Highland Holiday Rentals from NZ$143: 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 spacious living area with a staircase, a dining table, and a sofa.

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

Highland

Pinal

includes taxes & fees

21 Nov - 22 Nov

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

16 Nov - 17 Nov

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

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

Highland

Laurie G.

includes taxes & fees

16 Nov - 17 Nov

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

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

Stone Ridge

Michael C.

includes taxes & fees

1 Dec - 2 Dec

A wooden vanity with a mirror, two pendant lights, and a folded towel.

5. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

Stone Ridge

Catherine

includes taxes & fees

22 Nov - 23 Nov

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.

includes taxes & fees

16 Nov - 17 Nov

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

7. A Cozy Private Suite in a Country Home near New Paltz

Wallkill

Carrie

includes taxes & fees

16 Nov - 17 Nov

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

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

Fishkill

Anonymous traveller

includes taxes & fees

29 Nov - 30 Nov

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

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

Staatsburg

elizabeth

includes taxes & fees

1 Dec - 2 Dec

A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

10. 1 King Bed | Non-Smoking, Kitchen, Shower

Fishkill

Anonymous traveller

includes taxes & fees

11 Dec - 12 Dec

A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

11. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Rhinebeck Village

Heather O.

includes taxes & fees

6 Dec - 7 Dec

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

12. Mid-Century DJ’s Dream

Staatsburg

Alexandra R.

includes taxes & fees

18 Nov - 19 Nov

13. 2 Full Beds | Non-Smoking, Kitchen

Fishkill

Anonymous traveller

includes taxes & fees

29 Nov - 30 Nov

A building entrance with a brick facade, a double door, and a sign labeled 'Lobby.'

14. Studio 6 Fishkill|King bed|Hearing Access|Kitchen

Fishkill

Anonymous traveller

includes taxes & fees

3 Dec - 4 Dec

A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

15. Campfire Cottage: Fireplace, fire pit & no chores!

Kingston

Jim R.

includes taxes & fees

19 Nov - 20 Nov

16. 1 Queen Bed | Non-Smoking, Kitchen

Fishkill

Ray

includes taxes & fees

29 Nov - 30 Nov

A hotel lobby with a reception desk, seating area, and a wall-mounted television.

17. 1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen

Fishkill

Anonymous traveller

includes taxes & fees

10 Dec - 11 Dec

A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

18. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Stone Ridge

Tarun

includes taxes & fees

1 Dec - 2 Dec

A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

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

Newburgh

George J.

includes taxes & fees

29 Nov - 30 Nov

A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

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

Newburgh

Albert

includes taxes & fees

16 Nov - 17 Nov

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Find holiday rentals that suit your style

Top Highland Hotel Reviews

A modern bathroom with a white sink, mirror, and toilet.

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

8/10 Good

Bridget

A courtyard with a fire pit, outdoor seating, and a covered area with string lights.

Homewood Suites by Hilton Poughkeepsie

Poughkeepsie

10/10 Excellent

Jeremy

A modern hotel lobby with wooden flooring, yellow chairs, a long dining table, and pendant lighting.

Hampton Inn & Suites Poughkeepsie

Crown Heights

10/10 Excellent

Anna

A hotel entrance with a brick facade, a glass door entrance, and a paved walkway.

Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

10/10 Excellent

Anne

A Courtyard by Marriott hotel with a modern design, large windows, and a well-maintained lawn.

Courtyard by Marriott Poughkeepsie

Poughkeepsie

10/10 Excellent

Anonymous traveller

A multi-story hotel with a central entrance, stone pillars, and a brick facade.

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Hyde Park

10/10 Excellent

Stephen

A spacious living area with a stone fireplace, comfortable seating, a kitchen with bar seating, and large windows.

Residence Inn by Marriott Poughkeepsie

Poughkeepsie

8/10 Good

Peter

A hotel room with a large bed, two bedside tables with lamps, a headboard with a mirror, a window with curtains, and an air conditioning unit.

Roosevelt Inn of Hyde Park

Hyde Park

10/10 Excellent

CornelisSmit

A buffet with various food items, including omelets and baked goods, served in metal containers.

Holiday Inn Express & Suites Kingston-Ulster by IHG

Lake Katrine

8/10 Good

Andrew

A hotel reception area with a reception desk, a waiting area with sofas, and a glass door entrance.

Quality Inn Poughkeepsie

Arlington

8/10 Good

I stayed at the Quality Inn Poughkeepsie just as it was completing renovations in June, 2022, so everything was sparkling new and in perfect working order -- except, as usual, the hotel internet. I would have given the property a 5-star review, except they have farmed out their internet to a dodgy provider, and it simply doesn't work. The property is on the very edge of Poughkeepsie, a few walkable blocks from Vassar College and one block from a 24-hour diner. Strangely, the Quality Inn (with...

Anonymous traveller

A spacious lobby with a high ceiling, a reception desk, a seating area with blue sofas and armchairs, and a visible Pepsi refrigerator.

Comfort Suites Fishkill near Interstate 84

Fishkill

8/10 Good

David

An outdoor patio with a fire pit, seating, and a building in the background.

Courtyard by Marriott Kingston

Kingston

10/10 Excellent

Robert

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 favorite 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 depends 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 NZ$143 per night. Entering your travel dates in the search wizard you might find 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.

Highland Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Highland holiday rentals

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

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

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

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

5. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

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

7. A Cozy Private Suite in a Country Home near New Paltz

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

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

10. 1 King Bed | Non-Smoking, Kitchen, Shower

11. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

12. Mid-Century DJ’s Dream

13. 2 Full Beds | Non-Smoking, Kitchen

14. Studio 6 Fishkill|King bed|Hearing Access|Kitchen

15. Campfire Cottage: Fireplace, fire pit & no chores!

16. 1 Queen Bed | Non-Smoking, Kitchen

17. 1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen

18. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

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

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

Find holiday rentals that suit your style

Top Highland Hotel Reviews

Home2 Suites By Hilton Poughkeepsie

8/10 Good

Find out more about Highland

Highland holiday rentals: An excellent choice for every season

How to find incredible deals on Highland rentals

Frequently Asked Questions

Can I find holiday rentals in Highland?

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

How many holiday rentals will I find in Highland?

What can I see and do in Highland?

What are holiday rentals like in Highland?

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