Best Holiday rentals and Airbnb offers in Highland
9.8 78 reviews
Highland
15/07 – 27/07
£439/nighttotal: £5268 (12 )
Luxurious Private Log Cabin Retreat In Nature
1 2
cabin , Haviland
This charming log cabin is situated in the serene Hudson Valley, just 130 kilometres from New York City and a 20-minute drive from Poughkeepsie train station. It has received excellent ratings for location, cleanliness, and overall experience, making it a popular choice for travellers seeking a tranquil getaway. The cabin has three bedrooms and one bathroom, comfortably accommodating up to six guests. You'll enjoy a fully equipped kitchen, a cosy fireplace, a spacious garden, and a fitness centre, ensuring a relaxing and enjoyable stay.
9.9 153 reviews
Highland
15/07 – 27/07
£140/nighttotal: £1680 (12 )
Historic Hyde Park Studio | Minutes From Fdr & Cia
1 2
apartment , Hyde Park
This studio apartment is situated in Hyde Park, just a short walk from the Hudson River and the Vanderbilt Estate, offering easy access to the area's attractions. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment offers a comfortable and stylish space for two guests, with a private bathroom and a well-equipped kitchen. Amenities include air conditioning, parking, internet access, and keyless entry, ensuring a convenient and enjoyable stay.
9.9 146 reviews
Highland
15/07 – 27/07
£192/nighttotal: £2304 (12 )
2br|1 King 1 Queen Bed|balcony|parking|strong Wifi
2 2
apartment , Poughkeepsie
This two-bedroom flat is ideally located in Poughkeepsie, just a short walk from the Walkway Over the Hudson and local restaurants and breweries. It has received excellent ratings for its cleanliness, location, and overall user experience. The apartment has a spacious layout, comfortably accommodating up to six guests. Guests can enjoy a fully equipped kitchen, two balconies, cable TV and Roku, and a peaceful ambiance, making it a great choice for families and groups of friends.
10 6 reviews
Highland
15/07 – 27/07
£821/nighttotal: £9852 (12 )
Cliffside Luxury: Hot Tub, Sun & River Views!
1 2
apartment , Highland
This recently renovated riverside dwelling in Highland offers unobstructed Hudson River views from every room, with expansive private outdoor spaces including a deck, patio, and stone terrace with a fire pit, situated just a short drive from local amenities and approximately 145 kilometres from NYC. This luxurious property boasts three bedrooms, two bathrooms, and accommodates up to six guests, featuring a chef's kitchen with high-end appliances, two fireplaces, a spa bathroom with steam shower and whirlpool bath, and a 4-season sunroom, with easy access to outdoor pursuits like kayaking and hiking, as well as local breweries and wineries.
9.5 191 reviews
Highland
15/07 – 27/07
£175/nighttotal: £2100 (12 )
Historic 1 Br Family Home Near Buttermilk Falls
1 2
apartment , Milton
This charming 1790 Stagecoach Stop is situated in Milton, New York, directly across the street from Buttermilk Falls Resort & Spa and just a short drive from Walkway Over The Hudson. The property has received excellent ratings for location, cleanliness, and overall user experience. This one-bedroom, one-bathroom cottage can comfortably accommodate up to four guests and features a spacious kitchen, living room, and a sunroom with stunning views. Guests can enjoy a private garden, a fire pit, and modern conveniences like air conditioning, a coded deadbolt, and Roku Guest Mode for streaming entertainment.
Highland
15/07 – 27/07
£211/nighttotal: £2532 (12 )
Tranquil 1-bedroom Apartment With Ac In Charming Poughkeepsie
1 2
apartment , Poughkeepsie
This Poughkeepsie flat offers a convenient base, located near Locust Grove and the Clinton House State Historic Site, with Franny Reese State Park and James Baird State Park also within reach. This one-bedroom flat accommodates up to four guests, featuring air conditioning and heating for year-round comfort, and is situated a short distance from the Frances Lehman Loeb Art Centre and the Mid-Hudson Civic Centre.
