Highland holiday lettings

We found 1,732 holiday rentals — enter your dates for availability
Discover a selection of 25 homes and other holiday rentals in Highland that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Highland

Showing deals for:20 Nov - 27 Nov

Interior
Interior
Private kitchen
Property grounds
Exceptional
(11 reviews)

Farmette Roquette Hudson Valley

Germantown

7% off
£4,094
for 7 nights, 1 room
£585 per night
includes taxes & fees
Farmette Roquette Hudson Valley
Property grounds
Rear Deck, Hot Tub and Screened Porch
Our Sunny Living Room with Wood Stove
A beautiful spot for our comfortable cabin
Exceptional
(119 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off
£2,572
for 7 nights, 1 cabin
£367 per night
includes taxes & fees
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
Room
Interior
Interior
Private kitchen
Exceptional
(10 reviews)

Mountain Brook Cabin w/ 4-bedroom in lovely Cornwall with Jacuzzi Tub and Sauna

Mountainville

13% off
£5,229
for 7 nights, 1 cabin
£747 per night
includes taxes & fees
Mountain Brook Cabin w/ 4-bedroom in lovely Cornwall with Jacuzzi Tub and Sauna
Pool
Interior
Private kitchen
Outdoor dining
Exceptional
(28 reviews)

Elegant Waterfront Hudson River 12-acre Estate w/ Amazing Views. Sleeps 14

Saugerties

8% off
£12,853
for 7 nights, 1 home
£1,836 per night
includes taxes & fees
Elegant Waterfront Hudson River 12-acre Estate w/ Amazing Views. Sleeps 14
Property grounds
Living area
Outdoor dining
Exterior
Exceptional
(7 reviews)

6 Acre Private Hudson Valley Estate

Highland

8% off
£7,660
for 7 nights, 1 home
£1,094 per night
includes taxes & fees
6 Acre Private Hudson Valley Estate
Great Room/Kitchen Area
Interior
Private kitchen
Living area
Exceptional
(26 reviews)

Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals

Saugerties

8% off
£4,676
for 7 nights, 1 home
£668 per night
includes taxes & fees
Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals
Dinning room & Kitchen. Original exposed beams.
Exterior
View from front lawn
Main bedroom with king bed and private full bath and walk in closet.
Exceptional
(10 reviews)

Cheerful Circa 1700 3 Bedroom Farmhouse

Hyde Park

30% off
£2,277
for 7 nights, 1 home
£325 per night
includes taxes & fees
Cheerful Circa 1700 3 Bedroom Farmhouse
Living area
Room
Living area
Outdoor dining
Exceptional
(6 reviews)

Cozy and bright 2-bedroom cabin in charming Elka Park

Tannersville

8% off
£1,109
for 7 nights, 1 cabin
£158 per night
includes taxes & fees
Cozy and bright 2-bedroom cabin in charming Elka Park
Through the front door to spectacular lake beauty
Breathtaking View, Situated on Orange Lake
Front of house. Lake in back.
Winter beauty
Exceptional
(328 reviews)

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

Newburgh

8% off
£3,077
for 7 nights, 1 home
£440 per night
includes taxes & fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Living area
Exterior
Pool
Outdoor dining
Exceptional
(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off
£2,428
for 7 nights, 1 home
£347 per night
includes taxes & fees
Secluded family retreat within minutes of Woodstock village
Master suite balcony
Living area
Dining
Interior
Exceptional
(34 reviews)

Luxury secluded Catskill log cabin on creek-ski hike great restaurants mins away

Catskill

8% off
£2,927
for 7 nights, 1 cabin
£418 per night
includes taxes & fees
Luxury secluded Catskill log cabin on creek-ski hike great restaurants mins away
Living area
Living area
Dining
Dining
Exceptional
(125 reviews)

