A suspension bridge over a river with autumn foliage and distant hills.

Highland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Highland vacation rentals

A bedroom with a bed, a window, a heater, and a door leading to another room.

1. Hudson Valley Duplex: Hike, Sip + Explore!

Hudson Valley Duplex: Hike, Sip + Explore!
3.0 star property
Highland
Hudson Valley Duplex: Hike, Sip + Explore!
A porch with white railings and multiple chairs.

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

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Highland
10.0 out of 10, Exceptional, (2 reviews)
"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"
United States
Rebecca D.
The price is CA $242
CA $562 total
includes taxes & fees
Oct 8 - Oct 9
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
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

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (13 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is CA $365
CA $1,051 total
includes taxes & fees
Oct 13 - Oct 14
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A wooden porch with white rocking chairs and a hanging flower basket.

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

Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
Highland
9.6 out of 10, Exceptional, (11 reviews)
"Would definitely stay again"
United States
Laurie G.
The price is CA $284
CA $619 total
includes taxes & fees
Oct 12 - Oct 13
Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

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

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is CA $94
CA $193 total
includes taxes & fees
Nov 3 - Nov 4
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is CA $228
CA $617 total
includes taxes & fees
Oct 8 - Oct 9
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.4 out of 10, Exceptional, (10 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is CA $160
CA $300 total
includes taxes & fees
Oct 19 - Oct 20
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
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

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Stone Ridge
8.8 out of 10, Excellent, (19 reviews)
"Clean cozy will be staying again"
United States
Michael C.
The price is CA $130
CA $240 total
includes taxes & fees
Oct 28 - Oct 29
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

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

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is CA $102
CA $115 total
includes taxes & fees
Nov 3 - Nov 4
1 King Bed | Non-Smoking, Kitchen, Shower
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

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

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is CA $212
CA $336 total
includes taxes & fees
Oct 15 - Oct 16
Cabin in the heart of the Hudson Valley, Cabin 4
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

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

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is CA $98
CA $352 total
includes taxes & fees
Oct 14 - Oct 15
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A forest campsite with a tent, a fire pit, and a bench.

12. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
The price is CA $122
CA $216 total
includes taxes & fees
Oct 12 - Oct 13
Glamping Tent & Campsite by Minnewaska State Park
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

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

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
The price is CA $178
CA $324 total
includes taxes & fees
Oct 8 - Oct 9
Cabin in the Heart of the Hudson Valley, Cabin 1
A brick building with a sign reading 'Lobby' in front.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is CA $124
CA $143 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

15. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very good, (46 reviews)
"The pictures are misleading"
United States
Jia
The price is CA $160
CA $386 total
includes taxes & fees
Oct 8 - Oct 9
The Studio at the Inn at High Falls
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

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

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is CA $245
CA $319 total
includes taxes & fees
Oct 8 - Oct 9
Hudson Valley Farm Getaway- West/Llama Lover Lane
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is CA $125
CA $380 total
includes taxes & fees
Nov 3 - Nov 4
Campfire Cottage: Fireplace, fire pit & no chores!
A deck with a red umbrella, wooden chairs, and a table with potted plants.

18. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (60 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is CA $264
CA $413 total
includes taxes & fees
Nov 3 - Nov 4
Mid-Century DJ’s Dream
A cozy living room with a sofa, a coffee table with candles, and a fireplace.

19. Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (31 reviews)
"Wonderful property will definitely book again."
United States
Jane G.
The price is CA $115
CA $255 total
includes taxes & fees
Nov 3 - Nov 4
Dream getaway apartment in the foot of Gunks Ridge
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

20. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is CA $176
CA $410 total
includes taxes & fees
Nov 3 - Nov 4
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Highland Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"Hot breakfast. Quiet room."
Marlene 2-night trip
Posted 16 hours ago
Holiday Inn Express Poughkeepsie by IHG

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland vacation rentals we have selected for you start as low as CA $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 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. 

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.