities while enjoying a home-like environment.
  • Chalets: Offering a blend of style and comfort, these alpine-style lodgings are perfect for those wanting a touch of luxury amidst stunning surroundings.**

Top attractions near Highland

Highland, New York, offers a charming escape with its rich historical legacy and scenic outdoor adventures. Visitors can explore historic sites, bridges, and houses that celebrate the area's cultural heritage. Whether seeking an adventure or a peaceful retreat, the city's blend of outdoor experiences and historical allure provides a delightful setting for all travellers.

Things to do recommended for couples

Discover Highland's charm with scenic walks and cosy dining spots. Enjoy a relaxing day exploring local hidden gems and winding streets, perfect for couples seeking a romantic retreat.

Things to do recommended for families

Families visiting Highland can explore the scenic Walkway Over the Hudson, where children can enjoy stunning views and fresh air. The nearby Franklin D. Roosevelt Presidential Library and Museum offers engaging exhibits, making it a perfect spot for curious minds to learn about history together.

Things to do recommended for groups

In Highland, New York, groups can savour local culinary delights, explore scenic parks, and partake in historical walking tours, ensuring an engaging and immersive visit tailored for group travellers.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Highland

If you're travelling with a group, as a family, bringing along your pets, or seeking extended stays, be sure to apply the appropriate filters according to your priorities. Here are some helpful booking tips for Stayz.

  • Traveling to Highland with a group: Consider how many bedrooms you require, as well as facilities like a fully-equipped kitchen or an outdoor area for social gatherings. Fortunately, Stayz allows you to filter for all these features and more.
  • Traveling to Highland with young kids: Traveling with young children can be demanding. You must ensure their comfort and safety, along with age-suitable facilities, such as a private swimming pool. It is also advisable to consider your closeness to family-friendly attractions.
  • Taking your pets with you to Highland: For many, a family holiday is not complete without the presence of their four-legged companion. If you identify with this, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at ease.
  • Planning for a long term stay visiting Highland: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Highland

Highland, New York offers a delightful escape for those who appreciate outdoor adventures and scenic landscapes. Visitors can explore charming neighbourhoods with a family-friendly atmosphere, enjoy sunny weather, and take in the local vistas while experiencing the unique appeal of Highland town. The area provides a relaxed, business-friendly ambience with opportunities to appreciate local real estate and homes, perfect for a memorable and serene holiday.

  • Poughkeepsie: Poughkeepsie, a bustling city merely 3km from Highland, offers an enticing blend of outdoor adventures and family-friendly activities. Visitors can explore modern educational institutions, scenic lakes and historic colleges, all within convenient reach. The city’s vibrant shopping areas and recreational spaces provide ample opportunities for both leisurely strolls and spirited family outings, making it a charming destination for any traveller.
  • New Paltz: Situated 11km from Highland, New Paltz is a picturesque city that invites you to embrace the great outdoors. Known for its captivating scenery and adventurous spirit, this locale offers a variety of recreational areas, ski fields, and even a dedicated ski area for winter enthusiasts. The proximity of a serene lake, a nature reserve, and a majestic mountain ensures that every visit is filled with natural splendour and exhilarating experiences.
  • Hudson Valley: Located 16km from Highland, the Hudson Valley is a region celebrated for its breathtaking landscapes and outdoor pursuits. It presents a harmonious mix of scenic beauty and adventure, with opportunities to enjoy ski resorts, ski fields and more adventurous ventures. With a lovely lake, a towering mountain, and a welcoming beach nearby, travellers will find that this area offers a remarkable setting for both relaxation and active exploration.

Best time to go to Highland

If you're planning a trip to Highland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January26.8°F (-2.9°C)Light RainMostly SunnyModerately LowAverage
February28.6°F (-1.9°C)Light RainMostly SunnyAverageSlightly Low
March36.3°F (2.4°C)Light RainMostly SunnyModerately HighSlightly Low
April48.0°F (8.9°C)Light RainMostly SunnyModerately HighSlightly Low
May59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
June67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
July73.2°F (22.9°C)Light RainMostly SunnyModerately HighSlightly High
August71.1°F (21.7°C)Light RainMostly SunnyAverageSlightly High
September64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
October52.9°F (11.6°C)Light RainMostly SunnyAverageAverage
November40.6°F (4.8°C)Light RainMostly SunnyModerately LowAverage
December32.7°F (0.4°C)Light RainMostly SunnyModerately LowSlightly High

Booking with Stayz is simple

If you're keen to cut costs on your upcoming journey, consider keeping your travel dates flexible as prices can vary. Additionally, opting for an extended stay often translates to considerable savings. To discover the ideal Stayz property that meets your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board offers a user-friendly platform where you can easily create new trips, resume your planning, or manage your existing itineraries. Here, you can find your saved or booked properties neatly organised into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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)
  • SplashDown Beach (12.3 mi / 19.8 km)
  • Whitecliff Vineyard (12.6 mi / 20.3 km)
  • Beekman Golf Course (13 mi / 20.9 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)
  • 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)
  • Minnewaska State Park (14.4 mi / 23.2 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. Stayz 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 Stayz 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 Stayz.
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, Stayz 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 Stayz.
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 Stayz 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 Stayz 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.