57+ Vacation Rentals & Holiday Homes in Highland |
  1. USA
  2. New York
  3. Poughkeepsie
  4. Highland

Highland Accommodations - Hotels & Rentals

About Highland Vacation Rentals

Discover More than 57 Incredible Getaway Rentals Available in Highland. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Highland.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Highland, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Highland. The Average Size of Places to Stay Near Highland is 1706.62 ft², with Prices Averaging US $855 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Highland. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

Show more
Show less

Top Hotels & Vacation Rentals in Highland

Type Count
Vacation Homes 35
Holiday Apartments 10
Villas 2
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Highland

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Highland with Online Reservations.

Weather in Highland, NY

View the weather forecast for Highland before booking your Highland Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities HighlandGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World HighlandGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Walkway Over the Hudson State Historic Park
Olana
Vanderbilt Mansion
Berean Park Beach
Harriman State Park
Apple Greens Golf Course
Dia Beacon
Kykuit
Lyndhurst Castle
West Park Winery
Francis Lehman Loeb Art Center
Franklin D Roosevelt Library & Museum
Storm King Art Center
Val-Kill
Catskill Mountains
United States Military Academy
Marist College
Train Station

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Lyndhurst Castle 198 Properties
Vanderbilt Mansion 198 Properties
Dia Beacon 198 Properties
Harriman State Park 198 Properties
Olana 198 Properties
Storm King Art Center 198 Properties
Franklin D Roosevelt Library & Museum 198 Properties
Francis Lehman Loeb Art Center 198 Properties
Kykuit 198 Properties
Clintondale 34 Properties
Town of Lloyd 33 Properties
West Park 29 Properties

Frequently Asked Questions About Highland?

What are the top hotels, lake houses & vacation rentals in Highland?

We provide an array of great vacation destinations in Highland. If you are looking to stay in or around the Highland area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Highland:

Which hotel, lake house, or vacation rental in Highland is best for families?

Searching for a family-friendly getaway in Highland? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Highland?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 57 in the Highland area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Highland.


People Also Ask

Online Reservation in Highland

Recently Booked Hotels, Resorts, or Rentals in Highland