Photo by Karen Wirtz

Holiday Rentals in Highland

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Holiday Rentals in Highland

Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (198)
"Spent two nights and wanted a place where we could easily bike into town and got exactly that! The sound of the creek outside was so relaxing, accommodations were clean and comfy. Definitely would return!"
The price is €315
includes taxes & fees
3 Jun - 4 Jun
Streamside Cottage Walking Distance to Town of Woodstock
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (153)
"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!
Exterior
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (37)
"A perfect location and the cottage was set up with great attention to detail. Everything was very clean and comfortable. The property is beautiful too. John and Mollie are very responsive hosts and provided us with anything we needed. Could not ask for more. Highly recommend!"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
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Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (35)
"This sweet little apartment was perfect for my solo stay. Comfortable, quiet, and very easy to get to. Lovely view from the deck. It had a feeling of security and privacy. Vicky was quick with answering my emails."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Property grounds
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (82)
"Very clean home. Had everything we needed. Quiet location. All beds were extremely comfortable. Host was very helpful and quick to reply. Good location that was close to area attractions. Would definitely look to stay here again! Thank you Cristiana!"
The price is €301
includes taxes & fees
20 Jun - 21 Jun
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (65)
"Very relaxing and enjoyable with excellent views and tranquility!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (16)
"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 €221
includes taxes & fees
2 Jun - 3 Jun
Campfire Cottage: Fireplace, fire pit & no chores!
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Property grounds
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
10.0 out of 10, Exceptional, (11)
"Perfect spot to visit grandkids Lots to do"
The price is €247
includes taxes & fees
23 May - 24 May
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Property grounds
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (13)
"Our stay was quite nice, the place looked as the pictures showed it to be which is just amazing. everything was music themed and our host had an amazing selection of vinyls. The only complaints I would say I had was the small flying bugs near the Tv and we weren’t provided paper towels. Overall it was a nice place for the night and the property itself was beautiful."
The price is €197
includes taxes & fees
27 May - 28 May
Mid-Century DJ’s Dream
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (30)
"It was a nice location to spend time with family."
Cozy Relaxing Retreat in Saugerties, NY
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior
5-Star New Barn Home - Music Studio, Views & Hot Tub
10.0 out of 10, Exceptional, (18)
"The house is amazing, it delivers on everything stated in the listing and then some. This was our second time staying at Stephen's place and it just keeps getting better. Can't wait for the next one. If you love to listen and play music, its a must."
5-Star New Barn Home - Music Studio, Views & Hot Tub
Fridge, microwave, oven, stovetop
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay! We had a large group of 24 friends, and the house met all of our needs. It was very clean, had enough bedrooms for everyone, and a large dining table that accommodated everyone for big dinners. We spent a lot of time throughout the weekend outside playing lawn games and sitting by the fire. The place was close enough to grab amenities or go to a grocery store, but off the beaten path and quiet. It was exactly what was listed and made for a where enjoyable time....
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (48)
"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
1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"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
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"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
Property grounds
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
9.8 out of 10, Exceptional, (18)
"My recent weekend getaway to the Catskills was truly unforgettable, thanks to our wonderful host and their charming retreat nestled in the heart of this picturesque mountain region. From the moment we arrived, we were greeted with warm hospitality and a sense of tranquility that immediately set the tone for our stay. The accommodations were nothing short of perfect – cozy yet spacious, with rustic charm and modern amenities seamlessly blended together. Our host went above and beyond to ensure...
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (6)
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
Bar (on property)
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (69)
"We love the place it was even more beautiful and peaceful than we expected .It was home away from home with the most gorgeous view . Ms.Karen was wonderful very welcoming . It was all my partner and I need to get away from stressful week . Thanks again Ms.Karen and p.s we love the ice cream Sunday . We are not only highly recommended but soon we will be back . All the best we are very grateful for this staying ."
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.

Other types of properties in Highland you may be interested in

Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1001)
"Easy and safe area . Major highway nearby."
The price is €146
includes taxes & fees
3 Jun - 4 Jun
HYATT house Fishkill/Poughkeepsie
Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building
Quality Inn Poughkeepsie
2.5 star property
8.0 out of 10, Very good, (232)
"N/A"
The price is €111
includes taxes & fees
27 May - 28 May
Quality Inn Poughkeepsie
Front of property
SureStay Plus Hotel by Best Western Highland Poughkeepsie
2.5 star property
7.6 out of 10, Good, (705)
"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 €102
includes taxes & fees
17 Jun - 18 Jun
SureStay Plus Hotel by Best Western Highland 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, apart-hotels, 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 favorite 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 depends 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 €155 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 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

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

5/5 Excellent
"We had an amazing stay ! The hotel is super clean, modern and comfortable. Delicious breakfast. Friendly staff. So far the best hotel we have ever stayed in."
A verified traveller stayed at Hyatt Place Poughkeepsie / Hudson Valley
Posted 2 days ago
Hyatt Place Poughkeepsie / Hudson Valley