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Highland vacation rentals

We found 1,748 vacation rentals — enter your dates for availability

Discover a selection of 19 homes and other vacation rentals in Highland that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you need and want for your stay, such as air conditioning and WiFi. No matter what you're looking for, you're sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Highland

Showing deals for:Aug 14 - Aug 21

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

8% off
Price is $686
$4,800 for 7 nights
All fees included
Farmette Roquette Hudson Valley

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Find out more about Highland

Why visit Highland

  • Outdoor Adventures: Highland is perfect for nature enthusiasts, offering stunning scenery and a variety of outdoor activities.
  • Historic Attractions: Explore local historic sites and bridges that showcase the rich heritage of the area.
  • Family-Friendly Atmosphere: Highland provides a welcoming environment, ideal for families seeking adventure and relaxation.
  • Charming Accommodations: Choose from cozy cottages, spacious rentals, and charming cabins for a memorable stay.
  • Vibrant Local Community: Experience the friendly vibe and create lasting memories while exploring the nearby neighborhoods.

Popular types of accommodation in Highland

Planning a getaway to Highland? The next exciting step is selecting your perfect accommodation. Whether you're looking for houses, charming cottages, or cozy cabins, Highland offers a variety of highland homes for rent. Explore furnished apartments and houses to find the ideal spot for your stay, ensuring a comfortable and memorable experience. Start your adventure with us and discover the best home rentals that Highland has to offer.

  • Houses: The top choice among travelers heading to Highland, these homes offer spacious accommodations perfect for families or groups.
  • Cottages: Second in popularity, these quaint and cozy homes provide a charming escape for a peaceful stay.
  • Cabins: A favorite retreat for outdoor enthusiasts, cabins offer a rustic ambiance surrounded by nature.
  • Apartments: Ideal for couples or solo travelers, apartments are a convenient option for a comfortable stay.
  • Chalets: These inviting mountain-style homes rank fifth, perfect for those seeking a unique vacation experience.**

Top attractions in and around Highland

Highland, New York, is perfect for outdoor and adventure enthusiasts, offering stunning scenery and cultural experiences. Visitors can explore local attractions such as historic sites, bridges, and medical centers, making it ideal for families and travelers seeking adventure. Whether you're looking for history or outdoor activities, Highland has a variety of points of interest to enrich your vacation experience.

  • Franklin D Roosevelt Library & Museum: This engaging library offers a deep dive into the life and legacy of President FDR, with rich historical exhibits and family-friendly activities that foster a sense of community and culture.
  • Franny Reese State Park: Nestled in stunning natural scenery, this state park invites adventure enthusiasts to explore its trails while enjoying breathtaking views of the Hudson River and surrounding landscapes.
  • Mohonk Lake: A picturesque destination 11 miles away, Mohonk Lake boasts beautiful beaches, romantic settings, and outdoor activities, perfect for relaxation and exploration in a serene environment.

Things to do recommended for couples

Highland offers a charming escape for couples. Enjoy a scenic hike at the nearby Walkway Over the Hudson, savor a wine tasting at local wineries, or take a romantic sunset cruise on the Hudson River. These experiences make for unforgettable moments together in this beautiful area.

Things to do recommended for families

Families visiting Highland can explore the scenic Walkway Over the Hudson, enjoy picnics at the beautiful Highland Landing Park, and embark on a fun-filled apple-picking adventure at nearby orchards during the fall. Don’t miss the local farms offering hands-on experiences for kids.

Things to do recommended for groups

Explore the scenic Walkway Over the Hudson for stunning views, or enjoy a wine tasting at a local vineyard. For adventure, take a group hike in the nearby Shawangunk Mountains, or unwind with a picnic at the beautiful Highland Landing Park.