9.6 4 reviews
Highland
15/07 – 27/07
£444/nighttotal: £5328 (12 )
Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny
5 2
apartment , Poughkeepsie
This Poughkeepsie property is a five-bedroom dwelling situated near Franny Reese State Park and Vanderbilt Mansion National Historic Site, with attractions such as the Mid-Hudson Civic Centre and McCann Ice Arena also easily accessible. This residence accommodates up to 18 guests across four queen beds and one king bed, offering air conditioning, heating, an iron, and a hairdryer, with a host available to assist during your stay.
9.7 52 reviews
Highland
15/07 – 27/07
£517/nighttotal: £6204 (12 )
Charming Townhouse In Historic District
5 2
apartment , Poughkeepsie
This charming five-bedroom townhouse is situated in the Poughkeepsie Historic District, just a short walk from Vassar College and the Walkway Over the Hudson, offering stunning views of the Hudson River. The apartment has received excellent ratings for cleanliness, user experience and location, making it an ideal choice for travellers seeking a comfortable and well-maintained home away from home. The spacious property features multiple levels, including a media room and a parlor level perfect for gatherings, accommodating up to eight guests. The townhouse boasts a fully equipped kitchen with a freezer, microwave oven and dishwasher, as well as air conditioning, a garden and internet access, ensuring a comfortable and enjoyable stay.
9.9 98 reviews
Highland
15/07 – 27/07
£178/nighttotal: £2136 (12 )
Magical Charming 1850s Barn On Idyllic Former Farm
1 2
farm , Rifton
This charming 19th-century barn is situated in Highland, just a short drive from New Paltz and minutes from I-87, offering easy access to the Hudson Valley's attractions. The property has received excellent ratings for its cleanliness, location, and overall experience. The charming cottage sleeps two guests in one bedroom and one bathroom. Guests can enjoy a wood-burning stove, clawfoot tub, farmhouse sink, outdoor fire pit, bistro table, grill, and gazebo, as well as access to a washer/dryer and iron in the main farmhouse.
9.7 13 reviews
Highland
15/07 – 27/07
£307/nighttotal: £3684 (12 )
Pleasant Lane Family Retreat
1 2
apartment , Red Oaks Mill
This three-bedroom, two-bathroom apartment at 9 Pleasant Lane, Poughkeepsie, offers family-friendly accommodation a short drive from Red Oaks Mill. Sleeping seven guests, the property features a full kitchen, in-unit laundry, a finished basement with a large TV, a patio with fire pit, and kid-friendly amenities including a crib and bunk bed; access is provided to the entire house (excluding the garage).
9.7 27 reviews
Highland
15/07 – 27/07
£1035/nighttotal: £12420 (12 )
Modern Designer Cabin In Woods W/ 5-star Amenities
1 2
cabin , Highland
This Highland, New York log cabin retreat is situated on a secluded 0.8-hectare wooded plot, a short 16-kilometre drive from both New Paltz and Poughkeepsie. The four-bedroom, four-bathroom property sleeps eight guests and boasts a 100-inch screen cinema room, games room, private gym, saltwater pool, cedar sauna, and hot tub, alongside a fully equipped kitchen and ample parking.
8.9 11 reviews
Highland
15/07 – 27/07
£212/nighttotal: £2544 (12 )
Quiet Hudson Valley Escape
1 2
apartment , Highland
This Highland, New York apartment is situated near the Mid-Hudson Bridge, offering easy access to Marist College and Vassar College (distances not specified). The three-bedroom, three-bathroom property sleeps six guests and includes a fully equipped kitchen with dishwasher, air conditioning, parking, and internet access; nearby attractions include the Walkway Over the Hudson.
Best Holiday Rentals for Families in Highland
These family-friendly holiday rentals in Highland offer plenty of room and city attractions within easy reach.
