Discover Your Ideal Highland, New York Vacation Rental for a Memorable Getaway
Discover Your Perfect Highland Vacation Homes
Best Vacation Homes in Highland
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Highland Luxury Rentals
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Highland Pet Friendly Vacation Rentals
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Highland Large Vacation Homes
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Why Choose Rent By Owner for your Highland Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Highland
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here can enhance your experience, as seasonal variations in this destination influence the ambiance and activities available, making it essential to consider your preferred weather and crowd levels when booking your vacation rentals in Highland, New York.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer days, making it ideal for exploring outdoor activities in this scenic region. Many visitors choose this time to experience the area’s natural beauty at its peak.
Fall (September to November)
Autumn brings vibrant foliage and crisp air, attracting those seeking a picturesque retreat in this destination. It’s a popular season for experiencing the region's natural transformation and enjoying seasonal festivities.
Off-Season Highlights
Winter (December to February)
Cold winter months offer a quieter period with fewer visitors, providing a peaceful escape. The winter scenery adds charm for those interested in cozy getaways or winter sports nearby.
Spring (March to May)
Early spring is a tranquil time to visit as the region awakens from winter. Fewer tourists mean more relaxed explorations of the area's natural sights and outdoor experiences.
Weekly Weather Forecast for Highland
How to Book Your Highland Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Highland
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining on a private patio or deck with scenic views of the surrounding landscape.
- Take advantage of a spacious yard for family games, picnics, or relaxing under the open sky.
- Relax by a fire pit during cool evenings to gather and share stories in a cozy outdoor setting.
- Explore nearby hiking trails directly from your rental for outdoor adventures in the region.
- Make use of an outdoor swimming pool to cool off and unwind during warmer months.
- Benefit from well-maintained grounds ideal for morning yoga or outdoor fitness routines.
- Utilize available outdoor grilling facilities for preparing delicious meals with a view of the outdoors.
Top Attractions Around Highland
What attractions are nearby?
Discover nearby outdoor adventures, scenic parks, and cultural attractions that make this destination in Highland, New York, a perfect spot for your next getaway.

Family Activities
- Walkway Over the Hudson State Historic Park: Experience stunning river views and open-air walks on one of the world's longest elevated pedestrian bridges, perfect for family outings in this scenic region.
- The Mid-Hudson Children's Museum: Engage your kids with hands-on exhibits and interactive play spaces that make exploring the local culture both fun and educational here.
- Discover outdoor adventures like hiking and picnicking amidst breathtaking natural landscapes that are ideal for family activities in the area.
- Haviland Hollow Farm: Enjoy a family-friendly farm experience with opportunities for animal interactions and seasonal activities within this charming part of the region.
Adult Activities
- Hiking along the Hudson River waterfront: Explore scenic trails offering breathtaking views, perfect for outdoor enthusiasts seeking active adventures here.
- Visiting local wineries and breweries: Enjoy tasting tours at nearby vineyards and breweries that highlight the region's rich agricultural heritage and craft beverage scene.
- Discovering historical sites and museums: Engage with the area's history through well-preserved landmarks and educational exhibits that provide cultural insights.
- Enjoying outdoor recreational activities in state parks: Take advantage of parks offering opportunities for picnicking, birdwatching, and relaxing amidst natural beauty nearby.
Other Places to Stay in Highland, NY
Highland Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Outdoor Adventures: Take advantage of the region’s scenic parks and trails by scheduling outdoor activities early to enjoy the best weather and avoid crowds during your stay.
- Explore Local Cuisine: Savor the authentic flavors offered in nearby eateries or consider booking a vacation rental with a fully equipped kitchen to prepare regional dishes at your own pace.
- Discover Hidden Gems: Engage with local guides or hosts to uncover lesser-known spots that showcase the area’s unique charm and natural beauty beyond the typical tourist attractions.
- Maximize Your Comfort and Convenience: Choose a well-located vacation rental that offers amenities tailored to your needs, ensuring a relaxing and hassle-free experience here in the region.
Transportation Options
- New York State Thruway (Interstate 87): This major highway provides convenient access to Highland and the surrounding region, making road trips straightforward from nearby cities and attractions.
- Local Bus Services: Local bus options connect the area with neighboring towns and transportation hubs, offering an affordable way to explore without driving yourself.
- Amtrak Station in Poughkeepsie: The Amtrak train station offers convenient rail travel for visitors coming from major cities across the country, with easy connections to Highland's regional transportation network.
- Taxi and Ride-Sharing Services: Reliable taxi companies and ride-sharing options are available here, providing flexible and direct transportation for your travel convenience within the area.
Local Customs Options
- Local Brewmaster Traditions: You can experience the region's renowned craft beer heritage through local breweries that celebrate Highland's distinctive brewing techniques.
- Seasonal Harvest Celebrations: Participating in seasonal festivals around here allows you to enjoy time-honored customs centered on the area's abundant agricultural bounty.
- Historic Architectural Styles: The region showcases unique architectural designs that reflect its rich history, offering a glimpse into Highland's cultural evolution.
- Community Arts and Crafts: Engaging with locally produced arts and crafts provides insight into the area's creative traditions and community pride.
Frequently Asked Questions About Highland?
1. What are the top vacation rentals in Highland?
There are a lot of options in Highland. If you plan on staying in the Highland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland:
- Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs.
- Highland Home 4BR Near New Paltz, Wedding Venues & Hudson Valley
- Mountain Ridge Retreat - Private & Peaceful Getaway. Family & Pet Friendly
- Spacious 4BD Country Gem - Fire Pit & Chill Vibes
- Studio with private pool, firepit, cabana, grill, & washer/dryer-Dogs ok
- Bright & Spacious Hudson Valley Home with Pool
- 5 miles from New Paltz, close to Vassar, SUNY ideal for weddings and graduations
- 13k Sq Ft Family Compound Around Pvt 37-Acre Lake - 164 Acre Retreat
- Beautiful modern villa with pool suana hot tub.
- Private 37 Acre Lake Estate On 164 Acres - 11 Br
2. Which vacation homes in Highland are best for families?
If you are looking for a family-friendly vacation home in Highland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland:
3. How many Rentbyowner vacation rentals are available in Highland?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 57 in the Highland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Highland.
4. What is the cancellation policy for vacation rentals in Highland, New York?
5. How do I secure my reservation at a Highland vacation rental?
6. Are there any additional fees associated with booking a vacation rental here?
7. What amenities can I expect in a vacation rental in this region?
8. How close are Highland vacation rentals to popular transportation options?
Highland Top Rated Vacation Rentals
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