Best Vacation Homes in Highland
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
5 Guests
650 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $424/Night
7 Nights - US $2,971
House
10.0(1 Review)
11 Bedrooms
9 Baths
29 Guests
10763.91 ft²
EV Charge Station- Parking
View- Air Conditioner
US $9,099/Night
7 Nights - US $63,692
Hotel
8.0(1004 Reviews)
1 Bath
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $100/Night
7 Nights - US $700
House
9.8(16 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
Internet
US $246/Night
7 Nights - US $1,725
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
2497.23 ft²
- Parking
Pool- Balcony/Terrace
- Internet
US $551/Night
7 Nights - US $3,855
Apartment
9.4(8 Reviews)
1 Bedroom
1 Bath
6 Guests
850 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $427/Night
7 Nights - US $2,987
New
Cottage
2 Bedrooms
1 Bath
6 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $349/Night
7 Nights - US $2,442
House
10.0(75 Reviews)
4 Bedrooms
5 Baths
8 Guests
4100 ft²
Private Pool
Hot Tub- Parking
- Pool
US $2,171/Night
7 Nights - US $15,197
Highland Luxury Rentals
House
9.4(3 Reviews)
14 Bedrooms
8 Baths
29 Guests
10764 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $6,423/Night
7 Nights - US $44,958
House
10.0(6 Reviews)
6 Bedrooms
6 Baths
15 Guests
8000 ft²
- Private Pool
- Parking
- Pool
Spa
US $4,080/Night
7 Nights - US $28,557
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
2078 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,145/Night
7 Nights - US $8,017
New
House
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $992/Night
7 Nights - US $6,942
House
9.6(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
2700 ft²
- Hot Tub
- Air Conditioner
- Internet
Child Friendly
US $967/Night
7 Nights - US $6,766
House
4 Bedrooms
3 Baths
10 Guests
2701.74 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $950/Night
7 Nights - US $6,650
House
1 Bedroom
3 Baths
8 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Pet Friendly
US $900/Night
7 Nights - US $6,300
Villa
10.0(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $800/Night
7 Nights - US $5,598
Highland Pet Friendly Vacation Rentals
House
10.0(34 Reviews)
4 Bedrooms
3 Baths
8 Guests
2400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $606/Night
7 Nights - US $4,241
Apartment
8.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $252/Night
7 Nights - US $1,764
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
Ocean View- Balcony/Terrace
- View
- Kitchen
US $260/Night
7 Nights - US $1,817
US $325/Night
7 Nights - US $2,275
House
9.6(12 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $795/Night
7 Nights - US $5,562
New
Apartment
1 Bedroom
1 Bath
2 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $226/Night
7 Nights - US $1,582
New
House
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $582/Night
7 Nights - US $4,076
House
8.2(22 Reviews)
4 Bedrooms
5 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $406/Night
7 Nights - US $2,843
Highland Large Vacation Homes
Cabin
10.0(17 Reviews)
5 Bedrooms
3 Baths
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $645/Night
7 Nights - US $4,517
House
9.5(4 Reviews)
5 Bedrooms
5 Baths
10 Guests
2002.09 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $389/Night
7 Nights - US $2,725
House
10.0(1 Review)
5 Bedrooms
5 Baths
16 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $660/Night
7 Nights - US $4,623
House
9.6(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $585/Night
7 Nights - US $4,092
House
4.7(3 Reviews)
4 Bedrooms
4 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,196/Night
7 Nights - US $8,372
House
5 Bedrooms
3 Baths
11 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $913/Night
7 Nights - US $6,389
House
10.0(2 Reviews)
11 Bedrooms
8 Baths
16 Guests
12800 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $1,877/Night
7 Nights - US $13,141
Villa
10.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $525/Night
7 Nights - US $3,672
Why Choose Rent By Owner for your Highland Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
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.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
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.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
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.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Highland
How to Book Your Highland Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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
Walkway Over the Hudson State Historic Park
Apple Greens Golf Course
Berean Park Beach
Clintondale
West Park Winery
West Park
Lyndhurst Castle
Vanderbilt Mansion
Harriman State Park
Dia Beacon
Town of Lloyd
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.
Highland Vacation Rental Frequently Asked Questions
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.
- Private 4BR Retreat on 10 Acres Near New Paltz - The Cherry House
- Spacious 4BD Country Gem - Fire Pit & Chill Vibes
- Mountain Ridge Retreat - Private & Peaceful Getaway. Family & Pet Friendly
- 5 miles from New Paltz, close to Vassar, SUNY ideal for weddings and graduations
- Bright & Spacious Hudson Valley Home with Pool
- Charming Vacation House w/Pool & HotTub
- 1850s Barn Studio on 4.5 Hudson Valley Acres!
- Beautiful modern villa with pool suana hot tub.
- Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
2. How many vacation rentals have private pools in Highland?
There are 2 vacation rentals with private pools near Highland. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Highland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 69 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.
5. What is the cancellation policy for vacation rentals in Highland, New York?
Cancellation policies vary depending on the property listing. You should review the specific cancellation terms listed with the rental before booking or contact the property owner directly to clarify any questions.
6. How do I secure my reservation at a Highland vacation rental?
Reservations are typically secured through a secure booking process on the listing page. Make sure to provide accurate information and complete all required steps, or reach out to the host if you need assistance.
7. Are there any additional fees associated with booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or local taxes are usually detailed on the property listing. It’s advisable to read the full breakdown or ask the owner for clarification before confirming your reservation.
8. What amenities can I expect in a vacation rental in this region?
Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. For specific amenities, consult the individual listing or contact the host directly to ensure it meets your needs.
9. How close are Highland vacation rentals to popular transportation options?
Most rentals are conveniently located near key transportation routes within the area. To find out about proximity to airports, train stations, or bus stops, review the property details or contact the owner for detailed location information.
Highland Top Rated Vacation Rentals
House
9.8(29 Reviews)
3 Bedrooms
2 Baths
6 Guests
3600 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $501/Night
7 Nights - US $3,504
New
House
8.0(1 Review)
4 Bedrooms
1 Bath
8 Guests
2500 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $468/Night
7 Nights - US $3,277
House
3 Bedrooms
2 Baths
7 Guests
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
US $661/Night
7 Nights - US $4,627
House
10.0(15 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $375/Night
7 Nights - US $2,625
Apartment
10.0(11 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $185/Night
7 Nights - US $1,296
Apartment
9.8(33 Reviews)
3 Bedrooms
1 Bath
4 Guests
800 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $268/Night
7 Nights - US $1,876
Apartment
9.8(26 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $323/Night
7 Nights - US $2,258
House
5.0(3 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $759/Night
7 Nights - US $5,313
