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Highland Holiday Rentals

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Holiday Rentals in Highland

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

9.8 out of 10, Exceptional, (6)
"My family and I had a great time at this property. Located on a beautiful property. Very relaxing and coordinating with the property owner was very easy. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

The Scenic Mansion With Breathtaking View

8.8 out of 10, Excellent, (18)
"This was a extended work visit, and the property was perfect for us and the host was very accommodating whenever needed. I can see a wedding, reunion or a quiet getaway for a large family at this location."
The Scenic Mansion With Breathtaking View

Private 37 Acre Lake Estate on 164 Acres - 11 BR

9.4 out of 10, Exceptional, (3)
"Work & Play getaway for myself and some close friends. The weather, property and location near New Paltz, NY could not have been better."
Private 37 Acre Lake Estate on 164 Acres - 11 BR

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

10.0 out of 10, Exceptional, (194)
"Wonderful place to rest and recharge."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (44)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is AU$485
includes taxes & fees
5 Oct - 6 Oct
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (55)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
The price is AU$373
includes taxes & fees
1 Oct - 2 Oct
Esopus Creek modern Tiny house Retreat!

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (36)
"Great place for a quiet stay"
The price is AU$541
includes taxes & fees
1 Oct - 2 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (17)
"The property was perfectly secluded while being close to town. We observed lots of wildlife including deer, a woodchuck family, and a turtle laying eggs! The house was roomy and comfortable with just enough upscale elegance that made us feel pampered."
The price is AU$914
includes taxes & fees
2 Oct - 3 Oct
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (30)
"Lovely property, well-maintained, clean and comfortable, and the host was especially responsive to all communications. Highly recommend."
Hamptons on the Hudson in South Saugerties

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is AU$346
includes taxes & fees
13 Oct - 14 Oct
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

The Farm at Hyde Park

9.8 out of 10, Exceptional, (79)
"This was the perfect option for us for a nearby wedding. We ate twice at the River & Post (excellent) and went into Rhinebeck for the Sunday market. The property itself was very accommodating and had everything we needed. The kitchen was well equipped, beds comfortable, and plenty of seating options in the main room. The outside area was also a perfect place for coffee in the morning and we loved the chickens running around. Glenn could not have been nicer. Highly recommend!"
The Farm at Hyde Park

Chestnut on Willow Lake

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is AU$893
includes taxes & fees
1 Oct - 2 Oct
Chestnut on Willow Lake

‘A Quiet Place’ 3-bedrm house. Mid-Hudson Valley.

10.0 out of 10, Exceptional, (17)
"Our stay was great."
‘A Quiet Place’ 3-bedrm house. Mid-Hudson Valley.

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (16)
"The gatehouse was a perfect spot for a girls trip getaway. Secluded enough, but close to some local activities and restaurants! Cozy vibe and place had everything we needed!"
Charming Cottage in the Heart of the Shawangunks

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (74)
"Nice property Very clean and comfortable "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (308)
"We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

3 bedroom house. AC in Village of Montgomery. Safe location. Gourmet kitchen.

2.0 star property
3 bedroom house. AC in Village of Montgomery. Safe location. Gourmet kitchen.

New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

10.0 out of 10, Exceptional, (21)
"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

10.0 out of 10, Exceptional, (93)
"We loved this stay! The yurt was absolutely charming! Such an amazing location within easy distance of hiking and the Empire State Trail bicycle path, plus great dining in New Paltz and Kingston."
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
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

Find out more about Highland

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$346 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?

Our home is perfect for relaxing and having lots of fun, with near by activity’s: This highly rated holiday home rental in Highland offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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 19 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 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 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.