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Highland Holiday Rentals

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Tonight
8 Sept - 9 Sept
Tomorrow
9 Sept - 10 Sept
This weekend
12 Sept - 14 Sept
Next weekend
19 Sept - 21 Sept

Holiday Rentals in Highland

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

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

9.8 out of 10, Exceptional, (6)
"Enjoyed the stay. Nice place to relax for a weekend."
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Studio with private pool, firepit, cabana, grill, & washer/dryer-Dogs ok
Terrace/patio

Studio with private pool, firepit, cabana, grill, & washer/dryer-Dogs ok

10.0 out of 10, Exceptional, (9)
"Great place to stay and beautiful grounds. "
Studio with private pool, firepit, cabana, grill, & washer/dryer-Dogs ok
The Scenic Mansion With Breathtaking View
Outdoor dining

The Scenic Mansion With Breathtaking View

8.8 out of 10, Excellent, (18)
"This house is so grand and perfect for a destination wedding, corprate retreat or family reunion. Host was wonderful!"
The Scenic Mansion With Breathtaking View
Private 37 Acre Lake Estate on 164 Acres - 11 BR
14 bedrooms, iron/ironing board, travel cot, WiFi

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
Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (51)
"We enjoyed our stay. It was very comfortable and very clean and communication with the host was always available, when needed. We look forward to staying here again!!"
The price is HK$1,157
HK$1,872 total
includes taxes & fees
22 Sept - 23 Sept
Esopus Creek modern Tiny house Retreat!
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (27)
"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
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

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

9.8 out of 10, Exceptional, (31)
"Great place for a quiet stay"
The price is HK$2,020
HK$2,593 total
includes taxes & fees
21 Sept - 22 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.8 out of 10, Exceptional, (13)
"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
Living area

1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

2.0 star property
9.0 out of 10, Wonderful, (8)
"Gary is a great host and provides a wonderful experience. He is the best and it was a very nice stay. Best host I have had before."
The price is HK$1,358
HK$1,590 total
includes taxes & fees
10 Sept - 11 Sept
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (76)
"We enjoyed our stay...lots to do in the area. Glen was very friendly and accommodating. "
The Farm at Hyde Park
Charming Cottage in the Heart of the Shawangunks
Fridge, microwave, oven, stovetop

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (15)
"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
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (88)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Cozy Bedroom With Fireplace
Fireplace

Cozy Bedroom With Fireplace

10.0 out of 10, Exceptional, (1)
"Very nice and cozy room. Golden was great."
The price is HK$1,286
HK$1,702 total
includes taxes & fees
8 Oct - 9 Oct
Cozy Bedroom With Fireplace
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

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

10.0 out of 10, Exceptional, (307)
"Perfect place to enjoy family and rest. Open floor plan and scenic lake made it so enjoyable for us. Don is a great communicator with easy check in and check out. A"
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
2 bedrooms, iron/ironing board, WiFi, bed sheets

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
Large,Cozy,Bright Apartment, Business Themed.
Interior

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is HK$3,156
HK$5,220 total
includes taxes & fees
21 Sept - 22 Sept
Large,Cozy,Bright Apartment, Business Themed.
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
1 bedroom, travel cot, free WiFi, bed sheets

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

10.0 out of 10, Exceptional, (92)
"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
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Private kitchen

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

2.0 star property
The price is HK$1,102
HK$1,802 total
includes taxes & fees
14 Sept - 15 Sept
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
Outdoor pool

NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool

10.0 out of 10, Exceptional, (131)
"The house was comfortable for a large group, beautiful setting, private, clean, etc. We enjoyed our stay."
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Children’s area

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (43)
"This was a wonderful place to stay right by the center of woodstock."
The price is HK$1,404
HK$2,419 total
includes taxes & fees
14 Sept - 15 Sept
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

  • View our selection of featured holiday rentals in Highland
  • Use the map to find apartments and other holiday homes in the Highland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland while they last

Look no further and take a look at our great range of rental properties in Highland!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.