Highland Vacation Rentals
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
Our top choices for Highland vacation rentals
1. Amazing 3-bedroom house with AC in adorable Highland
Amazing 3-bedroom house with AC in adorable Highland
2. Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
3. Our home is perfect for relaxing and having lots of fun, with near by activity’s
Our home is perfect for relaxing and having lots of fun, with near by activity’s
4. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
5. Cabin in the Heart of the Hudson Valley, Cabin 1
Cabin in the Heart of the Hudson Valley, Cabin 1
6. Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
7. Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
8. Many perfect sunsets at the magical house on the lake
Many perfect sunsets at the magical house on the lake
Find vacation rentals that suit your style
Top Highland Hotel Reviews
Comfort Suites Fishkill near Interstate 84
Find out more about Highland
Everything you need to know about Highland vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Highland vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $86 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Highland rentals
At Expedia, we put the best Highland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Explore a world of travel with Expedia
- Luxury Hotels in Poughkeepsie
- Fishkill Hotels
- Poughkeepsie Hotels
- Cheap Hotels in Poughkeepsie
- Cabin Rentals in Hudson Valley
- Cold Spring Hotels
- Hotels near Culinary Institute of America
- Hotels near LEGOLAND® New York
- Kingston Hotels
- Rhinebeck Hotels
- Hotels near Marist College
- Middletown Hotels
- New Paltz Hotels
- Newburgh Hotels
- Motels in Poughkeepsie
- Beacon Hotels
- Cabin Rentals in The Catskills
- Hyde Park Hotels
- Highland Hotels
- Flights to Poughkeepsie
- Flights from Tampa (TPA) to New York (NYC)
- Flights from NYC-All Airports
- Flights from Cincinnati (CVG) to New York (NYC)
- Flights from San Antonio (SAT) to New York (NYC)
- Flights from Pittsburgh (PIT) to New York (NYC)
- Flights from Charleston (CHS) to New York (NYC)
- Flights from Seattle (SEA) to New York (NYC)
- Flights from Stewart Intl.
- Flights from Indianapolis (IND) to New York (NYC)
- Flights from St. Louis (STL) to New York (NYC)
- Flights from Portland (PDX) to New York (NYC)
- Flights from Columbus (CMH) to New York (NYC)
- Flights from Chicago (ORD) to New York (NYC)
- Flights from Richmond (RIC) to New York (NYC)
- Flights from Toronto (YYZ) to New York (NYC)
- Flights from London (LON) to New York (NYC)
- Flights from Cleveland (CLE) to New York (NYC)
- Flights from Los Angeles (LAX) to New York (NYC)
- Flights from Fort Lauderdale (FLL) to New York (NYC)
- Flights from Raleigh (RDU) to New York (NYC)
- Flights from San Diego (SAN) to New York (NYC)
- Flights from Detroit (DTW) to New York (NYC)
- Flights to Newburgh
- Flights from Poughkeepsie
- Flights from Austin (AUS) to New York (NYC)
- Flights from Miami (MIA) to New York (NYC)
- Flights from Atlanta (ATL) to New York (NYC)
- Flights from Kansas City (MCI) to New York (NYC)
- Flights from New Orleans (MSY) to New York (NYC)
- Flights from Houston (HOU) to New York (NYC)
- Flights from Boston (BOS) to New York (NYC)
- Flights from Minneapolis (MSP) to New York (NYC)
- Flights from Dutchess County
- Flights from Sacramento (SMF) to New York (NYC)
- Flights from Orlando (MCO) to New York (NYC)
- Flights from Westchester County
- Flights from Tel Aviv (TLV) to New York (NYC)
- Flights from Dallas (DFW) to New York (NYC)
- Stone Ridge Vacation Rentals
- Staatsburg Vacation Rentals
- Pleasant Valley Vacation Rentals
- Clinton Corners Vacation Rentals
- Hopewell Junction Vacation Rentals
- Kerhonkson Vacation Rentals
- Millbrook Vacation Rentals
- Clintondale Vacation Rentals
- New Paltz Vacation Rentals
- Wappingers Falls Vacation Rentals
- Pine Bush Vacation Rentals
- Fishkill Vacation Rentals
- Kingston Vacation Rentals
- Wallkill Vacation Rentals
- New Windsor Vacation Rentals
- High Falls Vacation Rentals
- Port Ewen Vacation Rentals
- Beacon Vacation Rentals
- Hyde Park Vacation Rentals
- Lake Katrine Vacation Rentals
- Walden Vacation Rentals
- Newburgh Vacation Rentals
- Red Hook Vacation Rentals
- Accord Vacation Rentals
- Poughkeepsie Vacation Rentals
- Orange Lake Vacation Rentals
- Hudson Valley Vacation Rentals
- Hurley Vacation Rentals
- Rhinebeck Vacation Rentals
- Cornwall-On-Hudson Vacation Rentals
