Highland Vacation Rentals from $95: Search Short-Term Rentals

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

The Church : Visitors like this Highland vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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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

$432 nightly

Sep 9 - Sep 10

Total with taxes and fees

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.

$381 nightly

Aug 27 - Aug 28

Total with taxes and fees

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

$627 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

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

Staatsburg

jay c.

$175 nightly

Sep 1 - Sep 2

Total with taxes and fees

A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

5. Private, Cozy, Clean apartment in lovely Hyde Park

Hyde Park

Janet M.

$185 nightly

Aug 31 - Sep 1

Total with taxes and fees

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

6. Mid-Century DJ’s Dream

Staatsburg

Alexandra R.

$199 nightly

Aug 31 - Sep 1

Total with taxes and fees

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

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

Stone Ridge

Michael C.

$159 nightly

Sep 7 - Sep 8

Total with taxes and fees

A compact kitchen with blue cabinets, a white stove, and yellow chairs.

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

Kingston

Brendan B.

$222 nightly

Aug 31 - Sep 1

Total with taxes and fees

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Top Highland Hotel Reviews

Beekman Arms and Delamater Inn

10/10 Excellent

"I have a habit of calling ahead a day or two before my arrival to make sure my reservation is confirmed. I made numerous attempts to to so and no one was answering the phones? It took from 1.30pm - 8.30pm to reach someone.... Other than the trash can missed being empty, all was very nice. I will gladly stay again!"

DoubleTree by Hilton Poughkeepsie Convention Center

8/10 Good

"First-class hotel, except for the breakfast. My spouse and child waited for 40 minutes to be fed until they gave up and left. They observed other patrons not getting any breakfast, either. Probably just as well, as the prices were outrageously high (even if the service had been even remotely competent). The drive-thru window at Dunkin' Donuts provided better service and at much more reasonable prices. I would stay at the Doubletree again, but I would plan to avoid their restaurant at all costs."

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Everything was great...fun bar, very nice rooms with kitchen small living room area. But the reason we stayed was the Culinary Institute. The staff told us it was a 5 min walk, Please be advised it is not 5 min more like 10-15 min. The hill from the hotel is step and it's also steep to go up to the Culinary Institute. If your young its fine. But people who don't walk to well should expect to take and Uber maybe 7-10.00$ We took and Uber home because it was dark out after we had our dinner. You can pick up and Uber very easy by the students dorms."

Studio 6 Extended Stay Fishkill Route 9 NY

8/10 Good

"Not fancy, but very clean and it looks like it was updated recently. The location is good, as the many hotels in the area show. This is a budget friendly place, but nicer than most in that category. The staff was great, and Mike at the front desk was especially helpful. I wasn’t thrilled with the $10 fee for staying less than a week, and the $2 housekeeping fee is strange (especially since there wasn’t any during my four night stay… I didn’t need it or miss it but if you go out the way to charge for it… ). Anyway if you want a clean and safe budget stay, it’s a great option."

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 $95 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?

The Church: Visitors like this Highland vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Highland?

With 25 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 scenic spots to enjoy the outdoors, whereas Franklin D Roosevelt Library & Museum is one of the cultural attractions. 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.

Highland Vacation Rentals

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

5. Private, Cozy, Clean apartment in lovely Hyde Park

6. Mid-Century DJ’s Dream

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

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

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

10. The Studio at the Inn at High Falls

11. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

12. Studio6 Fishkill 2 Full Beds, Mobil Tub, Nsmk Kitchen

13. 1 King Bed | Non-Smoking, Kitchen, Shower

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

15. Glamping Tent & Campsite by Minnewaska State Park

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

17. 1 Queen Bed | Non-Smoking, Kitchen

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

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

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

Find vacation rentals that suit your style

Top Highland Hotel Reviews

Beekman Arms and Delamater Inn

Find out more about Highland

Explore a world of travel with Expedia

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