Highland Vacation Rentals from $93: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Highland?

Private 37 Acre Lake Estate on 164 Acres - 11 BR : This highly rated vacation home rental in Highland is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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In two weeks

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Our top choices for Highland vacation rentals

A modern kitchen with white cabinets, a built-in toaster, a blender, and a window with a view of trees.

1. Amazing 3-bedroom house with AC in adorable Highland

Highland

$470 nightly

Oct 5 - Oct 6

Total with taxes and fees

A wooden porch with white rocking chairs and a hanging flower basket.

2. Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley

Highland

Ellen E.

$326 nightly

Sep 29 - Sep 30

Total with taxes and fees

A porch with white railings and multiple chairs.

3. Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Highland

Rebecca D.

$325 nightly

Oct 5 - Oct 6

Total with taxes and fees

A spacious living area with a staircase, a dining table, and a sofa.

4. Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland

Pinal

$604 nightly

Sep 29 - Sep 30

Total with taxes and fees

5. Hudson Escape W/ Hot Tub + Bridge View

Highland

$814 nightly

Oct 1 - Oct 2

Total with taxes and fees

A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

6. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie

Nicole Y.

$348 nightly

Sep 29 - Sep 30

Total with taxes and fees

A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

7. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

Wallkill

Carrie

$114 nightly

Sep 29 - Sep 30

Total with taxes and fees

A deck with a red umbrella, wooden chairs, and a table with potted plants.

8. Mid-Century DJ’s Dream

Staatsburg

Alexandra R.

$219 nightly

Oct 4 - Oct 5

Total with taxes and fees

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Top Highland Hotel Reviews

Ramada by Wyndham Newburgh/West Point

10/10 Excellent

"Was a pleasant overnight stay"

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"First the good....the hotel was very clean. That is paramount to me, so I gave a very good rating due to that. There is no elevator so if you cannot do the stairs, you need to ask for a first-floor room. Even though we can easily do the stairs, taking up suitcases can be a challenge. Our room was pretty small, but it had all the amenities (TV, microwave, fridge). Breakfast was better than expected being the area was pretty small. No wheat bread - only white and plain bagels. Eggs and sausage were really good as was the waffle maker. All in all, although the beds were comfortable, I'm glad we were only there one night. Best for a brief layover......"

SureStay Plus Hotel by Best Western Highland Poughkeepsie

8/10 Good

"This is a cost-effective option for the region. The rooms are clean, but the motel has a run-down feel to it. When we arrived, the card-key generator wasn't working. Staff let us in to our room, and we got working keys the next morning, but I haven't run into that problem anywhere else. Likewise, the card-reader on a side entrance, which would have been very useful for accessing our room, was broken, necessitating a longer walk around to the front of the motel. In the shower, the plate behind the dial had come away from the wall. It didn't affect the quality of the shower (which was fine in terms of heat and pressure), but it's not a good look. Breakfast was good and plentiful (I had scrambled eggs and sausages, but there's also cereal, various breads, and a waffle-maker, with orange and apple juice). My wife and I would come back, and thus the "Good" overall rating."

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 $93 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.

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Frequently asked questions

Can I find vacation rentals in Highland?

Yes, we offer vacation rentals close to the most popular points of interest in Highland, or you can select a more remote option if you want a relaxing place to stay. Highland is known for its riverfront and mountain views.

What are some of the best vacation home rentals in Highland?

Private 37 Acre Lake Estate on 164 Acres - 11 BR: This highly rated vacation home rental in Highland is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Highland?

With 30 Expedia vacation rentals, you're sure to find just the right place for your Highland stay.

What can I see and do in Highland?

Walkway Over the Hudson State Historic Park and Berean Park Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Franny Reese State Park and Apple Greens Golf Course are other places worth a visit.

What are vacation rentals like in Highland?

Vacation rentals are privately owned properties you can book for a couple days or more in Highland. Vacation rentals offer extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Highland vacation rentals

1. Amazing 3-bedroom house with AC in adorable Highland

2. Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley

3. Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

4. Our home is perfect for relaxing and having lots of fun, with near by activity’s

5. Hudson Escape W/ Hot Tub + Bridge View

6. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

7. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

8. Mid-Century DJ’s Dream

9. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

10. The Studio at the Inn at High Falls

11. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

12. Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

13. Cabin in the heart of the Hudson Valley, Cabin 2

14. Hudson Valley Farm Getaway- West/Llama Lover Lane

15. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

16. Cabin in the Heart of the Hudson Valley, Cabin 1

17. Dream getaway apartment in the foot of Gunks Ridge

18. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

19. Mossy Moody Cabin in High Falls, NY

20. Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Find vacation rentals that suit your style

Top Highland Hotel Reviews

Ramada by Wyndham Newburgh/West Point

Hyatt Place Poughkeepsie / Hudson Valley

Quality Inn Hyde Park Poughkeepsie North

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Beekman Arms and Delamater Inn

Find out more about Highland

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