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Highland, NY place to stay
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38 Lodgings in Highland, NY

Best family friendly Highland, NY lodging

Among the 38 accommodations in Highland, NY, here are the 4 best for families

Hudson Escape W/ Hot Tub + Bridge View - Highland, NY
9.8 48 reviews

Hudson Escape W/ Hot Tub + Bridge View

apartment, Highland
This Highland apartment boasts stunning Hudson River and bridge views, offering easy access to the Hudson Valley's attractions.
The three-bedroom property sleeps six, features a full kitchen with dishwasher, a jacuzzi, private parking for up to three cars, and a private deck; pets are welcome (fee applies).
Hudson Escape W/ Hot Tub + Bridge View - Highland, NY
No reviews

Hudson Escape W/ Hot Tub + Bridge View

apartment, Highland
This family-friendly holiday home in Highland offers a rural, waterfront setting, a 4-minute drive from the Walkway Over the Hudson State Historic Park and a 15-minute walk from the Hudson River.
The spacious 170-square-meter accommodation features 3 bedrooms, 1.5 bathrooms, and accommodates up to 6 guests with amenities including a hot tub, garden, Wi-Fi, air conditioning, and a full kitchen with a washer and dryer.
Beautiful 3 Bedroom Home With Hudson River Views - Highland, NY
10 13 reviews

Beautiful 3 Bedroom Home With Hudson River Views

apartment, Hyde Park
This Hyde Park cottage is located on a scenic street, directly opposite the Vanderbilt Estate's Lower Gate and within 500 meters of Crum Elbow Creek's waterfall and trails, with Franklin D. Roosevelt's Home & Library a short drive south and Rhinebeck less than 15 kilometers north.
This family-friendly apartment offers accommodation for up to seven guests, featuring three bedrooms, one bathroom, air conditioning, a fully equipped kitchen with a Vitamix blender, Omega juicer, and Waring Professional waffle maker, and entertainment options including a 55-inch LG TV, Sonos, a record player, and a wood-burning fireplace, alongside sweeping Hudson River views and a sun-filled porch overlooking a waterfall.
Outdoor Hot Tub And Scenic Views - Luxurious Hudson Valley Escape - Highland, NY
No reviews

Outdoor Hot Tub And Scenic Views - Luxurious Hudson Valley Escape

house, Highland
This renovated historic residence in Highland, Hudson Valley, offers mesmerising views of the Hudson River and bridge, located just minutes from the Walkway Over the Hudson and a short drive to New Paltz and Poughkeepsie.
This family-friendly detached house accommodates up to six guests with three bedrooms and one bathroom, featuring a full kitchen, air conditioning, Wi-Fi, a hot tub, a garden, and on-site parking for three vehicles.

Best Highland, NY lodging with a pool

Among the 38 accommodations in Highland, NY, here are the 4 best ones with a pool

Hudson Riverfront Retreat - Highland, NY
9.1 30 reviews

Hudson Riverfront Retreat

apartment, Hyde Park
This luxurious eight-bedroom Hyde Park apartment boasts a stunning riverfront location with a private beach, situated approximately 16 kilometres from New Paltz, Kingston, and Poughkeepsie.
Sleeping up to 18 guests comfortably in 13 beds, this self-catering property features a dishwasher, air conditioning, a swimming pool, jacuzzi, sauna, parking, and is within walking distance of the Hudson House Distillery and a local winery.
Hyde Park Luxury A-frame - Pool/chef Kitchen - Highland, NY
10 59 reviews

Hyde Park Luxury A-frame - Pool/chef Kitchen

apartment, Haviland
This A-frame house is located in Hyde Park, just 145 kilometres from New York City, making it a convenient base for exploring the Hudson Valley. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The house has three bedrooms and three bathrooms, comfortably accommodating up to six guests. Amenities include a private pool, a spa, a screened-in cabana, dual fireplaces, game and movie rooms, a fully equipped kitchen, and a fitness centre.
Hudson Valley Estate 90 Min From Nyc Pool&gameroom - Highland, NY
10 52 reviews

Hudson Valley Estate 90 Min From Nyc Pool&gameroom

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.
Classic Hudson Valley Riverfront House With Pool - Highland, NY
9.7 26 reviews

Classic Hudson Valley Riverfront House With Pool

apartment, Highland
This spacious house is located on the Hudson River, just 90km north of New York City, offering easy access to the Hudson Valley's attractions, including Mohonk Mountain House and the towns of Beacon and New Paltz. The property boasts excellent user, location, and cleanliness ratings, making it an ideal choice for travellers seeking a comfortable and enjoyable stay.
The house has four bedrooms and two bathrooms, accommodating up to six guests. It offers a range of amenities, including a swimming pool, a garden, a fully equipped kitchen, and a game room, providing everything you need for a relaxing and entertaining holiday.

Frequently asked questions about accommodations in Highland, NY

  • What outdoor activities can visitors enjoy in and around Highland, NY?

    Highland is a haven for outdoor enthusiasts! Hiking, biking, and kayaking are all popular activities. You can explore the trails of the Shawangunk Ridge, go for a swim in Lake Minnewaska, or rent a kayak on the Hudson River.
  • When is the ideal time to plan a trip to Highland, NY?

