Holiday Rentals Highland from £70: Find Short-Term Rentals & Holiday Accommodations

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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In two weeks

In two months

In three months

In four months

Our top choices for Highland holiday 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

includes taxes & fees

29 Sept - 30 Sept

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.

includes taxes & fees

29 Sept - 30 Sept

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.

includes taxes & fees

5 Oct - 6 Oct

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

includes taxes & fees

29 Sept - 30 Sept

5. Hudson Escape W/ Hot Tub + Bridge View

Highland

includes taxes & fees

1 Oct - 2 Oct

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

29 Sept - 30 Sept

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

includes taxes & fees

29 Sept - 30 Sept

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

8. Mid-Century DJ’s Dream

Staatsburg

Alexandra R.

includes taxes & fees

4 Oct - 5 Oct

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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 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, apart-hotels, 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 £70 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.

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Our top choices for Highland holiday 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 holiday 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

Frequently asked questions

Go further with the Expedia app

Search Holiday Rentals in Highland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Highland holiday 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 holiday rentals that suit your style

Top Highland Hotel Reviews

Ramada by Wyndham Newburgh/West Point

Find out more about Highland

Frequently asked questions

Go further with the Expedia app