9.4 3 reviews
Highland
15/07 – 27/07
£404/nighttotal: £4848 (12 )
Black Walnut Tree Farm: 50-acres + Private Pond
4 2
apartment , Clintondale
This Highland countryside farmhouse, a 33-minute (53km) drive from Mohonk Lake and 12-minute (19km) drive from the Walkway Over the Hudson State Historic Park, offers a convenient rural location near major attractions. Sleeping up to eight guests, the property boasts three bathrooms, a fully equipped kitchen including dishwasher and microwave, Wi-Fi, laundry facilities, a private garden, and barbecue facilities, all within easy reach of Quartz Rock Vineyard and Franny Reese State Park.
Top Holiday Rentals with Parking in Highland
Free on-site parking comes with these holiday rentals in Highland, allowing you to focus on the city centre from day one.
9.5 191 reviews
Highland
15/07 – 27/07
£175/nighttotal: £2100 (12 )
Historic 1 Br Family Home Near Buttermilk Falls
1 2
apartment , Milton
This charming 1790 Stagecoach Stop is situated in Milton, New York, directly across the street from Buttermilk Falls Resort & Spa and just a short drive from Walkway Over The Hudson. The property has received excellent ratings for location, cleanliness, and overall user experience. This one-bedroom, one-bathroom cottage can comfortably accommodate up to four guests and features a spacious kitchen, living room, and a sunroom with stunning views. Guests can enjoy a private garden, a fire pit, and modern conveniences like air conditioning, a coded deadbolt, and Roku Guest Mode for streaming entertainment.
9.4 3 reviews
Highland
15/07 – 27/07
£404/nighttotal: £4848 (12 )
Black Walnut Tree Farm: 50-acres + Private Pond
4 2
apartment , Clintondale
This Highland countryside farmhouse, a 33-minute (53km) drive from Mohonk Lake and 12-minute (19km) drive from the Walkway Over the Hudson State Historic Park, offers a convenient rural location near major attractions. Sleeping up to eight guests, the property boasts three bathrooms, a fully equipped kitchen including dishwasher and microwave, Wi-Fi, laundry facilities, a private garden, and barbecue facilities, all within easy reach of Quartz Rock Vineyard and Franny Reese State Park.
9.6 4 reviews
Highland
15/07 – 27/07
£444/nighttotal: £5328 (12 )
Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny
5 2
apartment , Poughkeepsie
This Poughkeepsie property is a five-bedroom dwelling situated near Franny Reese State Park and Vanderbilt Mansion National Historic Site, with attractions such as the Mid-Hudson Civic Centre and McCann Ice Arena also easily accessible. This residence accommodates up to 18 guests across four queen beds and one king bed, offering air conditioning, heating, an iron, and a hairdryer, with a host available to assist during your stay.
9.7 52 reviews
Highland
15/07 – 27/07
£517/nighttotal: £6204 (12 )
Charming Townhouse In Historic District
5 2
apartment , Poughkeepsie
This charming five-bedroom townhouse is situated in the Poughkeepsie Historic District, just a short walk from Vassar College and the Walkway Over the Hudson, offering stunning views of the Hudson River. The apartment has received excellent ratings for cleanliness, user experience and location, making it an ideal choice for travellers seeking a comfortable and well-maintained home away from home. The spacious property features multiple levels, including a media room and a parlor level perfect for gatherings, accommodating up to eight guests. The townhouse boasts a fully equipped kitchen with a freezer, microwave oven and dishwasher, as well as air conditioning, a garden and internet access, ensuring a comfortable and enjoyable stay.
Frequently asked questions about holiday rentals in Highland
Which walking or cycling routes are the best in Highland, NY?
For a scenic walk, try the Highland Recreation Area. There are many trails to choose from, ranging in difficulty. If you prefer cycling, the Pacific Crest Trail passes through the area, offering stunning views of the mountains. You could also try the paved bike path along Base Line Road.
What are the best Airbnb and holiday rentals in Highland?
What sports or outdoor activites can visitors enjoy in and around Highland, NY?
Hiking, mountain biking, and rock climbing are popular activities in the nearby San Bernardino Mountains. If you're looking for something less strenuous, there are several parks and lakes in the area perfect for picnicking, fishing, and kayaking.