Modern, Artsy, & Lofty Log Home

Wallkill

20% off
£7,218
for 7 nights, 1 home
£1,031 per night
includes taxes & fees
Modern, Artsy, & Lofty Log Home
Great room featuring a wonderful wall of windows
Private kitchen
Exterior
Kitchen with everything you'll need
Exceptional
(52 reviews)

Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres

Woodstock

12% off
£2,744
for 7 nights, 1 home
£392 per night
includes taxes & fees
Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres
Original mahogany wood work and French Chandliers though out the house
View of the dining room
Living room through Mahogany pocket doors
Walk way to back yard from side of the house
Exceptional
(16 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

20% off
£4,383
for 7 nights, 1 home
£626 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
French Doors leading to a veranda offer a wonderful connection to the outdoors, making it the perfect spot to start your day with a cup of morning coffee or tea.
Dining
For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.
A Special Place for Your Special Times! 4 bedroom, 3.5 baths, Full Kitchen, Kitchenette, 2 Living Areas, 2 Dining Areas, Full access to backyard with dining area, fire pit with adirondack chairs, BBQ grill, hammock on 2 acres of land.
Exceptional
(25 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
£3,944
for 7 nights, 1 home
£563 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
In winter, stay toasty warm by the fire
Welcome to Bridge House
Fern garden in summer
Cooking is a breeze in this recently remodeled kitchen
Exceptional
(128 reviews)

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

Willow

8% off
£1,928
for 7 nights, 1 home
£275 per night
includes taxes & fees
Waterfront Mid-century Modern Gem Surround by Forever Wild Land
Stone steps to the pool
Master bedroom with TV
Property grounds
Kitchen Entrance and dining room
Exceptional
(30 reviews)

HIKE, SWIM, STARGAZE IN WOODS SIDING MINNEWASKA STATE PARK SHAWANGUNK MOUNTAINS

Wallkill

10% off
£2,036
for 7 nights, 1 cottage
£291 per night
includes taxes & fees
HIKE, SWIM, STARGAZE IN WOODS SIDING MINNEWASKA STATE PARK SHAWANGUNK MOUNTAINS
5 star ensuite bathroom with tub, hand shower, and rain shower.
450sqft of living space: super comfy kingsize bed (+ 2 optional twin beds)
Enjoy your private deck, lawn, firepit, and grill!
Private, luxurious retreat in the heart of an organic farm in the Hudson Valley
Exceptional
(25 reviews)

Luxury retreat w/ private deck, garden, firepit on organic farm

Gardiner

8% off
£1,305
for 7 nights, 1 cabin
£186 per night
includes taxes & fees
Luxury retreat w/ private deck, garden, firepit on organic farm
Exterior
Interior
Living area
Private kitchen
Exceptional
(8 reviews)

Catskill Penthouse center of town

Catskill

15% off
£2,996
for 7 nights, 1 apartment
£428 per night
includes taxes & fees
Catskill Penthouse center of town
Open Plan Kitchen / Dining Area with French Doors and Screen Porch in Distance
Terraced Rock Garden with Rustic Stone Walls and Massive Steps
Entrance to Tannery Brook Cottage in July with Front Porch and Day Lilies
Dining Area with Curio Cabinet, Book Shelf and Office Nook with Computer Station
Exceptional
(18 reviews)

Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

Woodstock

11% off
£2,131
for 7 nights, 1 cottage
£304 per night
includes taxes & fees
Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.
Interior
Exterior
Living area
Property grounds
Wonderful
(12 reviews)

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

8% off
£1,066
for 7 nights, 1 home
£152 per night
includes taxes & fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Living area
Property grounds
Living area
Dining
Exceptional
(18 reviews)

Stylish Saugerties Retreat with Hot Tub + Game Room + Theater + Firepit

Saugerties

8% off
£3,168
for 7 nights, 1 home
£453 per night
includes taxes & fees
Stylish Saugerties Retreat with Hot Tub + Game Room + Theater + Firepit
Interior
Exterior
Property grounds
Terrace/patio
Exceptional
(46 reviews)

