Highland Holiday Rentals from AU$131: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Highland has to offer?

Private 37 Acre Lake Estate on 164 Acres - 11 BR : This highly rated holiday home rental in Highland is located on the waterfront, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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Our top choices for Highland holiday rentals

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

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

Highland

Laurie G.

includes taxes & fees

12 Oct - 13 Oct

A porch with white railings and multiple chairs.

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

Highland

Rebecca D.

includes taxes & fees

12 Oct - 13 Oct

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

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

Highland

Pinal

includes taxes & fees

13 Oct - 14 Oct

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

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

Poughkeepsie

Nicole Y.

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Staatsburg

jay c.

includes taxes & fees

19 Oct - 20 Oct

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

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

Wallkill

Carrie

includes taxes & fees

3 Nov - 4 Nov

A brick building with a sign reading 'Lobby' in front.

7. 2 Full Beds | Non-Smoking, Kitchen

Fishkill

Anonymous traveller

includes taxes & fees

5 Nov - 6 Nov

A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

8. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

Stone Ridge

Michael C.

includes taxes & fees

3 Nov - 4 Nov

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Top Highland Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

8/10 Good

"The place was clean and the breakfast good. It was quite expensive though."

Beekman Arms and Delamater Inn

8/10 Good

"This was my first time at this property. My room was not in the Beekman Arms but in its sister property a few blocks away. The room was large and nicely decorated, it was very clean and the bed was comfortable. The bathroom was very nice and soap, shampoo and towels were supplied in abundance. Breakfast was included and consisted of all sorts of breads, fruit, yogurt, hard boiled eggs, juiced coffee and teas. This was served in a separate building near the residential building Our room was on the third floor so the lack of an elevator pushed my 94 year old body a bit. I would definitely come back to the Beeckman Arms but next time I’ll request a downstairs room."

The Thayer Hotel at West Point

10/10 Excellent

"Incredible staff. Great location. Attention to guests superlative.West Point tours were fantastic. Only complaint was that it is extremely pricey. Which is understandable considering where we stayed. We ate there for 2 dinners, one lunch, and 1 breakfast. Meals are expensive but were great except for a breakfast that was stone-cold for $24 each."

Find out more about Highland

Everything you need to know about Highland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Highland holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland holiday rentals we have selected for you start as low as AU$131 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland holiday 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 holiday.

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.

Frequently asked questions

Can I find holiday rentals in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. Highland is known for its riverfront and mountain views.

What are some of the best holiday rentals that Highland has to offer?

Private 37 Acre Lake Estate on 164 Acres - 11 BR: This highly rated holiday home rental in Highland is located on the waterfront, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Highland?

With 30 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Highland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Highland holiday rentals

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

2. 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

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

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

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

7. 2 Full Beds | Non-Smoking, Kitchen

8. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

9. 1 King Bed | Non-Smoking, Kitchen, Shower

10. Cabin in the heart of the Hudson Valley, Cabin 3

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

12. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

13. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

14. Mid-Century DJ’s Dream

15. 2 Queen Beds | Non-Smoking, Kitchen

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

17. Cabin in the heart of the Hudson Valley, Cabin 4

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

19. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

20. 1 Queen Bed | Non-Smoking, Kitchen

Find holiday rentals that suit your style

Top Highland Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

Beekman Arms and Delamater Inn

Kingston Regency Inn

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Hyatt Place Poughkeepsie / Hudson Valley

The Thayer Hotel at West Point

DoubleTree by Hilton Poughkeepsie Convention Center

Red Roof Inn PLUS+ Poughkeepsie

Studio 6 Extended Stay Fishkill Westage Center NY

Find out more about Highland

Frequently asked questions

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