What other towns or cities can be easily accessed from Highland, NY?
Highland is conveniently located near several other towns and cities. You can easily drive to San Bernardino, which is about 15 minutes away, or head to the larger city of Los Angeles, about an hour and a half drive.
What are the best holiday rentals with a pool in Highland?
What amenities are commonly available in vacation rentals in Highland, NY?
Vacation rentals in Highland usually offer amenities like Wi-Fi, air conditioning, and a fully equipped kitchen. Many also have private patios or balconies, perfect for relaxing and enjoying the views. You can also find rentals with pools, hot tubs, and fire pits.
What are the best rentals for families and kids in Highland?
What time of year is best to rent a vacation rental Highland, NY?
Spring and autumn are the best times to visit Highland, as the weather is pleasant and the crowds are smaller. Summer can get very hot, and winter can bring snow, so it's best to check the weather forecast before you go.
What are the best rentals or Airbnbs with a jacuzzi in Highland?
The Highland region is known for its Mexican cuisine. Be sure to try some of the local tacos, burritos, and enchiladas. There are also several restaurants serving classic American dishes, such as burgers, fries, and pizza.
Destinations nearby
Check Out Holiday Rentals with a Balcony in Highland
A terrace with city skyline views is a fantastic reason to book a holiday rental in Highland. View our top picks and start comparing now.
Highland
15/07 – 27/07
£211/nighttotal: £2532 (12 )
Industry Style Open Concept Downtown
2 2
apartment , Poughkeepsie
This Poughkeepsie flat offers easy access to local attractions from its convenient district, a short drive from the Walkway Over the Hudson State Historic Park and close to Vassar College, with the Poughkeepsie Train Station facilitating travel to and from New York City. This two-bedroom, one-bathroom flat accommodates up to six guests and features air conditioning, internet, and a kitchen, making it suitable for group travel, families, and business trips with ample dining and entertainment options nearby.
Find the Best Dog-Friendly Self-Catering Rentals in Highland
These dog-friendly holiday rentals in Highland feature city walks on the doorstep. Your dog will love the trip as much as you do.
9.7 111 reviews
Highland
15/07 – 27/07
£110/nighttotal: £1320 (12 )
Your Own Pied-a-terre "Walkway Over The Hudson"#2
1 2
apartment , Poughkeepsie
This charming flat is situated in the heart of Poughkeepsie, just under 10 kilometres from Vassar College, Marist College, and the Walkway Over the Hudson, making it a convenient base for exploring the city. The property has consistently received excellent ratings for location, cleanliness, and overall experience, making it a popular choice for travellers. The apartment is a one-bedroom, one-bathroom flat with a private entrance and can accommodate up to two guests. Features include a well-equipped kitchen, air conditioning, complimentary bicycles, a garden, and parking, ensuring a comfortable and enjoyable stay.
10 74 reviews
Highland
15/07 – 27/07
£415/nighttotal: £4980 (12 )
Wooded Rhinebeck-beacon Area Escape W/outdoor Spa
1 2
apartment , Fairview
This Fairview apartment is situated in Hyde Park, New York, just a short drive from Poughkeepsie and Rhinebeck, making it a great base for exploring the Hudson Valley. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment is a comfortable and spacious property with two bedrooms, sleeping up to four guests. It offers a range of amenities, including a hot tub, a fully equipped kitchen, and a screened-in porch, perfect for relaxing after a day of exploring the local attractions.
10 47 reviews
Highland
15/07 – 27/07
£1195/nighttotal: £14340 (12 )
Hudson Valley Estate 90 Min From Nyc Pet Friendly
4 2
apartment , Highland
This spacious waterfront estate is situated in the Hudson Valley, just 90 minutes from New York City, offering a peaceful retreat from the city's hustle and bustle. The property has received excellent ratings for its location, cleanliness, and overall experience. This large holiday home boasts four bedrooms and two bathrooms, comfortably accommodating up to 10 guests. The estate features a chef's kitchen, a private garden, a swimming pool, and a host of other amenities perfect for relaxation and entertainment.