Cosy lakefront cottage in Hudson Valley

Walden

7% off
£1,272
for 7 nights, 1 cottage
£182 per night
includes taxes & fees
Cosy lakefront cottage in Hudson Valley
Exterior detail
Exterior detail
Living area
Room
Exceptional
(8 reviews)

Heart of the Village Victorian Saugerties NY

Saugerties

5% off
£2,643
for 7 nights, 1 home
£378 per night
includes taxes & fees
Heart of the Village Victorian Saugerties NY

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The scenic city of Highland awaits you

The riverfront, wildlife and mountains are the perfect backdrop to your holiday home in Highland. This scenic city attracts visitors thanks to its boating and hiking. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Highland

Are you hoping to discover attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Highland a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • New Paltz Golf Course (7.1 mi / 11.4 km)
  • Benmarl Vineyards and Winery (8.9 mi / 14.4 km)
  • Mohonk Golf Course (9.9 mi / 15.9 km)
  • SplashDown Beach (12.3 mi / 19.8 km)
  • Beekman Golf Course (13 mi / 20.9 km)
  • Millbrook Vineyards and Winery (16.3 mi / 26.3 km)

Exploring the natural features in Highland

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Highland is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Walkway Over the Hudson State Historic Park (0.9 mi / 1.4 km)
  • Mohonk Lake (10.6 mi / 17.1 km)
  • Mohonk Preserve Visitor Center (11.7 mi / 18.9 km)
  • Shawangunk Mountains (13.4 mi / 21.6 km)
  • Lake Minnewaska Beach (14.3 mi / 23.1 km)
  • Minnewaska State Park (14.4 mi / 23.2 km)

