Highland holiday lettings

We found 1,695 holiday rentals — enter your dates for availability

Discover a selection of 18 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 Mar - 13 Mar

Image gallery for Farmette Roquette Hudson Valley

Property grounds
9.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Farmette Roquette Hudson Valley

Germantown, NY

7% off
Price is £4,051
for 7 nights, 1 room
£579 per night
includes taxes & fees
Farmette Roquette Hudson Valley

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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:

  • 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)
  • Millbrook Vineyards and Winery (16.3 mi / 26.3 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 best area to stay in Highland when booking a holiday rental?
When considering a holiday rental in Highland, New York, the area around the Hudson River offers a delightful experience. This picturesque location is not only scenic but also conveniently situated near some of the region's top attractions. Staying here will allow you easy access to the Walkway Over the Hudson State Historic Park, a stunning pedestrian bridge that provides breathtaking views of the river and surrounding landscapes. Additionally, the nearby Franklin D. Roosevelt Presidential Library and Museum is a fascinating destination for history enthusiasts, offering insights into the life and legacy of one of America's most popular presidents.
How much does it cost to rent a holiday home in Highland?
Prices for holiday rentals in Highland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Highland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Highland holiday house rentals?
You can find great discounts on house rentals in Highland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Highland ski resort rentals?
For ski resort rentals near Highland, New York, the best options can be found in the nearby area of Kingston and the Catskills region. Specifically, the town of Hunter, located roughly 30 minutes from Highland, is home to the popular Hunter Mountain ski resort. Here, visitors can find a variety of rental properties, including condos and cabins that cater to different group sizes. Many of these accommodations feature amenities such as fully equipped kitchens, spacious living areas with fireplaces, and easy access to ski lifts and trails.

In addition to Hunter, the towns of Tannersville and Windham also offer excellent rental options. Tannersville is known for its quaint village atmosphere and proximity to the slopes, with several lodges and chalets that often include amenities like hot tubs, ski storage, and outdoor decks with beautiful mountain views. Windham, another popular ski destination, provides a range of properties from modern condos to rustic cabins, many of which come with additional perks such as game rooms, spacious dining areas, and ample parking.
What is the most popular type of holiday rental accomodation in Highland?
In Highland, holiday houses are the most popular type of rental, with around 17 available in the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces ideal for enjoying the picturesque surroundings. In addition to holiday houses, several apartments and cottages are also offered, providing a range of options for travellers seeking a more compact or quaint stay. Many of these accommodations are situated near local attractions, such as the scenic Walkway Over the Hudson and the beautiful landscapes of the Hudson Valley, making them great bases for exploring the region.
Are there any family house rentals in Highland?
In Highland, New York, there are quite a few family-friendly house rentals available—around 18 in total. This charming area offers a variety of properties suitable for families, with many located near the scenic Hudson River and the picturesque landscapes of the Hudson Valley.

Visitors can expect spacious living areas, fully equipped kitchens for family meals, and outdoor spaces where children can play safely. Common amenities include Wi-Fi and air conditioning, ensuring a comfortable stay for all.
Can I rent a holiday home with a pool or hot tub in Highland?
In Highland, New York, there are several holiday homes available for rent that feature pools or hot tubs, making it a delightful choice for those seeking relaxation and recreation. The area is known for its scenic views and proximity to the Hudson River, providing a peaceful backdrop for a getaway.

Travellers can expect a variety of amenities in these rentals, such as private pools, spacious outdoor areas for lounging, and hot tubs superb for unwinding after a day of exploring. Many properties also come equipped with modern kitchens, ideal for preparing meals, and comfortable living spaces for family gatherings.
Can I find long-stay holiday rentals in Highland?
A long-stay holiday rental in Highland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Highland?
In Highland, there are several pet-friendly house rentals available, making it a great choice for travellers accompanied by their furry friends. Many of these holiday rentals feature spacious living areas, fully equipped kitchens, and private outdoor spaces, allowing guests to relax comfortably during their stay.
Are there any remote work holiday rentals in Highland?
In Highland, New York, there are several remote work holiday rentals available, with around 23 options to choose from. This picturesque town, set against the backdrop of the scenic Hudson River Valley, offers a variety of properties that cater to those looking to work remotely while enjoying the tranquillity of the area. Many of these rentals come equipped with dedicated office spaces, high-speed Wi-Fi, and comfortable desks and chairs, ensuring a productive working environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Highland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Highland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Highland?
In Highland, popular rental amenities include kitchens equipped with cookware, dishware, and utensils, allowing guests to prepare their own meals. Many properties also feature microwaves for convenience, and patios where travellers can relax and enjoy the outdoors. Additionally, free Wi-Fi is commonly available in the rentals, ensuring guests can stay connected during their stay.
When is the best time to visit Highland for a holiday rental?
April marks the height of the travel season in Highland, New York, making it an ideal time for holiday rentals. This month is particularly vibrant as the landscape bursts into bloom, inviting visitors to enjoy the scenic beauty of the Hudson Valley. The peak season runs from March to May, during which outdoor enthusiasts flock to the area for hiking, cycling, and exploring the picturesque surroundings.

With average temperatures in April hovering around 15°C, the weather is generally mild and pleasant, great for sightseeing and outdoor activities. The charming local parks and the nearby Walkway Over the Hudson State Historic Park offer fantastic views and leisurely walks, ideal for those who appreciate nature's splendour.

For travellers looking for a more budget-friendly option, December is a delightful alternative. Although it's the low season, visitors can experience the enchanting winter atmosphere, complete with holiday decorations and local festivities. The quieter streets provide a chance to explore the area's unique shops and cosy eateries without the usual crowds.
How early should I book a Highland holiday rental?
Book your Highland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Highland?
In Highland, New York, visitors can explore several noteworthy attractions that showcase the area's natural beauty and history. The Walkway Over the Hudson State Historic Park is a prominent feature, offering breathtaking views of the Hudson River from its elevated walkway, making it a popular spot for walkers and cyclists alike. Nearby, the historic Mid-Hudson Bridge connects Highland to Poughkeepsie and is an iconic landmark worth visiting.

For those who enjoy the outdoors, the scenic trails of the Hudson Highlands State Park are superb for hiking and nature walks, with opportunities to see local wildlife and stunning vistas. The area is also home to the beautiful Highland Landing Park, which features picnic areas and access to the river, providing a lovely spot for relaxation.
Can I change or cancel my Highland home rental booking on Vrbo?
To find Highland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Highland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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