*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 traveling with a group, family, pets, or planning an extended stay, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Highland with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Highland with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Highland: For many families, a trip isn’t truly enjoyable without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Highland: If you're seeking vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Highland

Highland, New York, offers an unforgettable outdoor adventure with its stunning scenery and family-friendly atmosphere. Explore the nearby neighborhoods for a relaxing getaway filled with friendly faces and breathtaking views. From spacious rentals to charming local spots, you'll find the perfect blend of adventure and tranquility. Don't miss the opportunity to experience Highland's vibrant vibes and create lasting memories in this beautiful region.

  • Poughkeepsie: Located a mere 2 miles from Highland, Poughkeepsie offers a blend of outdoor adventure and family-friendly activities. The city is known for its vibrant shopping areas and recreational spaces, making it an ideal spot for those looking to enjoy both leisure and fun. Visitors can explore educational institutions, including a modern college and a historic university, or relax by the scenic lakes that dot the landscape. Don't miss the chance to stroll along the Walkway Over the Hudson, a stunning park that provides breathtaking views of the river and surrounding areas.
  • New Paltz: Just 7 miles away from Highland, New Paltz is a charming town famed for its outdoor adventures and stunning scenery. This city is a haven for nature lovers, offering recreational areas perfect for hiking, skiing, and exploring the beautiful mountain landscapes. The nearby nature reserve is ideal for those looking to immerse themselves in the great outdoors. Additionally, the town's vibrant culture and quaint shops make it a delightful stop for visitors seeking unique experiences alongside its natural attractions.
  • Hudson Valley: Situated 10 miles from Highland, the Hudson Valley is renowned for its picturesque landscapes and outdoor adventures. This region is a popular destination for skiing, with several ski fields and resorts offering thrilling winter sports. Beyond skiing, visitors can enjoy the stunning views of lakes, mountains, and even beaches that make the Hudson Valley a diverse and beautiful area to explore. Whether you're hitting the slopes or relaxing by the water, the Hudson Valley promises an unforgettable experience in nature.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Also, booking an extended stay can lead to significant savings. To help you find the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental. We're here to support you in finding the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform where you can plan new adventures, resume your previous work, or manage your travel itinerary. You'll easily find your saved or booked properties organized under categories such as Potential, Upcoming, or Current Trips. To begin exploring the benefits of Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Walk on New York's wild side in Highland

Hidden away in Ulster County, Highland is a friendly hamlet known for its scenic trails, historic ranches, and rolling fruit orchards. Unlike the Big Apple, Highland is all about reconnecting with nature. Highland vacation rentals put you in the heart of New York State, with beautiful country cottages surrounded by grassy pastures. There is a string of country towns and pretty villages to explore, as well as a fine selection of wineries and orchards to visit.

Activities and attractions in Highland

Are you hoping to find attractions to visit while you're in town? Venture out of your cozy vacation rental and experience everything that makes Highland a one-of-a-kind vacation spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Ice Time Sports Complex (15.7 mi / 25.2 km)
  • Millbrook Vineyards and Winery (16.3 mi / 26.3 km)
  • Brotherhood Winery (22.5 mi / 36.2 km)

Town-hopping to Highland and beyond

In Highland, relaxation is the order of the day. From morning coffees on your private dock to board game nights by the fireplace, there's no better place to unwind than a Highland vacation rentals property. Beyond Highland itself, Ulster County is dotted with characterful towns. From historic Lloyd and orchard strewn Marlborough to laid-back Esopus and artsy New Paltz, getting to know Ulster's towns is all part of the fun. Highland is also an easy drive from Kingston's trendy Rondout District, a vibrant neighborhood known for its chic restaurants, quirky museums, and eclectic antique stores.

Balmy nights in the Highland countryside

Summer brings sunshine and sultry weather to New York State, making it a favorite with local vacationers. Highland vacation rentals maximise balmy summer evenings with sun-drenched decks and outdoor fire pits. This means you can throw your own BBQs and s'more roasting sessions. If you're planning on hiking, spring is a fantastic time to visit, with a sea of wildflowers to admire. In winter, New York State is dusted in a blanket of snow. Highland is no exception, and, while it can get chilly, it's a magical time to enjoy a staycation in New York state.