How to get to and around Highland

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 16.6 mi (26.7 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Highland?
Prices for holiday rentals in Highland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Highland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Highland holiday house rentals?
You can find great discounts on house rentals in Highland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Highland ski resort rentals?
For the best ski resort rentals in Highland, New York, visitors should consider accommodations in the nearby town of New Paltz, which is a short drive from the slopes at Mohonk Mountain House and the nearby ski areas in the Catskills. In New Paltz, you can find a variety of rental properties, including cosy cabins and spacious homes that often feature amenities such as wood-burning stoves, fully equipped kitchens, and outdoor spaces great for après-ski relaxation.Additionally, properties in this area often come with easy access to hiking trails and scenic views of the Shawangunk Ridge, making them ideal for those who enjoy both skiing in the winter and outdoor activities in the warmer months. Some rentals may also offer modern conveniences like Wi-Fi, laundry facilities, and outdoor grills, suiting families and groups looking for a comfortable stay.Further along the Hudson River, towns like Kingston and Saugerties provide additional options, where visitors can find charming historic homes and modern apartments, often equipped with amenities such as hot tubs or fire pits, great for unwinding after a day on the slopes.
What is the most popular type of holiday rental accomodation in Highland?
In Highland, holiday houses are the predominant holiday rental choice, with approximately 64 available throughout the area. These properties typically offer spacious layouts, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or decks, making them ideal for families or groups seeking a comfortable retreat. Additionally, there are around 16 apartments that provide a more compact living option, often equipped with essential amenities like kitchen facilities and cosy living areas. While there are several cottages and villas as well, these tend to be fewer in number and often provide a charming, rustic experience.
Are there any family house rentals in Highland?
In Highland, New York, there is a good selection of family-friendly homes available, with around 17 properties to choose from. This charming area offers a delightful mix of natural beauty and convenient access to local attractions. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play. Visitors can also expect amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.Nearby points of interest include the scenic Walkway Over the Hudson, superb for family outings and enjoying panoramic views of the river. The vibrant town centre is home to various shops and restaurants, making it easy to immerse oneself in the local culture. Additionally, the surrounding landscapes are ideal for hiking and exploring, providing families with plenty of opportunities for adventure.
Can I rent a holiday home with a pool or hot tub in Highland?
In Highland, New York, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located along the Hudson River, offers a peaceful retreat with beautiful natural surroundings. Many of the rental properties in the area come with amenities such as private pools, hot tubs, outdoor decks, and spacious living areas, making them superb for families or groups seeking relaxation and leisure.Travellers can also expect fully equipped kitchens for self-catering, as well as comfortable bedrooms and modern bathrooms. The scenic views of the surrounding landscape add to the appeal, providing a tranquil atmosphere for a getaway.
Can I find long-stay holiday rentals in Highland?
A long-stay holiday rental in Highland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Highland?
In Highland, there are several pet-friendly house rentals available, making it a great choice for travellers looking to bring their furry companions along. The area features charming properties that often come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces, great for enjoying the scenic surroundings. Many rentals also provide comfortable sleeping arrangements and access to private gardens or patios where pets can roam freely.Highland is located near the picturesque Hudson River, offering numerous outdoor activities. The nearby Walkway Over the Hudson State Historic Park is a fantastic spot for walks with pets, providing stunning views and ample space for exploration. Additionally, the region is dotted with local parks and hiking trails, inviting pet owners to enjoy the natural beauty of the area.
Are there any remote work holiday rentals in Highland?
In Highland, New York, there are numerous options for remote work holiday rentals, with around 84 properties available to suit your needs. Many of these rentals come equipped with essential amenities for a comfortable working environment, such as reliable Wi-Fi, dedicated workspaces with desk and chair setups, and access to printing facilities.The town is located along the scenic Hudson River and offers beautiful landscapes, making it an inspiring place to work remotely. Additionally, Highland is conveniently situated near points of interest like the Walkway Over the Hudson State Historic Park, which provides stunning views and recreational opportunities for breaks from work. The area's charming local cafes and restaurants also make it easy to find a change of scenery while enjoying a meal or coffee. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Highland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Highland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Highland?
In Highland, popular rental amenities typically include kitchens, which allow guests to prepare their own meals, and blenders for those who enjoy smoothies or soups. Many rentals also feature decks or patios where visitors can relax and take in the scenic surroundings. A fireplace is common in these accommodations, providing a warm and inviting atmosphere, especially during cooler months. Additionally, onsite parking is often available, making it convenient for travellers with vehicles.
When is the best time to visit Highland for a holiday rental?
April is the most popular month to visit Highland, as it marks the peak season running from March to May. During this time, the area comes alive with vibrant spring foliage, making it an ideal backdrop for outdoor adventures such as hiking and exploring the scenic trails of the Hudson Valley. Visitors can enjoy the pleasant temperatures, typically ranging from 5 to 15 degrees Celsius, which enhances the experience of sightseeing, whether you're wandering through charming local markets or taking in the stunning views along the Hudson River.If you're looking for a more tranquil experience, consider planning your trip in December. This month offers a unique charm as Highland embraces the winter season, where you can enjoy cozy evenings and festive decorations without the crowds. While it's cooler, the serene atmosphere allows for peaceful walks along the river and enjoying local holiday events.Ultimately, the best time to book a holiday rental in Highland depends on your preferences.
How early should I book a Highland holiday rental?
Book your Highland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Highland?
In Highland, visitors can enjoy a variety of attractions that highlight the area's natural beauty and historical significance. The Walkway Over the Hudson, an impressive pedestrian bridge, offers stunning views of the Hudson River and is great for leisurely walks or cycling. Nearby, the historic Hudson Valley Rail Trail provides a scenic route for outdoor enthusiasts.The area is also known for its proximity to the beautiful Minnewaska State Park Preserve, where guests can explore hiking trails, waterfalls, and breathtaking vistas. For those interested in history, the Mid-Hudson Children's Museum is a delightful spot, particularly for families, featuring interactive exhibits and activities for children.
Can I change or cancel my Highland home rental booking on Vrbo?
To find Highland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Highland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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