Photo by Karen Wirtz

Highland Holiday Rentals

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Holiday Rentals in Highland

The Scenic Mansion With Breathtaking View
9.6 out of 10, Exceptional, (11)
"So nice we keep coming back. Can't recommend highly enough and will be back in the spring. "
The Scenic Mansion With Breathtaking View
Our home is perfect for relaxing and having lots of fun, with near by activity’s
10.0 out of 10, Exceptional, (1)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, (26)
"This place was great! The apartment itself is a great size for 2 people. The yard was pretty big with lots of seating, firepit, an awesome guitar shaped chiminea, nice sized pool, outdoor tv in the gazebo. The owner, Ryan, came later at night and left the next morning. He was super nice and very helpful!"
The price is AU$483
includes taxes & fees
30 Nov - 1 Dec
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Streamside Cottage Half Mile to Town of Woodstock
10.0 out of 10, Exceptional, (224)
"We had a wonderful time at this comfy cottage by the water. Just a few minutes from tow but totally peaceful and laid back. Cottage lives up to its fine reviews. We were lucky to have unusually warm weather so we could enjoy the outside more than we expected for November."
Streamside Cottage Half Mile to Town of Woodstock
The Farm at Hyde Park
9.8 out of 10, Exceptional, (63)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (42)
"2nd time around here-perfect location to everything.Great place and grounds.Will be back."
Cozy Relaxing Retreat in Saugerties, NY
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
9.6 out of 10, Exceptional, (50)
"Our family enjoyed our time at the property- it was a great place for us all to gather. The property managers were incredibly helpful and responsive to the few things that needed attention during our stay. The pool area is the shining star of this home. You can expect the house/ furnishings to be in mostly good shape and as photographed-. The layout of the bedrooms/ shared bathrooms did surprise us a bit despite careful review of photos and listing video tour. Overall great stay!"
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (23)
"Every thing was good! Thank you for quickly responding to my request to add an additional night. Thank you for being pet friendly."
The price is AU$249
includes taxes & fees
30 Nov - 1 Dec
Mid-Century DJ’s Dream
Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (34)
"This house was adorably charming and perfect for a weekend getaway in Woodstock. We loved watching wildlife from the beautiful kitchen windows and the privacy the property provided. Our pup loved the front sun room and keeping an eye on the yard. Thank you for sharing your home!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (169)
" Beautiful house! Great location! The house overall exceeded our expectations! A bit bright in the mornings, good to know in case you are looking to try and sleep in. King bed in the master is super comfortable and the shower is awesome! Would definitely stay again."
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Esopus Escape: Pool, Hot Tub & Media Room
9.6 out of 10, Exceptional, (18)
"We were in the area for a wedding. The house was great. Hot tub was fabulous. Beautiful couple of days. Just one note for safety: the metal railing on the left side of the steps from the driveway heading up to the house is coming loose or rather, is very, very loose so as to not be useable. Just could be a bit dangerous particularly at night. Otherwise, was absolutely lovely."
Esopus Escape: Pool, Hot Tub & Media Room
The Studio at the Inn at High Falls
7.8 out of 10, Good, (22)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The Studio at the Inn at High Falls
Hamptons on the Hudson in South Saugerties
10.0 out of 10, Exceptional, (12)
"Our group of 7 women had a great time in the house. Beautiful property. Nice view of the Hudson. Lots of amenities. Well stocked kitchen. Cozy and comfortable. We enjoyed the Nespresso machine. Lots of room for us to spread out and to hang out together in the living room and enjoy a meal in the dining room. We would definitely stay again. "
Hamptons on the Hudson in South Saugerties
5-Star New Barn Home - Music Studio, Views & Hot Tub
10.0 out of 10, Exceptional, (25)
"Perfect house and perfect location. Look forward to this trip yearly. Stephen makes everything easy and is always available. Great escape and property! "
5-Star New Barn Home - Music Studio, Views & Hot Tub
Kingston Crawfish Cottage Near Catskills!
9.8 out of 10, Exceptional, (10)
"We enjoyed our stay at the crawfish cottage. It was clean and had everything we needed. The host, Diane, was great, friendly and very responsive. "
Kingston Crawfish Cottage Near Catskills!
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (32)
"This is a very nice home with a well equipped kitchen. The living room and dining areas are spacious. We could have used more closet space but it wasn’t that much of an issue. The driveway could use grading but had ample parking."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is AU$532
includes taxes & fees
18 Nov - 19 Nov
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Sexiest Lil Cabin in Saugerties, NY
8.6 out of 10, Excellent, (7)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
Sexiest Lil Cabin in Saugerties, NY
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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Other types of properties in Highland you may be interested in

Rodeway Inn & Suites New Paltz - Hudson Valley
2.0 star property
7.2 out of 10, Good, (660)
"Our experience was excellent! Our room was clean and comfortable, the beds were very comfortable and the shower had nice water pressure. The office personnel was very helpful with anything that we needed. Rodeway Inn was also centrally located for visiting family at the college, wandering and eating in New Paltz and kayaking!! All within 10 minutes!! We will definitely stay here again! Last but not least, the price was reasonable. "
The price is AU$139
includes taxes & fees
18 Nov - 19 Nov
Rodeway Inn & Suites New Paltz - Hudson Valley
SureStay Plus Hotel by Best Western Highland Poughkeepsie
2.5 star property
7.6 out of 10, Good, (791)
"The front desk clerk was very helpful and friendly "
The price is AU$194
includes taxes & fees
3 Dec - 4 Dec
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Best Western Plus Kingston Hotel And Conference Center
2.5 star property
7.8 out of 10, Good, (1005)
"Good and convenient"
The price is AU$243
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Kingston Hotel And Conference Center
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.

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?

The Farm at Hyde Park: This holiday home rental outside of Highland is located in a rural location, and has a fireplace, a patio and a BBQ 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 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.