Photo by Karen Wirtz

Highland Holiday Rentals

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Holiday Rentals in Highland

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, 21 reviews
"place was great, exactly as described...ryan was great, no issues all was as described...however sent 2 notes via vrbo but rec'd no response and ryan apologized...so all good...if needed place up that way again would stay."
The price is AU$434
includes taxes & fees
3 June - 4 June
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
The Scenic Mansion With Breathtaking View
9.4 out of 10, Exceptional, 3 reviews
"We loved staying in this large home for a weekend wedding in the area. All couples had plenty of room, with a bathroom in every bedroom, comfy beds, lots of living spaces, and gorgeous views of the valley below. The fall colors were so pretty!"
The Scenic Mansion With Breathtaking View
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, 199 reviews
"Very clean, just as advertised. The stream behind the cottage is beautiful! Will stay there again if we get a chance to revisit the area. The host was extremely accommodating and available🙂"
The price is AU$508
includes taxes & fees
3 June - 4 June
Streamside Cottage Walking Distance to Town of Woodstock
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The Farm at Hyde Park
9.8 out of 10, Exceptional, 48 reviews
"We thoroughly enjoyed our stay. It was a unique setting. Glen was very accommodating for our check in & out needs. Great location & central to everything we wanted to do & see. Definitely would come back."
The Farm at Hyde Park
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 35 reviews
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, 153 reviews
"We had a great time, and the space was great. The house is so spacious, and that was perfect for us. We would have liked a few more towels, a bit more soap and shampoo, and the grill didn't get hot enough to cook the steak we had brought. Overall a wonderful time. Thank you very much."
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, 32 reviews
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is AU$427
includes taxes & fees
2 June - 3 June
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, 36 reviews
"Very nice. A lot of attention to detail"
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, 38 reviews
"We spent the weekend and had a wonderful time. The property was conveniently located near the center of town while still being very quiet and private. The cottage is perfect for a couple’s weekend getaway. Great spot if you want to have a jumping off point to explore the area. Would definitely stay again."
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, 84 reviews
"A perfect getaway retreat! Gorgeous grounds with garden, firepit with adirondack chairs, flowers and tree-li ed view as far as the eye can see from upper and lower decks equipped with seating, umbrella shade and dining area with bbq grill. All the comforts of home--and that's before you enter!! The home is very clean, bright with A-frame windows in the family room Updated kitchen and fine wood flooring as well as beautiful bathrooms. Downstairs bedrooms were small but had very comfortable...
The price is AU$471
includes taxes & fees
20 June - 21 June
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, 35 reviews
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, 31 reviews
"The house is secluded and peaceful with a huge deck for a cool breeze with morning coffee or an evening glass of wine. The house was spotless and well equipped with anything you could possibly need. Restaurants, grocery, and Katterskill Falls for hiking all within a 15-20 minute drive. Our host, Nick, was very attentive making sure everything was as we expected ( and it was). Would stay here again if the opportunity arises. I highly recommend this property for your vacation getaway."
Cozy Relaxing Retreat in Saugerties, NY
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, 65 reviews
"Very relaxing and enjoyable with excellent views and tranquility!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, 28 reviews
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, 16 reviews
"An unassuming setting belies the well-appointed interior and thoughtful extras you’ll find within. Parking is tight but it is off-street and the location offers come-and-go convenience for exploring the area."
The price is AU$340
includes taxes & fees
2 June - 3 June
Campfire Cottage: Fireplace, fire pit & no chores!
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 168 reviews
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, 8 reviews
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, 11 reviews
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is AU$249
includes taxes & fees
2 June - 3 June
Cabin in the heart of the Hudson Valley, Cabin 4
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, 3 reviews
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is AU$249
includes taxes & fees
3 June - 4 June
Cabin in the heart of the Hudson Valley, Cabin 2
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, 70 reviews
"Fantastic, loved everytbing about it"
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Don't see what you're looking for?
See all available properties in Highland
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.

Highland Holiday Home Travel Info

Number of holiday homes
2
Popular accommodation
Highland private holiday homes
Known landmarks
Benmarl Vineyards and Winery, Glorie Farm Winery and Benmaryle Wineries
International airport
Newburgh, NY (SWF-Stewart Intl.)

Other types of properties in Highland you may be interested in

Rodeway Inn & Suites New Paltz - Hudson Valley
2.0 star property
7.0 out of 10, Good, 557 reviews
"The property was large and clean the location was descolate "
The price is AU$127
includes taxes & fees
4 June - 5 June
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, 707 reviews
"This hotel is a hidden gem and pet friendly. The staff was great and had coffee or tea available at all times and comfortable seating area to eat or just relax. No microwaves in rooms but available in lobby. Will go back soon. Convenient to highways. "
The price is AU$166
includes taxes & fees
5 June - 6 June
SureStay Plus Hotel by Best Western Highland Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, 1,000 reviews
"Liked how the room was a suite! They we’re accommodating and let us check in a little early, too. Would recommend for a good spot in the area!"
The price is AU$239
includes taxes & fees
30 June - 1 July
HYATT house Fishkill/Poughkeepsie
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.

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$249 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?

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 18 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, Apple Greens Golf Course and Franny Reese State Park 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.

Recent reviews of Highland properties
Expedia verified reviews