    Spring and autumn are the most pleasant times to visit Highland, with mild temperatures and vibrant foliage. Summer can be hot and humid, while winter brings snow and cold temperatures, making it perfect for skiing and snowboarding.
  • What are the best walking or cycling routes in Highland, NY?

    The Overlook Mountain Trail is a popular hike with stunning views of the surrounding area. For a more leisurely stroll, try the Walkway Over the Hudson, a pedestrian bridge spanning the Hudson River. Cyclists will enjoy the Wallkill Valley Rail Trail, a paved path that follows the old rail line.
  • What nearby towns or cities can be explored from Highland, NY?

    New Paltz, a charming college town with a vibrant arts scene, is just a short drive away. Poughkeepsie, a larger city with a historic downtown and the Vassar College campus, is also worth exploring. And of course, you can easily get to New York City for a day trip.
  • What amenities can travelers expect from accommodations in Highland, NY?

    Highland offers a range of accommodations, from cozy bed and breakfasts to spacious hotels. Many accommodations offer amenities like swimming pools, fitness centers, and on-site restaurants. You can also find cabins and vacation rentals in the surrounding area.

Popular destinations

Best Highland, NY accommodations with a garden

Wake-up To Hudson River Sunrises- Historic Riverfront Retreat. - Highland, NY
10 1 review

Wake-up To Hudson River Sunrises- Historic Riverfront Retreat.

apartment, Highland
This riverside flat in Highland offers spectacular Hudson River sunrises and direct riverfront access, located across from the Marist Boathouse and minutes from Marist University, Vassar College, and the Culinary Institute of America.
This 127 square meter residence accommodates four guests across two bedrooms and two bathrooms, boasting modern comforts, a fully equipped kitchen, Sonos sound system, solar power, and a unique river-view attic space, with parking for one vehicle in a garage.
The Hudsy Home - Highland, NY
9.8 111 reviews

The Hudsy Home

apartment, Fairview
This Poughkeepsie flat, in Fairview, offers easy access to the Walkway Over the Hudson (less than 1km away) and is a short drive (around 3.2km) from Vassar and Marist Colleges.
The self-catering suite comprises one bedroom, one bathroom, sleeps two guests, includes a 65-inch TV, designated parking, and a full kitchen with fridge, freezer and microwave; nearby amenities include Starbucks, Chipotle, CVS and ShopRite.
S'mores Studio Hideaway - Highland, NY
No reviews

S'mores Studio Hideaway

studio, Highland
This Highland apartment, a studio, is located a 13-minute walk from the Franklin D Roosevelt Library & Museum and a 14-minute drive from the Walkway Over the Hudson State Historic Park.
This pet-friendly, family-approved accommodation for two includes air conditioning, Wi-Fi, a fridge, microwave, and access to a communal swimming pool and barbecue facilities.
Vintage Farmhouse In The Heart Of Hudson Valley - Highland, NY
9.7 100 reviews

Vintage Farmhouse In The Heart Of Hudson Valley

apartment, Clintondale
This 1901 farmhouse, situated in Clintondale in the Hudson Valley, is 145km from New York City, 16km from Poughkeepsie's Metro-North station, and 24km from New Paltz, offering easy access to the Walkway Over the Hudson and other Hudson Valley attractions.
The property, sleeping up to six guests in two queen bedrooms and a sofa bed, features a renovated kitchen with modern appliances, a spacious deck overlooking a private garden, a fire pit, and a grill, alongside Wi-Fi, streaming services, and a Nintendo Classic.

Best Highland, NY accommodations with a kitchen

Two Tillson - Highland, NY
10 18 reviews

Two Tillson

apartment, Highland
This apartment is situated on the grounds of the historic Inn at Twaalfskill, directly adjacent to the Hudson Valley Rail Trail, and within minutes of Vassar College, Marist University, and the Culinary Institute of America, offering convenient access to significant historic sites.
This stylish two-bedroom, two-bathroom flat sleeps up to five guests and features air conditioning, Wi-Fi, a kitchen equipped with a fridge and dishwasher, and off-street parking, with a garden also available for use.
Wooded Rhinebeck-beacon Area Escape W/outdoor Spa - Highland, NY
10 80 reviews

Wooded Rhinebeck-beacon Area Escape W/outdoor Spa

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.
Charming Home Near Walkway Over The Hudson - Highland, NY
9.9 414 reviews

Charming Home Near Walkway Over The Hudson

apartment, Poughkeepsie
This charming house is located in Poughkeepsie, just a short walk from the train station, Marist College, Vassar College, and the Walkway over the Hudson. It has been awarded excellent ratings for its location, cleanliness and overall experience.
The house has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Enjoy modern amenities like a fully equipped kitchen, a laundry unit, WiFi, a smart TV, and keyless entry.
Historic Hyde Park Studio | Minutes From Fdr & Cia - Highland, NY
9.9 162 reviews

Historic Hyde Park Studio | Minutes From Fdr & Cia

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.
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