A Hudson River highlight

Sitting on the banks of the Hudson River, Highland is a beautiful introduction to rural New York. The region is dotted with easy hiking trails which means you can take the whole family along for a stroll. To the west you'll find the scenic Hudson Valley Rail Trail, another family-friendly gem that'll take you past creeks, ponds, and pine forests. The nearby Shawangunk Mountains region is a big draw for rock climbers, while parks like Black Creek Preserve and Shaupeneak Ridge are eternal favorites with picnickers.

How to get to and around Highland

Fly into Stewart Intl. Airport (SWF), the closest airport, located 16.6 mi (26.7 km) from the city center.

Frequently asked questions

What is the best area to stay in Highland, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Highland, New York, the best area to stay is near the scenic Hudson River waterfront. This charming neighborhood offers a serene atmosphere and beautiful views, making it an ideal spot for relaxation and exploration. You'll find a variety of vacation rentals, from cozy cottages to spacious homes, providing options that cater to different group sizes and preferences.

One of the top attractions in this area is the Walkway Over the Hudson State Historic Park, which features a stunning elevated walkway that spans the Hudson River and offers breathtaking views of the surrounding landscape. It's great for walking, biking, or simply enjoying a leisurely stroll. Additionally, the nearby Hudson Valley Rail Trail provides a picturesque route for outdoor enthusiasts, making it easy to immerse yourself in the natural beauty of the region.

Staying in this neighborhood not only places you close to these attractions but also ensures you have access to quaint local shops and delightful dining options.
How much does it cost to rent a vacation home in Highland?
Prices for vacation 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 vacation 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, travelers should focus on the nearby area of Kingston and the Catskill Mountains. The closest ski facilities are located at Hunter Mountain, about a 30-minute drive from Highland. In the Kingston area, vacation rentals typically include charming cabins and cozy cottages that offer the rustic charm of the Catskills. Many of these properties come with essential amenities such as fully equipped kitchens, fireplaces, and outdoor spaces for relaxation.

Additionally, you can find more modern condominiums and lodges in and around Hunter Village, which provide convenient access to the slopes. These accommodations often feature amenities like ski storage, hot tubs, and communal lounges, superb for unwinding after a day of skiing. Many properties also offer stunning mountain views, and some even have direct shuttle services to the ski resort, enhancing the overall experience for winter sports enthusiasts.

Travelers can also enjoy the natural beauty of the surrounding area, with opportunities for hiking and exploring the scenic beauty of the Catskills during the off-season.
What is the most popular type of vacation rental accomodation in Highland?
In Highland, vacation houses are the most popular type of rental, with about 16 available throughout the area. These homes offer spacious rooms with multiple bedrooms, fully equipped kitchens, and often outdoor spaces such as decks or patios, great for enjoying the scenic views of the Hudson Valley. Additionally, there are several apartments, villas, and cottages that provide alternative lodging options, each typically featuring cozy living areas and essential amenities to ensure a comfortable stay.
Are there any family house rentals in Highland?
In Highland, New York, families will find plenty of options with around 17 rentals available that cater to their needs. The area is known for its scenic beauty and outdoor activities, making it an excellent choice for family getaways. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to enjoy. Common amenities include Wi-Fi, air conditioning, and sometimes even game rooms or backyard areas for recreation.

Visitors will appreciate the proximity to nearby attractions, such as the Walkway Over the Hudson, which offers stunning views and a chance for family walks or bike rides. Additionally, the charming local parks provide ample opportunities for picnicking and outdoor fun. See all family-friendly rentals in Highland.
Can I rent a vacation home with a pool or hot tub in Highland?
In Highland, New York, there are several vacation homes available for rent that feature pools and hot tubs. This charming area, located along the Hudson River, offers a tranquil setting for travelers looking to relax and unwind. Many of these properties come equipped with amenities such as private pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, superb for both leisure and entertaining.

