Highland Holiday Rentals from €201: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Highland has to offer?

The House In Highland-Secluded Retreat : This highly rated holiday home rental in Highland offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Our travellers also rate Our home is perfect for relaxing and having lots of fun, with near by activity’s as a favourite home for rent in Highland.

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Holiday Rentals in Highland

Enjoy outdoor dining and relaxation on the spacious deck with comfortable seating and a barbecue grill.

Relax on the covered porch with comfortable seating and a small table, perfect for casual dining or unwinding.

"Really liked that each room had it's own temperature control"

Set amidst lush greenery and mature trees, this charming building features a steeply pitched roof and a brick facade.

"We were visiting the Culinary Institute highly recommend it."

Enjoy a romantic dinner for two on this deck with a beautiful floral arrangement and a bottle of wine.

"Had a fantastic stay for a quick overnight trip to ski."

includes taxes & fees

16 Jul - 17 Jul

Relax on the serene deck, surrounded by bare trees and a frozen lake.

"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "

includes taxes & fees

13 Jul - 14 Jul

Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

"Communication was easy, location and parking was great! Very clean and cozy!"

includes taxes & fees

13 Jul - 14 Jul

Relax in a cozy outdoor space with a fireplace, wicker furniture, and a scenic view.

"Beautiful property- not too far from Hunter Mt or Woodstock. House has a lot to offer for adults and/or families with kids. Would highly recommend!"

"Incredible location and comfortable space. Would make this my exclusive place to stay everytime I visit woodstock."

Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel range hood.

"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "

includes taxes & fees

16 Jul - 17 Jul

Set amidst a serene wooded area, this two-story house offers a retreat with a well-manicured lawn and a small deck.

"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "

Enjoy a peaceful forest view from the large window, featuring a comfortable bed below.

"We loved our stay at this home! It is full of so much light and good vibes. We planned the weekend around a concert at Levon Helms studio, which was right down the street. The owners/management were wonderful & easy to get in touch with (not that we needed anything). The deck & music room were enjoyed the most :)"

Enjoy meals in the kitchen with a large window, coffee maker, and dining area.

Situated in a lush forest, this cabin offers a serene retreat with a symmetrical facade and a well-manicured lawn.

"This was a very nice place, great value and comfortable. I would definitely return."

includes taxes & fees

13 Jul - 14 Jul

Compact kitchen with a central island, black stove, and dining table for two.

"Very cool place everything u need is just a short drive away "

Cozy living room with a fireplace, flat-screen TV, and comfortable seating area.

"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."

Escape to a serene river setting surrounded by lush foliage and towering trees.

"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."

includes taxes & fees

13 Jul - 14 Jul

Relax in this inviting living area with a plush sofa, wooden floor, and ceiling fan.

"Our stay was great."

Relax by the serene pool surrounded by lush greenery and a children's play area.

includes taxes & fees

20 Jul - 21 Jul

Two comfortable beds with white bedding, a large window offering a view of a lush outdoor area, and a mirror complete this serene retreat.

includes taxes & fees

14 Jul - 15 Jul

Relax in a spacious bedroom with a large bed, bedside table, and lamp, offering a view of the balcony and adjacent room.

"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"

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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, 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 €201 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.

Recent reviews of Highland properties

5/5 Excellent

"Great, clean pool, clean rooms, no complaints. One thing to note: there is no elevator to the second floor! So if you have luggage or have walking difficulties or injuries , there’s no way to get on second floor, other than stairs. If hotel is fully booked you also may not have an option to switch to the first level, which is what we had to deal with. Staff helped us with luggage, but there’s no bellman, so that was challenging. Breakfast was also below average, but waffles were good. Need fruit and protein.."

A verified traveller stayed at Quality Inn Poughkeepsie

Posted 2 days ago

Best Western Plus Kingston Hotel And Conference Center

5/5 Excellent

"I liked the skylight above the swimming pool. However, the pool is not heated. It felt cold going in the pool. Only one of the exercise bikes and thread mills worked. Also, the equipment is very limited. Not a lot of weights and exercise machines. The continental breakfast is great."

A verified traveller stayed at Best Western Plus Kingston Hotel And Conference Center

Posted 2 days ago

5/5 Excellent

"Check-in was easy. The gentleman who checked is in on 7/4 at about 4:30pm was really great through out our stay. Very helpful and attentive. Breakfast was good. Hot food along with cold breakfast options were available. My children enjoyed the pool and hot tub. The cook at the bar recommended great food places to check out"

A verified traveller stayed at HYATT house Fishkill/Poughkeepsie

Posted 3 days ago

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 House In Highland- Secluded Retreat: This highly rated holiday home rental in Highland offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Our travellers also rate Our home is perfect for relaxing and having lots of fun, with near by activity’s as a favourite home for rent in Highland.

How many holiday rentals will I find in Highland?

With 21 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.

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Holiday Rentals in Highland

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Holiday Rentals in Highland

The House In Highland- Secluded Retreat

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

The Farm at Hyde Park

Esopus Creek modern Tiny house Retreat!

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

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

Hamptons on the Hudson in South Saugerties

Streamside Cottage Half Mile to Town of Woodstock

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

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

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8

The Studio at the Inn at High Falls

The Chicken Coop

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

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

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Indoor Pool Paradise | 6BR + Huge Decks

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

Find out more about Highland

Recent reviews of Highland properties

Quality Inn Poughkeepsie

Best Western Plus Kingston Hotel And Conference Center

Hampton Inn by Hilton New Paltz

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

HYATT house Fishkill/Poughkeepsie

Holiday Inn Express Poughkeepsie by IHG

Quality Inn & Suites Fishkill South near I-84

The Thayer Hotel at West Point

Americas Best Value Inn New Paltz

Frequently asked questions