Travelers can enjoy the scenic beauty of the surrounding region, with opportunities for hiking, exploring local parks, and visiting nearby attractions. Find your rental in Highland with a pool or a hot tub.
Can I find long-stay vacation rentals in Highland?
A long-stay vacation rental in Highland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Highland?
In Highland, there are several pet-friendly house rentals available, offering a great option for travelers looking to enjoy the scenic beauty of the Hudson Valley with their furry companions. Many of these vacation rentals come equipped with amenities such as spacious backyards, outdoor seating areas, and fully stocked kitchens, making them comfortable for families or groups.

The area is known for its picturesque landscapes and outdoor activities, with nearby attractions like the Walkway Over the Hudson, a scenic pedestrian bridge that provides stunning views of the river and surrounding hills. This location is great for leisurely walks or bike rides with pets. Additionally, the nearby Kingston area features pet-friendly parks and nature trails, providing plenty of opportunities for outdoor adventures. See all pet-friendly rentals in Highland.
Are there any remote work vacation rentals in Highland?
In Highland, New York, there are about 21 vacation rentals suitable for remote work. This charming town, located along the Hudson River, offers a serene environment for those looking to blend work and leisure. Many properties come equipped with high-speed internet, making it easy to stay connected, as well as dedicated office spaces or areas where you can set up a workstation.

Travelers can expect amenities such as free Wi-Fi, comfortable living areas, and fully equipped kitchens, allowing for a pleasant work-from-home experience. The scenic surroundings provide opportunities for relaxation after work hours, with access to local parks and outdoor activities along the river. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Highland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Highland with parking available—perfect for families or travelers 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 vacation rental amenities typically include fully equipped kitchens, which allow guests to prepare their own meals and enjoy the convenience of home dining. Many rentals also feature blenders for smoothie lovers or those who enjoy homemade drinks. Outdoor spaces like decks or patios are common, providing a ideal setting for relaxation or outdoor dining. Additionally, a fireplace is often included in these rentals, creating a cozy atmosphere during cooler evenings. Onsite parking is also a standard amenity, ensuring easy access for guests traveling by car.
When is the best time to visit Highland for a vacation rental?
April marks the height of the travel season in Highland, New York, making it an ideal time to book a vacation rental. As spring unfolds, the landscape comes alive with vibrant blooms and mild temperatures, typically ranging from the low 40s to mid-60s Fahrenheit. This is a great backdrop for outdoor activities like hiking in nearby parks and enjoying the scenic beauty of the Hudson Valley.

The peak season runs from March through May, attracting visitors who are eager to experience the region's natural beauty and partake in various festivals and events. During April, outdoor enthusiasts can explore local trails, visit charming farms, and enjoy the blossoming scenery that characterizes this time of year.

For those considering a more budget-friendly option, December presents a quieter atmosphere, ideal for cozy getaways and enjoying the peaceful charm of Highland. While it may be less bustling, the beauty of the winter landscape and the opportunity for local winter activities still provide memorable experiences.

Ultimately, the best time to visit Highland for a vacation rental depends on your personal preferences. If you enjoy vibrant spring activities and a lively option, April is your best bet. Alternatively, if you prefer a more tranquil escape in a winter wonderland, December offers its own unique charm.
How early should I book a Highland vacation rental?
Book your Highland vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Highland, New York, United States of America?
In Highland, New York, visitors can enjoy a variety of attractions that showcase the area's natural beauty and rich history. The Walkway Over the Hudson, a remarkable pedestrian bridge, offers stunning views of the Hudson River and is superb for walking or biking. Nearby, the historic Huguenot Street in New Paltz features well-preserved 18th-century stone houses and museums that highlight the region's historic past.

For outdoor enthusiasts, the Mohonk Preserve provides a wealth of hiking trails and scenic vistas, making it a great spot for nature walks and photography. The area is also close to the picturesque Minnewaska State Park Preserve, which boasts waterfalls, cliffs, and beautiful lakes for swimming and picnicking.

Additionally, the charming downtown area of Highland features local shops and eateries, providing a delightful atmosphere for leisurely strolls and dining experiences.
Can I change or cancel my Highland home rental booking on Vrbo?
To find Highland vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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